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

As product managers, one of our best sets of skills is curiosity and empathy and trying to understand our users. But

the moment that we're talking to an executive, we forget those skills and those talents.

>> It's your fault if the leaders didn't buy into your ideas.

>> People completely misunderstand how executives make decisions. What is going on in the heads? I describe an executive's calendar as a strobe light going off. You wake up at 8:00 a.m.,

going off. You wake up at 8:00 a.m.,

you've already got a huge list of urgent things going on. They have not had the time, the energy, the wherewithal to center your problems. >> What are their goals? What are they trying to do? How are they measured?

Connect the thing you're pitching them with that success.

>> There's ways for us to ask much more interesting questions of our executives.

Tell me what the board is pushing you on. Execs want to be successful, too.

on. Execs want to be successful, too.

They want to be good at their jobs.

>> Sometimes you have the best idea and they just don't bite.

>> One of the biggest things you can do to build trust is kill things. Dep

Prioritize things. If you're thinking about how do you be more senior, how do you show up in a way that is in a leadership mindset, you get paid to be a domain expert, your executive is looking

for you to be the deepest person in the room. Bringing your expertise to bear is

room. Bringing your expertise to bear is absolutely crucial. You have to act like

absolutely crucial. You have to act like a CPO.

Today my guest is Jessica Feain who's been a product leader at Box and Slack and Brightitewheel and now at Webflow and she has gotten very very uniquely

good at the art and science of influence and in particular influencing executives. Influence might be the

executives. Influence might be the single highest leveraged skill for product leaders outside of AI. We

actually get into how AI is changing the skill of influence. I've never heard a podcast conversation get deep into the art and science of influence, how to actually change people's minds and the

mistakes that people make when they're trying to influence leaders. We get very tactical and very specific. There's a

bunch of stuff in this conversation that I've never heard before or thought about. I am very excited for you to

about. I am very excited for you to learn from Jessica. Before we get into it, don't forget to check out lennisproduct.com for an incredible set of deals available exclusively to Lenny's newsletter

subscribers. Now, let's get into it.

subscribers. Now, let's get into it.

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>> Jessica, thank you so much for being here. Welcome to the podcast.

here. Welcome to the podcast.

>> Thanks for having me. It's my pleasure.

Let's set this conversation up. We're

going to be talking about the skill and the art of influence and in particular uh influencing executives and leaders, people above you that you want to convince to do things you want them to

do. Help us understand why this is worth

do. Help us understand why this is worth people's time. Why is this worth the

people's time. Why is this worth the next hour of someone listening to this?

Why is this skill so important to people's careers? I think as product

people's careers? I think as product builders, there's almost not a skill that's more important. Influence and

building a momentum behind great ideas is the way that great products actually get built. And if you don't have that

get built. And if you don't have that influence, if you don't have the buyin and the backing of your key stakeholders, of your executives, you can't build great products.

>> Something that I personally went through is just like I I was in a period of like I don't need to work on this skill. I'm

just like, I'm just going to do amazing work. I'm just going to it's going to

work. I'm just going to it's going to show itself. Everyone's going to

show itself. Everyone's going to recognize it. And you just everyone run

recognize it. And you just everyone run into this wall of like, oh man, all these other people are getting promoted.

Maybe talk about that because it feels like that's a big trap. People run into you.

>> I think why I wanted to talk to you about this is, you know, when I was an ICPM, I was putting forth ideas. I was

trying to reflect what I was hearing from my customers. I was trying to get sort of buyin and excitement about the work that I thought was really going to move us forward. And at the time that

I'm thinking about, I was a PM at Slack.

And some of my ideas got people really excited, you know, got me funding and backing and just really a sense that we could accomplish something great. And

some of my ideas and the things that I really really believed in died on the vine. They went nowhere. And I was so

vine. They went nowhere. And I was so confused and frustrated honestly because I felt like, hey, I really get this user base. I really understand what's going

base. I really understand what's going to move the ball forward. And I don't understand how these decisions are actually being made behind the scenes.

And uh I was uh eight months pregnant, eight and a half months pregnant. April

Underwood, who had just been named CPO of Slack, um she had just come back from maternity leave. We had a two-day

maternity leave. We had a two-day overlap. And I sort of got up my courage

overlap. And I sort of got up my courage and I said to her, "April, I've admired you for a long time. I love the way you work. I I really love the way you think.

work. I I really love the way you think.

Um, and I really want to understand it better. If you'd ever consider having a

better. If you'd ever consider having a chief of staff, I'd love for you to consider me. And when I came back from

consider me. And when I came back from that maternity leave, I came into a stint as April's chief of staff and was later chief of staff to Tamario Hoshua.

Um, who succeeded succeeded April, >> who's been on the podcast, >> who's been on the podcast, right? And is

now a CPO and head of AI at Atlassian.

Tamar, don't um be mad if I mess up your title. And what I learned through that

title. And what I learned through that process is that people completely misunderstand how executives make decisions, what is going on in the

heads, in the calendars, in the incentive structures of executives. And

instead of really understanding where that exec or stakeholder is coming from, they center themselves. They center

their own desires, their own motivations, their own slice of the world, and they end up just not being as successful both in their career, but also in the types of products that they're building.

>> What's an example of that when you talk about people don't understand how product leaders actually make decisions, how they decide what to do, what to listen to. What's an example?

listen to. What's an example?

>> Oh my gosh. I think the biggest example of this is people don't understand executive calendars, right? A lot of times on Google calendar, it's blocked.

you can't see what they're working on.

But I describe an executive's calendar as like a strobe light going off. You

know, you wake up at 8 a.m., you've

already got a huge list of urgent things going on. You go from a meeting with

going on. You go from a meeting with finance on a budget to an interview for another executive to a people problem to a legal problem to a product review. And

the product manager coming to that product review or the leader who's trying to make a pitch thinks I've been prepping for this meeting for two weeks, three weeks, maybe six weeks since we

last spoke. But the executive coming

last spoke. But the executive coming into that session hasn't thought about you since. They may not have gone to the

you since. They may not have gone to the bathroom today, right? And you have to understand that they have not had the time, the energy, the wherewithal to

center your problems. and you have to help them get into that mindset. So,

this is as simple as execs are people too, right? They are running around

too, right? They are running around context switching in the most insane ways I've ever seen. And everything that comes across their plate is an emergency. So, one of the biggest

emergency. So, one of the biggest tactics I think is so important is just take 30 seconds at the top of a meeting.

Why are we here? What happened the last time we talked? Why is this important to you? Why is this meaningful? and really

you? Why is this meaningful? and really

remember that they are not thinking just about you. They are optimizing for a

about you. They are optimizing for a global maximum and not for the local that you're you're optimizing for.

>> Essentially, this is how to help someone in this world that is running around from meeting to meeting without context on most things, maybe hasn't had time to go to the bathroom. How do we help them see what you want them to see and maybe

buy into your vision and suggestions?

Yeah, I think that um you know, one of the ways that I phrase this is how do you get the best out of your exec? How

do you help them be their best selves?

We often think about how we show up in a meeting or the doc that we wrote or the prototype that we've got ready, but we don't think about how they can be at their best. How do we give them the

their best. How do we give them the right kind of information in the way that they communicate? You know, we as product leaders have to be communication

chameleons. We have to be speaking their

chameleons. We have to be speaking their language like love languages, right? But

appropriate for work. Um, and you have to think about do they really uh turn a spark with a design, with a customer story, with a dashboard, with an

experiment, and how do you understand how their best brain, how their best expertise gets turned on to give you the best of themselves. But part of that is literally just setting up the meeting

effectively so that they can have the context, the wherewithal, the sort of breath at the beginning of the meeting to to dive into it.

>> The other thing I always tell uh people I managed is it's your fault if the leaders didn't buy into your idea. Like

it's not you can't just be like ah they never they just don't see it. It's not

my fault. I they they agreed to do something else. I always tell them like

something else. I always tell them like that's just you're not able to influence them and convince them that you're right.

>> Yeah. And I Annie Pearl who was my first PM manager back at Box. Uh she's

>> also former podcast guest.

>> Also former podcast guest, a former CPO at Calendarly and Glass Door and now at Microsoft and Annie's just the best. She

always said to me, "It's not my fault, but it is my problem." And I think that that's the vantage point that a product leader has to have, especially if they're trying to put themselves in the

in the shoes of an executive. As product

managers, one of our best sets of skills is curiosity and empathy and trying to understand our users. But the moment that we're talking to an executive or to

a stakeholder, we forget those skills and those talents and we begin to think about our ideas, getting that approval, getting to the next meeting, whatever it might be, the incentive that we are

driving. We don't think about the

driving. We don't think about the curiosity and empathy for what they're thinking about, for what their incentives are, for how their day has been. And if we can take some of those

been. And if we can take some of those skills of building great products and think about our executive as our key user here, then we can have a much much more productive conversation. You know,

I think one of the most disastrous things you can do is going into a meeting just looking for approval for your plan. Instead, if what you go in

your plan. Instead, if what you go in with is how can I learn, how can I strengthen this plan, how can I use the domain expertise, the context, the um

the experience that this person brings to the table and imbue that into my product work. Both the executive will

product work. Both the executive will like you better because they will feel like you have actually built product alongside them, but you will also end up with a with a better product. You know,

I often hear people say to me, "Oh, they just don't get it, right? They don't see what I see. They're not in my meetings.

