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

[00:00] 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 head. So I describe an executive's calendar as a strobe light going off. You wake up at 8 m. You've already got a huge list of urgent things going on. [00:30] 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. They want to be good at their jobs. Sometimes you have the best idea and they just don't buy. One of the biggest things you can do to build trust [01:00] 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 absolutely crucial. You have to act like a CPO. [01:17] Today my guest is Jessica Fain, who's been a product leader at Box and Slack and Brightwheel and now at Webflow. [01:24] and she has gotten very, very [01:27] uniquely good, [01:28] at the Art and Science of Influence. [01:31] and in particular influencing executives. [01:33] 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, [01:49] change people's minds, and the mistakes that people make when they're trying to influence leaders. [01:53] we get very tactical and very specific [01:55] There's a bunch of stuff in this conversation that I've never heard before or thought about [02:00] I am very excited for you to learn from Jessica. Before we get into it, don't forget to check out Lenny's Product Pass dot com. [02:05] for an incredible set of deals available exclusively to Lenny's newsletter subscribers.

Now let's get into it after a short word from our wonderful sponsors. [02:15] This episode is brought to you by Omni. Many product teams today are in the process of debating how to ship AI analytics. The hard part is obvious. Having an LLM guess at SQL in production is a huge mess and just a bad idea. Omni takes a different approach. They have a semantic layer built in so that when you embed their analytics, the AI actually knows your business definitions, not just your raw tables. [02:45] production. If you want AI analytics in your product without building the whole stack from scratch, check out

co slash Lenny for a free three-week trial. Companies like Perplexity, DBT, and BuzzFeed use Omni to ship analytics their customers can trust. That's co slash Lenny. [03:04] This episode is brought to you by Lovable. Not only are they the fastest growing company in history, I use it regularly and I could not recommend it more highly. If you've ever had an idea for an app but didn't know where to start, Lovable is for you. Lovable lets you build working apps and websites by simply chatting with AI. Then you can customize it, add automations, and deploy it to live domain.

It's perfect for marketers spinning up tools, product managers prototyping new ideas, [03:34] tools. Lovable isn't about static pages. It builds full apps with real functionality. And it's fast. What used to take weeks, months, or years, you can now do over a weekend. So if you've been sitting on an idea, now is the time to bring it to life. [03:49] Get started for free at dev. [03:52] That's dev. [03:57] Jessica, thank you so much for being here. Welcome to the podcast. Thanks for having me. [04:02] It's my pleasure. Let's set this conversation up.

[04:05] We're going to be talking about the skill and the art of influence. [04:11] And in particular, influencing executives and leaders, people above you that you want to convince to do things you want them to do. [04:18] Help us understand why this is worth people's time. Why is this worth the next hour of someone listening to this? [04:24] Why is this skill so important to people's careers? - I think as product builders, there's almost not a skill that's more important. Influence and building momentum behind great ideas is the way that great products actually get built.

And if you don't have that influence, if you don't have the buy-in and the backing of your key stakeholders, of your executives, [04:46] You can't build great products. [04:48] Something that I personally went through [04:51] is just like 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. [04:57] I'm just going to it's going to show itself. Everyone's going to recognize it. [05:01] 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. 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 buy in 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.

[05:31] 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 confused and frustrated, honestly, because I felt like, hey, I really get this user 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. [06:01] eight months pregnant, eight and a half months pregnant. April Underwood, who had just been named CPO of Slack, she had just come back from maternity leave.

We had a two-day 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 really love the way you think. And I really want to understand it better. If you'd ever consider having a chief of staff, [06:26] I'd love for you to 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 Tamar Yehoshua, who 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 be mad if I mess up your title. And what I learned through that process [06:56] 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 [07:26] Thank you.

[07:26] decide what to do, what to listen to, what's an example. [07:29] 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 m. You've already got a huge list of urgent things 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

[07:59] to a product review. And the product manager coming to that product review, or the leader who's trying to make a pitch, [08:06] Thanks, I've been prepping for this meeting for two weeks, three weeks, maybe six weeks since we last spoke. [08:13] But the executive coming into that session hasn't thought about you since. [08:18] So, [08:18] They may not have gone to the bathroom today. [08:20] 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 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 tactics i think is so important is [08:48] Just take 30 seconds at the top of a meeting.

