---
url: "https://youtube.com/watch?v=RP4vJeIb7WU&is=0rUhm81woGx-3agp"
title: "The art of influence: The single most important skill left that AI can’t replace | Jessica Fain"
source_kind: youtube
author: "Lenny's Podcast"
captured: "2026-08-17T00:36:36+00:00"
comment_tree: false
topics: [ai-impact]
summary: "Jessica Fain discusses the art of influencing executives as a critical skill AI can't replace, offering tactical advice on building trust and connecting ideas to leaders' goals."
status: ok
---

# The art of influence: The single most important skill left that AI can’t replace | Jessica Fain

Channel: Lenny's Podcast

## Transcript

[0s] As product managers, one of our best
[1s] sets [music] of skills is curiosity and
[4s] empathy and trying to understand our
[6s] users. But the moment that we're talking
[8s] to an executive, we forget those skills
[10s] and those talents.
[11s] >> It's your fault if the leaders didn't
[13s] buy into your ideas.
[14s] >> People completely misunderstand [music]
[16s] how executives make decisions. What is
[19s] going on in the heads? I describe
[20s] [music] an executive's calendar as a
[22s] strobe light going off. You wake up at
[24s] 8:00 a.m., you've already got a huge
[27s] list of [music] urgent things going on.
[29s] They have not had the time, the energy,
[32s] [music] the wherewithal to center your
[34s] problems.
[34s] >> What are their goals? What are they
[35s] trying to do? How are they measured?
[37s] Connect the thing you're pitching them
[38s] with that success.
[39s] >> There's ways for [music] us to ask much
[42s] more interesting questions of our
[44s] executives. Tell me what the board is
[46s] pushing you on. Execs want to be
[48s] successful, too. They want to be good at
[49s] their jobs.
[50s] >> Sometimes you have the best idea and
[52s] they just don't bite.
[52s] >> One of the biggest things you can do to
[54s] build trust is kill things. Dep
[57s] Prioritize [music] things. If you're
[58s] thinking about how do you be more
[60s] senior, how do you show up in a way that
[63s] is in a leadership mindset, you get paid
[65s] to be a domain expert, your executive is
[68s] looking [music] for you to be the
[70s] deepest person in the room. Bringing
[71s] your expertise to bear is absolutely
[74s] crucial. [music] You have to act like a
[76s] CPO.
[77s] Today my guest is Jessica Feain who's
[79s] been a product leader at Box and Slack
[82s] and Brightitewheel and now at Webflow
[84s] and she has gotten very very uniquely
[88s] good at the art and science of influence
[91s] and in particular influencing
[92s] executives. Influence might be the
[95s] single highest leveraged skill for
[97s] product leaders outside of AI. We
[99s] actually get into how AI is changing the
[101s] skill of influence. I've never heard a
[103s] podcast [music] conversation get deep
[105s] into the art and science of influence,
[108s] how to actually change people's minds
[110s] and the mistakes that people make when
[111s] they're trying to influence leaders. We
[113s] get very tactical and very specific.
[116s] There's a bunch of stuff in this
[117s] conversation that I've never heard
[118s] [music] before or thought about. I am
[120s] very excited for you to learn from
[121s] Jessica. Before we get into it, don't
[123s] forget to check out lennisproduct.com
[126s] for an incredible set of deals available
[128s] exclusively to Lenny's newsletter
[130s] subscribers. Now, let's get into it.
[132s] after a short word from our wonderful
[134s] sponsors. This episode is brought to you
[136s] by Omni. Many product teams today are in
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[237s] >> Jessica, thank you so much for being
[239s] here. Welcome to the podcast.
[240s] >> Thanks for having me. It's my pleasure.
[243s] Let's set this conversation up. We're
[246s] going to be talking about the skill and
[249s] the art of influence and in particular
[253s] uh influencing executives and leaders,
[255s] people above you that you want to
[256s] convince to do things you want them to
[257s] do. Help us understand why this is worth
[261s] people's time. Why is this worth the
[262s] next hour of someone listening to this?
[264s] Why is this skill so important to
[265s] people's careers? I think as product
[267s] builders, there's almost not a skill
[270s] that's more important. Influence and
[273s] building a momentum behind great ideas
[276s] is the way that great products actually
[278s] get built. And if you don't have that
[280s] influence, if you don't have the buyin
[283s] and the backing of your key
[284s] stakeholders, of your executives, you
[287s] can't build great products.
[289s] >> Something that I personally went through
[291s] is just like I I was in a period of like
[294s] I don't need to work on this skill. I'm
[296s] just like, I'm just going to do amazing
[297s] work. I'm just going to it's going to
[299s] show itself. Everyone's going to
[300s] recognize it. And you just everyone run
[303s] into this wall of like, oh man, all
[304s] these other people are getting promoted.
[306s] Maybe talk about that because it feels
[307s] like that's a big trap. People run into
[309s] you.
[309s] >> I think why I wanted to talk to you
[311s] about this is, you know, when I was an
[312s] ICPM, I was putting forth ideas. I was
[315s] trying to reflect what I was hearing
[317s] from my customers. I was trying to get
[319s] sort of buyin and excitement about the
[322s] work that I thought was really going to
[324s] move us forward. And at the time that
[325s] I'm thinking about, I was a PM at Slack.
[329s] And some of my ideas got people really
[331s] excited, you know, got me funding and
[334s] backing and just really a sense that we
[337s] could accomplish something great. And
[339s] some of my ideas and the things that I
[341s] really really believed in died on the
[343s] vine. They went nowhere. And I was so
[347s] confused and frustrated honestly because
[349s] I felt like, hey, I really get this user
[352s] base. I really understand what's going
[354s] to move the ball forward. And I don't
[355s] understand how these decisions are
[357s] actually being made behind the scenes.
[360s] And uh I was uh eight months pregnant,
[362s] eight and a half months pregnant. April
[364s] Underwood, who had just been named CPO
[367s] of Slack, um she had just come back from
[369s] maternity leave. We had a two-day
[371s] overlap. And I sort of got up my courage
[374s] and I said to her, "April, I've admired
[376s] you for a long time. I love the way you
[378s] work. I I really love the way you think.
[381s] Um, and I really want to understand it
[383s] better. If you'd ever consider having a
[385s] chief of staff, I'd love for you to
[387s] consider me. And when I came back from
[389s] that maternity leave, I came into a
[391s] stint as April's chief of staff and was
[393s] later chief of staff to Tamario Hoshua.
[396s] Um, who succeeded succeeded April,
[398s] >> who's been on the podcast,
[399s] >> who's been on the podcast, right? And is
[401s] now a CPO and head of AI at Atlassian.
[404s] Tamar, don't um be mad if I mess up your
[407s] title. And what I learned through that
[410s] process is that people completely
[412s] misunderstand how executives make
[415s] decisions, what is going on in the
[418s] heads, in the calendars, in the
[419s] incentive structures of executives. And
[422s] instead of really understanding where
[425s] that exec or stakeholder is coming from,
[427s] they center themselves. They center
[429s] their own desires, their own
[431s] motivations, their own slice of the
[434s] world, and they end up just not being as
[436s] successful both in their career, but
[438s] also in the types of products that
[440s] they're building.
[441s] >> What's an example of that when you talk
[442s] about people don't understand how
[444s] product leaders actually make decisions,
[446s] how they decide what to do, what to
[448s] listen to. What's an example?
[449s] >> Oh my gosh. I think the biggest example
[451s] of this is people don't understand
[454s] executive calendars, right? A lot of
[456s] times on Google calendar, it's blocked.
[458s] you can't see what they're working on.
[460s] But I describe an executive's calendar
[462s] as like a strobe light going off. You
[464s] know, you wake up at 8 a.m., you've
[466s] already got a huge list of urgent things
[469s] going on. You go from a meeting with
[472s] finance on a budget to an interview for
[474s] another executive to a people problem to
[477s] a legal problem to a product review. And
[481s] the product manager coming to that
[482s] product review or the leader who's
[484s] trying to make a pitch thinks I've been
[487s] prepping for this meeting for two weeks,
[489s] three weeks, maybe six weeks since we
[491s] last spoke. But the executive coming
[495s] into that session hasn't thought about
[497s] you since. They may not have gone to the
[500s] bathroom today, right? And you have to
[502s] understand that they have not had the
[506s] time, the energy, the wherewithal to
[508s] center your problems. and you have to
[511s] help them get into that mindset. So,
[513s] this is as simple as execs are people
[515s] too, right? They are running around
[517s] context switching in the most insane
[519s] ways I've ever seen. And everything that
[522s] comes across their plate is an
[523s] emergency. So, one of the biggest
[525s] tactics I think is so important is just
[528s] take 30 seconds at the top of a meeting.
[531s] Why are we here? What happened the last
[533s] time we talked? Why is this important to
[535s] you? Why is this meaningful? and really
[537s] remember that they are not thinking just
[540s] about you. They are optimizing for a
[542s] global maximum and not for the local
[545s] that you're you're optimizing for.
[546s] >> Essentially, this is how to help someone
[548s] in this world that is running around
[550s] from meeting to meeting without context
[552s] on most things, maybe hasn't had time to
[554s] go to the bathroom. How do we help them
[556s] see what you want them to see and maybe
[558s] buy into your vision and suggestions?
[561s] Yeah, I think that um you know, one of
[563s] the ways that I phrase this is how do
[565s] you get the best out of your exec? How
[567s] do you help them be their best selves?
[569s] We often think about how we show up in a
[571s] meeting or the doc that we wrote or the
[573s] prototype that we've got ready, but we
[576s] don't think about how they can be at
[578s] their best. How do we give them the
[580s] right kind of information in the way
[581s] that they communicate? You know, we as
[584s] product leaders have to be communication
[587s] chameleons. We have to be speaking their
[590s] language like love languages, right? But
[592s] appropriate for work. Um, and you have
[594s] to think about do they really uh turn a
[598s] spark with a design, with a customer
[601s] story, with a dashboard, with an
[603s] experiment, and how do you understand
[605s] how their best brain, how their best
[607s] expertise gets turned on to give you the
[611s] best of themselves. But part of that is
[613s] literally just setting up the meeting
[614s] effectively so that they can have the
[617s] context, the wherewithal, the sort of
[619s] breath at the beginning of the meeting
[621s] to to dive into it.
[623s] >> The other thing I always tell uh people
[625s] I managed is it's your fault if the
[628s] leaders didn't buy into your idea. Like
[629s] it's not you can't just be like ah they
[631s] never they just don't see it. It's not
[632s] my fault. I they they agreed to do
[635s] something else. I always tell them like
[637s] that's just you're not able to influence
[638s] them and convince them that you're
[639s] right.
[640s] >> Yeah. And I Annie Pearl who was my first
[643s] PM manager back at Box. Uh she's
[645s] >> also former podcast guest.
[647s] >> Also former podcast guest, a former CPO
[649s] at Calendarly and Glass Door and now at
[651s] Microsoft and Annie's just the best. She
[654s] always said to me, "It's not my fault,
[655s] but it is my problem." And I think that
[657s] that's the vantage point that a product
[659s] leader has to have, especially if
[661s] they're trying to put themselves in the
[663s] in the shoes of an executive. As product
[666s] managers, one of our best sets of skills
[668s] is curiosity and empathy and trying to
[670s] understand our users. But the moment
[673s] that we're talking to an executive or to
[675s] a stakeholder, we forget those skills
[677s] and those talents and we begin to think
[680s] about our ideas, getting that approval,
[683s] getting to the next meeting, whatever it
[685s] might be, the incentive that we are
[687s] driving. We don't think about the
[689s] curiosity and empathy for what they're
[692s] thinking about, for what their
[694s] incentives are, for how their day has
[696s] been. And if we can take some of those
[698s] skills of building great products and
[700s] think about our executive as our key
[702s] user here, then we can have a much much
[706s] more productive conversation. You know,
[708s] I think one of the most disastrous
[709s] things you can do is going into a
[711s] meeting just looking for approval for
[714s] your plan. Instead, if what you go in
[716s] with is how can I learn, how can I
[719s] strengthen this plan, how can I use the
[721s] domain expertise, the context, the um
[724s] the experience that this person brings
[726s] to the table and imbue that into my
[728s] product work. Both the executive will
[731s] like you better because they will feel
[733s] like you have actually built product
[734s] alongside them, but you will also end up
[738s] with a with a better product. You know,
[740s] I often hear people say to me, "Oh, they
[743s] just don't get it, right? They don't see
[745s] what I see. They're not in my meetings.
[747s] They don't know how hard this is."