They don't know how hard this is."

Fine. If you don't respect that person, if you don't believe they know something you don't, you need to quit. You need to go work somewhere else. But if you respect them, if you think they have something to offer you, that they got to

the place that they're at because they learned and they developed a skill that you're trying to gain, awesome. Take the

feedback, take the insight, ask questions, and don't just treat it like a rubber stamp because that's a failure state and it's a failure state that they don't like. I want to dive deeper into

don't like. I want to dive deeper into this stuff, but first something on my mind is some people might be turned off by this topic in terms of it may feel

icky of just like uh I don't want to try to be this like manipulative person and you know deal with politics and influence like I just want to do awesome work. Why do I have to do this? Speak to

work. Why do I have to do this? Speak to

that person that's kind of just like feels icky about building this and working on this and being this person.

>> Yeah. I think that when people frame this as politics, they're completely missing the point. Politics is

manipulating outcomes in people for your own gain. Influence is about increasing

own gain. Influence is about increasing the odds that your good ideas survive.

And I think what happens is people actually let ego and let their own narrative, their own scope of influence get in the way of empathy. Right? So

this isn't politicking. This is

learning. If we treat our stakeholder conversations, as discovery interviews as a way to strengthen our ideas, then we end up in a much much better place.

And if we do that in a in a genuine and low ego way, um I'll give an example here. Um Noah Weiss who succeeded um uh

here. Um Noah Weiss who succeeded um uh Tamario Suez, CPO of Slack and also former podcast.

What a what a run we're on here.

>> Oh, I uh No. Yeah, I I've learned so much from Noah. We sat down uh to write product principles for Slack and uh Ethan Eisman, our head of design um was

leading that initiative. But really this was a lot about codifying the early ideas that made Slack great, especially from a product principles and and sort

of craft perspective. And we started talking about this um and Noah had been at Slack early on and he he pulls out like a small notebook that he kept in his bag and he said, "You know, I actually have a section of this notebook

that I've been keeping things I learned from Stuart over the years." Now, he hadn't been keeping that notebook because he said to himself, "Oh, one day we're going to write product principles and I'm going to want these quotes on

hand or I'm going to show off that I have this." No, it was for genuine

have this." No, it was for genuine learning and growth of his own ideas and place as a product leader that he was taking those and and what it allowed him

to do was reflect back to Stuart ideas and principles that he had, but also grow his own product sense intuition.

And as an organization, it then allowed us to scale those principles. Um, and

and I think was a really really important part. And we worked with a lot

important part. And we worked with a lot of the sort of early Slack folks and the people that had really developed that culture, but it was folks who had really tried to grow and learn. They weren't

trying to politic. They were trying to build great products. And that's the approach we have to take.

>> Okay. So, what if you're not working for Stewart, which most people, you know, Stuart also former podcast guest? I feel

like uh just the alumni of Slack. Holy

moly. Just like this is a just the fact that >> what a just the fact that I have so many of these people on the podcast. What a

sign of an incredible team. Okay, so

yeah. So most people do not work for a steward that has incredible product sense, really cares about craft and uh you know most people are like I he's so or she is so wrong about what we're

doing. This is such a mistake. They

doing. This is such a mistake. They

don't listen. They don't know what they're talking about. How do you deal with that? One assumption I have of of

with that? One assumption I have of of how folks may misunderstand this skill is that they have to be a yes man. They

have to take everything that the um the leader said and do exactly that. That is

absolutely wrong. You get paid to have an opinion. You get paid to be a domain

an opinion. You get paid to be a domain expert. And in a lot of ways, your

expert. And in a lot of ways, your executive is looking for you to be the deepest person in the room, especially if they're good at their job, right?

they're looking for you to be the expert. And so bringing your expertise

expert. And so bringing your expertise to bear is absolutely crucial. Um, you

know, Elon Frank who was who was my boss at Slack as well is now CPO of Checker, he always had a customer anecdote in his back pocket. Like I can hear him in my

back pocket. Like I can hear him in my head saying, "I was just on site last week with so- and so and they said blah blah blah." Right? He always brought his

blah blah." Right? He always brought his expertise to bear and many of the executives at Slack were not from a strong enterprise background. so he

could bring that to the forefront. I

think that has to be married again with that curiosity and empathy. If you hear something that you don't agree with, this is something that on a guy my team does super super well right now. You

know, he'll hear something that flies in the face of of what he's the data he's seeing, the insights he's gotten, his experience in his domain expertise, and

he'll say, "That's so interesting. What

led you to believe that?"

That kind of question is actually curious about this person said something that I think is dumb, but there must be something behind it. And so if I

actually care what's behind it, and what you end up doing in that in that question is co-creating with the person who offered the opinion in the first place, you're able to say to them, I'm

interested in what led you to that belief, your experience. Did you have a meeting last week? Are you getting pressure from the board right now in a certain way? What is leading you to that

certain way? What is leading you to that belief? I think one thing that really

belief? I think one thing that really trips people up is execs are so good at seeming certain.

They say things in an authoritative way with confidence with shity because so much of their work is having to make those ultra fast decisions with little

information.

But if this is someone who is also a learner, who is also has a growth mindset, then if you are able to help them unpack why they believe something and then respond with your own domain

expertise, you are able to get to a better solution together.

>> I love these very tactical phrases and tips for how to deal with someone, say a leader, say you're, let's just say this is like, you know, they're a director of product, VP of product, CEO that you're trying to convince to agree to a plan.

So, one phrase, the phrase you're suggesting here is, uh, that's so interesting. What led you to believe

interesting. What led you to believe that? Um, anything else along these

that? Um, anything else along these lines? Say you're pitching your product

lines? Say you're pitching your product or an idea to say a VP of product and they're just like, what what else would what else what else works?

>> The earlier that you can understand the belief system and the things that are important to them, the better off you're going to be. So, very, very early on in

this process, what is top of mind for them? I can count on one hand when I was

them? I can count on one hand when I was chief of staff, how many people asked me for advice before going into our product review with our CPO or other executive team to say, "What do you think is most

important to them right now?" Use the people around them, their EA, their chief of staff, the people who have successfully pitched ideas in the past and say, "What worked? What do you think they're worried about? What are the

risks?" And in an age of the tools of AI

risks?" And in an age of the tools of AI that we have, this is so much easier than it's ever been, right? You can ask Slackbot, "What has Rachel been posting about lately? What what do you think is

about lately? What what do you think is most important to her?" A colleague of mine, a peer on on our product leadership team trained a GPT on a bunch of um transcripts from past product

reviews that are all publicly available.

And we expect that our PMs are running their PRDS or their their pitches through that to say, "What's Rachel going to push back on? Where are their weaknesses in this ideas?" You can also train things on where are your own

weaknesses? I know I've gotten feedback

weaknesses? I know I've gotten feedback in the past that my data is a little thin or that this kind of UX thinking is thin. Give me feedback on that. Cloud's

thin. Give me feedback on that. Cloud's

amazing for this. And so I think that the the first step is actually just saying what's important to them. What do

they want to hear? And anchor on that. I

think the second piece is going in to learn, not to convince. And the earlier on you do that, the better. So we have something at Webflow uh called office

hours. as early as you can you are

hours. as early as you can you are having these conversations to align on strategic direction maybe even before you have a one-pager you know uh we implemented something at Slack with

Stuart because we realized we were coming to him with like done designs and he was like what the [ __ ] is this I this is completely different than how I had this in my mind so Ali Rail early Slack

employee implemented something called hey Stuart what do you think and we would just sit with him for half an hour and say what do you think on this topic what's your belief system, what's your past experience? And we started with a

past experience? And we started with a user interview, right? We started with we actually want to download your expertise here. And I think that when

expertise here. And I think that when you engage execs in that way, it's really, really valuable. Like one of the things I see people do poorly is they don't ask for the time. They, you know,

this is sort of in counterpoint to what we were talking about before with how busy their calendars are, but they're afraid to ask for more time to get that insight. But sometimes if you don't, you

insight. But sometimes if you don't, you miss the point.

>> Something that we hear a lot on this podcast is as a product leader, as a leader of any kind, you want to have a point of view. You want to come into a discussion with here's here's our

options. Here's what I think is the

options. Here's what I think is the right solution. And then at the same

right solution. And then at the same time, as you're describing, you want to come across as I want to learn. I'm not

here to convince you. I'm here to just like help understand your worldview and where you think the right path is. How

do you think about just those two kind of that balance of I have something I believe is right and okay but I'm here to learn and get your feedback and see what you think makes sense.

>> Okay. So my advice on this may be a little paradoxical because um I think people make mistakes in both directions on the polls here. On the one hand I think there's an error people make of

trying to show too much work trying to tow too much upfront proof point. We

talked to 16 participants from these 15 geos and this is the statistically significant and the exec is like I'm so bored I'm going to die. I remember I did

this in a review once and literally the person I was most trying to convince glazed over got on their phone and I totally blew the meeting because I was trying to prove that I had done my

homework. Put it in the appendix. Right?

homework. Put it in the appendix. Right?

They don't need to know every single detail. the baseline expectation is that

detail. the baseline expectation is that you did your job and that you this that this is built on a solid foundation of your domain expertise. On the flip side,

I think there's some balance of showing your work that helps elucidate why your solution is best. So, one of the mistakes I see people giving is is doing

is giving only one option.

