Influence is the highest-leverage skill for product leaders outside of AI, and it’s the single most important skill that AI cannot replace. Jessica Fain, a product leader who has worked at Box, Slack, Brightcove, and now Webflow, spent time as chief of staff to Slack’s CPO April Underwood and later Tamar Yehoshua. That experience gave her a rare window into how executives actually think, make decisions, and spend their time. She discovered that most product managers fundamentally misunderstand this, and it’s the reason great ideas die on the vine.
Why great ideas fail without executive buy-in
Product managers often believe that doing great work is enough, that the quality of their ideas will speak for itself. But without executive backing, even the best ideas go nowhere. Jessica experienced this firsthand at Slack: some of her ideas got funding and excitement, while others she deeply believed in were ignored. The difference wasn’t the quality of the ideas, it was her ability to understand and influence the decision-makers.
The core mistake is centering yourself instead of the executive. PMs are trained in curiosity and empathy for users, but they forget to apply those same skills when talking to executives. They walk into meetings focused on getting approval for their plan rather than understanding what the executive is dealing with.
How executives actually think
An executive’s calendar is like a strobe light: they wake up to a huge list of urgent things and go from meeting to meeting, context-switching between finance, hiring, people problems, legal issues, and product reviews. The PM may have spent weeks preparing, but the executive hasn’t thought about it since the last meeting. They may not have even had time to go to the bathroom.
Everything that lands on an executive’s desk feels like an emergency. They are optimizing for a global maximum across the entire business, not for the local problem you’re bringing them. Your job is to help them get into your mindset quickly and connect your pitch to what they’re already trying to accomplish.
The fundamentals: context-setting, communication, and empathy
Spend 30 to 60 seconds at the top of every meeting setting context: why you’re here, where you left off last time, the goals of today’s meeting, and how you’ll run it. Then stop talking. If you go over 60 seconds, you’ve lost them. End by asking, “Was there anything else you were hoping to cover today?”
Be a communication chameleon. Understand how each executive processes information best. Some want a doc with 10 minutes of silent reading time before discussion. Some want to see data first. Some want customer stories. Some hate PowerPoint. Ask them directly what they prefer, or ask their EA, chief of staff, or peers who have successfully pitched to them before.
Use AI tools to simulate executive feedback. One product leader trained a GPT on transcripts from past product reviews so PMs could run their PRDs through it and predict where the exec would push back. You can also use Slackbot to see what an executive has been posting about lately to understand their current priorities.
Stop pitching for approval—start co-creating with execs
The most disastrous thing you can do is walk into a meeting looking for a rubber stamp. Instead, go in to learn. Treat stakeholder conversations as discovery interviews that strengthen your ideas. When an executive offers an opinion you disagree with, say, “That’s so interesting. What led you to believe that?” This disarms them, helps you understand their reasoning, and lets you co-create a better solution together using your domain expertise.
If you don’t respect an executive’s knowledge and experience, you should quit. But if you do respect them, recognize they have context and skills you don’t. Take their feedback seriously. Annie Pearl, Jessica’s first manager at Box, always said: “It’s not my fault, but it is my problem.” If the leader didn’t buy in, that’s on you.
Influence vs. politics (and why people get it wrong)
People often conflate influence with politics and find it icky. But politics is manipulating outcomes for your own gain. Influence is about increasing the odds that good ideas survive. If you approach it with genuine curiosity and low ego, it’s learning, not manipulation.
Noah Weiss at Slack kept a notebook of things he learned from Stewart Butterfield over the years, not to show off, but to genuinely grow his own product sense. That allowed him to reflect ideas back to leadership and scale principles across the organization. That’s the right mindset: trying to build great products, not politicking.
How to disagree with execs without losing trust
You get paid to have an opinion and to be the deepest person in the room on your domain. Good executives want your expertise. The key is to marry your domain expertise with curiosity about theirs. When they say something that contradicts your data, ask what led them to believe it. They may be getting pressure from the board, or they may have information you don’t.
Executes are very good at seeming certain because they have to make fast decisions with little information. But if they have a growth mindset, helping them unpack why they believe something, and then responding with your own expertise, gets you to a better solution together.
How to present ideas
Don’t show too much upfront proof. Executives don’t need to know you talked to 16 participants across 15 geographies. They trust that you did your homework. Put the detailed process in an appendix. The baseline expectation is that your work is built on solid domain expertise.
Do present multiple options, not just one. Giving three options (like classic pricing strategy) shows you’ve considered the space and didn’t miss something obvious. It also gives you a forum to debate the merits of each approach. At Slack, after a design review with Stewart, the team would present “Stewart plus two more”: exactly what he asked for, plus two alternatives they felt good about.