[750s] Fine. If you don't respect that person,
[752s] if you don't believe they know something
[754s] you don't, you need to quit. You need to
[756s] go work somewhere else. But if you
[758s] respect them, if you think they have
[760s] something to offer you, that they got to
[762s] the place that they're at because they
[764s] learned and they developed a skill that
[766s] you're trying to gain, awesome. Take the
[769s] feedback, take the insight, ask
[772s] questions, and don't just treat it like
[775s] a rubber stamp because that's a failure
[777s] state and it's a failure state that they
[779s] don't like. I want to dive deeper into
[781s] this stuff, but first something on my
[783s] mind is some people might be turned off
[785s] by this topic in terms of it may feel
[789s] icky of just like uh I don't want to try
[792s] to be this like manipulative person and
[794s] you know deal with politics and
[796s] influence like I just want to do awesome
[798s] work. Why do I have to do this? Speak to
[800s] that person that's kind of just like
[801s] feels icky about building this and
[802s] working on this and being this person.
[804s] >> Yeah. I think that when people frame
[806s] this as politics, they're completely
[808s] missing the point. Politics is
[810s] manipulating outcomes in people for your
[813s] own gain. Influence is about increasing
[816s] the odds that your good ideas survive.
[819s] And I think what happens is people
[822s] actually let ego and let their own
[826s] narrative, their own scope of influence
[829s] get in the way of empathy. Right? So
[831s] this isn't politicking. This is
[833s] learning. If we treat our stakeholder
[836s] conversations, as discovery interviews
[838s] as a way to strengthen our ideas, then
[841s] we end up in a much much better place.
[844s] And if we do that in a in a genuine and
[846s] low ego way, um I'll give an example
[848s] here. Um Noah Weiss who succeeded um uh
[852s] Tamario Suez, CPO of Slack and also
[855s] former podcast.
[857s] What a what a run we're on here.
[859s] >> Oh, I uh No. Yeah, I I've learned so
[862s] much from Noah. We sat down uh to write
[865s] product principles for Slack and uh
[868s] Ethan Eisman, our head of design um was
[870s] leading that initiative. But really this
[872s] was a lot about codifying the early
[875s] ideas that made Slack great, especially
[877s] from a product principles and and sort
[880s] of craft perspective. And we started
[882s] talking about this um and Noah had been
[884s] at Slack early on and he he pulls out
[886s] like a small notebook that he kept in
[888s] his bag and he said, "You know, I
[890s] actually have a section of this notebook
[891s] that I've been keeping things I learned
[893s] from Stuart over the years." Now, he
[896s] hadn't been keeping that notebook
[897s] because he said to himself, "Oh, one day
[899s] we're going to write product principles
[901s] and I'm going to want these quotes on
[902s] hand or I'm going to show off that I
[905s] have this." No, it was for genuine
[907s] learning and growth of his own ideas and
[910s] place as a product leader that he was
[913s] taking those and and what it allowed him
[914s] to do was reflect back to Stuart ideas
[918s] and principles that he had, but also
[920s] grow his own product sense intuition.
[923s] And as an organization, it then allowed
[925s] us to scale those principles. Um, and
[927s] and I think was a really really
[929s] important part. And we worked with a lot
[931s] of the sort of early Slack folks and the
[933s] people that had really developed that
[935s] culture, but it was folks who had really
[937s] tried to grow and learn. They weren't
[940s] trying to politic. They were trying to
[941s] build great products. And that's the
[944s] approach we have to take.
[945s] >> Okay. So, what if you're not working for
[948s] Stewart, which most people, you know,
[950s] Stuart also former podcast guest? I feel
[952s] like uh just the alumni of Slack. Holy
[954s] moly. Just like this is a just the fact
[956s] that
[957s] >> what a just the fact that I have so many
[959s] of these people on the podcast. What a
[960s] sign of an incredible team. Okay, so
[962s] yeah. So most people do not work for a
[965s] steward that has incredible product
[966s] sense, really cares about craft and uh
[969s] you know most people are like I he's so
[972s] or she is so wrong about what we're
[974s] doing. This is such a mistake. They
[975s] don't listen. They don't know what
[977s] they're talking about. How do you deal
[978s] with that? One assumption I have of of
[981s] how folks may misunderstand this skill
[984s] is that they have to be a yes man. They
[986s] have to take everything that the um the
[989s] leader said and do exactly that. That is
[994s] absolutely wrong. You get paid to have
[996s] an opinion. You get paid to be a domain
[999s] expert. And in a lot of ways, your
[1001s] executive is looking for you to be the
[1004s] deepest person in the room, especially
[1005s] if they're good at their job, right?
[1006s] they're looking for you to be the
[1008s] expert. And so bringing your expertise
[1010s] to bear is absolutely crucial. Um, you
[1014s] know, Elon Frank who was who was my boss
[1016s] at Slack as well is now CPO of Checker,
[1019s] he always had a customer anecdote in his
[1022s] back pocket. Like I can hear him in my
[1024s] head saying, "I was just on site last
[1026s] week with so- and so and they said blah
[1028s] blah blah." Right? He always brought his
[1030s] expertise to bear and many of the
[1032s] executives at Slack were not from a
[1034s] strong enterprise background. so he
[1035s] could bring that to the forefront. I
[1037s] think that has to be married again with
[1039s] that curiosity and empathy. If you hear
[1042s] something that you don't agree with,
[1043s] this is something that on a guy my team
[1045s] does super super well right now. You
[1047s] know, he'll hear something that flies in
[1049s] the face of of what he's the data he's
[1052s] seeing, the insights he's gotten, his
[1054s] experience in his domain expertise, and
[1057s] he'll say, "That's so interesting. What
[1060s] led you to believe that?"
[1062s] That kind of question is actually
[1064s] curious about this person said something
[1068s] that I think is dumb, but there must be
[1071s] something behind it. And so if I
[1074s] actually care what's behind it, and what
[1075s] you end up doing in that in that
[1078s] question is co-creating with the person
[1080s] who offered the opinion in the first
[1081s] place, you're able to say to them, I'm
[1084s] interested in what led you to that
[1086s] belief, your experience. Did you have a
[1088s] meeting last week? Are you getting
[1089s] pressure from the board right now in a
[1091s] certain way? What is leading you to that
[1093s] belief? I think one thing that really
[1096s] trips people up is
[1098s] execs are so good at seeming certain.
[1102s] They say things in an authoritative way
[1105s] with confidence with shity because so
[1109s] much of their work is having to make
[1111s] those ultra fast decisions with little
[1114s] information.
[1115s] But if this is someone who is also a
[1117s] learner, who is also has a growth
[1119s] mindset, then if you are able to help
[1122s] them unpack why they believe something
[1124s] and then respond with your own domain
[1126s] expertise, you are able to get to a
[1129s] better solution together.
[1130s] >> I love these very tactical phrases and
[1132s] tips for how to deal with someone, say a
[1134s] leader, say you're, let's just say this
[1136s] is like, you know, they're a director of
[1138s] product, VP of product, CEO that you're
[1140s] trying to convince to agree to a plan.
[1142s] So, one phrase, the phrase you're
[1144s] suggesting here is, uh, that's so
[1145s] interesting. What led you to believe
[1147s] that? Um, anything else along these
[1149s] lines? Say you're pitching your product
[1150s] or an idea to say a VP of product and
[1154s] they're just like, what what else would
[1156s] what else what else works?
[1157s] >> The earlier that you can understand the
[1160s] belief system and the things that are
[1162s] important to them, the better off you're
[1164s] going to be. So, very, very early on in
[1168s] this process, what is top of mind for
[1170s] them? I can count on one hand when I was
[1172s] chief of staff, how many people asked me
[1175s] for advice before going into our product
[1177s] review with our CPO or other executive
[1179s] team to say, "What do you think is most
[1181s] important to them right now?" Use the
[1183s] people around them, their EA, their
[1185s] chief of staff, the people who have
[1187s] successfully pitched ideas in the past
[1189s] and say, "What worked? What do you think
[1191s] they're worried about? What are the
[1192s] risks?" And in an age of the tools of AI
[1195s] that we have, this is so much easier
[1198s] than it's ever been, right? You can ask
[1200s] Slackbot, "What has Rachel been posting
[1203s] about lately? What what do you think is
[1205s] most important to her?" A colleague of
[1206s] mine, a peer on on our product
[1208s] leadership team trained a GPT on a bunch
[1211s] of um transcripts from past product
[1213s] reviews that are all publicly available.
[1215s] And we expect that our PMs are running
[1218s] their PRDS or their their pitches
[1220s] through that to say, "What's Rachel
[1222s] going to push back on? Where are their
[1224s] weaknesses in this ideas?" You can also
[1226s] train things on where are your own
[1227s] weaknesses? I know I've gotten feedback
[1229s] in the past that my data is a little
[1231s] thin or that this kind of UX thinking is
[1234s] thin. Give me feedback on that. Cloud's
[1236s] amazing for this. And so I think that
[1238s] the the first step is actually just
[1240s] saying what's important to them. What do
[1243s] they want to hear? And anchor on that. I
[1246s] think the second piece is going in to
[1248s] learn, not to convince. And the earlier
[1251s] on you do that, the better. So we have
[1253s] something at Webflow uh called office
[1256s] hours. as early as you can you are
[1259s] having these conversations to align on
[1261s] strategic direction maybe even before
[1263s] you have a one-pager you know uh we
[1266s] implemented something at Slack with
[1267s] Stuart because we realized we were
[1269s] coming to him with like done designs and
[1271s] he was like what the [ __ ] is this I this
[1273s] is completely different than how I had
[1275s] this in my mind so Ali Rail early Slack
[1278s] employee implemented something called
[1280s] hey Stuart what do you think and we
[1282s] would just sit with him for half an hour
[1284s] and say what do you think on this topic
[1286s] what's your belief system, what's your
[1287s] past experience? And we started with a
[1289s] user interview, right? We started with
[1292s] we actually want to download your
[1293s] expertise here. And I think that when
[1295s] you engage execs in that way, it's
[1298s] really, really valuable. Like one of the
[1299s] things I see people do poorly is they
[1302s] don't ask for the time. They, you know,
[1305s] this is sort of in counterpoint to what
[1307s] we were talking about before with how
[1308s] busy their calendars are, but they're
[1311s] afraid to ask for more time to get that
[1313s] insight. But sometimes if you don't, you
[1316s] miss the point.
[1317s] >> Something that we hear a lot on this
[1320s] podcast is as a product leader, as a
[1323s] leader of any kind, you want to have a
[1325s] point of view. You want to come into a
[1327s] discussion with here's here's our
[1329s] options. Here's what I think is the
[1330s] right solution. And then at the same
[1332s] time, as you're describing, you want to
[1334s] come across as I want to learn. I'm not
[1336s] here to convince you. I'm here to just
[1337s] like help understand your worldview and
[1340s] where you think the right path is. How
[1341s] do you think about just those two kind
[1342s] of that balance of I have something I
[1345s] believe is right and okay but I'm here
[1347s] to learn and get your feedback and see
[1349s] what you think makes sense.
[1350s] >> Okay. So my advice on this may be a
[1352s] little paradoxical because um I think
[1354s] people make mistakes in both directions
[1356s] on the polls here. On the one hand I
[1359s] think there's an error people make of
[1361s] trying to show too much work trying to
[1364s] tow too much upfront proof point. We
[1367s] talked to 16 participants from these 15
[1370s] geos and this is the statistically
[1372s] significant and the exec is like I'm so
[1374s] bored I'm going to die. I remember I did
[1376s] this in a review once and literally the
[1380s] person I was most trying to convince
[1381s] glazed over got on their phone and I
[1384s] totally blew the meeting because I was
[1387s] trying to prove that I had done my
[1389s] homework. Put it in the appendix. Right?
[1391s] They don't need to know every single
[1393s] detail. the baseline expectation is that
[1395s] you did your job and that you this that
[1397s] this is built on a solid foundation of
[1399s] your domain expertise. On the flip side,
[1402s] I think there's some balance of showing
[1405s] your work that helps elucidate why your
[1408s] solution is best. So, one of the
[1410s] mistakes I see people giving is is doing
[1412s] is giving only one option.
[1415s] I think that people if you say I mean
[1417s] this is also like classic pricing and
[1419s] packaging strategy uh give three options
[1422s] and the goldilocks in the middle is the
[1424s] perfect one. Right? But I think that
[1426s] what that actually allows you to do is
[1428s] say hey we considered we are not dumb.