[08:51] Why are we here? What happened the last time we talked? Why is this important to you? Why is this meaningful? And really remember that they are not thinking just about you. They are optimizing for a global maximum and not for the local that 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. [09:13] maybe hasn't had time to go to the bathroom. How do we help them see what you want them to see? [09:17] and maybe buy into your vision and suggestions.

Yeah. [09:21] I think that, 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 right kind of information in the way that they communicate? You know, we as product leaders have to be communication chameleons.

[09:51] is right, but appropriate for work. And you have to think about [09:55] Do they really 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 [10:25] Managed as it's your fault. [10:27] 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. They... [10:34] They agreed to do something else. [10:36] I always tell them that's just you not able to influence them and convince them that you're right. Yeah. And Annie Pearl, who was my first PM manager back at Box, she's now- Also a former podcast guest. Also a former podcast guest, a former CPO at Calendly and Glassdoor 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 shoes of an executive. [11:05] 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.

[11:35] their day has 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. [12:05] that this person brings to the table and imbue that into my product work, [12:09] Both? [12:10] 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 better product. You know, I often hear people say to me, [12:22] 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. [12:30] 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, [12:47] Awesome. [12:48] 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 this stuff, but first, something on my mind is, [13:04] some people might be turned off by this topic. [13:07] in terms of [13:08] it may feel icky of just like, "I don't want to try to be this manipulative person." [13:14] you know deal with politics and like I just want to do awesome work why do I have to do this [13:19] Speak to that person that's kind of just like feels icky about building this and working on this and being this person. [13:24] Yeah, I think that when people frame this as politics, they're completely missing the point.

Politics is manipulating outcomes and people for your own gain. [13:34] 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. 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 [14:04] We do that in a genuine and low ego way. I'll give an example here. Noah Weiss, who seceded Tamari Oshue as CPO of Slack.

Also former podcast guest. - What a runner on here. - I've learned so much from Noah. We sat down to write product principles for Slack. [14:27] and Ethan Eisman, our head of design, was leading that initiative. But really, this was a lot about codifying the early ideas that made Slack great, especially from product principles and sort of craft perspective. And we started talking about this and Noah had been at Slack early on. And 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.

[14:57] 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 learning and growth of his own ideas and place as a product leader that he was taking those. 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 [15:27] and I think was a really, really 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 [15:39] 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... [15:46] not working for a Stuart, which most people, you know, Stuart also a former podcast guest. I feel like just the alumni of Slack, holy moly, just like this is a, just the fact that I've had, 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 Stuart that has incredible product sense, really cares about craft and, [16:09] You know, most people are like, she is so wrong about what we're doing. This is such a mistake. They don't listen. They don't know what they're talking about. [16:17] How do you deal with that? One assumption I have of how folks may misunderstand this skill is that they have to be a yes man. They have to take everything that the leader said and do exactly that. That is. [16:33] absolutely wrong.

You get paid to have an opinion, you get paid to be a domain 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 to bear is absolutely crucial. You know, Elon Frank, who was who was my boss at Slack as well as now CPO of Checker, he always had a customer anecdote in his back pocket. Like I can [17:03] in my head saying, "I was just on site last week with so-and-so and they said blah, blah, blah."

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. [17:21] If you hear something that you don't agree with, this is something that a guy on my team does super, super well right now, he'll hear something that, [17:29] flies in the face of what he's, the data he's seeing, the insights he's gotten, his experience in his domain expertise, and he'll say, [17:38] That's so interesting.

What led you to believe that? [17:42] That kind of question is actually curious about this person said something that I think is dumb. [17:50] 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 [17:57] in that question is co-creating with the person who offered the opinion in the first place. You're able to say to them, [18:04] 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 belief? [18:14] I think one thing that really trips people up is [18:18] Execs are so good at seeming certain. [18:21] They say things in an authoritative way, with confidence, with surety, because so much of their work is having to make those ultra fast decisions with little information. [18:35] But if this is someone who is also a learner, who is also has a growth mindset, then you [18:41] 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... [18:52] tips for how to deal with someone say a leader say you're let's just say this is like you know they're [18:57] 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, [19:05] That's so interesting what led you to believe that. [19:08] Anything else along these lines, say you're pitching your product or an idea to [19:12] say a VP of product. [19:13] and they're just like, "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 [19:26] very, very early on in this process, [19:29] What is top of mind for them? [19:31] I can count on one hand when I was chief of staff, how many people asked me for advice before going into a product review with our CPO or other executive team to say, [19:40] "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, [19:50] "What worked?