I think that people if you say I mean this is also like classic pricing and packaging strategy uh give three options and the goldilocks in the middle is the perfect one. Right? But I think that

perfect one. Right? But I think that what that actually allows you to do is say hey we considered we are not dumb.

We did not miss something. You think we missed something but no no we actually considered this. So we had a recent

considered this. So we had a recent product review with my manager Rachel Woolen. uh she was a recent guest on how

Woolen. uh she was a recent guest on how I AI and we uh brought a doc a sort of reasonable approach to what we thought was the sort of problem and strategic

space we were going after.

It didn't go well. it really didn't match her expectations and the feedback she gave us which was really really the right feedback was I don't understand how you're thinking about the

permutations of possible here because we had only given one option set and so what we did following that review is we said hey we really want to sort this out

we want to get moving we want to show um that we can really get building on this on this product and alignment is the next stepping stone for that can you

meet in two days and we turned around a new doc in two days that actually showed all of the options we had considered but hadn't brought to that first review. And

once we elucidated all the things we considered and why we thought they would or wouldn't serve the outcomes we were driving and the technical complexity behind them, she was like, "Oh yeah,

okay. I see why the solution that you're

okay. I see why the solution that you're proposing makes the most sense for what we're trying to accomplish." But in the first version, in the first meeting, we hadn't kind of shown that and we hadn't

workshopped it through her. And so

sometimes, you know, really tactically, you you want to have that available to you. It's not necessary to put all 15

you. It's not necessary to put all 15 options you considered, but at least be ready to show them. Have them in an appendix, have them in a draft Figma file, whatever it is. Um, we uh we we

used to have this rule after a design review with Stuart. We'd go through the design review and he'd say, "No, do it exactly like this. I want, you know, the button here and the interaction to be

this." And frankly, he always had better

this." And frankly, he always had better ideas than than we did, but we would come back and we called it Stuart plus two more. So, we did exactly what he

two more. So, we did exactly what he asked for and then two other versions that we felt good about. And then it gave us a a forum for conversation to

debate the merits of each type of approach. Awesome. Okay. So, there's a

approach. Awesome. Okay. So, there's a bunch of advice here. One is the default is don't go in with here's our whole process that landed on this suggestion.

Uh but have that ready because they may ask for that if they don't buy into it.

Another is present options. And then

there's a here's my point of view.

Here's why I think this is the right one. And then if they dig in, you have

one. And then if they dig in, you have be ready for more options. Have you have you ever looked into the Mento pyramid way of presenting stuff?

>> No, I don't know what that is.

>> Okay. So, this is there's this uh lady Barbara Mento. she uh she's like from

Barbara Mento. she uh she's like from the 50s I think she was the first female uh consultant at McKenzie or something like that and she kind of figured out the best way to present information to

execs is is uh backwards essentially it's instead of here's our process here's all the things we did here's our set of conclusions and then here's our recommendation it's flip it start with

here's our recommendation and then here's the things we explored and then here's the evidence behind that feels like that's kind of what you're describing Yeah, I think that's a really

good way of doing it. I think my only gloss on that would be that people are really different, right? Like execs are people too. And so one of the things

people too. And so one of the things that I think is really important is understanding what is the literal format, storytelling, pre-work that is

going to work for that person. You know,

some people hate a PowerPoint and it's just going to crush their soul if you start doing that. Um, some people only want to see the data and not the user,

you know, the the qualitative research.

Um, and so I do think it is about really understanding their communication style.

And execs, if you're listening to this, it's really [ __ ] helpful if you tell people because you actually know what you like and don't like. And so just tell people, I prefer a doc. I want no

upfront explanation. I want 10 minutes

upfront explanation. I want 10 minutes of quiet reading time and then we can come back together. That's a

particularly effective um means for for very busy people and short meetings um and especially in remote work where presentations just don't work very well.

Some execs are willing to do pre-ereads, some aren't. Um and I I think you just

some aren't. Um and I I think you just have to be willing to accept that they are also human and you're trying to give them the best shot at inculcating the information in the way that is

meaningful to them. So, there's a bunch of uh tips here that I want to summarize for how to kind of set yourself up for

success. One is what you just described,

success. One is what you just described, which is just think about how do they respond best? What kind of setup do they

respond best? What kind of setup do they respond best to? Is it a presentation?

Is it a here's what we recommend. Here's

three options. Is it uh data? Something

else? So, there's like just understand here's what this person likes. They they

don't want a they want like five minutes fast conclusion. Why? Uh then there's

fast conclusion. Why? Uh then there's your advice of ask people that know them what is top of mind for them right now because they may be like this is the big

bet we're making right now if it's not align with that they're not going to care. So it's like either either ask

care. So it's like either either ask them or ask people around them what's top of mind for them right now and then there's this idea of simulate almost simulate them feed all the previous meetings with them into say cloud

project or something like that create a little GPT and run your idea by them and like what would you say >> I will tell you I am not a big fan of the what's top of mind for you uh

question this a hot take because I think that what often people do is they think through their top priorities their top experiences is, you know, if we were

trying to do a research study uh to understand the day-to-day lives of our users, we probably wouldn't say, "What's top of mind for you?" We'd say, "Tell me how you spent your day." We'd say,

"What's the most urgent priority for you right now that you're really scared about messing up? What um pressures are you facing?" And so, I think there's

you facing?" And so, I think there's ways for us to ask much more interesting questions of our executives. Um, I

recently did this with our CEO. I said,

"Tell me what the board is pushing you on because everyone's got a boss and uh even a CEO who seems so powerful and

competent and um and and sure is getting pressures, right? What are you seeing as

pressures, right? What are you seeing as the the the key inputs to your success?"

The other thing people don't realize is excepts want to be successful, too. They

want to be good at their jobs. And how

can you help them? I mean, in the best case scenario, your incentives at a local team level or product organization level really closely align with their incentives that you're working on

something that really matters to the company. If you're not, you really

company. If you're not, you really should be having that conversation because you'll be in misalignment from the start. But if you actually have

the start. But if you actually have alignment, point out that alignment. How

is the metric that they're trying to move? The OKR they're responsible for

move? The OKR they're responsible for the board pressure that they're under going to be improved by the thing that you are proposing and how do you get

there together. So I think that one of

there together. So I think that one of the things people really miss out on here is what are the success criteria for an

exec and how do you model your world to amplify that success so that both of you can be more successful.

>> Okay, that is such an important lesson before we I follow that thread just to clarify this question of what is top of mind. Your advice uh was ask people

mind. Your advice uh was ask people around them what is top of mind for them. Don't ask them directly this

them. Don't ask them directly this question. top of mind has become this

question. top of mind has become this sort of trope, right? It's uh it's execs write a weekly write up of what's top of mind and it sort of becomes this generic

uninteresting sort of neutralized frame.

And so I think the question what's top of mind for you has actually lost some of its firepower and instead we have to

get at what is the emotion the um the sort of drive behind it and and what's the spicier question that'll get a more interesting answer. So then but going

interesting answer. So then but going back to this incentives piece such a powerful lever for getting anyone basically to get anyone to agree to what

you want which is what is what are they what are their goals? What are they trying to do? How are they measured?

How's success for them? And then how's the thing you're pitching them aligning with that and will help them achieve that specific goal.

>> Right? And in a product in building products together, your incentives should be making your users successful, making your business successful because of that. And so what do they actually

of that. And so what do they actually believe about that? It's not just about, oh, they want a promotion or they don't want to get fired or they want to hit their KR. Those are very very real human

their KR. Those are very very real human things. But in an ideal world, in

things. But in an ideal world, in product work, it is really based on building incredible products for your users and therefore great outcomes for your business. And so I think a big part

your business. And so I think a big part of this is actually understanding their strategic insights and what they believe is going to move the business forward um most effectively. So after I was chief

most effectively. So after I was chief of staff, I took over Slack's core product team. We worked on channels and

product team. We worked on channels and emoji and search and messaging. And

there was a real feeling from our executive team that we had a bit lost our mojo around product craft. And we

talked about, you know, painting the insides of the cabinets. We really

wanted such an amazing experience for our users. That was one of the things

our users. That was one of the things that makes made Slack great in the first place was just it really felt like a product that took that

usability to a 10x place. And there was a sense that I had heard from our leadership that we weren't quite there and we had lost some of that. And that

was so so important to who we were and how we showed up for our users. And so

we implemented something uh called the customer love sprint. Uh we said, "Okay, engineering, stop what you're doing. As

an entire team, we're going to spend two weeks just painting the inside of the cabinets." The only rule was engineers

cabinets." The only rule was engineers got to pick what they worked on. We we

supported them from a PM and design and and customer support perspective. We

gave them tons of ideas, but engineers could pick what they worked on. The only

rule was that you had to ship something.

You had to ship something that was good for users. And what we did is, you know,

for users. And what we did is, you know, you could call this a bug bash. You

could say, "Okay, you gotta fix these uh, you know, these these rough edges, these these misses in the product, but we made it a huge deal. We made it

really exciting and fun, and we had a big really fun judging competition that our executives took part of, and we really brought back that part of our

culture that we had lost out on a bit.

And it spoke to what our executives believed was a differentiation for us and how we were going to show up in the market, show up to our users, grow our

user base by making it feel special. And

we were able to say, "Oh, we shipped 65 improvements this week, this this sprint." And and that felt really really

sprint." And and that felt really really aligned with what they were trying to accomplish from a company perspective as well.