[1431s] We did not miss something. You think we
[1434s] missed something but no no we actually
[1435s] considered this. So we had a recent
[1437s] product review with my manager Rachel
[1440s] Woolen. uh she was a recent guest on how
[1442s] I AI and we uh brought a doc a sort of
[1447s] reasonable approach to what we thought
[1449s] was the sort of problem and strategic
[1451s] space we were going after.
[1453s] It didn't go well. it really didn't
[1455s] match her expectations and the feedback
[1457s] she gave us which was really really the
[1459s] right feedback was I don't understand
[1463s] how you're thinking about the
[1464s] permutations of possible here because we
[1466s] had only given one option set and so
[1468s] what we did following that review is we
[1471s] said hey we really want to sort this out
[1473s] we want to get moving we want to show um
[1476s] that we can really get building on this
[1478s] on this product and alignment is the
[1481s] next stepping stone for that can you
[1483s] meet in two days and we turned around a
[1486s] new doc in two days that actually showed
[1488s] all of the options we had considered but
[1490s] hadn't brought to that first review. And
[1492s] once we elucidated all the things we
[1494s] considered and why we thought they would
[1497s] or wouldn't serve the outcomes we were
[1499s] driving and the technical complexity
[1500s] behind them, she was like, "Oh yeah,
[1503s] okay. I see why the solution that you're
[1506s] proposing makes the most sense for what
[1508s] we're trying to accomplish." But in the
[1510s] first version, in the first meeting, we
[1512s] hadn't kind of shown that and we hadn't
[1514s] workshopped it through her. And so
[1517s] sometimes, you know, really tactically,
[1519s] you you want to have that available to
[1522s] you. It's not necessary to put all 15
[1524s] options you considered, but at least be
[1526s] ready to show them. Have them in an
[1528s] appendix, have them in a draft Figma
[1530s] [clears throat] file, whatever it is.
[1532s] Um, we uh we we used to have this rule
[1535s] after a design review with Stuart. We'd
[1537s] go through the design review and he'd
[1539s] say, "No, do it exactly like this. I
[1542s] want, you know, the button here and the
[1543s] interaction to be this." And frankly, he
[1546s] always had better ideas than than we
[1548s] did, but we would come back and we
[1550s] called it Stuart plus two more. So, we
[1553s] did exactly what he asked for and then
[1556s] two other versions that we felt good
[1558s] about. And then it gave us a a forum for
[1561s] conversation to debate the merits of
[1564s] each type of approach. Awesome. Okay.
[1567s] So, there's a bunch of advice here. One
[1568s] is the default is don't go in with
[1571s] here's our whole process that landed on
[1573s] this suggestion. Uh but have that ready
[1575s] because they may ask for that if they
[1577s] don't buy into it. Another is present
[1579s] options. And then there's a here's my
[1581s] point of view. Here's why I think this
[1582s] is the right one. And then if they dig
[1584s] in, you have be ready for more options.
[1586s] Have you have you ever looked into the
[1588s] Mento pyramid way of presenting stuff?
[1591s] >> No, I don't know what that is.
[1592s] >> Okay. So, this is there's this uh lady
[1594s] Barbara Mento. she uh she's like from
[1596s] the 50s I think she was the first female
[1598s] uh consultant at McKenzie or something
[1600s] like that and she kind of figured out
[1601s] the best way to present information to
[1603s] execs is is uh backwards essentially
[1607s] it's instead of here's our process
[1609s] here's all the things we did here's our
[1611s] set of conclusions and then here's our
[1613s] recommendation it's flip it start with
[1616s] here's our recommendation
[1618s] and then here's the things we explored
[1620s] and then here's the evidence behind that
[1622s] feels like that's kind of what you're
[1623s] describing Yeah, I think that's a really
[1625s] good way of doing it. I think my only
[1628s] gloss on that would be that people are
[1631s] really different, right? Like execs are
[1633s] people too. And so one of the things
[1635s] that I think is really important is
[1638s] understanding what is the literal
[1640s] format, storytelling, pre-work that is
[1643s] going to work for that person. You know,
[1645s] some people hate a PowerPoint and it's
[1647s] just going to crush their soul if you
[1649s] start doing that. Um, some people only
[1653s] want to see the data and not the user,
[1655s] you know, the the qualitative research.
[1657s] Um, and so I do think it is about really
[1660s] understanding their communication style.
[1662s] And execs, if you're listening to this,
[1664s] it's really [ __ ] helpful if you tell
[1666s] people because you actually know what
[1668s] you like and don't like. And so just
[1670s] tell people, I prefer a doc. I want no
[1673s] upfront explanation. I want 10 minutes
[1675s] of quiet reading time and then we can
[1678s] come back together. That's a
[1679s] particularly effective um means for for
[1682s] very busy people and short meetings um
[1684s] and especially in remote work where
[1686s] presentations just don't work very well.
[1688s] Some execs are willing to do pre-ereads,
[1690s] some aren't. Um and I I think you just
[1693s] have to be willing to accept that they
[1696s] are also human and you're trying to give
[1698s] them the best shot at inculcating the
[1700s] information in the way that is
[1702s] meaningful to them. So, there's a bunch
[1704s] of uh tips here that I want to summarize
[1707s] for how to kind of set yourself up for
[1710s] success. One is what you just described,
[1714s] which is just think about how do they
[1716s] respond best? What kind of setup do they
[1718s] respond best to? Is it a presentation?
[1720s] Is it a here's what we recommend. Here's
[1722s] three options. Is it uh data? Something
[1724s] else? So, there's like just understand
[1726s] here's what this person likes. They they
[1728s] don't want a they want like five minutes
[1730s] fast conclusion. Why? Uh then there's
[1734s] your advice of ask people that know them
[1737s] what is top of mind for them right now
[1739s] because they may be like this is the big
[1742s] bet we're making right now if it's not
[1743s] align with that they're not going to
[1745s] care. So it's like either either ask
[1747s] them or ask people around them what's
[1749s] top of mind for them right now and then
[1751s] there's this idea of simulate almost
[1752s] simulate them feed all the previous
[1755s] meetings with them into say cloud
[1756s] project or something like that create a
[1758s] little GPT and run your idea by them and
[1760s] like what would you say
[1762s] >> I will tell you I am not a big fan of
[1764s] the what's top of mind for you uh
[1766s] question this a hot take because I think
[1769s] that what often people do is they think
[1772s] through their top priorities their top
[1774s] experiences is, you know, if we were
[1777s] trying to do a research study uh to
[1779s] understand the day-to-day lives of our
[1781s] users, we probably wouldn't say, "What's
[1783s] top of mind for you?" We'd say, "Tell me
[1785s] how you spent your day." We'd say,
[1787s] "What's the most urgent priority for you
[1791s] right now that you're really scared
[1792s] about messing up? What um pressures are
[1795s] you facing?" And so, I think there's
[1798s] ways for us to ask much more interesting
[1800s] questions of our executives. Um, I
[1803s] recently did this with our CEO. I said,
[1806s] "Tell me what the board is pushing you
[1808s] on because everyone's got a boss and uh
[1812s] even a CEO who seems so powerful and
[1815s] competent and um and and sure is getting
[1818s] pressures, right? What are you seeing as
[1821s] the the the key inputs to your success?"
[1824s] The other thing people don't realize is
[1827s] excepts want to be successful, too. They
[1829s] want to be good at their jobs. And how
[1831s] can you help them? I mean, in the best
[1834s] case scenario, your incentives at a
[1837s] local team level or product organization
[1839s] level really closely align with their
[1841s] incentives that you're working on
[1843s] something that really matters to the
[1844s] company. If you're not, you really
[1846s] should be having that conversation
[1848s] because you'll be in misalignment from
[1850s] the start. But if you actually have
[1852s] alignment, point out that alignment. How
[1855s] is the metric that they're trying to
[1856s] move? The OKR they're responsible for
[1859s] the board pressure that they're under
[1861s] going to be improved by the thing that
[1864s] you are proposing and how do you get
[1866s] there together. So I think that one of
[1870s] the things people really miss out on
[1872s] here is
[1875s] what are the success criteria for an
[1877s] exec and how do you model your world to
[1881s] amplify that success so that both of you
[1884s] can be more successful.
[1885s] >> Okay, that is such an important lesson
[1887s] before we I follow that thread just to
[1889s] clarify this question of what is top of
[1891s] mind. Your advice uh was ask people
[1894s] around them what is top of mind for
[1895s] them. Don't ask them directly this
[1896s] question. top of mind has become this
[1899s] sort of trope, right? It's uh it's execs
[1902s] write a weekly write up of what's top of
[1904s] mind and it sort of becomes this generic
[1908s] uninteresting sort of neutralized frame.
[1911s] And so I think the question what's top
[1914s] of mind for you has actually lost some
[1916s] of its firepower and instead we have to
[1919s] get at what is the emotion the um the
[1925s] sort of drive behind it and and what's
[1928s] the spicier question that'll get a more
[1930s] interesting answer. So then but going
[1932s] back to this incentives piece such a
[1933s] powerful lever for getting anyone
[1936s] basically to get anyone to agree to what
[1939s] you want which is what is what are they
[1942s] what are their goals? What are they
[1943s] trying to do? How are they measured?
[1945s] How's success for them? And then how's
[1947s] the thing you're pitching them aligning
[1949s] with that and will help them achieve
[1951s] that specific goal.
[1952s] >> Right? And in a product in building
[1955s] products together, your incentives
[1957s] should be making your users successful,
[1959s] making your business successful because
[1961s] of that. And so what do they actually
[1963s] believe about that? It's not just about,
[1965s] oh, they want a promotion or they don't
[1967s] want to get fired or they want to hit
[1969s] their KR. Those are very very real human
[1971s] things. But in an ideal world, in
[1975s] product work, it is really based on
[1977s] building incredible products for your
[1979s] users and therefore great outcomes for
[1981s] your business. And so I think a big part
[1983s] of this is actually understanding their
[1986s] strategic insights and what they believe
[1987s] is going to move the business forward um
[1990s] most effectively. So after I was chief
[1993s] of staff, I took over Slack's core
[1994s] product team. We worked on channels and
[1997s] emoji and search and messaging. And
[2000s] there was a real feeling from our
[2003s] executive team that we had a bit lost
[2005s] our mojo around product craft. And we
[2008s] talked about, you know, painting the
[2009s] insides of the cabinets. We really
[2011s] wanted such an amazing experience for
[2013s] our users. That was one of the things
[2015s] that makes made Slack great in the first
[2017s] place was just it really felt like a
[2020s] product that took that
[2023s] usability to a 10x place. And there was
[2027s] a sense that I had heard from our
[2029s] leadership that we weren't quite there
[2032s] and we had lost some of that. And that
[2034s] was so so important to who we were and
[2036s] how we showed up for our users. And so
[2038s] we implemented something uh called the
[2041s] customer love sprint. Uh we said, "Okay,
[2044s] engineering, stop what you're doing. As
[2046s] an entire team, we're going to spend two
[2049s] weeks just painting the inside of the
[2051s] cabinets." The only rule was engineers
[2054s] got to pick what they worked on. We we
[2055s] supported them from a PM and design and
[2057s] and customer support perspective. We
[2060s] gave them tons of ideas, but engineers
[2061s] could pick what they worked on. The only
[2063s] rule was that you had to ship something.
[2065s] You had to ship something that was good
[2066s] for users. And what we did is, you know,
[2069s] you could call this a bug bash. You
[2071s] could say, "Okay, you gotta fix these
[2074s] uh, you know, these these rough edges,
[2076s] these these misses in the product, but
[2078s] we made it a huge deal. We made it
[2080s] really exciting and fun, and we had a
[2084s] big really fun judging competition that
[2086s] our executives took part of, and we
[2088s] really brought back that part of our
[2090s] culture that we had lost out on a bit.
[2093s] And it spoke to what our executives
[2096s] believed was a differentiation for us
[2098s] and how we were going to show up in the
[2101s] market, show up to our users, grow our
[2103s] user base by making it feel special. And
[2106s] we were able to say, "Oh, we shipped 65
[2110s] improvements this week, this this
[2111s] sprint." And and that felt really really
[2114s] aligned with what they were trying to
[2115s] accomplish from a company perspective as
[2117s] well.
[2118s] >> Okay. So to summarize the kind of
[2120s] tactics so far, one is align your pitch
[2124s] with the person you're trying to pitch
[2128s] is incentives. I don't know if the
[2130s] grammar on that sentence works, but what
[2132s] are they trying what does success look
[2133s] like for them? Connect the thing you're
[2135s] pitching them with that success.
[2137s] >> Yeah, I think that um aligning your
[2140s] incentives is yes really really
[2142s] important in a product pitch. If you're
[2144s] thinking about a product pitch, how does
[2145s] it connect to the company goals? Are you
[2147s] trying to um improve conversion rates?
