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

Why does it matter? Because the skill that separates good PMs from great ones has nothing to do with their roadmap.

Jessica Fain spent years watching brilliant product ideas die at Slack, Box, and Brightwheel — not because they were wrong, but because the people pitching them forgot to treat executives like humans. The insight she unlocked as chief of staff to two Slack CPOs is both obvious and routinely ignored: the same curiosity and empathy PMs apply to users gets completely switched off the moment they walk into an exec review.

• Executives operate on a strobe-light calendar — they may not have thought about your pitch since your last meeting six weeks ago
• Going in for approval is a failure mode; going in to learn produces better products and better relationships simultaneously
• Mapping your pitch to an exec's OKRs and board pressures is the single highest-leverage alignment move — and most PMs skip it entirely
• In an AI world, execution complexity is collapsing; the scarce resource is now the judgment and alignment needed to fund V2 through V4

Executives haven't thought about your pitch since your last meeting — and you have 30 seconds to fix that

An executive's calendar is a strobe light, Fain says. By the time they walk into your product review, they've already been through a finance budget session, an executive interview, a people problem, and a legal issue. The PM has been preparing for six weeks. The exec may not have had time to use the bathroom.

The fix is brutally simple and almost never done: spend 30 seconds at the top of the meeting re-orienting them. Fain's exact script — why are we here, what happened last time we talked, why does this matter to you, here's how we'll run the meeting — and then stop before 60 seconds. The moment you go past a minute, you've lost them.

She adds one move most people forget: end that setup with "Was there anything else you were hoping to cover today?" That single question changes the dynamic from presentation to collaboration before a single slide has been shown.

The underlying principle is what Fain calls being a "communication chameleon" — understanding whether a given exec lights up for customer stories, dashboards, design mocks, or raw data, and leading with that format. Some hate PowerPoint. Some want 10 minutes of silent reading time before any conversation. Learning the format is as important as crafting the content.

Treating your executive as a user — and every meeting as a discovery interview — produces better products, not just better politics

PMs apply curiosity and empathy to customers as a matter of professional religion. The moment they face an executive, those skills evaporate and get replaced by a single drive: approval. Fain calls this "one of the most disastrous things you can do."

The reframe she learned partly from Annie Pearl, her first PM manager at Box: "It's not my fault, but it is my problem." Ownership without blame. That mindset forces you out of victimhood ("they just don't see it") and into genuine curiosity about what the exec actually knows that you don't.

At Slack, Noah Weiss — later CPO, now head of AI at Atlassian — carried a small notebook with a section dedicated to things he'd learned from Stewart Butterfield over the years. Not to perform diligence. Not to impress anyone. Because he genuinely wanted that knowledge for his own product thinking. When the team eventually sat down to write Slack's product principles, those notes became the foundation.

For everyone who isn't working for a Stewart Butterfield: Fain's advice is direct. If you don't respect the exec's judgment, quit. If you do respect them, treat their pushback as signal, not obstacle. Her PM on the current team at Webflow does this with a single phrase when he hears something that contradicts his data: "That's so interesting — what led you to believe that?" It disarms, it invites, and it almost always surfaces something genuinely useful.

Ask the CEO what the board is pushing them on — then show exactly how your pitch moves that needle

Incentive misalignment doesn't announce itself. It quietly kills pitches that should have sailed.

Fain goes further than the standard "align to company goals" advice. She recently sat down with Webflow's CEO and asked directly: "Tell me what the board is pushing you on." Everyone has a boss. Even the most confident, decisive executive is under pressure from somewhere, and surfacing that pressure — rather than guessing at it — is what turns a pitch from a favor request into a shared problem.

The questions she pushes PMs toward are more specific than "what's top of mind?" That phrase has become so neutralized by weekly executive writeups that it generates generic answers. Instead: what are you most afraid of messing up right now? What pressures are you facing? What would a failure state look like?

Once you have that, the alignment move is explicit: how does the metric you're trying to move, the OKR you're responsible for, the board pressure you're under get improved by the thing I'm proposing? If you can't answer that, Fain's follow-on question is equally sharp — do you need to change course entirely? Working on something that doesn't shift one of those outcomes or isn't urgent for the business isn't a resourcing problem. It's a direction problem.

One option signals you didn't do the work — the Goldilocks three-option structure proves rigor without burying them in process

Presenting a single recommendation forces a yes/no and leaves the exec wondering what you missed. Fain's team at Webflow learned this the hard way.

They brought a product doc to CPO Rachel Wolan that laid out one option set. It didn't land. Wolan's feedback: "I don't understand how you're thinking about the permutations of possible here." Rather than waiting for the next scheduled review, Fain's team asked for a meeting in two days and turned around a new doc that showed all the options they'd considered but hadn't surfaced — along with why each would or wouldn't serve the outcomes they were driving and the technical complexity behind them. Wolan's response: "Oh yeah, I see why the solution you're proposing makes the most sense."