>> Okay. So to summarize the kind of tactics so far, one is align your pitch with the person you're trying to pitch

is incentives. I don't know if the

is incentives. I don't know if the grammar on that sentence works, but what are they trying what does success look like for them? Connect the thing you're pitching them with that success.

>> Yeah, I think that um aligning your incentives is yes really really important in a product pitch. If you're

thinking about a product pitch, how does it connect to the company goals? Are you

trying to um improve conversion rates?

Are you trying to grow enterprise customers? Are you trying to be

customers? Are you trying to be perceived in brand? Are you trying to break into some new category? Of course,

you have to align on a new pitch. I

think the inverse of this is how do you use that incentive structure to also inform regular roadmap? not uh you know

just net new product ideas or net new pitches but you're actually imbuing your entire team and your thought process with that incentive structure it's a deep understanding how did the OKRs get

to be the way they are how did the positioning statement get to be that way how do I understand that and deeply embed it into my team's culture so that we're reflecting what our exec team our

leadership has said is important >> so basically Everything should feel like it's a cohesive set of priorities based on some outcome you all agreed to in the mission.

>> Yeah. And I think a a big part of this is also metrics and data and what you're actually measuring your your own teams on. You know, we talk a lot about uh

on. You know, we talk a lot about uh leading and lagging indicators. Um or in the nonprofit world, this is called theory of change. Uh there are many steps. You yourself and your individual

steps. You yourself and your individual team may not be able to directly move enterprise revenue or directly move conversion rate. But you believe and the

conversion rate. But you believe and the company has a belief that painting the inside of the cabinets having an exceptional customer experience will be the thing that leads to customer

retention, customer conversion, um user satisfaction. And so how do you make

satisfaction. And so how do you make sure that your metrics and the things that you are proposing to actually shift ladder up really really clearly to those

and that your executive agrees to that.

>> Okay. And then the a second lever is trying to not go into a conversation even though you are trying to influence them. It's to go into it with an open

them. It's to go into it with an open mind and and a learning mindset. You use

this phrase uh that's so interesting.

What led you to believe that?

>> Right. And I think in that is um a disarming of the executive. You know,

again going back to like how do you get the best out of them? You want them to feel comfortable. You want them to feel

feel comfortable. You want them to feel like they can be honest with you. I

think something I see people miss often is they don't follow the subtle threads that executives lead them, the sort of breadcrumbs of opinions. you know, in a

in a sort of more clear-cut scenario, your leader, your executive will say to you, "Okay, I'd like a brief on exactly this thing. Write it generally this way.

this thing. Write it generally this way.

Let's review it in a week." That's a very clear-cut ask, but very very often the asks are more subtle. I wonder if I'm thinking about, have you considered?

And what I find is that people don't take the bait and the best people do. So

I'll give you an example. Just last week um you know we've been working a lot on as uh skills get democratized across web flow everyone can do design everyone can

ship code uh everyone can write a PRD how are we enabling people to move as fast as their brains and tools will make them. Uh Rachel our CPO said you know

them. Uh Rachel our CPO said you know hey Kev our head of design we're going to have to think about design reviews at some point. And within an hour, Kev had

some point. And within an hour, Kev had had a loom put together of, hey, here's a framework of high-risisk design changes, lowrisisk design changes, blast radius, release processes, and how we

might allow anyone in the organization to have designs shipped to production.

That was a thread. She didn't ask him to do that. he didn't need to follow up in

do that. he didn't need to follow up in that time frame, but he recognized that the organization's incentives are to keep empowering people, to keep everyone moving fast, to keep everyone um really

excited about what they're building as well. And he knew that he could slot in

well. And he knew that he could slot in and respond to this feedback really really quickly. A lot of times I see

really quickly. A lot of times I see people don't take that invitation from the executive to actually engage on the feed, the subtle feedback they're giving. you know, uh, an example from my

giving. you know, uh, an example from my past where this didn't go as well was, um, we were in a strategy review, you know, sort of a quarterly strategy review, and it was probably the fourth

time I had heard Tamar ask, I want to see, I'm interested in seeing the top 10 use cases on X. And the fourth time it happened, she got really frustrated. She

said, we've talked about this so many times before. Why don't we have this

times before. Why don't we have this documented? And I think it's because

documented? And I think it's because people are not picking up on the cue that there's really something deep underneath. There's really an important

underneath. There's really an important piece of feedback or a question that they're not pulling on. Maybe you think that that's not an important thing to do. And then you need more information

do. And then you need more information about why they think it's important.

Because if you just let it go and you don't respond to the feedback or respond to the ask, that person loses faith in you that you're going to follow up on the thing that they believe is important.

>> It also sounds like a really good way to influence is you take the reigns and here's where I think we could go with this and here's the answer to your question.

>> Absolutely. I mean, I think if you're thinking about how do you be more senior, how do you show up in a way that is in a leadership mindset, you have to act like a CPO, you have to come in with

that perspective. You have to come in

that perspective. You have to come in with a solution. You have to follow the thread that they've asked about. You

have to do it quickly. Um, one of the missteps here is, you know, people treat these interactions as so high seeks and sometimes they are, but one of the ways

that you you fail at that interaction is you wait too long to to engage on the feedback. If you wait a week for the

feedback. If you wait a week for the follow-up items that you discussed in the meeting, that exec has moved on and you've missed your chance to actually respond to the feedback in a in a in a

quick manner. you will get so much more

quick manner. you will get so much more excitement, enthusiasm, brain power from them if you keep the ball rolling in a in a timely manner.

>> And obviously there's like, you know, everyone's so busy, there's already so much work on their plates, you can't just hop on everything an exec says.

There's also this like classic advice of sometimes exacts just say something and everyone takes it so seriously. Oh, I

have to do that. And sometimes they're just saying it in passing. So, it's

probably all, you know, it's a balance of like take the opportunities, don't have fun every single thing.

>> Yeah. And a great question to ask in that in that scenario is how strongly do you feel about this? So if you hear something that they say really strongly

um or how urgent do you think that is or hey here's what the team is working on now. Do you think that that trumps these

now. Do you think that that trumps these priorities? And if they say yes, listen,

priorities? And if they say yes, listen, do the thing that they say trumps it.

Right? It's not about jumping on every request or taking every piece of feedback. It's about contextualizing it

feedback. It's about contextualizing it in why they believe that, what they think the urgency is, and then actually responding to that. So, more often than not, they'll say, "I wonder if we could

do this kind of study." And people will go and say, "Oh my gosh, we have to go run that study right now. We have to dep prioritize everything else." But if you say to them, hey, that's a really cool idea. I I like that. Do you think that

idea. I I like that. Do you think that that's more important than these three other studies or three other projects that we're working on now? And they'll

say, "Oh, no, no. That's just like a random idea. put it on the backlog. I

random idea. put it on the backlog. I

think that um execs are moving so quickly that they won't always give you that context of urgency and so you have to ask for it. This is something I've been working on getting better at as a

leader. This is just an idea. Um this is

leader. This is just an idea. Um this is a mandate. This is something I want to

a mandate. This is something I want to see. But uh it's hard sometimes it's

see. But uh it's hard sometimes it's hard to remember to do that because your brain is spinning with ideas.

>> This comes back to your point about uh getting into the mind of the person in the meeting, the leader. They're running

around all day. I think you call it a strobe. You're just like bam, another

strobe. You're just like bam, another meeting, next meeting, next meeting, next meeting without a lot of context and they just say things and sometimes it's import to them, sometimes not.

Which comes back to one of your tips at the beginning of this chat is >> spend 30 to 60 seconds at the beginning just giving them a little context on what the heck. What would you recommend in that 30 60 seconds? What are some

kind of key bullet points of what you want to communicate? Yeah, in the 30 seconds I would say we're here to discuss XYZ. Last time we met, we left

discuss XYZ. Last time we met, we left it off here. The goals of today's meetings are ZYX.

We're going here's how we're going to run this meeting and then stop talking because the moment you go off over 60 seconds, you've lost them. And and oh, I think the other really important thing I would add there is to say, was there

anything else you were hoping to cover today?

>> That was awesome. I love this advice. I

am excited to tweet this out just to summarize these bullet points you just shared. Uh that is so cool. I love that.

shared. Uh that is so cool. I love that.

And to your point, if 60 seconds flies by, you may think you're talking for 60 seconds. It often ends up being 5

seconds. It often ends up being 5 minutes. So the advice of keep it under

minutes. So the advice of keep it under 60 seconds. Just like try to actually do

60 seconds. Just like try to actually do that.

>> Try to actually do that. I think the other thing here is, you know, this often depends on what kind of meeting what what you're actually doing. You

know, in our culture, we do a lot of sort of silent read of docs or watching a loom um in the meeting and then coming back for conversation. I think one of the things that I've seen be really

effective in coming back for that conversation is often times a a leader will smatter your doc with a hundred comments and you're like, "Oh my gosh, what is actually important here?" So,

what I often do is I have a section at the top to say themes for discussion. I

bubble up some of the biggest and most controversial pieces that can only be discussed live. And anything they've

discussed live. And anything they've said that they're just curious about, what's the time frame for this? What's

the staffing need for why, I can answer offline, I can answer a follow-up. What

I can't get again is the time for discussion with that group. And the

safer that they feel in that discussion and the more that they think that you've understood what is the most sort of spicy or controversial, that's where you get to the good stuff and you really get

their insight and input. So I, you know, put a section at the top and say topics for discussion that I'm reading through the comments. Rachel, was that right?

the comments. Rachel, was that right?