"What do you think they're worried about? "What are the risks?" And in an age of the tools of AI that we have, [19:56] This is so much easier than it's ever been, right? You can ask Slackbot, what has Rachel been posting about lately? What do you think is most important to her? A colleague of mine, a peer on our product leadership team, trained a GPT on a bunch of transcripts from past product reviews that are all publicly available. And we expect that our PMs are running their PRDs or their pitches through that to say, what's Rachel going to push back on?

Where are their weaknesses in this idea? [20:26] on where are your own 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. Claude's amazing for this. And so I think that the first step is actually just saying, what's important to them? What do they wanna hear and anchor on that? [20:45] 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 called Office Hours. As early as you can, you are having these conversations to align on strategic direction, maybe even before you have a one pager. We implemented something at Slack with Stuart because we realized we were coming to him [21:10] done designs and he was like what the is this this is completely different than how i had this in my mind so ally rail early slack employee implemented something called hey stuart what do you think [21:21] 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 user interview, right? We started with, we actually want to download your expertise here. I think that when you engage execs in that way, it's really, really valuable. Like one of the things I see people [21:40] do poorly is they don't ask for the time. They, you know, this is sort of a 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. [21:54] But sometimes if you don't, you miss the point.

[21:57] Something that [21:59] we hear a lot on this podcast is as a product leader, as a leader of any kind, [22:04] You want to have a point of view. [22:06] You want to come into a discussion with here's our options, here's what I think is the right solution. [22:12] And then at the same time, as you're describing, you want to [22:14] come across as I want to learn. I'm not here to convince you. I'm here to just like [22:18] 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, [22:24] I have something I believe is right. [22:26] And OK, but I'm here to learn and get your feedback and see what you think makes sense. [22:30] 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 [22:41] trying to show too much work, trying to show too much upfront proof point. We talked to 16 participants from these 15 GOs 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 [22:59] 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? They don't need to know every single detail. The baseline expectation is that you did your job and 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.

[23:29] So one of the mistakes I see people doing is giving only one option. [23:34] I think that people, if you say, I mean, this is also like classic pricing and packaging strategy, give three options and the Goldilocks in the middle is the 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, no, we actually considered this. So we had a recent product review with my manager, Rachel Wolin.

She was a recent guest on How I AI. [24:03] And we brought a sort of reasonable approach to what we thought was the sort of problem and strategic space we were going after. [24:13] 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, [24:21] 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. [24:35] that we can really get building on this product. And alignment is the next stepping stone for that. [24:43] "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 proposing makes the most sense for what we're trying to accomplish." [25:13] 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 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. 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, [25:43] and the interaction to be this, and frankly, he always had better ideas than we did, but we would come back and we called it Stuart + 2 more. So we did exactly what he asked for, [25:55] and then two other versions that we felt good about. And then it gave us a forum for conversation to debate the merits of each type of approach. [26:06] 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.

[26:13] Suggestion. [26:14] But have that ready because they may ask for that if they don't buy into it. [26:18] 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. [26:23] And then if they dig in, [26:24] be ready for more options. [26:26] Have you ever looked into the Minto pyramid way of presenting stuff? [26:31] No, I don't know what that is. Okay, so this is, there's this lady, Barbara Minto, she's like from the 50s, I think. She was the first female [26:38] consultant at McKinsey or something like that.

[26:40] And she kind of figured out the best way to present [26:43] Information to execs is [26:45] backwards. Essentially it's [26:47] Instead of here's our process, here's all the things we did, [26:50] here's our set of conclusions and then here's our recommendation [26:54] It's flip it. Start with, here's a recommendation. [26:57] And then here's the things we explored. And then here's the evidence behind that. [27:02] It feels like that's kind of what you're describing. [27:04] Yeah, I think that's a really good way of doing it. I think my only... [27:08] gloss on that would be that people are really different right like execs are 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

[27:38] you think it is about really understanding their communication style and execs if you're listening to this it's really fucking 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 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 [28:08] Some execs are willing to do pre-reads, some aren't.