The framework Fain recommends: three options, with your recommendation clearly labeled as the Goldilocks middle. It's borrowed from classic pricing and packaging strategy, but the logic is the same — it signals analytical depth, creates a collaborative conversation, and preempts the "what did you miss?" objection before it's raised.

At Slack, the team ran a version of this called "Stuart plus two more." After any design review where Stewart Butterfield came back with a specific direction, they'd return with exactly what he asked for — plus two alternatives they felt good about. That created the forum for real debate rather than a rubber stamp in either direction.

Voluntarily killing something does more for your credibility than any pitch you'll ever make

Executives are culturally the only ones expected to kill projects. When a PM does it proactively, the signal it sends is disproportionate to the act.

"One of the biggest things you can do to build trust is kill things, deprioritize things," Fain says. It demonstrates that your incentives are aligned with company outcomes, not just your local team's output. That's a senior signal. It's the difference between being seen as a resource-acquirer and being seen as a strategic peer.

She traces this back to something Lenny has called the CPO mindset — thinking like the person whose job it is to optimize the whole portfolio, not just your slice. Stuart Butterfield has noted that CEOs are often the only ones culturally empowered to kill things across an organization. Fain thinks that's a mistake in how most teams operate. "If we each think of ourselves as owners and contributors to the business, we will bring those opportunities up as well — to both amplify the business or save it from itself."

The practical version: in your next roadmap review, find one thing your team should stop doing and make the case for it before anyone asks. That one act builds more trust than any new pitch in your backlog.

Executives drop breadcrumbs, not mandates — and the best PMs respond within hours

"I wonder if... I'm thinking about... Have you considered?" These are not casual asides. They're invitations — and most people don't take the bait.

At Webflow, Rachel Wolan mentioned in passing to Kev, the head of design, that the team would need to think about design reviews at some point. Within an hour, Kev had a Loom recorded: a framework for high-risk versus low-risk design changes, blast radius analysis, release processes, and a model for letting anyone in the organization ship designs to production. She hadn't asked for it. There was no deadline. He recognized the organizational signal and ran at it.

The failure mode is the inverse. Fain watched Tamar Yehoshua ask four separate times across quarterly reviews to see the top 10 use cases on a particular topic documented. By the fourth time, Yehoshua was visibly frustrated: "We've talked about this so many times before. Why don't we have this?" The ask had been a breadcrumb every time. Nobody pulled on it.

Fain's rule: if you wait a week to follow up on items discussed in a meeting, the exec has moved on and you've missed your window. Her practical system — log any "I wonder if" or "have you considered" comments after every exec interaction, then respond within 24 hours, even if only to say "here's how I'm thinking about this."

AI trained on past product review transcripts is already standard prep at Webflow — and it's simulating your exec's objections before you walk in

A colleague on Webflow's product leadership team trained a custom GPT on transcripts from past product reviews — all publicly available. The expectation is now that PMs run their PRDs and pitches through it before any major review, asking: what will this exec push back on, and where are the weaknesses in this idea?

You can also train it on your own blind spots. Fain's example: if you've gotten consistent feedback that your data is thin or your UX thinking needs depth, feed that history in and ask for targeted critique before you present. Claude is particularly strong here, she notes. And Slackbot can tell you what a given executive has been posting about recently — surfacing their current preoccupations without requiring a direct ask.

The broader implication Fain draws is structural, not tactical. As execution complexity collapses — "everyone can be a builder" — the leverage point shifts from doing the synthesis work to deciding what work actually survives and gets funded past V1. "The act of influence, the act of stakeholder management, the act of learning is the 10x skill." We're entering a golden age of product management, she argues, not of product managers. The function's core capabilities — discovery, user empathy, strategy clarity — become more valuable precisely as everything else becomes cheap.

The bottleneck is shifting from building to deciding what deserves to exist

When anyone can ship a V1 over a weekend, the question of what gets funded through V2, V3, and sustained operation becomes the real game. Strategy clarity isn't a nice-to-have in that world — it's the mechanism that lets empowered teams move at the speed their tools now allow without compounding mistakes.

The PMs who will matter most in this environment aren't the ones who optimize for execution speed. They're the ones who've deliberately invested in the skills that don't get cheaper: reading an organization, surfacing what an executive actually needs, knowing when to kill something, and making the case for what survives.

Influence, it turns out, was always the job. AI just made that impossible to ignore.

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Topics: executive influence, stakeholder management, product management, career growth, AI and product management, communication, presentation skills, organizational dynamics, trust building