Did I sort of get your thoughts right?

Anything you would add to this? And then

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We've talked about aligning your incentives and goals with their goals.

Uh going in with an open mind, setting context at the beginning of the meeting, understanding how they like to be presented to. What else can we learn to

presented to. What else can we learn to become better at influencing execs? And

let me just do a quick tangent. As

people are listening to this, they may again be like, "Oh my god, all this BS I have to do. I just want to do awesome work. Why am I spending all this time

work. Why am I spending all this time learning all this meta work of how to convince someone of a freaking thing? I

just want to build awesome products, drive, you know, growth for the business and the product and this sucks." I think it's again important to remind people this is just the way things go. You need

to influence people in power to agree with your approach. That's just the way it is. You can't just be like, "Nah, no

it is. You can't just be like, "Nah, no one no one understands me. It sucks."

So, it's not my fault.

>> I mean, it's literally your job, right?

They uh I think the way that product management has has worked for a long time is you basically get funding for your ideas in the form of engineering,

design, uh you know, crossunctional resourcing, right? that is you should

resourcing, right? that is you should consider that VC money that's been invested in you and your CFO, your CPO, your CEO is expecting a return. And so

what is the way that you are showing that you are building great products that that honors that investment in you and sure you can go into a startup and be

the sole decision maker and that is a very very valid way to work. But if you work with other people, having them excited interested passionate um

bought in to what you're doing will make everything easier. I It is also the job, right? You you also have to, but I think I think the thing I want

people to take away is that it's really the way to build well. You know, when people are motivated, when they feel purpose, when they feel like this is really something that I believe in, they

work harder. They support you more. They

work harder. They support you more. They

talk about you in rooms that you're not in. And so, it's it's just actually the

in. And so, it's it's just actually the way you deliver great results.

>> I I think that's such an important framing. Okay. What other tactics, what

framing. Okay. What other tactics, what other techniques work in helping leaders uh get influenced?

>> Yeah. put get influenced. I love that. I

love that. Um

>> yeah, we should we should have like a stamp like influenced uh at the end.

>> So I think one of the things that people misunderstand is the constraints that they are bound by versus their

leadership. you know, execs are not um

leadership. you know, execs are not um they they don't have the same boundaries of budget and headcount and um and timeline that you feel. They can move

people around in the organization. They

can ask for more resourcing. They can

get creative. They can elevate projects, kill projects. Um and so you know you

kill projects. Um and so you know you have to come to them with that mindset of hey with today's resourcing with this many engineers or this kind of tooling

or this kind of investment here's what what I can get but I'm thinking of the 10x case I'm thinking of the accelerated case and if that's what you want and if

that's aligned with your incentives here's what I need to be successful and so I think that people think okay well I've got my pizza team and I've got my four engineers and what you're asking is

not possible. Well, if it's not

not possible. Well, if it's not possible, tell them why not. Come back

and say, you know, the thing that you're asking for, I'm super stoked about that.

I need eight more people. I need you twice a week for an hour. I need much closer alignment with our marketing team and I'm not sure how to get that. You

have to think about what are the constraints that hold you back that they can actually help you a lot with. And

people miss out on this all the time of not asking for what they need to be successful, especially when the ask from the executive seems unreasonable.

>> This is such a good adi piece of advice of just if you get them excited enough, things can significantly change in terms of resourcing and prioritization. Like

your job is to help them see that how massive an opportunity this is and go and not just give you what you want, but just like wow, okay, here's the way to unblock this thing. Uh here's how we can go. like, okay, this is going to be our

go. like, okay, this is going to be our new bet big bet. Let's let's go big here.

>> Yeah, absolutely. This is going to be our new big bet. And this comes back to aligning with what the company's trying to to accomplish. And also the urgency.

So some things if you added a dozen more people or perfect alignment with go to market, yeah, you could get them to market faster, but is that the most important thing for the company goals?

is right now the answer is accelerating this in this way actually going to do more or is it something else that's actually more aligned and so I think it's still being so rooted in the

company goals in what the exec is trying to accomplish in what your users really need to be successful so that you can say in order to accelerate our goals here's what we can here's what we can do

>> like you know if you were in charge of a company you were you'd be so excited if someone came to you with a 10x next idea that's going to change the trajectory of your product like that's what everybody

wants.

>> Uh and so uh that is a really powerful way of approaching all these things.

Obviously not every idea is going to be a big idea. Not every idea is a great idea. A lot of times these take time.

idea. A lot of times these take time.

Also maybe speak to that just like say you have a big idea and they're like nah. What what are some expectations to

nah. What what are some expectations to set for people that come up with a big idea that just isn't getting any traction? You know, it really depends on

traction? You know, it really depends on what kind of organization you're working in. You know, if you're working in a

in. You know, if you're working in a smaller organization, if that big idea is something that you can build on your own or you can build within versus if you need, you know, a large large scale

investment. I think the real thing about

investment. I think the real thing about um uh building toward a big idea towards something net new, the key is really

outside and around the executive. So if

the executive is the decision maker on whether we're going to invest here, they also want to understand from their peers, from other experts what why this

actually matters. If you have something

actually matters. If you have something net new that you want to bring to market and customer success thinks it would really accelerate expansion rates or you

know the the marketing team thinks that uh signups would be 10xed because of this. if you have that cross functional

this. if you have that cross functional alignment. And this is where a lot of

alignment. And this is where a lot of these lessons don't just apply if you're going into a a product executive meeting, but that if you're influencing your cross functional execs and your cross functional stakeholders to be

advocates on your behalf. I I think that, you know, we now have more tools than ever to as as product folks build out the V1, right? prototype something,

build your own app, build the messy version of it, get feedback, iterate, and be socializing that in a way that

creates a ground swell of buyin. Um, to

the point that, you know, the exact can't say no to the funding. Along those

lines, it feels like to me the biggest reason that a leader doesn't buy into your pitch is you just have different information. They don't see what you

information. They don't see what you see. They don't you don't see what they

see. They don't you don't see what they see, right? They have all this other

see, right? They have all this other stuff that they're looking at and trying to decide. Maybe speak to just like that

to decide. Maybe speak to just like that skill of trying to clarify information on both sides.

>> I'm thinking about a a a tool April Underwood taught me. Um, she said she used to go into product strategy meetings with Stuart and was really trying to extract some of his ideas, but

she was always holding the whiteboard marker. And so there was this back and

marker. And so there was this back and forth between them in the conversation of I'm trying to imbue I'm trying to understand deeply what you're seeing in

the market, what you're feeling in the business, what your instincts are, but I'm also going to package that in a way that is translatable, is actionable, is

in a framework that you might not have had in your head. And so that is like a great tool for marrying that leader's instincts with your ability to sort of

not synthesize their approach but really um take that approach and and accelerate it for marrying what you know about the world and what they know about the world.

>> So it's kind of what I'm hearing is kind of take it upon yourself to help them to kind of align your world view with their worldview. And there's this question

worldview. And there's this question coming back just like like help me understand what I don't what was the question you had? Uh oh that's so interesting. What led you to believe

interesting. What led you to believe that? Like these are kind of questions

that? Like these are kind of questions that help you extract what you don't know that they know.

>> Yes. And I think there are also really different phases of a relationship.

There's a phase when you're new. You may

not have so much facetime with that person. You don't really know them that

person. You don't really know them that well. But I think that this is a place

well. But I think that this is a place where time spent together really just accelerates your trust with them, your um ability to speak freely, to ask

difficult questions to get real feedback. And so um especially if you're

feedback. And so um especially if you're in a position where you can ask for that time, more casual time, less fraught that you're not always pitching an idea,

but you can have real conversations.

that is also the groundwork for the pitch down the line. I think people devalue that that time upfront spent together because it pays dividends for the later pitch.

>> Yeah, I'm glad you went there. That's

exactly where I was going to actually go is this idea of trust and building and having, you know, giving the person a reason to kind of assume that you know

what you're doing. Um, obviously hard to build trust. And the reason I think this

build trust. And the reason I think this is important is sometimes you have the best idea and they just don't buy it because they just don't know anything about they don't they don't know what you've been up to. They don't know how awesome you are, how smart you are, how successful you've been your whole life

and career. Uh maybe because you're new.

and career. Uh maybe because you're new.

What are some tips for trying to build trust with the leader so that these things become easier?

>> I think in terms of building trust, it's really important to ground yourself in what they believe. If you are pitching an idea that is wildly

different than something they believe, don't bother. You probably have nine

don't bother. You probably have nine other good ideas that are more aligned with the beliefs that they already h that they already hold. Follow those

instead. So, there's something about just engaging uh from a baseline assumption. If they feel strongly about

assumption. If they feel strongly about something, okay, maybe you can come back to them once or twice and say, "Are you sure you feel strongly about that? I

really see this data." And if they say, "Yeah, I feel really strongly." you

probably have to drop it. But in terms of building that long-term trust, I think the biggest things that do that are really hearing them out and actioning on the feedback that you've

gotten in the past, having results. You

know, it cannot be overstated that impact in the organization, building great products, shipping amazing things quickly, feeding that back to the leader

to say, "Hey, we worked with you on this. We shipped it. It went well.

this. We shipped it. It went well.