The Minto Pyramid approach works well: start with your recommendation, then show the options you considered, then the evidence. But tailor the format to the person. Some execs want the conclusion first, some want data, some want stories.
When an executive gives subtle feedback like “I wonder if…” or “Have you considered…”, take the bait. These are invitations to engage. At Slack, Tamar Yehoshua asked four times to see the top 10 use cases for something, and when nobody acted on it, she got frustrated. Follow up on these threads quickly. Speed matters: if you wait a week to follow up, the executive has moved on.
Understanding incentives to unlock buy-in
The most powerful lever for getting anyone to agree is understanding their goals, how they’re measured, and what success looks like for them. Then explicitly connect your pitch to that success. What are their OKRs? What is the board pushing them on? How will the thing you’re proposing help them move the metrics they care about?
Don’t ask “What’s top of mind for you?” directly, it’s become a generic trope that gets generic answers. Instead, ask spicier questions: “What are you most scared about messing up right now?” “What pressures are you facing?” “Tell me what the board is pushing you on.” Even CEOs have bosses and pressures.
Execs want to be successful too. If your incentives align with theirs, point that out explicitly. If they don’t align, you need to have that conversation because you’ll be misaligned from the start.
Aligning product work with company strategy
Embed the company’s incentive structure into your entire team’s thought process, not just individual pitches. Understand how the OKRs were set, how the positioning was chosen, and reflect that in your team’s culture. Everything should feel like a cohesive set of priorities based on agreed-upon outcomes.
Make sure your metrics ladder up clearly to executive goals. You may not directly move enterprise revenue, but if the company believes that exceptional customer experience leads to retention and conversion, show that chain of logic and get your executive to agree to it.
At Slack, when leadership felt the team had lost its product craft mojo, Jessica’s team ran a “customer love sprint” where engineers picked their own user-facing improvements and shipped 65 of them in two weeks. This directly aligned with the executive belief that exceptional user experience was Slack’s market differentiation.
Disarming the executive
Go into meetings with an open mind and a learning mindset, even though your goal is to influence. The phrase “That’s so interesting, what led you to believe that?” is disarming because it shows genuine curiosity rather than defensiveness.
Follow the subtle threads executives leave. When Rachel Woolen at Webflow mentioned offhand that the team would need to think about design reviews, her head of design had a Loom with a full framework put together within an hour. She didn’t ask him to do it, but he recognized the organizational incentive to keep empowering people to move fast.
When you’re not sure how strongly an executive feels about something, ask: “How strongly do you feel about this?” or “How urgent is this compared to our current priorities?” Execs move so fast they don’t always give context about urgency, and you need to ask so you don’t either over-index or under-index on their offhand comments.
How to run high-impact meetings
Keep context-setting under 60 seconds. State what you’re discussing, where you left off, the meeting goals, and how you’ll run it. Then stop.
If you’re doing a doc review, include a “themes for discussion” section at the top that bubbles up the most controversial or important points that can only be discussed live. Answer simple follow-up questions offline. This makes the executive feel like you’ve understood what matters and creates a safer space for the real conversation.
When an executive leaves dozens of comments on your doc, don’t try to address every one. Summarize the themes and confirm you got it right: “Here’s what I’m hearing. Did I capture your thoughts?” Then focus the live discussion on the spicy stuff.
Why influencing execs is part of your job
This isn’t optional meta-work. Getting funding for your ideas in the form of engineering, design, and cross-functional resources is literally your job. Your CPO and CEO are expecting a return on that investment. If you work with other people, having them excited and bought in makes everything easier.
When people are motivated and believe in what they’re building, they work harder, support you more, and advocate for you in rooms you’re not in. Influence is how you deliver great results, not a distraction from them.
Asking for resources and thinking in 10x bets
PMs often constrain themselves to their current team and budget. But executives can move people around, get more funding, elevate projects, and kill projects. Come to them with the 10x case: “With today’s resources, here’s what I can get. But if we’re going after the accelerated case aligned with your incentives, here’s what I need to be successful.”
If an executive’s ask seems unreasonable, tell them why and what you’d need to make it possible. Don’t just say it’s impossible. Come back and say, “I’m super stoked about this. I need eight more people, or I need you twice a week for an hour, or I need closer alignment with marketing.”
Not every idea is a big idea, and not every idea will get traction. If you’re working on something net new, build cross-functional alignment first. Get customer success, marketing, and other teams to be advocates. Prototype a V1 yourself, iterate, and create a groundswell of buy-in so the executive can’t say no.
Clarifying information and building shared context
The biggest reason leaders don’t buy into your pitch is that you have different information. They see things you don’t, and you see things they don’t. Your job is to extract their insights and apply them to your ideas.