And I think you just have to [28:14] 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. [28:23] So there's a bunch of tips here that I want to summarize. [28:27] for how to [28:29] kind of set yourself up for success. [28:31] One is... [28:32] what you just described, which is just [28:34] think about how do they respond best? What kind of setup do they respond best to? Is it a [28:39] presentation?

Is it a [28:41] Here's what we recommend. Here's three options. Is it? [28:43] data, something else. So there's like just [28:46] Understand, here's what this person likes. They want it like five minutes fast [28:50] Conclusion. [28:51] Why? [28:53] Then there's your advice of [28:55] ask people that know them what is top of mind for them right now [28:59] because they may be like, this is the big bet we're making right now. If it's not aligned with that, they're not going to care. [29:05] So it's like either either ask them or ask people around them.

What's top of mind for them right now? [29:10] And then there's this idea of simulate almost, simulate them. [29:13] feed all the previous meetings with them into, say, cloud projects or something like that. [29:17] create a little GPT and [29:19] run your idea by them and like what would you say? [29:21] I will tell you, I am not a big fan of the what's top of mind for you. [29:26] question, this a hot take, because I think that what often people do is they think through their top priorities, their top experiences.

You know, if we were trying to do a research study 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? [29:53] "What pressures are you facing?" And so I think there's ways for us to ask much more interesting questions of our executives. I recently did this with our CEO, I said, [30:06] "Tell me what the board is pushing you on."

Because everyone's got a boss. And even a CEO who seems so powerful and competent and sure is getting pressures, right? What are you seeing as the key inputs to your success? The other thing people don't realize is, [30:26] if sets want to be successful too they want to be good at their jobs and how can you [30:32] 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 should be having that conversation because you'll be in misalignment from 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, the board pressure that they're under going to [31:02] be improved by the thing that you are proposing and how do you get there together so i think that [31:09] One of the things people really miss out on here is [31:15] What are the success criteria for an exec? [31:18] And how do you model your world to amplify that success so that both of you can be more successful?

[31:25] Okay, that is such an important lesson. Before we follow that thread, just to clarify this question of what is top of mind, [31:31] Your advice was ask people around them what is top of mind for them. Don't ask them directly this question. [31:37] Top of mind has become this sort of trope. [31:40] right it's uh it's exact right a weekly write-up of what's top of mind and it sort of becomes this generic [31:47] 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 [32:04] the [32:05] sort of drive behind it? And what's the spicier question that'll get a more interesting answer? So then, but going back to those incentives piece, such a powerful [32:14] Lever. [32:15] for getting anyone, basically to get anyone to [32:18] agree to what you want, which is [32:21] What are their goals? What are they trying to do? How are they measured? [32:25] How's the success for them? And then how's the thing you're pitching them? [32:29] aligning with that and will help them achieve [32:31] that specific goal.

[32:32] Right. And 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 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 care. Those are very, very real human things. [32:52] 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 of this is actually understanding their strategic insights and what they believe is going to move the business forward most effectively.

So after I was chief of staff, I took over Slack's core product team. We worked on channels and emoji and search and messaging. [33:22] 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 that made Slack great in the first place was just, it really felt like a product that took that, [33:43] 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 called the customer love sprint. 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. [34:13] engineers got to pick what they worked on. We supported them from a PM and design and customer support perspective. We gave them tons of ideas that 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. What we did is, you could call this a bug bash. You could say, "Okay, you got to fix these [34:35] rough edges, these misses in the product," but we made it a huge deal. We made it really exciting [34:43] 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 sprint. [35:13] felt really, really aligned with what they were trying to accomplish from a company perspective as well. [35:17] Okay, so to summarize the kind of tactics so far, [35:22] One is align your pitch with [35:25] the person you're trying to pitch [35:28] is incentives i don't know if the grammar on that sentence works but what do they try what does success look like for them connect the thing you're pitching them with that [35:36] Success. [35:37] Yeah, I think that [35:39] 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 improve conversion rates? Are you trying to grow enterprise 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, [36:09] product ideas or net new pitches, but you're actually [36:14] 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 [36:31] 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 and the mission. [36:42] Yeah. And I think a big part of this is also metrics and data and what you're actually measuring your own teams on.