Here's the results." that builds you momentum to be able to go back with the uh the more novel approach or the scarier one. I think the other thing I

scarier one. I think the other thing I would say is um one of my favorite well actually one of the only business books I've ever liked is called Switch. Uh

it's about change management and they talk a lot about shrinking the change um which is this brilliant idea. If

something seems scary and overwhelming, how do you make it so much smaller so that it's an experiment? It's uh a oneweek uh proof of concept. It's

something that feels really small that can get people over the hump of well I'm not going to invest in six months for this project if I don't know if it's going to work. So shrinking the change

is a huge way to build momentum and trust. And I think this applies to the

trust. And I think this applies to the way that we develop all products especially if you're doing something that lasts longer than a month. What are

your milestones? What are the chunks at which you're showing outcomes and fit?

And this is easier than ever to do with the tools that we have at our disposal.

How are we showing that we are taking a much more iterative approach so that you can build that momentum, build that buyin and get that trust to to do the bigger thing. That's an awesome very

bigger thing. That's an awesome very tactical piece of advice here to convince someone to do something is just reduce the risk essentially reduce the investment to help build trust in okay

this is showing success because obviously it's much easier to bite off on something that's going to take two weeks or have very low risk and impact if it's not a good idea.

>> Yeah, I think that's absolutely right and I think what is the type of risk that they are most afraid of too, right?

Is it wasting time? Is it time to market? Is it that they don't actually

market? Is it that they don't actually think this is going to work with customers? So, if you can start to and

customers? So, if you can start to and and you can and should ask this, what are the outcomes you're most afraid of, right? What would a failure state be um

right? What would a failure state be um for you in in this experiment? You know,

there's there's a concept of red teaming, which is originally a military tactic and and now being applied to businesses. How do you take an outsers's

businesses. How do you take an outsers's perspective to your idea and not just be so obsessed with your own thinking, with your own concept? Because so often we

get wrapped around the axle. Especially

I I I actually find this happens even more with prototyping. You build a prototype and you're like, "Oh, looks so beautiful. I would have never been able

beautiful. I would have never been able to build that before." That's actually like not a very good idea, but um but you get obsessed with it and you're unwilling to accept that it could fail.

I think one of the biggest things you can do to build trust is kill things, deprioritize things. That is a very very

deprioritize things. That is a very very senior way of thinking, right? And it

shows that you have the same aligned incentives as the executive who's thinking about the good of the company outcome, the user outcome, and not just your own. That is such a good one

your own. That is such a good one because everyone's always just trying to acquire more resources, more investment, just like more features, and showing that, okay, this is a terrible idea. I

know I spent like months on this, but no, we should kill this because it's not working, >> right? It's not working. And and here's

>> right? It's not working. And and here's how I'm going to know that's not working. And here's when I'm going to

working. And here's when I'm going to come back to you with a decision. Right?

So, sometimes we don't know the a lot of times we don't know the outcome, especially with AI native products. And

if we can say, we're going to test this.

here's how we're going to know it's working. We'll come back to you on X

working. We'll come back to you on X date. I think one thing that really

date. I think one thing that really spirals people out of control is is a desire for certainty. You know, as human beings, many of us have have a huge desire for certainty. Now more than

ever, that is not possible. Um and so, uh one trick that I learned, especially working with engineers who often have a very very high, uh desire for certainty, um is to say, I don't know the answer

right now. I don't know if this is going

right now. I don't know if this is going to be successful. I'm going to check in with you on X date. That's when we're going to come back and have another conversation. And so at least there's

conversation. And so at least there's certainty about the next check-in point.

And that can be a really powerful uh tool for sort of deescalating the fears and risks around a given initiative or idea.

>> Okay. Before we get into AI's impact and all this stuff, are there any other common mistakes people make when they are trying to get better at the skill of

influence or just any other really powerful tactics for increasing your ability to influence leaders?

>> Something people miss is the extremely broad context that execs bring to bear from not only their experiences but the things that they are hearing in their

day-to-day life. They understand what

day-to-day life. They understand what other product teams are working on better than you. They understand the conversation at the E staff level.

They've been to executive roundts and they are hearing and one of your jobs is to extract that insight and information and apply it to your ideas and they want

to feel like you care, like you respect that, like you can apply it to your own thinking. And so this this keeps coming

thinking. And so this this keeps coming back to that curiosity and empathy. What

if they know that you don't that you can actually apply to strengthen your thinking or inform the direction that you want to take your team? Um, and I think people just often don't ask those

things um of of their executives. They

don't uh show a curiosity for the expertise that that person has has brought to bear. And frankly, I think often they don't really care, which is

the chief mistake. um they should really actually take it into account to strengthen their own thinking.

>> Yeah. So much of this is about just uh coming into it with like here's what I it's just like having the same information. And I think this point

information. And I think this point about just like believe they know what they're doing is is so underappreciated.

Like there's a reason they're in this role. There's a reason you're not there.

role. There's a reason you're not there.

There's a reason this company's doing as well as it is. Uh and so and even if they are wrong like they believe they are right. So it's important to

are right. So it's important to understand what they think and know and what information they have access to.

>> Yeah. And I I think the other piece of this is for anyone thinking about how they grow their career.

How did that person get into the role that they are in? They broadened their context. They saw you know sort of had

context. They saw you know sort of had great peripheral vision. And that is a way to show up in a room that is much more senior than you are is keep your

domain expertise, keep the things that you know best, but broaden your perspective, broaden your um vantage point to think about it in the context

of the whole ecosystem, the whole organization, the whole industry, which you often don't get a a chance to say it. And what happens at that point is

it. And what happens at that point is you get seen as a strategic thinker. you

get seen as somebody who really cares about the company's success and not just your own and so it is actually a really really important tool for growth especially you know I had told April

when I originally pitched her on being our chief of staff that I I wanted to take the job because I wanted to know if I if I wanted to be CPO when I grew up and and it's true I still don't know um

because it's a really really hard job and I have just way more respect than I ever did before before that but I think that if you want to grow into a product

leadership role. Expanding your

leadership role. Expanding your viewpoint, expanding the way that you see problems and thinking about it from a global perspective is a way to show up

as that strategic leader that you say you want to be.

>> I love this advice just to make it very clear for people because it's easy to just like, yeah, okay, I'll just like expand my horizon. Like basically the advice here is uh just like think on

behalf of the entire business, not just your feature, not just your little goal.

It's like what is the business trying to do? Here's how this fits into it. Here's

do? Here's how this fits into it. Here's

what the here's what the CEO broadly is thinking about. Like here the epitome of

thinking about. Like here the epitome of this to me is Jeff Weinstein, I think is how I pronounce his last name, or Weinstein at Stripe. like he's just like a PM on a product and he's just

constantly tweeting and sharing uh Stripe as a business. Like he's just like thinking about Stripe as the company and then here's this thing I work on that helps the company.

>> Absolutely. And Jeff and I work together at Box.

>> Oh, you did? Oh, that is so cool. Right.

Okay. Would you agree he's like the epitome of this?

>> Oh, yeah. I mean, he's so charismatic and able to to really put himself in other people's shoes. I mean, I think that um it is just a way to, you know,

we we just redid our PM career ladder for this year. Um, and I led that effort. And one of the things that we

effort. And one of the things that we noted as a a trait of becoming more senior is your product citizenship and how much you are embedding back in the

organization and giving back best practices, mentoring others, um, broadening people's horizons on tooling,

technology, storytelling, and and of course strategy. And I think that this

course strategy. And I think that this is such an important part of people's growth that uh they often underell but

you can do it at every level in your own area and it's about connecting the dots back up to what is important to the company. So you know so many times I see

company. So you know so many times I see docs that are like okay our KR is to ship this thing and I'm like

why does that matter? Like does anyone care? um you have to tell a story and

care? um you have to tell a story and even if that's true that shipping is the car sometimes that's the case right but even if that's true why are you doing that what is the outcome for the

business why would the CEO be excited about shipping that uh it's usually because of some business outcome or user outcome that you have to tie back to

their perspective of and then I think the flip side of is if you're working on something that doesn't shift one of those outcomes or isn't urgent for the business, do you need to change course?

Do you need to say, "Hey, actually, I don't think this is the highest leverage thing right now." Um, we could actually do X uh to to be much more effective for our broader goals.

>> That that's where I was going to go is just like that's the ultimate trust building move is to tell the leaders, okay, here's our goal. Here's all these ideas, but we don't think this is the right goal, and here's how this doesn't fit in, and here's why we should kill

this product.

>> Right. Exactly. Right. Think like a CPO.

put yourself in their shoes. I mean, you had Stuart on a few weeks ago and he talked about how the CEO is kind of the only one who can really kill things across a,

you know, things that already exist or um really make some of those super super tough decisions. I think that is often

tough decisions. I think that is often times our culture, but is a mistake. If

we each think of ourselves as owners and as contributors to the business and as leaders, we will bring those opportunities up as well to both amplify

the business or save it from itself.

>> Do the job you want versus the job you have.

>> Classic.

>> Yes.

>> Okay, let's talk AI. I feel like you can't have a you cannot do anything these days without mentioning AI in some way. Uh, how is AI changing the skill of

way. Uh, how is AI changing the skill of influence? What's changed in the past

influence? What's changed in the past couple years in trying to convince people to do the things you're hoping them to do?