[2149s] Are you trying to grow enterprise
[2151s] customers? Are you trying to be
[2153s] perceived in brand? Are you trying to
[2155s] break into some new category? Of course,
[2156s] you have to align on a new pitch. I
[2159s] think the inverse of this is how do you
[2162s] use that incentive structure to also
[2164s] inform regular roadmap? not uh you know
[2168s] just net new product ideas or net new
[2171s] pitches but you're actually imbuing your
[2175s] entire team and your thought process
[2177s] with that incentive structure it's a
[2179s] deep understanding how did the OKRs get
[2181s] to be the way they are how did the
[2183s] positioning statement get to be that way
[2185s] how do I understand that and deeply
[2187s] embed it into my team's culture so that
[2189s] we're reflecting what our exec team our
[2193s] leadership has said is important
[2195s] >> so basically Everything should feel like
[2196s] it's a cohesive set of priorities based
[2199s] on some outcome you all agreed to in the
[2202s] mission.
[2203s] >> Yeah. And I think a a big part of this
[2205s] is also metrics and data and what you're
[2207s] actually measuring your your own teams
[2210s] on. You know, we talk a lot about uh
[2212s] leading and lagging indicators. Um or in
[2215s] the nonprofit world, this is called
[2216s] theory of change. Uh there are many
[2219s] steps. You yourself and your individual
[2221s] team may not be able to directly move
[2224s] enterprise revenue or directly move
[2226s] conversion rate. But you believe and the
[2229s] company has a belief that painting the
[2231s] inside of the cabinets having an
[2232s] exceptional customer experience will be
[2235s] the thing that leads to customer
[2237s] retention, customer conversion, um user
[2240s] satisfaction. And so how do you make
[2243s] sure that your metrics and the things
[2245s] that you are proposing to actually shift
[2248s] ladder up really really clearly to those
[2250s] and that your executive agrees to that.
[2252s] >> Okay. And then the a second lever is
[2256s] trying to not go into a conversation
[2258s] even though you are trying to influence
[2261s] them. It's to go into it with an open
[2263s] mind and and a learning mindset. You use
[2266s] this phrase uh that's so interesting.
[2268s] What led you to believe that?
[2270s] >> Right. And I think in that is um a
[2273s] disarming of the executive. You know,
[2277s] again going back to like how do you get
[2279s] the best out of them? You want them to
[2281s] feel comfortable. You want them to feel
[2284s] like they can be honest with you. I
[2286s] think something I see people miss often
[2289s] is they don't follow the subtle threads
[2291s] that executives lead them, the sort of
[2293s] breadcrumbs of opinions. you know, in a
[2296s] in a sort of more clear-cut scenario,
[2300s] your leader, your executive will say to
[2301s] you, "Okay, I'd like a brief on exactly
[2304s] this thing. Write it generally this way.
[2306s] Let's review it in a week." That's a
[2309s] very clear-cut ask, but very very often
[2311s] the asks are more subtle. I wonder if
[2315s] I'm thinking about, have you considered?
[2318s] And what I find is that people don't
[2320s] take the bait and the best people do. So
[2324s] I'll give you an example. Just last week
[2326s] um you know we've been working a lot on
[2328s] as uh skills get democratized across web
[2331s] flow everyone can do design everyone can
[2333s] ship code uh everyone can write a PRD
[2336s] how are we enabling people to move as
[2339s] fast as their brains and tools will make
[2341s] them. Uh Rachel our CPO said you know
[2344s] hey Kev our head of design we're going
[2346s] to have to think about design reviews at
[2348s] some point. And within an hour, Kev had
[2351s] had a loom put together of, hey, here's
[2353s] a framework of high-risisk design
[2356s] changes, lowrisisk design changes, blast
[2358s] radius, release processes, and how we
[2360s] might allow anyone in the organization
[2363s] to have designs shipped to production.
[2366s] That was a thread. She didn't ask him to
[2368s] do that. he didn't need to follow up in
[2370s] that time frame, but he recognized that
[2372s] the organization's incentives are to
[2374s] keep empowering people, to keep everyone
[2376s] moving fast, to keep everyone um really
[2378s] excited about what they're building as
[2380s] well. And he knew that he could slot in
[2383s] and respond to this feedback really
[2385s] really quickly. A lot of times I see
[2387s] people don't take that invitation from
[2390s] the executive to actually engage on the
[2393s] feed, the subtle feedback they're
[2394s] giving. you know, uh, an example from my
[2396s] past where this didn't go as well was,
[2399s] um, we were in a strategy review, you
[2402s] know, sort of a quarterly strategy
[2403s] review, and it was probably the fourth
[2406s] time I had heard Tamar ask, I want to
[2408s] see, I'm interested in seeing the top 10
[2410s] use cases on X. And the fourth time it
[2414s] happened, she got really frustrated. She
[2416s] said, we've talked about this so many
[2418s] times before. Why don't we have this
[2419s] documented? And I think it's because
[2422s] people are not picking up on the cue
[2425s] that there's really something deep
[2427s] underneath. There's really an important
[2429s] piece of feedback or a question that
[2431s] they're not pulling on. Maybe you think
[2434s] that that's not an important thing to
[2435s] do. And then you need more information
[2437s] about why they think it's important.
[2439s] Because if you just let it go and you
[2442s] don't respond to the feedback or respond
[2444s] to the ask, that person loses faith in
[2447s] you that you're going to follow up on
[2449s] the thing that they believe is
[2450s] important.
[2451s] >> It also sounds like a really good way to
[2452s] influence is you take the reigns and
[2456s] here's where I think we could go with
[2458s] this and here's the answer to your
[2459s] question.
[2460s] >> Absolutely. I mean, I think if you're
[2461s] thinking about how do you be more
[2463s] senior, how do you show up in a way that
[2466s] is in a leadership mindset, you have to
[2469s] act like a CPO, you have to come in with
[2471s] that perspective. You have to come in
[2473s] with a solution. You have to follow the
[2476s] thread that they've asked about. You
[2478s] have to do it quickly. Um, one of the
[2480s] missteps here is, you know, people treat
[2483s] these interactions as so high seeks and
[2485s] sometimes they are, but one of the ways
[2488s] that you you fail at that interaction is
[2491s] you wait too long to to engage on the
[2494s] feedback. If you wait a week for the
[2496s] follow-up items that you discussed in
[2498s] the meeting, that exec has moved on and
[2501s] you've missed your chance to actually
[2502s] respond to the feedback in a in a in a
[2505s] quick manner. you will get so much more
[2508s] excitement, enthusiasm, brain power from
[2510s] them if you keep the ball rolling in a
[2512s] in a timely manner.
[2514s] >> And obviously there's like, you know,
[2515s] everyone's so busy, there's already so
[2517s] much work on their plates, you can't
[2519s] just hop on everything an exec says.
[2521s] There's also this like classic advice of
[2523s] sometimes exacts just say something and
[2524s] everyone takes it so seriously. Oh, I
[2526s] have to do that. And sometimes they're
[2527s] just saying it in passing. So, it's
[2529s] probably all, you know, it's a balance
[2530s] of like take the opportunities, don't
[2532s] have fun every single thing.
[2533s] >> Yeah. And a great question to ask in
[2536s] that in that scenario is how strongly do
[2538s] you feel about this? So if you hear
[2540s] something that they say really strongly
[2543s] um or how urgent do you think that is or
[2546s] hey here's what the team is working on
[2548s] now. Do you think that that trumps these
[2550s] priorities? And if they say yes, listen,
[2555s] do the thing that they say trumps it.
[2557s] Right? It's not about jumping on every
[2559s] request or taking every piece of
[2561s] feedback. It's about contextualizing it
[2563s] in why they believe that, what they
[2565s] think the urgency is, and then actually
[2567s] responding to that. So, more often than
[2569s] not, they'll say, "I wonder if we could
[2571s] do this kind of study." And people will
[2574s] go and say, "Oh my gosh, we have to go
[2575s] run that study right now. We have to dep
[2577s] prioritize everything else." But if you
[2579s] say to them, hey, that's a really cool
[2581s] idea. I I like that. Do you think that
[2584s] that's more important than these three
[2585s] other studies or three other projects
[2587s] that we're working on now? And they'll
[2588s] say, "Oh, no, no. That's just like a
[2589s] random idea. put it on the backlog. I
[2592s] think that um execs are moving so
[2593s] quickly that they won't always give you
[2596s] that context of urgency and so you have
[2599s] to ask for it. This is something I've
[2601s] been working on getting better at as a
[2603s] leader. This is just an idea. Um this is
[2606s] a mandate. This is something I want to
[2607s] see. But uh it's hard sometimes it's
[2610s] hard to remember to do that because your
[2611s] brain is spinning with ideas.
[2613s] >> This comes back to your point about uh
[2615s] getting into the mind of the person in
[2617s] the meeting, the leader. They're running
[2618s] around all day. I think you call it a
[2620s] strobe. You're just like bam, another
[2622s] meeting, next meeting, next meeting,
[2623s] next meeting without a lot of context
[2625s] and they just say things and sometimes
[2627s] it's import to them, sometimes not.
[2629s] Which comes back to one of your tips at
[2630s] the beginning of this chat is
[2632s] >> spend 30 to 60 seconds at the beginning
[2634s] just giving them a little context on
[2636s] what the heck. What would you recommend
[2638s] in that 30 60 seconds? What are some
[2640s] kind of key bullet points of what you
[2641s] want to communicate? Yeah, in the 30
[2643s] seconds I would say we're here to
[2646s] discuss XYZ. Last time we met, we left
[2649s] it off here. The goals of today's
[2651s] meetings are ZYX.
[2654s] We're going here's how we're going to
[2655s] run this meeting and then stop talking
[2657s] because the moment you go off over 60
[2660s] seconds, you've lost them. And and oh, I
[2662s] think the other really important thing I
[2664s] would add there is to say, was there
[2665s] anything else you were hoping to cover
[2667s] today?
[2667s] >> That was awesome. I love this advice. I
[2670s] am excited to tweet this out just to
[2672s] summarize these bullet points you just
[2674s] shared. Uh that is so cool. I love that.
[2676s] And to your point, if 60 seconds flies
[2678s] by, you may think you're talking for 60
[2680s] seconds. It often ends up being 5
[2682s] minutes. So the advice of keep it under
[2683s] 60 seconds. Just like try to actually do
[2685s] that.
[2686s] >> Try to actually do that. I think the
[2687s] other thing here is, you know, this
[2690s] often depends on what kind of meeting
[2692s] what what you're actually doing. You
[2693s] know, in our culture, we do a lot of
[2695s] sort of silent read of docs or watching
[2697s] a loom um in the meeting and then coming
[2700s] back for conversation. I think one of
[2703s] the things that I've seen be really
[2704s] effective in coming back for that
[2706s] conversation is often times a a leader
[2710s] will smatter your doc with a hundred
[2712s] comments and you're like, "Oh my gosh,
[2714s] what is actually important here?" So,
[2716s] what I often do is I have a section at
[2718s] the top to say themes for discussion. I
[2721s] bubble up some of the biggest and most
[2723s] controversial pieces that can only be
[2725s] discussed live. And anything they've
[2727s] said that they're just curious about,
[2728s] what's the time frame for this? What's
[2730s] the staffing need for why, I can answer
[2732s] offline, I can answer a follow-up. What
[2734s] I can't get again is the time for
[2736s] discussion with that group. And the
[2738s] safer that they feel in that discussion
[2740s] and the more that they think that you've
[2742s] understood what is the most sort of
[2745s] spicy or controversial, that's where you
[2747s] get to the good stuff and you really get
[2749s] their insight and input. So I, you know,
[2752s] put a section at the top and say topics
[2754s] for discussion that I'm reading through
[2755s] the comments. Rachel, was that right?
[2757s] Did I sort of get your thoughts right?
[2759s] Anything you would add to this? And then
[2761s] we can talk about uh the the the really
[2764s] good stuff that gets us to a better
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[2821s] We've talked about aligning your
[2823s] incentives and goals with their goals.
[2826s] Uh going in with an open mind, setting
[2829s] context at the beginning of the meeting,
[2831s] understanding how they like to be
[2832s] presented to. What else can we learn to
[2836s] become better at influencing execs? And
[2838s] let me just do a quick tangent. As
[2840s] people are listening to this, they may
[2841s] again be like, "Oh my god, all this BS I
[2843s] have to do. I just want to do awesome
[2844s] work. Why am I spending all this time
[2846s] learning all this meta work of how to
[2848s] convince someone of a freaking thing? I
[2849s] just want to build awesome products,
[2851s] drive, you know, growth for the business
[2853s] and the product and this sucks." I think
[2856s] it's again important to remind people
[2858s] this is just the way things go. You need
[2860s] to influence people in power to agree
[2864s] with your approach. That's just the way
[2867s] it is. You can't just be like, "Nah, no
[2868s] one no one understands me. It sucks."