You know, we talk a lot about leading and lagging indicators or in the nonprofit world. This is called theory of change. There are many steps. You yourself and your individual team may not be able to directly move enterprise revenue or directly move conversion rate. [37:12] customer experience will be the thing that leads to customer retention, customer conversion, user satisfaction. And so how do you [37:23] make sure that your metrics and the things that you're proposing to actually shift [37:27] ladder up really, really clearly to those and that your executive agrees to that.

[37:32] Okay, and then a second lever is... [37:36] trying to not go into a conversation, even though you are trying to [37:41] Influence them it's to go into it with an open mind and in a learning mindset use this phrase or [37:47] That's so interesting. What led you to believe that? [37:50] Right. And I think in that is, [37:52] um a disarming of the executive you know [37:56] 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 like they can be honest with you.

I think [38:06] 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 sort of more [38:18] 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 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 [38:40] and the best people do.

[38:43] So I'll give you an example. Just last week, you know, we've been working a lot on as skills get democratized across Webflow. Everyone can do design. Everyone can ship code. Everyone can write a PRD. How are we enabling people to move as fast as their brains and tools will make them? Rachel, our CPO, said, you know, hey, Kev, our head of design, we're going to have to think about, [39:07] design reviews at some point. And within an hour, Kev had had a loom put together of, hey, here's a framework of high risk design changes, low risk 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 that timeframe, but he recognized that the organization's incentives are to keep empowering people, [39:37] everyone really excited about what they're building as well. And he knew that he could slot in and respond to this feedback really, really quickly. A lot of times I see people don't take that invitation from the executive to actually engage on the subtle feedback they're giving. You know, an example from my past where this didn't go as well was, [40:00] We were in a strategy review, sort of a quarterly strategy review, and it was probably the fourth time I had heard Tamar ask, [40:08] I'm interested in seeing the top 10 use cases on X.

[40:12] 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 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 piece of feedback or a question that they're not pulling on. [40:33] Maybe you think that that's not an important thing to 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, [40:45] that person loses faith in you, that you're going to follow up on the thing that they believe is important.

[40:51] It also sounds like a really good way to influence [40:53] is you [40:54] take the reins 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 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

[41:21] you know, people treat these interactions as so high stakes. And sometimes they are, but one of the ways that you fail at that interaction is you wait too long to engage on the feedback. If you wait a week for the follow up items that you discussed in the meeting, [41:39] that exec has moved on and you've missed your chance to actually respond to the feedback in a quick manner, you will get so much more excitement, enthusiasm, brainpower from them if you keep the ball rolling in a timely manner. [41:53] 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.

[42:01] There's also this like classic advice of sometimes execs just say something and everyone takes it so seriously. Oh, I have to do that. [42:07] and sometimes they're just saying it in passing, [42:09] 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 scenario, is how strongly do you feel about this? [42:19] So if you hear something that they say really strongly, 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 priorities? And if they say yes. [42:33] 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 and why they believe that, [42:45] 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 deprioritize everything else.

But if you say to them, hey, that's a really cool idea. 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, no, that's just like a random idea. Put it on the backlog. I think that execs [43:15] 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, this is a mandate, this is something I want to see, but it's hard.

Sometimes it's hard to remember to do that because your brain is spinning with ideas. [43:33] This comes back to your point about [43:35] Getting into the mind of the person in the meeting, the leader, they're running around all day. I think you call that a strobe. You're just like, bam, another meeting, next meeting, next meeting, next meeting, without a lot of context. And they just... [43:46] Say things. [43:47] and sometimes it's more to them, sometimes not, which comes back to one of your tips at the beginning of this chat is, [43:52] spend 30 to 60 seconds at the beginning just giving them a little context on what the heck [43:57] What would you recommend in that 30, 60 seconds?