>> I think that we are entering a golden age of product management, not of product managers, but of product management and the core skills that made this function the thing that I love to

do. You know, more than ever, what we

do. You know, more than ever, what we have to do is have really interesting ideas that are grounded in user empathy,

curiosity, testing, iteration, but we will still be working in organizations where getting buy into those ideas uh and influencing people to fund not just

the V1, but the much more expensive V2, 3, 4, and ongoing support become 10x more important.

And as execution basically plummets in uh in complexity and everyone can be a builder, PMs can and and product

thinkers which I think is far beyond the product management function um can be so incredibly influenced by those

core skills of bringing people along for the ride. So I think that product

the ride. So I think that product managers for a long time have made their careers on being the most type A the

Gant chart master um the best notetaker in the business and if AI is better than you at analyzing data or taking meeting

notes or running experiments what's your job now so the leverage actually shifts from doing that work and being the synthesizer to deciding what work

actually survives lives and encouraging other people to buy into that process.

And I actually think it's just so incredibly exciting because PMs and other functions, engineers, designers are so empowered to bring that first

version to bear to get that momentum to get that signal on product market fit on user benefit and then build momentum from that point in a much faster cycle.

And so it's actually like an incredibly exciting place. But the act of

exciting place. But the act of influence, the act of stakeholder management, the act of learning is the 10x skill.

>> Awesome. This is such a fun topic with the way I've been thinking about this is just like where are human brains going to continue to be necessary and useful in this new world.

>> I'm terrified.

>> Maybe maybe nowhere.

>> Maybe nowhere. But the way you described it, which I totally agree with, is essentially it's deciding what to do and getting everyone on the same page, alignment uh around that. Here's we're

all on the same page. Here's what we're prioritizing. And then it's like, cool,

prioritizing. And then it's like, cool, now let's build it. And that happens so quickly now.

>> Yeah. And what can you notice that AI can't? You know, AI is not good at being

can't? You know, AI is not good at being an anthropologist yet, right? It is

based on a corpus of existing knowledge.

And I think the best product thinkers again across functions that I've I've worked with really are able to get to novel insights through that user empathy

through that understanding and through deep understanding of the business dynamics changing industry and bringing those together to prioritize ideas that

actually really really matter. You know,

we're going to have so much software we won't even know what to do with it. But

what software actually works? what

software actually matters, what software gets marketed or sold or you know we're we're gonna have to think about not just that the software exists but that it can

get to its final state and that is going to require people's buy in to that idea working.

>> Yeah. Uh the way I think about this right now is just like where humans are still necessary and uh great product thinkers are still necessary is uh on the front end deciding what to

prioritize and build on the back end determining if this is good and ready essentially judgment and taste and then there's distribution I think is such an

underappreciated like new bottleneck because as you said there's so much [ __ ] out there just like how do we get anyone to pay attention to any of this stuff every day there's is like a new life-changing product. So, I feel like

life-changing product. So, I feel like that's going to be a big problem.

>> Oh, I want you to do a whole episode on distribution because I feel this so much. Right. If everyone thinks they can

much. Right. If everyone thinks they can build the next Salesforce on their own, by the way, I don't believe that. Uh

then, you know, you're going to have just a flood of available tools. And who

gets the attention? It is still going to be who has the marketing dollars, who has the brand reputation, who is the existing customer base. distribution is

everything and I I think the quintessential example we've seen here is with Gemini and Google's tools and and just their total um continued dominance in that market because of

tools of distribution. Um and I think it's really fun to see. I think the other piece I would say is that's underrated there is trust building trust with your users but also with your

internal teams. You know we're seeing even model companies hire at a huge rate right now. So you are still working with

right now. So you are still working with colleagues. Uh you are still working

colleagues. Uh you are still working with millions of users and alongside distribution is trust and that is a a function of influence and empathy. Along

these lines what I wonder is we talked about these other two kind of areas.

Humans are still valuable and great product leaders are still valuable.

Deciding what to build knowing if it's ready and awesome. Uh, I wonder how good AI will get at those things because we never thought AI would be amazing at coding and now it's 100% of code will be

soon written by AI. And I've actually been building a bunch of stuff and I just find codeex and clock code are so good at actually giving you ideas for what to build. I'm just like, what should I do to make this better? And

it's like, here's 10 ideas and then they're like, that is a really good idea. So, I think it'll get there.

idea. So, I think it'll get there.

People underestimate how good it'll get at these things, I think. Yeah, I do think that as um as ideas proliferate and as there just becomes so many ideas

and so much feedback, you know, we're going through a strategy doc rewrite. I

think we have like 40 versions now because it's so easy to rev on a 15-page doc. Actually, when when these decisions

doc. Actually, when when these decisions are happening faster, building is happening faster. The flip side of that

happening faster. The flip side of that is mistakes compound faster as well. And

strategy clarity becomes so much more important to anchor people on if you want to have an empowered EPDI

organization or company. that that

clarity of what you believe, what are the most important problems to invest time and energy into what uh where we want to invest compute and dollars. Um

that is the mechanism for letting people go and run at as fast a velocity as they're capable of. Right? So if you have that corpus of shared beliefs that you update on a pretty fast clip because

uh I think that's that's the mode we're in. that is actually what enables teams

in. that is actually what enables teams to build the right stuff as opposed to just the idea that cloud had.

>> I love this point because there's a lot of talk on Twitter actually just today uh in the PM community about PRDS are dead and I think it's exactly the

opposite which is being very clear about what we are doing and the strategy is now the most important thing because once you have that then it's cool fire off 100 agents and we'll go build it and

launch it.

>> Totally. Strategy clarity is is so so important. I am not in the Twitter

important. I am not in the Twitter verse. I find it exhausting partially

verse. I find it exhausting partially because I think takes like PRDs are dead or software is dead is like really dumb.

Um I find it a little insufferable. uh

if I'm being spicy because I still think what matters is understanding users, understanding business and economic uh dynamics understanding

strategy and what we're trying to accomplish and then really thinking through what is the right way to do that together.

>> Okay, maybe one more question uh along these lines just agents now running as colleagues. Everyone's got all these

colleagues. Everyone's got all these clouds running, codeexes, all kinds of agent platforms now that agents are a part of kind of the workforce and increasingly

uh is there anything there around influence that is valuable for people to start thinking about to learn how to do?

>> I love that question. you know, uh, we talk about this a lot, especially when we think about identity security compliance that agents are a teammate for accelerating work um, and and the

risks that that also provides because of the um, places where agents fall down. I

I think agents are absolutely something we have to think about w with relation to um to influence because um, we are basically all directors of work now,

right? If we have an army of agents or

right? If we have an army of agents or this hundred new colleagues that joined our team, how would we onboard new junior team members who don't already understand our product philosophy?

What's important to us? And how do we codify that for ourselves? How do we take the time to say what's important to me as a product leader that I want to

inculcate into um anything that's developed for my team? What do I believe about um product market fit? what do I look for in terms of what success looks

like? How do I set metrics? And if we

like? How do I set metrics? And if we can do that upfront work to actually like analyze ourselves and where we've seen success, where we've seen downfalls, and then continue to train

our agent models with that um that data, that history, that context, they will be better off. But I also think the flip

better off. But I also think the flip side of this is guard rails. Where do

you need to be involved? Where do you need to catch hallucinations or missteps? Where do you uniquely have

missteps? Where do you uniquely have taste, uh, judgment, frame of reference, something intangible where you need to say, "Don't do this without me."

>> What's so funny about this, essentially, we're helping the agent learn the skills we've been talking about to influence you.

Here's context on my goals. Here's what

I understand about the customers. here's

our current priorities like help me tell me what to do and it's like influencing you to agree.

>> Absolutely. I think Wow, that's really the singularity, isn't it? Uh you should just feed this podcast to a bunch of agents and see if they can do this better than me. Um see see what their

advice is. No, but I really think at

advice is. No, but I really think at this point we are in a place where it is a back and forth and where we should be using agents and AI as um a really smart

colleague that never gets irritated by our questions. Poke holes in my ideas.

our questions. Poke holes in my ideas.

Um tell me what you would do differently. Um help me plan this out.

differently. Um help me plan this out.

Uh base this on more uh corporate context than I could ever have gone through myself. Um and and poke holes.

through myself. Um and and poke holes.

And I think that um that is a just like a really powerful way for amplifying our work.

>> Oh, it's like so interesting like one of your you know tips is come into an open mind and learn it's like exactly what an agent does. Tell me more. What else

agent does. Tell me more. What else

should I and then just like hopping on your ideas like okay cool we'll add that to the two like all the ideas you've shared agents are so good at. So that's

yeah >> I think that um one thing I'm really curious about you know you were talking about human brain chemistry is just how

we can protect our brains from overwhelm >> the the speed of ideas change um

building is we are diseolved for this pace of life we were evolved uh I I love this book um

Pachenko that tells the history of um a Korean family over several generations.

And in one of the generations sort of in the 1600s, 1700s, there are two wives that every day cook breakfast, then go to the market, buy rice, buy fish, buy

vegetables, go home, cook the rice, cook the fish, serve dinner, clean up dinner.

That's the day. And for the vast majority of human history, that was kind of our day. And the mental load that we are asking of our brains right now is

staggering. And so I think one of the

staggering. And so I think one of the ways that we actually have to use AI is and agents is to help our brains be most

effective is to clear out distraction to point out the most important things to and I I think this is where people really need to make some tough decisions. How much can we really focus

decisions. How much can we really focus on and how do we allow for that focus in the ways that are hopefully good for humanity?