[2870s] So, it's not my fault.
[2871s] >> I mean, it's literally your job, right?
[2874s] They uh I think the way that product
[2876s] management has has worked for a long
[2878s] time is you basically get funding for
[2882s] your ideas in the form of engineering,
[2885s] design, uh you know, crossunctional
[2888s] resourcing, right? that is you should
[2890s] consider that VC money that's been
[2892s] invested in you and your CFO, your CPO,
[2896s] your CEO is expecting a return. And so
[2898s] what is the way that you are showing
[2900s] that you are building great products
[2902s] that that honors that investment in you
[2906s] and
[2908s] sure you can go into a startup and be
[2910s] the sole decision maker and that is a
[2912s] very very valid way to work. But if you
[2914s] work with other people, having them
[2916s] excited, interested, passionate, um,
[2920s] bought in to what you're doing
[2923s] will make everything easier. I It is
[2926s] also the job, right? You you also have
[2928s] to, but I think I think the thing I want
[2931s] people to take away is that it's really
[2934s] the way to build well. You know, when
[2936s] people are motivated, when they feel
[2938s] purpose, when they feel like this is
[2939s] really something that I believe in, they
[2943s] work harder. They support you more. They
[2946s] talk about you in rooms that you're not
[2947s] in. And so, it's it's just actually the
[2951s] way you deliver great results.
[2954s] >> I I think that's such an important
[2956s] framing. Okay. What other tactics, what
[2959s] other techniques work in helping leaders
[2962s] uh get influenced?
[2964s] >> Yeah. put get influenced. I love that. I
[2967s] love that. Um
[2969s] >> yeah, we should we should have like a
[2971s] stamp like influenced uh [laughter]
[2974s] at the end.
[2975s] >> So I think one of the things that people
[2977s] misunderstand is the constraints that
[2981s] they are bound by versus their
[2983s] leadership. you know, execs are not um
[2988s] they they don't have the same boundaries
[2989s] of budget and headcount and um and
[2993s] timeline that you feel. They can move
[2996s] people around in the organization. They
[2998s] can ask for more resourcing. They can
[2999s] get creative. They can elevate projects,
[3002s] kill projects. Um and so you know you
[3005s] have to come to them with that mindset
[3008s] of hey with today's resourcing with this
[3011s] many engineers or this kind of tooling
[3013s] or this kind of investment here's what
[3016s] what I can get but I'm thinking of the
[3019s] 10x case I'm thinking of the accelerated
[3021s] case and if that's what you want and if
[3023s] that's aligned with your incentives
[3026s] here's what I need to be successful and
[3028s] so I think that people think okay well
[3031s] I've got my pizza team and I've got my
[3033s] four engineers and what you're asking is
[3035s] not possible. Well, if it's not
[3037s] possible, tell them why not. Come back
[3039s] and say, you know, the thing that you're
[3041s] asking for, I'm super stoked about that.
[3043s] I need eight more people. I need you
[3046s] twice a week for an hour. I need much
[3049s] closer alignment with our marketing team
[3051s] and I'm not sure how to get that. You
[3053s] have to think about what are the
[3055s] constraints that hold you back that they
[3057s] can actually help you a lot with. And
[3060s] people miss out on this all the time of
[3063s] not asking for what they need to be
[3064s] successful, especially when the ask from
[3067s] the executive seems unreasonable.
[3069s] >> This is such a good adi piece of advice
[3070s] of just if you get them excited enough,
[3073s] things can significantly change in terms
[3075s] of resourcing and prioritization. Like
[3077s] your job is to help them see that how
[3079s] massive an opportunity this is and go
[3081s] and not just give you what you want, but
[3083s] just like wow, okay, here's the way to
[3084s] unblock this thing. Uh here's how we can
[3086s] go. like, okay, this is going to be our
[3088s] new bet big bet. Let's let's go big
[3090s] here.
[3091s] >> Yeah, absolutely. This is going to be
[3092s] our new big bet. And this comes back to
[3094s] aligning with what the company's trying
[3096s] to to accomplish. And also the urgency.
[3099s] So some things if you added a dozen more
[3102s] people or perfect alignment with go to
[3104s] market, yeah, you could get them to
[3105s] market faster, but is that the most
[3108s] important thing for the company goals?
[3110s] is right now the answer is accelerating
[3114s] this in this way actually going to do
[3116s] more or is it something else that's
[3119s] actually more aligned and so I think
[3120s] it's still being so rooted in the
[3123s] company goals in what the exec is trying
[3124s] to accomplish in what your users really
[3127s] need to be successful so that you can
[3129s] say in order to accelerate our goals
[3131s] here's what we can here's what we can do
[3133s] >> like you know if you were in charge of a
[3136s] company you were you'd be so excited if
[3138s] someone came to you with a 10x next idea
[3140s] that's going to change the trajectory of
[3142s] your product like that's what everybody
[3145s] wants.
[3146s] >> Uh and so uh that is a really powerful
[3148s] way of approaching all these things.
[3150s] Obviously not every idea is going to be
[3152s] a big idea. Not every idea is a great
[3154s] idea. A lot of times these take time.
[3156s] Also maybe speak to that just like say
[3159s] you have a big idea and they're like
[3161s] nah. What what are some expectations to
[3163s] set for people that come up with a big
[3164s] idea that just isn't getting any
[3166s] traction? You know, it really depends on
[3168s] what kind of organization you're working
[3169s] in. You know, if you're working in a
[3170s] smaller organization, if that big idea
[3173s] is something that you can build on your
[3174s] own or you can build within versus if
[3176s] you need, you know, a large large scale
[3178s] investment. I think the real thing about
[3181s] um uh building toward a big idea towards
[3184s] something net new, the key is really
[3187s] outside and around the executive. So if
[3191s] the executive is the decision maker on
[3193s] whether we're going to invest here, they
[3196s] also want to understand from their
[3198s] peers, from other experts what why this
[3201s] actually matters. If you have something
[3203s] net new that you want to bring to market
[3206s] and customer success thinks it would
[3209s] really accelerate expansion rates or you
[3212s] know the the marketing team thinks that
[3215s] uh signups would be 10xed because of
[3217s] this. if you have that cross functional
[3219s] alignment. And this is where a lot of
[3221s] these lessons don't just apply if you're
[3222s] going into a a product executive
[3225s] meeting, but that if you're influencing
[3226s] your cross functional execs and your
[3228s] cross functional stakeholders to be
[3230s] advocates on your behalf. I I think
[3232s] that, you know, we now have more tools
[3234s] than ever to as as product folks build
[3238s] out the V1, right? prototype something,
[3241s] build your own app, build the messy
[3243s] version of it, get feedback, iterate,
[3246s] and be socializing that in a way that
[3250s] creates a ground swell of buyin. Um, to
[3254s] the point that, you know, the exact
[3257s] can't say no to the funding. Along those
[3259s] lines, it feels like to me the biggest
[3263s] reason that a leader doesn't buy into
[3265s] your pitch is you just have different
[3268s] information. They don't see what you
[3270s] see. They don't you don't see what they
[3273s] see, right? They have all this other
[3275s] stuff that they're looking at and trying
[3276s] to decide. Maybe speak to just like that
[3278s] skill of trying to clarify information
[3281s] on both sides.
[3282s] >> I'm thinking about a a a tool April
[3286s] Underwood taught me. Um, she said she
[3288s] used to go into product strategy
[3290s] meetings with Stuart and was really
[3291s] trying to extract some of his ideas, but
[3294s] she was always holding the whiteboard
[3296s] marker. And so there was this back and
[3298s] forth between them in the conversation
[3301s] of I'm trying to imbue I'm trying to
[3304s] understand deeply what you're seeing in
[3306s] the market, what you're feeling in the
[3308s] business, what your instincts are, but
[3310s] I'm also going to package that in a way
[3313s] that is translatable, is actionable, is
[3317s] in a framework that you might not have
[3319s] had in your head. And so that is like a
[3321s] great tool for marrying that leader's
[3324s] instincts with your ability to sort of
[3328s] not synthesize their approach but really
[3331s] um take that approach and and accelerate
[3335s] it for marrying what you know about the
[3339s] world and what they know about the
[3340s] world.
[3340s] >> So it's kind of what I'm hearing is kind
[3342s] of take it upon yourself to help them to
[3345s] kind of align your world view with their
[3346s] worldview. And there's this question
[3348s] coming back just like like help me
[3350s] understand what I don't what was the
[3352s] question you had? Uh oh that's so
[3353s] interesting. What led you to believe
[3355s] that? Like these are kind of questions
[3356s] that help you extract what you don't
[3359s] know that they know.
[3360s] >> Yes. And I think there are also really
[3362s] different phases of a relationship.
[3364s] There's a phase when you're new. You may
[3366s] not have so much facetime with that
[3368s] person. You don't really know them that
[3369s] well. But I think that this is a place
[3372s] where time spent together really just
[3375s] accelerates your trust with them, your
[3379s] um ability to speak freely, to ask
[3381s] difficult questions to get real
[3383s] feedback. And so um especially if you're
[3387s] in a position where you can ask for that
[3389s] time, more casual time, less fraught
[3391s] that you're not always pitching an idea,
[3394s] but you can have real conversations.
[3397s] that is also the groundwork for the
[3399s] pitch down the line. I think people
[3401s] devalue that that time upfront spent
[3404s] together because it pays dividends for
[3406s] the later pitch.
[3408s] >> Yeah, I'm glad you went there. That's
[3409s] exactly where I was going to actually go
[3411s] is this idea of trust and building and
[3414s] having, you know, giving the person a
[3416s] reason to kind of assume that you know
[3418s] what you're doing. Um, obviously hard to
[3421s] build trust. And the reason I think this
[3423s] is important is sometimes you have the
[3425s] best idea and they just don't buy it
[3426s] because they just don't know anything
[3427s] about they don't they don't know what
[3429s] you've been up to. They don't know how
[3430s] awesome you are, how smart you are, how
[3431s] successful you've been your whole life
[3432s] and career. Uh maybe because you're new.
[3435s] What are some tips for trying to build
[3437s] trust with the leader so that these
[3439s] things become easier?
[3440s] >> I think in terms of building trust, it's
[3443s] really important to ground yourself in
[3446s] what they believe. If you are pitching
[3449s] an idea that is wildly
[3452s] different than something they believe,
[3454s] don't bother. You probably have nine
[3456s] other good ideas that are more aligned
[3459s] with the beliefs that they already h
[3460s] that they already hold. Follow those
[3462s] instead. So, there's something about
[3464s] just engaging uh from a baseline
[3467s] assumption. If they feel strongly about
[3468s] something, okay, maybe you can come back
[3470s] to them once or twice and say, "Are you
[3472s] sure you feel strongly about that? I
[3473s] really see this data." And if they say,
[3475s] "Yeah, I feel really strongly." you
[3477s] probably have to drop it. But in terms
[3479s] of building that long-term trust, I
[3481s] think the biggest things that do that
[3482s] are really hearing them out and
[3484s] actioning on the feedback that you've
[3486s] gotten in the past, having results. You
[3489s] know, it cannot be overstated that
[3492s] impact in the organization, building
[3494s] great products, shipping amazing things
[3496s] quickly, feeding that back to the leader
[3500s] to say, "Hey, we worked with you on
[3502s] this. We shipped it. It went well.
[3504s] Here's the results." that builds you
[3506s] momentum to be able to go back with the
[3510s] uh the more novel approach or the
[3512s] scarier one. I think the other thing I
[3514s] would say is um one of my favorite well
[3516s] actually one of the only business books
[3518s] I've ever liked is called Switch. Uh
[3520s] it's about change management and they
[3522s] talk a lot about shrinking the change um
[3524s] which is this brilliant idea. If
[3526s] something seems scary and overwhelming,
[3529s] how do you make it so much smaller so
[3531s] that it's an experiment? It's uh a
[3534s] oneweek uh proof of concept. It's
[3537s] something that feels really small that
[3539s] can get people over the hump of well I'm
[3542s] not going to invest in six months for
[3543s] this project if I don't know if it's
[3545s] going to work. So shrinking the change
[3546s] is a huge way to build momentum and
[3549s] trust. And I think this applies to the
[3551s] way that we develop all products
[3553s] especially if you're doing something
[3554s] that lasts longer than a month. What are
[3556s] your milestones? What are the chunks at
[3558s] which you're showing outcomes and fit?