April Underwood used to go into strategy meetings with Stewart Butterfield holding a whiteboard marker. She was trying to deeply understand his market instincts and feelings about the business, but also packaging them into frameworks and actionable plans. This is a powerful tool for marrying a leader’s instincts with your ability to synthesize and accelerate.
Invest in casual, non-pitched time with executives, especially when you’re new. Time spent together accelerates trust and your ability to speak freely. People devalue this upfront investment, but it pays dividends when you later need to make a pitch.
How to build trust and make ideas stick
Ground yourself in what the executive already believes. If your idea is wildly different from their beliefs, don’t bother leading with it. Start with ideas that align, build trust, and then introduce more novel approaches over time.
The best way to build trust is to act on feedback you’ve received in the past and show results. Ship great things quickly, feed the results back, and say, “We worked with you on this, we shipped it, here’s what happened.” That builds momentum for the scarier, more novel ideas.
“Shrink the change” from the book Switch: if something seems scary and overwhelming, make it smaller. Propose a one-week proof of concept instead of a six-month project. Define what success looks like and when you’ll come back with results. This reduces risk and builds trust incrementally.
One of the most powerful trust-building moves is to kill things. Deprioritize things. Everyone is always trying to get more resources and ship more features. Showing that you’ll kill something that isn’t working, even if you spent months on it, demonstrates that you’re thinking like a CPO about the good of the company, not just your own agenda.
When you don’t know if something will work (especially with AI-native products), don’t pretend you do. Say, “I don’t know the answer right now, but here’s how we’ll know it’s working, and I’ll check in with you on X date.” Give certainty about the next check-in point, even if you can’t give certainty about the outcome.
Common mistakes people make
Not recognizing the broad context executives bring. They know what other teams are working on, they hear things at the E-staff level, and they’re getting input from executive roundtables. Your job is to extract that insight and apply it to your ideas. Show curiosity for their expertise.
Not believing that executives know what they’re doing. There’s a reason they’re in their role. Even if they’re wrong, they believe they’re right, so you need to understand what they think and what information they have access to.
Not broadening your own perspective. If you want to grow into a product leadership role, think about the whole ecosystem, the whole organization, the whole industry. Connect your work back to what matters to the company. When you write a doc, don’t just say “our KR is to ship this thing.” Explain why that matters to the business and why the CEO would be excited.
The ultimate trust-building move is to tell a leader that their current goal might be wrong and explain why, with evidence. Think like a CPO. Do the job you want, not just the job you have.
How AI is changing influence and product work
We’re entering a golden age of product management, not of product managers. As execution becomes cheaper and everyone can be a builder, the core skills that matter most are having great ideas grounded in user empathy, and getting buy-in to fund not just the V1 but the ongoing V2, V3, V4, and support.
AI is great at analyzing data, taking notes, and running experiments. What it can’t do yet is be an anthropologist. The best product thinkers get to novel insights through deep user empathy, understanding business dynamics, and bringing those together to prioritize ideas that actually matter.
Strategy clarity becomes more important, not less. With agents and AI making it easy to build fast, the bottleneck shifts to deciding what to build and getting alignment on it. PRDs aren’t dead; being very clear about strategy is now the most important thing because once you have that, you can fire off agents to build and launch quickly.
AI can be used as a smart colleague that never gets irritated by your questions. Feed it your corporate context, product philosophy, and past decisions, and use it to poke holes in your ideas, simulate executive feedback, and help you plan. But set guardrails for where you uniquely need to be involved: taste, judgment, and catching hallucinations.
Agents are now teammates, and you need to onboard them the way you’d onboard a junior team member. Codify your product philosophy, what you believe about product market fit, how you set metrics, and what success looks like. Analyze your own history of successes and failures and train your agent models with that context.
The human brain is not evolved for the current pace of ideas and change. Use AI to clear out distraction and point you toward the most important things. Make tough decisions about what you can really focus on and protect that focus.
Lightning round
Books Jessica recommends: She loves multigenerational historical fiction as a window into unfamiliar worlds. Pachinko (a Korean family over generations moving to Japan), Homegoing (West Africa and the slave trade’s impact across split family lines), and History of Burning (Indian indentured servants in Uganda). She also recommends The Overstory, a multigenerational story centered around a tree.
Favorite recent TV show: The Pit, which gives a vivid look at the incredibly difficult work of emergency healthcare workers and the broken system they operate under.
Favorite recent product: A $35 towel warmer from Amazon that has brought unexpected joy to her household. She’s also a loyal user of Casa, a household assistant service that catalogs everything in your home and handles maintenance, repairs, package pickup, and donations.
Life motto: “First the guests.” When hosting, guests always go first. It’s about being of service to others, being welcoming and kind, and putting others ahead of yourself.
Where to find her: LinkedIn is the main place she’s online. She’d love to hear what resonated and how people are applying these ideas in their work.