>> What a time to be alive, Jessica. Holy

Oh my god. Uh before we get to our very exciting lightning round, is there anything else that you wanted to share?

Anything else you want to double down on?

>> One thing I think that I'll say is I'm a people person. I love in-person

people person. I love in-person collaboration and I love talking ideas through and whiteboard sessions. I'm a

two-wing three. If there are any other anogram fans out there, it's uh it's a mix of like the people person, the sort of bringing to the communal thinker with

the achiever. Um that is my personality

the achiever. Um that is my personality type. I think that um sometimes I can

type. I think that um sometimes I can give this kind of advice and people say, "Oh, well Jess, you're you're good with people or like you kind of understand these things." I think that something

these things." I think that something that has taken me a while in my career is how to be authentic to myself in influence, in relationships, in trust

building. And I don't think that it's

building. And I don't think that it's one personality type or another. I think

that you could be shy and introverted or uh super data oriented and technical. I

think all types of personalities can in their own authentic way communicate with the people around them to build trust to build influence in the way that feels true to them. You know, I think when I

uh when I was younger in my career, I was starting out as a PM, I got a lot of feedback of, oh, Jess, how do you, you know, show up more like a man would?

Show up more aggressively, show up more um uh decisively. And I think there was some good nuggets in there, but I think it took me a while to feel like, hey,

who I am and how I show up is actually my superpower that I can double down on.

And I don't need to be like someone else. What I need to do is think about

else. What I need to do is think about what I want to accomplish and how I want to grow and do that in a way that is is true to me.

>> I could not agree more with that. I've

uh shared very sim similar sentiment on the pod a few times. Just like you can accomplish the same things other people can through your own strengths. You

don't have to do it the way they're doing it.

>> Exactly.

>> I so agree.

>> A beautiful way to end that. And with

that, we have reached our very exciting lightning round. I've got five questions

lightning round. I've got five questions for you. Are you ready?

for you. Are you ready?

>> I'm ready. I'm so excited.

>> What are two or three books that you find yourself recommending most to other people?

>> I think there's a genre of book I've really fallen in love with. Uh I

mentioned Pachenko before. Um, I love historical fiction because it really gives me access into worlds that I don't know. You know, they uh I can't remember

know. You know, they uh I can't remember who talks about um windows and mirrors.

Books are windows or mirrors for us. And

uh historical fiction, especially about places where I'm less familiar with that history, is really a window into someone else's experience. Um, and there's a

else's experience. Um, and there's a particular uh type of historical fiction that I just loved, which is multigenerational historical fiction.

Uh, Pachinko does this with a family in Korea over generations and moving to Japan. Uh, there's a book called

Japan. Uh, there's a book called Homegoing, which is about the west coast of Africa and the impact of the slave trade um, and the ongoing uh, life in

Africa from two uh, split parts of the family. Uh, history of burning is a is a

family. Uh, history of burning is a is a book that tells a story of um Indian indentured servants that were brought to

Uganda to build the um British railroad there. Um, and just parts of history

there. Um, and just parts of history that I was so much less familiar with and really treasure that sort of window into um a different world.

>> I think the book overstory is an example that. Have you heard of that?

that. Have you heard of that?

>> No, I haven't. I think I might be getting it wrong, but it's called overstory, which is around it's a concept of uh when you have a big tree like the overstory is the branches that kind of sit on top that kind of create a shade.

>> Oh, that's beautiful.

>> That's the book I'm thinking about and it's the story of a family over many generations and around a tree.

>> Oh, great. Now I have to pick that up.

>> Was popular. Okay. If it's the one I'm thinking about, I think you're going to love it.

>> Okay, great.

>> Uh favorite recent movie or TV show you've really enjoyed. You know, again, this is another window. I have been obsessively watching The Pit, which is probably a a lame answer. I wonder if

anyone else has given you that so far, but I just really um it's given me such a vantage point and a view into the incredibly difficult work that emergency

healthcare workers do and the stresses and the system and the brokenness that they operate under, but also the extreme care and love that they bring to their work. and has just given me so much

work. and has just given me so much admiration.

>> It is trending on this podcast. So, uh,

and I I'm watching.

>> It's really good.

>> It is really good.

>> Okay. Favorite recent product, favorite product you've recently discovered that you really love.

>> Okay. I I bought my husband a towel warmer. It was like 35 bucks on Amazon

warmer. It was like 35 bucks on Amazon and it has led to so much joy in our household. Just getting out of the

household. Just getting out of the shower to a warm towel is so great. Um,

it's a really fun addition to the to the family. So, highly recommend that. Um,

family. So, highly recommend that. Um,

it's a it's just a cheap and easy way to to brighten your day a little bit.

>> I want one. That sounds amazing. Does it

sit on top of an existing towel rack or is it a separate thing that you >> It's a separate thing. It's sort of like a basket that you put the towel in. You

could put it in for half an hour, an hour, set it on a timer. It's so cool.

>> Okay. I love this idea. Never been

mentioned before. But I think uh u more in the in the tech vein of products I've loved um I've been a loyal user of Casa which I believe you tweeted about as

well as a Kasa user. Um Casa comes in and they they have this idea of what if everyone had a household assistant. Um

and so they come in, they take stock of every paint color, every appliance, every light bulb. Um, and anytime something breaks or you need something repaired, you can just say, "I need new

light bulbs for this room." And they'll immediately send you them from Amazon. I

need a new dishwasher. Ours broke. And

they'll send you three options that fit your space um and are good quality. Um,

they also pick up your packages every Friday and your donations. So great. And

they're just the nicest people. So, I'm

really excited to see them see them thrive.

>> I love that pick. Uh, I was looking up their domain name, getcasa.com. And I

think they're only in the Bay Area right now, and I think they're expanding into LA right now.

>> Expanding into LA. Yep.

>> Sweet. That's a good pick. And their

website is very bare. I don't even know how you sign up, >> but uh yeah, I think I don't know. I

guess you could figure it out, but uh I I love Costa. Uh yeah, they also do like a filter rotation thing. So like every six months they come and replace all your filters or air purifiers and whatever. You can set you can set like

whatever. You can set you can set like maintenance for your dishwasher, for your air filters, for your uh washer dryer, which has been super cool to see.

Um they also you get handyman credits every month. So all the things that you

every month. So all the things that you put off do doing uh they can come in and and do it themselves and it's it's just wonderful.

>> Awesome. Okay, two more questions. Do

you have a favorite life motto that you often come back to in work or in life?

>> Um I asked my husband about this one. I

was like, "What's my life motto?" Um,

and he had such a nice answer that I I thought I'd go with it. Uh, we have this saying with our kids, first the guests.

Um, so if you have guests over, which we love to host people in our house, um, our rule with our three kids is guests always go first. And I think that um, it's really something that we think

about in terms of being of service to others, being respectful to others, being welcoming, being kind. Um, and I think that that has dictated a lot of

who I am as a person and and how we're trying to be as a family. When you are of service to others, when you are inclusive, um, when you can put them first ahead of yourself, I think it

actually brings a lot of joy to you. Um,

and it certainly makes the world a little bit better.

>> Oh, one of the core values at Airbnb was be a host.

>> Yeah.

>> Which is very appropriate for Airbnb, but such a broadly uh, useful lens, >> right? I've also recently heard uh if if

>> right? I've also recently heard uh if if you want a village, be a villager.

>> Um and so this idea of just building community, reaching out, being there for other people, and really taking that first step, even if it's scary or overwhelming, um can really can really

make a difference.

>> Final question, you have some cool posters behind you if people are watching on YouTube. Is there one that's like a favorite? Is there one that has a story per chance?

>> Ah, that's such a good question. So, uh,

these are all my husband's posters. He

is a musician. He loves guitar. Uh, so

he picked them all, but I think that I have to say my favorite one is probably, uh, Jimmyi Hendris plays the Greek. Uh,

so we live in Berkeley and uh, you can't, it's just slightly off camera, but it's just a great memory of sort of an incredible musician. Um, and the

iconic place that that we're lucky enough to live in and sort of the great access to culture that we have here, but also just how important music is to our lives, how much >> is such a cool venue. Just like if

people don't know, it's just like this outdoor amphitheater with grass. You can

get blankets.

>> Should everyone should go. It's such a fun spot. Right. right on UC Berkeley's

fun spot. Right. right on UC Berkeley's campus. Um, and they've got great music

campus. Um, and they've got great music and we're really lucky to live close by.

>> Well, with that, Jessica, I thank you so much for being here. Two final

questions. Where can folks find you online if they want to reach out at, maybe follow up on anything here? And

how can listeners be useful to you?

>> I am not a very online person, which is, you know, funny for being on this podcast. So, I think the main place I am

podcast. So, I think the main place I am online is on LinkedIn. Um, and so you could definitely find me there. Um, in

terms of being useful uh to me, I would love to hear what resonated for you, what's worked for you in the past, how you're seeing these things show up in your work, um, and how I can get better

at, um, you know, uplifting the tech community. And as we go through this

community. And as we go through this period of tremendous change, uh, how I can show up, uh, as a leader and as a a source of community for for this group

of folks.

>> What change are you speaking of?

Nothing.

>> It's called AI. We're still talking about AI.

>> Oh, man. All right. Well, Jessica, thank you so much for being here.

>> Yeah. Thanks.

>> Bye, everyone.

>> Thank you so much for listening. If you

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