[3560s] And this is easier than ever to do with
[3562s] the tools that we have at our disposal.
[3564s] How are we showing that we are taking a
[3568s] much more iterative approach so that you
[3570s] can build that momentum, build that
[3572s] buyin and get that trust to to do the
[3575s] bigger thing. That's an awesome very
[3576s] tactical piece of advice here to
[3579s] convince someone to do something is just
[3581s] reduce the risk essentially reduce the
[3583s] investment to help build trust in okay
[3586s] this is showing success because
[3588s] obviously it's much easier to bite off
[3589s] on something that's going to take two
[3591s] weeks or have very low risk and impact
[3593s] if it's not a good idea.
[3595s] >> Yeah, I think that's absolutely right
[3597s] and I think what is the type of risk
[3599s] that they are most afraid of too, right?
[3601s] Is it wasting time? Is it time to
[3603s] market? Is it that they don't actually
[3605s] think this is going to work with
[3606s] customers? So, if you can start to and
[3609s] and you can and should ask this, what
[3611s] are the outcomes you're most afraid of,
[3613s] right? What would a failure state be um
[3615s] for you in in this experiment? You know,
[3618s] there's there's a concept of red
[3620s] teaming, which is originally a military
[3621s] tactic and and now being applied to
[3623s] businesses. How do you take an outsers's
[3626s] perspective to your idea and not just be
[3629s] so obsessed with your own thinking, with
[3632s] your own concept? Because so often we
[3634s] get wrapped around the axle. Especially
[3637s] I I I actually find this happens even
[3639s] more with prototyping. You build a
[3641s] prototype and you're like, "Oh, looks so
[3643s] beautiful. I would have never been able
[3644s] to build that before." That's actually
[3646s] like not a very good idea, but um but
[3649s] you get obsessed with it and you're
[3650s] unwilling to accept that it could fail.
[3653s] I think one of the biggest things you
[3654s] can do to build trust is kill things,
[3658s] deprioritize things. That is a very very
[3660s] senior way of thinking, right? And it
[3662s] shows that you have the same aligned
[3666s] incentives as the executive who's
[3668s] thinking about the good of the company
[3670s] outcome, the user outcome, and not just
[3672s] your own. That is such a good one
[3674s] because everyone's always just trying to
[3676s] acquire more resources, more investment,
[3679s] just like more features, and showing
[3681s] that, okay, this is a terrible idea. I
[3682s] know I spent like months on this, but
[3684s] no, we should kill this because it's not
[3685s] working,
[3686s] >> right? It's not working. And and here's
[3688s] how I'm going to know that's not
[3689s] working. And here's when I'm going to
[3690s] come back to you with a decision. Right?
[3692s] So, sometimes we don't know the a lot of
[3695s] times we don't know the outcome,
[3696s] especially with AI native products. And
[3698s] if we can say, we're going to test this.
[3701s] here's how we're going to know it's
[3702s] working. We'll come back to you on X
[3704s] date. I think one thing that really
[3706s] spirals people out of control is is a
[3708s] desire for certainty. You know, as human
[3710s] beings, many of us have have a huge
[3712s] desire for certainty. Now more than
[3714s] ever, that is not possible. Um and so,
[3719s] uh one trick that I learned, especially
[3721s] working with engineers who often have a
[3723s] very very high, uh desire for certainty,
[3726s] um is to say, I don't know the answer
[3727s] right now. I don't know if this is going
[3729s] to be successful. I'm going to check in
[3731s] with you on X date. That's when we're
[3733s] going to come back and have another
[3735s] conversation. And so at least there's
[3737s] certainty about the next check-in point.
[3739s] And that can be a really powerful uh
[3741s] tool for sort of deescalating the fears
[3744s] and risks around a given initiative or
[3747s] idea.
[3748s] >> Okay. Before we get into AI's impact and
[3750s] all this stuff, are there any other
[3753s] common mistakes people make when they
[3756s] are trying to get better at the skill of
[3757s] influence or just any other really
[3760s] powerful tactics for increasing your
[3763s] ability to influence leaders?
[3765s] >> Something people miss is the extremely
[3768s] broad context that execs bring to bear
[3772s] from not only their experiences but the
[3775s] things that they are hearing in their
[3777s] day-to-day life. They understand what
[3779s] other product teams are working on
[3781s] better than you. They understand the
[3783s] conversation at the E staff level.
[3785s] They've been to executive roundts and
[3788s] they are hearing and one of your jobs is
[3790s] to extract that insight and information
[3793s] and apply it to your ideas and they want
[3795s] to feel like you care, like you respect
[3800s] that, like you can apply it to your own
[3804s] thinking. And so this this keeps coming
[3806s] back to that curiosity and empathy. What
[3808s] if they know that you don't that you can
[3810s] actually apply to strengthen your
[3812s] thinking or inform the direction that
[3814s] you want to take your team? Um, and I
[3816s] think people just often don't ask those
[3818s] things um of of their executives. They
[3821s] don't uh show a curiosity for the
[3823s] expertise that that person has has
[3826s] brought to bear. And frankly, I think
[3829s] often they don't really care, which is
[3831s] the chief mistake. um they should really
[3835s] actually take it into account to
[3837s] strengthen their own thinking.
[3839s] >> Yeah. So much of this is about just uh
[3841s] coming into it with like here's what I
[3843s] it's just like having the same
[3845s] information. And I think this point
[3847s] about just like believe they know what
[3849s] they're doing is is so underappreciated.
[3853s] Like there's a reason they're in this
[3854s] role. There's a reason you're not there.
[3856s] There's a reason this company's doing as
[3858s] well as it is. Uh and so and even if
[3860s] they are wrong like they believe they
[3862s] are right. So it's important to
[3863s] understand what they think and know and
[3866s] what information they have access to.
[3867s] >> Yeah. And I I think the other piece of
[3869s] this is for anyone thinking about how
[3871s] they grow their career.
[3874s] How did that person get into the role
[3876s] that they are in? They broadened their
[3879s] context. They saw you know sort of had
[3881s] great peripheral vision. And that is a
[3884s] way to show up in a room that is much
[3887s] more senior than you are is keep your
[3890s] domain expertise, keep the things that
[3892s] you know best, but broaden your
[3894s] perspective, broaden your um vantage
[3898s] point to think about it in the context
[3900s] of the whole ecosystem, the whole
[3902s] organization, the whole industry, which
[3905s] you often don't get a a chance to say
[3907s] it. And what happens at that point is
[3910s] you get seen as a strategic thinker. you
[3912s] get seen as somebody who really cares
[3915s] about the company's success and not just
[3916s] your own and so it is actually a really
[3919s] really important tool for growth
[3921s] especially you know I had told April
[3923s] when I originally pitched her on being
[3925s] our chief of staff that I I wanted to
[3927s] take the job because I wanted to know if
[3929s] I if I wanted to be CPO when I grew up
[3931s] and and it's true I still don't know um
[3933s] because it's a really really hard job
[3935s] and I have just way more respect than I
[3938s] ever did before before that but I think
[3940s] that if you want to grow into a product
[3943s] leadership role. Expanding your
[3946s] viewpoint, expanding the way that you
[3948s] see problems and thinking about it from
[3951s] a global perspective is a way to show up
[3954s] as that strategic leader that you say
[3956s] you want to be.
[3957s] >> I love this advice just to make it very
[3960s] clear for people because it's easy to
[3962s] just like, yeah, okay, I'll just like
[3964s] expand my horizon. Like basically the
[3966s] advice here is uh just like think on
[3969s] behalf of the entire business, not just
[3971s] your feature, not just your little goal.
[3973s] It's like what is the business trying to
[3975s] do? Here's how this fits into it. Here's
[3977s] what the here's what the CEO broadly is
[3980s] thinking about. Like here the epitome of
[3983s] this to me is Jeff Weinstein, I think is
[3985s] how I pronounce his last name, or
[3986s] Weinstein at Stripe. like he's just like
[3988s] a PM on a product and he's just
[3991s] constantly tweeting and sharing uh
[3994s] Stripe as a business. Like he's just
[3995s] like thinking about Stripe as the
[3997s] company and then here's this thing I
[3998s] work on that helps the company.
[4000s] >> Absolutely. And Jeff and I work together
[4002s] at Box.
[4002s] >> Oh, you did? Oh, that is so cool. Right.
[4004s] Okay. Would you agree he's like the
[4006s] epitome of this?
[4007s] >> Oh, yeah. I mean, he's so charismatic
[4009s] and able to to really put himself in
[4012s] other people's shoes. I mean, I think
[4014s] that um it is just a way to, you know,
[4017s] we we just redid our PM career ladder
[4019s] for this year. Um, and I led that
[4021s] effort. And one of the things that we
[4024s] noted as a a trait of becoming more
[4027s] senior is your product citizenship and
[4030s] how much you are embedding back in the
[4032s] organization and giving back best
[4034s] practices, mentoring others, um,
[4038s] broadening people's horizons on tooling,
[4041s] technology, storytelling, and and of
[4044s] course strategy. And I think that this
[4046s] is such an important part of people's
[4049s] growth that uh they often underell but
[4053s] you can do it at every level in your own
[4056s] area and it's about connecting the dots
[4059s] back up to what is important to the
[4061s] company. So you know so many times I see
[4065s] docs that are like okay our KR is to
[4067s] ship this thing and I'm like
[4070s] why does that matter? Like does anyone
[4074s] care? um you have to tell a story and
[4077s] even if that's true that shipping is the
[4080s] car sometimes that's the case right but
[4082s] even if that's true why are you doing
[4084s] that what is the outcome for the
[4086s] business why would the CEO be excited
[4088s] about shipping that uh it's usually
[4091s] because of some business outcome or user
[4094s] outcome that you have to tie back to
[4096s] their perspective of and then I think
[4098s] the flip side of is if you're working on
[4101s] something that doesn't shift one of
[4102s] those outcomes or isn't urgent for the
[4104s] business, do you need to change course?
[4107s] Do you need to say, "Hey, actually, I
[4109s] don't think this is the highest leverage
[4111s] thing right now." Um, we could actually
[4113s] do X uh to to be much more effective for
[4117s] our broader goals.
[4118s] >> That that's where I was going to go is
[4120s] just like that's the ultimate trust
[4121s] building move is to tell the leaders,
[4123s] okay, here's our goal. Here's all these
[4125s] ideas, but we don't think this is the
[4127s] right goal, and here's how this doesn't
[4129s] fit in, and here's why we should kill
[4130s] this product.
[4131s] >> Right. Exactly. Right. Think like a CPO.
[4133s] put yourself in their shoes. I mean, you
[4135s] had Stuart on a few weeks ago and he
[4138s] talked about how the CEO is kind of the
[4140s] only one who can really kill things
[4142s] across a,
[4144s] you know, things that already exist or
[4146s] um really make some of those super super
[4149s] tough decisions. I think that is often
[4152s] times our culture, but is a mistake. If
[4156s] we each think of ourselves as owners and
[4159s] as contributors to the business and as
[4162s] leaders, we will bring those
[4164s] opportunities up as well to both amplify
[4166s] the business or save it from itself.
[4169s] >> Do the job you want versus the job you
[4171s] have.
[4172s] >> Classic.
[4173s] >> Yes.
[4173s] >> Okay, let's talk AI. I feel like you
[4175s] can't have a you cannot do anything
[4177s] these days without mentioning AI in some
[4179s] way. Uh, how is AI changing the skill of
[4184s] influence? What's changed in the past
[4187s] couple years in trying to convince
[4189s] people to do the things you're hoping
[4190s] them to do?
[4191s] >> I think that we are entering a golden
[4194s] age of product management, not of
[4196s] product managers, but of product
[4198s] management and the core skills that made
[4201s] this function the thing that I love to
[4203s] do. You know, more than ever, what we
[4206s] have to do is have really interesting
[4209s] ideas that are grounded in user empathy,
[4213s] curiosity, testing, iteration, but we
[4217s] will still be working in organizations
[4219s] where getting buy into those ideas uh
[4222s] and influencing people to fund not just
[4225s] the V1, but the much more expensive V2,
[4228s] 3, 4, and ongoing support become 10x
[4232s] more important.