What are some kind of key bullet points of what you want to communicate? [44:02] Yeah. In the 30 seconds, I would say... [44:05] "We're here to discuss X, Y, Z. Last time we met, we left it off here. The goals of today's meetings are Z, Y, X. 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 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?"

[44:27] That was awesome. I love this advice. I'm excited to tweet this out just to summarize these bullet points you just shared. 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 five minutes. So the advice of keep it under 60 seconds, just like try to actually do that. [44:45] try to actually do that. I think the other thing here is, you know, this often depends on what kind of meeting, 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 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 oftentimes a leader will smatter your doc with a hundred comments and you're like, oh my gosh, what is [45:15] 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 said that they're just curious about, what's the timeframe for this? What's the staffing need for why? I can answer offline. I can answer to 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 [45:44] 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.

[45:56] Rachel, was that right? Did I sort of get your thoughts right? Anything you would add to this? And then we can talk about the really good stuff that gets us to a better outcome. My podcast guests and I love talking about craft and taste and agency and product market fit. You know what we don't love talking about? Sock 2. That's where Vanta comes in. Vanta helps companies of all sizes get compliant fast and stay that way with industry leading AI, automation, [46:26] first SOC 2 or ISO 27001, or an enterprise managing vendor risk.

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And let me just do a quick tangent. [47:19] As people are listening to this, they may again be like, [47:22] Oh my god, all this BS I have to do? I just want to do awesome work. Why am I... [47:26] 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. [47:32] growth for the business and the product and [47:35] This sucks. [47:36] I think it's, again, important to remind people this is just the way things go.

You need to... [47:41] influence people in power [47:43] to agree with your [47:45] approach. [47:46] That's just the way it is. You can't just be like, man, no one... [47:49] No one understands me. It sucks. It's not my fault. I mean, it's literally your job, right? They, I think the way that product management has worked for a long time is [48:00] you basically get funding for your ideas in the form of engineering, design, cross-functional resourcing. 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.

[48:17] And so what is the way that you are showing that you are building great products that [48:23] that honors that investment in you. [48:26] A. [48:27] 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, bought in to what you're doing, [48:43] will make everything easier, [48:45] It is also the job, right? You also have to. But 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... [49:01] that I believe in, they work harder, they support you more, they talk about you in rooms that you're not in, [49:08] And so it's just actually the way you deliver [49:13] Great results. [49:14] I think that's such an important framing. [49:17] Okay, what other... [49:18] tactics, what other techniques work in helping leaders work [49:23] Get influenced. Yeah, get influenced. I love that. I love that. Be influenced. [49:29] Yeah, we should we should have like a stamp like influence.

[49:35] 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. [49:47] They don't have the same boundaries of budget and headcount 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. 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 I can get.

[50:17] Thank you. [50:18] I'm thinking of the 10x case. [50:19] I'm thinking of the accelerated case. And if that's what you want, and if that's aligned with your incentives, [50:25] Here's what I need to be successful. And so I think that people think, OK, 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 possible, tell them why not come back and say, you know, the thing you're asking for. I'm super stoked about that. I need eight more people.

[50:45] 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. [51:09] This is such a good piece of advice of just if you get them excited enough, things can [51:14] significantly change in terms of resourcing and prioritization like your job is to help them see [51:19] how massive an opportunity this is and go, [51:21] And not just give you what you want, but just like, wow, OK, here's the way to unblock this thing.

[51:25] Here's how we can go like, okay, this is going to be our new big bet. Let's go big here. [51:30] - Yeah, absolutely. This is gonna be our new big bet, and this comes back to aligning with what the company's trying 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. [51:46] But... [51:47] 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 and what the exec is trying to accomplish and what your users really need to be successful so that you can say, in order to accelerate our goals, here's what we can do. [52:12] Here's what we can do. Like, you know, if you're in charge of a company, you are [52:17] You'd be so excited if someone came to you with a 10x idea that's going to change the trajectory of your product.

Like that's what everybody wants. [52:25] And so that is a really powerful way of... [52:29] approaching all these things. Obviously not every idea is going to be a big idea, not every idea is a great idea. [52:35] A lot of times these take time also [52:37] maybe speak to that just like say you have a big idea