[4233s] And as execution basically plummets in
[4238s] uh in complexity and everyone can be a
[4242s] builder, PMs can and and product
[4245s] thinkers which I think is far beyond the
[4248s] product management function um can
[4252s] be so incredibly influenced by those
[4255s] core skills of bringing people along for
[4259s] the ride. So I think that product
[4261s] managers for a long time have made their
[4264s] careers on being the most type A the
[4267s] Gant chart master um the best notetaker
[4270s] in the business and if AI is better than
[4274s] you at analyzing data or taking meeting
[4277s] notes or running experiments what's your
[4280s] job now so the leverage actually shifts
[4283s] from doing that work and being the
[4286s] synthesizer to deciding what work
[4288s] actually survives lives and encouraging
[4291s] other people to buy into that process.
[4295s] And I actually think it's just so
[4296s] incredibly exciting because PMs and
[4299s] other functions, engineers, designers
[4301s] are so empowered to bring that first
[4304s] version to bear to get that momentum to
[4307s] get that signal on product market fit on
[4310s] user benefit and then build momentum
[4313s] from that point in a much faster cycle.
[4316s] And so it's actually like an incredibly
[4318s] exciting place. But the act of
[4320s] influence, the act of stakeholder
[4322s] management, the act of learning is the
[4324s] 10x skill.
[4326s] >> Awesome. This is such a fun topic with
[4328s] the way I've been thinking about this is
[4330s] just like where are human brains going
[4331s] to continue to be necessary and useful
[4334s] in this new world.
[4335s] >> I'm terrified. [laughter]
[4337s] >> Maybe maybe nowhere.
[4339s] >> Maybe nowhere. But the way you described
[4340s] it, which I totally agree with, is
[4343s] essentially it's deciding what to do and
[4346s] getting everyone on the same page,
[4348s] alignment uh around that. Here's we're
[4350s] all on the same page. Here's what we're
[4352s] prioritizing. And then it's like, cool,
[4353s] now let's build it. And that happens so
[4354s] quickly now.
[4356s] >> Yeah. And what can you notice that AI
[4359s] can't? You know, AI is not good at being
[4361s] an anthropologist yet, right? It is
[4364s] based on a corpus of existing knowledge.
[4367s] And I think the best product thinkers
[4371s] again across functions that I've I've
[4373s] worked with really are able to get to
[4376s] novel insights through that user empathy
[4378s] through that understanding and through
[4380s] deep understanding of the business
[4382s] dynamics changing industry and bringing
[4385s] those together to prioritize ideas that
[4388s] actually really really matter. You know,
[4390s] we're going to have so much software we
[4392s] won't even know what to do with it. But
[4394s] what software actually works? what
[4396s] software actually matters, what software
[4398s] gets marketed or sold or you know we're
[4401s] we're gonna have to think about not just
[4403s] that the software exists but that it can
[4406s] get to its final state and that is going
[4408s] to require people's buy in to that idea
[4411s] working.
[4412s] >> Yeah. Uh the way I think about this
[4413s] right now is just like where humans are
[4416s] still necessary and uh great product
[4419s] thinkers are still necessary is uh on
[4421s] the front end deciding what to
[4423s] prioritize and build on the back end
[4425s] determining if this is good and ready
[4428s] essentially judgment and taste and then
[4430s] there's distribution I think is such an
[4433s] underappreciated like new bottleneck
[4436s] because as you said there's so much [ __ ]
[4438s] out there just like how do we get anyone
[4440s] to pay attention to any of this stuff
[4441s] every day there's is like a new
[4443s] life-changing product. So, I feel like
[4445s] that's going to be a big problem.
[4446s] >> Oh, I want you to do a whole episode on
[4448s] distribution because I feel this so
[4451s] much. Right. If everyone thinks they can
[4452s] build the next Salesforce on their own,
[4455s] by the way, I don't believe that. Uh
[4457s] then, you know, you're going to have
[4459s] just a flood of available tools. And who
[4462s] gets the attention? It is still going to
[4465s] be who has the marketing dollars, who
[4467s] has the brand reputation, who is the
[4469s] existing customer base. distribution is
[4471s] everything and I I think the
[4472s] quintessential example we've seen here
[4474s] is with Gemini and Google's tools and
[4476s] and just their total um continued
[4480s] dominance in that market because of
[4482s] tools of distribution. Um and I think
[4484s] it's really fun to see. I think the
[4486s] other piece I would say is that's
[4488s] underrated there is trust building trust
[4490s] with your users but also with your
[4492s] internal teams. You know we're seeing
[4495s] even model companies hire at a huge rate
[4498s] right now. So you are still working with
[4500s] colleagues. Uh you are still working
[4502s] with millions of users and alongside
[4505s] distribution is trust and that is a a
[4508s] function of influence and empathy. Along
[4511s] these lines what I wonder is we talked
[4514s] about these other two kind of areas.
[4515s] Humans are still valuable and great
[4518s] product leaders are still valuable.
[4519s] Deciding what to build knowing if it's
[4521s] ready and awesome. Uh, I wonder how good
[4523s] AI will get at those things because we
[4526s] never thought AI would be amazing at
[4528s] coding and now it's 100% of code will be
[4530s] soon written by AI. And I've actually
[4532s] been building a bunch of stuff and I
[4534s] just find codeex and clock code are so
[4536s] good at actually giving you ideas for
[4538s] what to build. I'm just like, what
[4540s] should I do to make this better? And
[4541s] it's like, here's 10 ideas and then
[4543s] they're like, that is a really good
[4544s] idea. So, I think it'll get there.
[4546s] People underestimate how good it'll get
[4547s] at these things, I think. Yeah, I do
[4550s] think that as um as ideas proliferate
[4554s] and as there just becomes so many ideas
[4557s] and so much feedback, you know, we're
[4559s] going through a strategy doc rewrite. I
[4561s] think we have like 40 versions now
[4563s] because it's so easy to rev on a 15-page
[4565s] doc. Actually, when when these decisions
[4568s] are happening faster, building is
[4569s] happening faster. The flip side of that
[4572s] is mistakes compound faster as well. And
[4576s] strategy clarity becomes so much more
[4579s] important to anchor people on if you
[4581s] want to have an empowered EPDI
[4584s] organization or company. that that
[4588s] clarity of what you believe, what are
[4591s] the most important problems to invest
[4593s] time and energy into what uh where we
[4596s] want to invest compute and dollars. Um
[4599s] that is the mechanism for letting people
[4602s] go and run at as fast a velocity as
[4604s] they're capable of. Right? So if you
[4606s] have that corpus of shared beliefs that
[4608s] you update on a pretty fast clip because
[4611s] uh I think that's that's the mode we're
[4613s] in. that is actually what enables teams
[4615s] to build the right stuff as opposed to
[4617s] just the idea that cloud had.
[4619s] >> I love this point because there's a lot
[4621s] of talk on Twitter actually just today
[4623s] uh in the PM community about PRDS are
[4625s] dead and I think it's exactly the
[4628s] opposite which is being very clear about
[4631s] what we are doing and the strategy is
[4634s] now the most important thing because
[4636s] once you have that then it's cool fire
[4638s] off 100 agents and we'll go build it and
[4639s] launch it.
[4640s] >> Totally. Strategy clarity is is so so
[4644s] important. I am not in the Twitter
[4645s] verse. I find it exhausting partially
[4648s] because I think takes like PRDs are dead
[4650s] or software is dead is like really dumb.
[4653s] Um I find it a little insufferable. uh
[4655s] if I'm being spicy because I still think
[4659s] what matters is understanding users,
[4662s] understanding business and economic uh
[4664s] dynamics, understanding
[4667s] strategy and what we're trying to
[4669s] accomplish and then really thinking
[4672s] through what is the right way to do that
[4675s] together.
[4676s] >> Okay, maybe one more question uh along
[4678s] these lines just agents now running as
[4680s] colleagues. Everyone's got all these
[4682s] clouds running, codeexes, all kinds of
[4685s] agent platforms
[4687s] now that agents are a part of kind of
[4688s] the workforce and increasingly
[4692s] uh is there anything there around
[4693s] influence that is valuable for people to
[4696s] start thinking about to learn how to do?
[4698s] >> I love that question. you know, uh, we
[4700s] talk about this a lot, especially when
[4702s] we think about identity security
[4704s] compliance that agents are a teammate
[4707s] for accelerating work um, and and the
[4710s] risks that that also provides because of
[4712s] the um, places where agents fall down. I
[4715s] I think agents are absolutely something
[4718s] we have to think about w with relation
[4720s] to um to influence because um, we are
[4725s] basically all directors of work now,
[4726s] right? If we have an army of agents or
[4729s] this hundred new colleagues that joined
[4731s] our team, how would we onboard new
[4734s] junior team members who don't already
[4736s] understand our product philosophy?
[4738s] What's important to us? And how do we
[4740s] codify that for ourselves? How do we
[4743s] take the time to say what's important to
[4745s] me as a product leader that I want to
[4747s] inculcate into um anything that's
[4750s] developed for my team? What do I believe
[4753s] about um product market fit? what do I
[4756s] look for in terms of what success looks
[4758s] like? How do I set metrics? And if we
[4760s] can do that upfront work to actually
[4762s] like analyze ourselves and where we've
[4765s] seen success, where we've seen
[4766s] downfalls, and then continue to train
[4769s] our agent models with that um that data,
[4773s] that history, that context, they will be
[4777s] better off. But I also think the flip
[4779s] side of this is guard rails. Where do
[4781s] you need to be involved? Where do you
[4782s] need to catch hallucinations or
[4785s] missteps? Where do you uniquely have
[4789s] taste, uh, judgment, frame of reference,
[4793s] something intangible where you need to
[4795s] say, "Don't do this without me."
[4797s] >> What's so funny about this, essentially,
[4800s] we're helping the agent learn the skills
[4802s] we've been talking about to influence
[4804s] you.
[4806s] Here's context on my goals. Here's what
[4808s] I understand about the customers. here's
[4810s] our current priorities like help me tell
[4814s] me what to do and it's like influencing
[4816s] you to agree.
[4817s] >> Absolutely. I think Wow, that's really
[4820s] the singularity, isn't it? Uh you should
[4822s] just feed this podcast to a bunch of
[4824s] agents and see if they can do this
[4826s] better than me. Um see see what their
[4828s] advice is. No, but I really think at
[4830s] this point we are in a place where it is
[4832s] a back and forth and where we should be
[4834s] using agents and AI as um a really smart
[4838s] colleague that never gets irritated by
[4840s] our questions. Poke holes in my ideas.
[4843s] Um tell me what you would do
[4845s] differently. Um help me plan this out.
[4847s] Uh base this on more uh corporate
[4851s] context than I could ever have gone
[4853s] through myself. Um and and poke holes.
[4856s] And I think that um that is a just like
[4858s] a really powerful way for amplifying our
[4860s] work.
[4861s] >> Oh, it's like so interesting like one of
[4863s] your you know tips is come into an open
[4864s] mind and learn it's like exactly what an
[4866s] agent does. Tell me more. What else
[4867s] should I and then just like hopping on
[4869s] your ideas like okay cool we'll add that
[4871s] to the two like all the ideas you've
[4873s] shared agents are so good at. So that's
[4876s] yeah
[4877s] >> I think that um one thing I'm really
[4879s] curious about you know you were talking
[4880s] about human brain chemistry is just how
[4884s] we can protect our brains from overwhelm
[4888s] >> the the speed of ideas change um
[4894s] building is
[4897s] we are diseolved for this pace of life
[4901s] we were evolved uh I I love this book um
[4905s] Pachenko that tells the history of um a
[4908s] Korean family over several generations.
[4910s] And in one of the generations sort of in
[4912s] the 1600s, 1700s, there are two wives
[4916s] that every day cook breakfast, then go
[4918s] to the market, buy rice, buy fish, buy
[4922s] vegetables, go home, cook the rice, cook
[4925s] the fish, serve dinner, clean up dinner.
[4928s] That's the day. And for the vast
[4930s] majority of human history, that was kind
[4933s] of our day. And the mental load that we
[4935s] are asking of our brains right now is
[4938s] staggering. And so I think one of the
[4940s] ways that we actually have to use AI is
[4943s] and agents is to help our brains be most
[4946s] effective is to clear out distraction to
[4949s] point out the most important things to
[4953s] and I I think this is where people
[4954s] really need to make some tough
[4956s] decisions. How much can we really focus
[4958s] on and how do we allow for that focus in
[4961s] the ways that are hopefully good for
[4963s] humanity?
[4965s] >> What a time to be alive, Jessica. Holy
[4967s] Oh my god. Uh before we get to our very
[4971s] exciting lightning round, is there
[4973s] anything else that you wanted to share?
[4976s] Anything else you want to double down
[4977s] on?
[4978s] >> One thing I think that I'll say is I'm a
[4982s] people person. I love in-person
[4985s] collaboration and I love talking ideas
[4988s] through and whiteboard sessions. I'm a
[4989s] two-wing three. If there are any other
[4992s] anogram fans out there, it's uh it's a
[4995s] mix of like the people person, the sort
[4997s] of bringing to the communal thinker with
[4999s] the achiever. Um that is my personality
[5001s] type. I think that um sometimes I can
[5004s] give this kind of advice and people say,
[5006s] "Oh, well Jess, you're you're good with
[5008s] people or like you kind of understand
[5009s] these things." I think that something
[5011s] that has taken me a while in my career
[5014s] is how to be authentic to myself in
[5017s] influence, in relationships, in trust
[5019s] building. And I don't think that it's
[5021s] one personality type or another. I think
[5024s] that you could be shy and introverted or
[5027s] uh super data oriented and technical. I
[5031s] think all types of personalities can in
[5034s] their own authentic way communicate with
[5036s] the people around them to build trust to
[5038s] build influence in the way that feels
[5040s] true to them. You know, I think when I
[5043s] uh when I was younger in my career, I
[5044s] was starting out as a PM, I got a lot of
[5046s] feedback of, oh, Jess, how do you, you
[5049s] know, show up more like a man would?
[5050s] Show up more aggressively, show up more
[5053s] um uh decisively. And I think there was
[5057s] some good nuggets in there, but I think
[5058s] it took me a while to feel like, hey,
[5061s] who I am and how I show up is actually
[5065s] my superpower that I can double down on.
[5068s] And I don't need to be like someone
[5069s] else. What I need to do is think about
[5073s] what I want to accomplish and how I want
[5076s] to grow and do that in a way that is is
[5078s] true to me.
[5079s] >> I could not agree more with that. I've
[5082s] uh shared very sim similar sentiment on
[5084s] the pod a few times. Just like you can
[5086s] accomplish the same things other people
[5088s] can through your own strengths. You
[5090s] don't have to do it the way they're
[5091s] doing it.
[5092s] >> Exactly.
[5092s] >> I so agree.
[5094s] >> A beautiful way to end that. And with
[5096s] that, we have reached our very exciting
[5098s] lightning round. I've got five questions
[5099s] for you. Are you ready?
[5100s] >> I'm ready. I'm so excited.
[5102s] >> What are two or three books that you
[5104s] find yourself recommending most to other
[5106s] people?
[5106s] >> I think there's a genre of book I've
[5108s] really fallen in love with. Uh I
[5109s] mentioned Pachenko before. Um, I love
[5112s] historical fiction because it really
[5114s] gives me access into worlds that I don't
[5118s] know. You know, they uh I can't remember
[5120s] who talks about um windows and mirrors.
[5124s] Books are windows or mirrors for us. And
[5127s] uh historical fiction, especially about
[5129s] places where I'm less familiar with that
[5131s] history, is really a window into someone
[5133s] else's experience. Um, and there's a
[5136s] particular uh type of historical fiction
[5138s] that I just loved, which is
[5140s] multigenerational historical fiction.
[5142s] Uh, Pachinko does this with a family in
[5145s] Korea over generations and moving to
[5148s] Japan. Uh, there's a book called
[5150s] Homegoing, which is about the west coast
[5152s] of Africa and the impact of the slave
[5154s] trade um, and the ongoing uh, life in
[5157s] Africa from two uh, split parts of the
[5160s] family. Uh, history of burning is a is a
[5163s] book that tells a story of um Indian
[5166s] indentured servants that were brought to
[5169s] Uganda to build the um British railroad
[5173s] there. Um, and just parts of history
[5175s] that I was so much less familiar with
[5177s] and really treasure that sort of window
[5179s] into um a different world.
[5181s] >> I think the book overstory is an example
[5183s] that. Have you heard of that?
[5184s] >> No, I haven't. I think I might be
[5186s] getting it wrong, but it's called
[5187s] overstory, which is around it's a
[5189s] concept of uh when you have a big tree
[5191s] like the overstory is the branches that
[5193s] kind of sit on top that kind of create a
[5195s] shade.
[5196s] >> Oh, that's beautiful.
[5197s] >> That's the book I'm thinking about and
[5198s] it's the story of a family over many
[5200s] generations and around a tree.
[5202s] >> Oh, great. Now I have to pick that up.
[5204s] >> Was popular. Okay. If it's the one I'm
[5205s] thinking about, I think you're going to
[5206s] love it.
[5207s] >> Okay, great.
[5208s] >> Uh favorite recent movie or TV show
[5210s] you've really enjoyed. You know, again,
[5212s] this is another window. I have been
[5214s] obsessively watching The Pit, which is
[5216s] probably a a lame answer. I wonder if
[5219s] anyone else has given you that so far,
[5221s] but I just really um it's given me such
[5224s] a vantage point and a view into the
[5227s] incredibly difficult work that emergency
[5230s] healthcare workers do and the stresses
[5232s] and the system and the brokenness that
[5234s] they operate under, but also the extreme
[5237s] care and love that they bring to their
[5239s] work. and has just given me so much
[5241s] admiration.
[5242s] >> It is trending on this podcast. So, uh,
[5244s] and I I'm watching.
[5245s] >> It's really good.
[5246s] >> It is really good.
[5247s] >> Okay. Favorite recent product, favorite
[5249s] product you've recently discovered that
[5250s] you really love.
[5251s] >> Okay. I I bought my husband a towel
[5254s] warmer. It was like 35 bucks on Amazon
[5258s] and it has led to so much joy in our
[5261s] household. Just getting out of the
[5263s] shower to a warm towel is so great. Um,
[5266s] it's a really fun addition to the to the
[5269s] family. So, highly recommend that. Um,
[5272s] it's a it's just a cheap and easy way to
[5275s] to brighten your day a little bit.
[5277s] >> I want one. That sounds amazing. Does it
[5279s] sit on top of an existing towel rack or
[5280s] is it a separate thing that you
[5282s] >> It's a separate thing. It's sort of like
[5283s] a basket that you put the towel in. You
[5285s] could put it in for half an hour, an
[5287s] hour, set it on a timer. It's so cool.
[5290s] >> Okay. I love this idea. Never been
[5292s] mentioned before. But I think uh u more
[5295s] in the in the tech vein of products I've
[5297s] loved um I've been a loyal user of Casa
[5301s] which I believe you tweeted about as
[5303s] well as a Kasa user. Um Casa comes in
[5306s] and they they have this idea of what if
[5309s] everyone had a household assistant. Um
[5311s] and so they come in, they take stock of
[5313s] every paint color, every appliance,
[5315s] every light bulb. Um, and anytime
[5318s] something breaks or you need something
[5320s] repaired, you can just say, "I need new
[5322s] light bulbs for this room." And they'll
[5324s] immediately send you them from Amazon. I
[5326s] need a new dishwasher. Ours broke. And
[5328s] they'll send you three options that fit
[5330s] your space um and are good quality. Um,
[5332s] they also pick up your packages every
[5334s] Friday and your donations. So great. And
[5337s] they're just the nicest people. So, I'm
[5339s] really excited to see them see them
[5341s] thrive.
[5342s] >> I love that pick. Uh, I was looking up
[5344s] their domain name, getcasa.com. And I
[5346s] think they're only in the Bay Area right
[5347s] now, and I think they're expanding into
[5348s] LA right now.
[5349s] >> Expanding into LA. Yep.
[5351s] >> Sweet. That's a good pick. And their
[5353s] website is very bare. I don't even know
[5354s] how you sign up,
[5356s] >> but uh yeah, I think I don't know. I
[5358s] guess you could figure it out, but uh I
[5360s] I love Costa. Uh yeah, they also do like
[5363s] a filter rotation thing. So like every
[5365s] six months they come and replace all
[5366s] your filters or air purifiers and
[5368s] whatever. You can set you can set like
[5370s] maintenance for your dishwasher, for
[5372s] your air filters, for your uh washer
[5374s] dryer, which has been super cool to see.
[5377s] Um they also you get handyman credits
[5379s] every month. So all the things that you
[5381s] put off do doing uh they can come in and
[5384s] and do it themselves and it's it's just
[5385s] wonderful.
[5386s] >> Awesome. Okay, two more questions. Do
[5388s] you have a favorite life motto that you
[5390s] often come back to in work or in life?
[5392s] >> Um I asked my husband about this one. I
[5395s] was like, "What's my life motto?" Um,
[5397s] and he had such a nice answer that I I
[5400s] thought I'd go with it. Uh, we have this
[5401s] saying with our kids, first the guests.
[5404s] Um, so if you have guests over, which we
[5405s] love to host people in our house, um,
[5408s] our rule with our three kids is guests
[5410s] always go first. And I think that um,
[5414s] it's really something that we think
[5416s] about in terms of being of service to
[5418s] others, being respectful to others,
[5420s] being welcoming, being kind. Um, and I
[5424s] think that that has dictated a lot of
[5426s] who I am as a person and and how we're
[5428s] trying to be as a family. When you are
[5430s] of service to others, when you are
[5432s] inclusive, um, when you can put them
[5435s] first ahead of yourself, I think it
[5437s] actually brings a lot of joy to you. Um,
[5439s] and it certainly makes the world a
[5441s] little bit better.
[5442s] >> Oh, one of the core values at Airbnb was
[5445s] be a host.
[5446s] >> Yeah.
[5447s] >> Which is very appropriate for Airbnb,
[5448s] but such a broadly uh, useful lens,
[5452s] >> right? I've also recently heard uh if if
[5455s] you want a village, be a villager.
[5457s] >> Um and so this idea of just building
[5459s] community, reaching out, being there for
[5462s] other people, and really taking that
[5464s] first step, even if it's scary or
[5466s] overwhelming, um can really can really
[5468s] make a difference.
[5469s] >> Final question, you have some cool
[5471s] posters behind you if people are
[5473s] watching on YouTube. Is there one that's
[5475s] like a favorite? Is there one that has a
[5477s] story per chance?
[5478s] >> Ah, that's such a good question. So, uh,
[5480s] these are all my husband's posters. He
[5483s] is a musician. He loves guitar. Uh, so
[5486s] he picked them all, but I think that I
[5489s] have to say my favorite one is probably,
[5492s] uh, Jimmyi Hendris plays the Greek. Uh,
[5495s] so we live in Berkeley and uh, you
[5497s] can't, it's just slightly off camera,
[5499s] but it's just a great memory of sort of
[5502s] an incredible musician. Um, and the
[5505s] iconic place that that we're lucky
[5507s] enough to live in and sort of the great
[5509s] access to culture that we have here, but
[5511s] also just how important music is to our
[5513s] lives, how much
[5514s] >> is such a cool venue. Just like if
[5516s] people don't know, it's just like this
[5517s] outdoor amphitheater with grass. You can
[5519s] get blankets.
[5521s] >> Should everyone should go. It's such a
[5522s] fun spot. Right. right on UC Berkeley's
[5524s] campus. Um, and they've got great music
[5527s] and we're really lucky to live close by.
[5529s] >> Well, with that, Jessica, I thank you so
[5532s] much for being here. Two final
[5533s] questions. Where can folks find you
[5534s] online if they want to reach out at,
[5536s] maybe follow up on anything here? And
[5537s] how can listeners be useful to you?
[5539s] >> I am not a very online person, which is,
[5542s] you know, funny for being on this
[5543s] podcast. So, I think the main place I am
[5545s] online is on LinkedIn. Um, and so you
[5548s] could definitely find me there. Um, in
[5550s] terms of being useful uh to me, I would
[5552s] love to hear what resonated for you,
[5555s] what's worked for you in the past, how
[5557s] you're seeing these things show up in
[5558s] your work, um, and how I can get better
[5561s] at, um, you know, uplifting the tech
[5563s] community. And as we go through this
[5565s] period of tremendous change, uh, how I
[5569s] can show up, uh, as a leader and as a a
[5572s] source of community for for this group
[5575s] of folks.
[5576s] >> What change are you speaking of?
[5578s] [laughter] Nothing.
[5579s] >> It's called AI. We're still talking
[5581s] about AI.
[5584s] >> Oh, man. All right. Well, Jessica, thank
[5586s] you so much for being here.
[5587s] >> Yeah. Thanks.
[5588s] >> Bye, everyone.
[5590s] >> Thank you so much for listening. If you
[5591s] found this valuable, you can subscribe
[5593s] to the show on Apple Podcasts, Spotify,
[5595s] or your favorite podcast app. Also,
[5598s] please consider giving us a rating or
[5600s] leaving a review as that really helps
[5602s] other listeners find the podcast. You
[5604s] can find all past episodes or learn more
[5606s] about the show at lennispodcast.com.
[5609s] See you in the next episode.