Jessica Fain, a Webflow product leader and former Slack chief of staff, says great products get built through influence, not politics, which manipulates outcomes for personal gain.
Fain says product managers should treat the executive as a key user, asking what drives them and what led them to a belief, and giving context in the first 30 to 60 seconds.
Fain says faster AI-driven decisions mean mistakes compound faster, so influence and learning become the 10X skill as execution gets cheaper.
Influence is the product skill AI will not replace
Influence decides whether good product ideas survive, and Fain argues it becomes more valuable as AI makes building cheaper. Executives decide in fragments between urgent meetings, so a PM who treats them as a key user and speaks to their incentives gets further than one seeking approval. Good ideas still need people to back them.
Takeaways
Influence is how great products get built. Fain says product managers drop the curiosity and empathy they show users once they face executives. An executive's day is a strobe light of urgent meetings, so a PM who prepped for weeks meets a leader who has not thought about it.
Treat the executive as a key user. Rachitsky argues it is the PM's fault when leaders do not buy in, and Fain agrees. Annie Pearl's line that it is not her fault but it is her problem captures the stance. Going in only to seek approval is disastrous.
Influence is not politics. Politics manipulates outcomes for personal gain, while influence raises the odds that good ideas survive. Fain learned from Noah Weiss, who kept a notebook of Stewart Butterfield's lessons, and from Ilan Frank, who brought customer anecdotes into executive discussions.
Tie pitches to executive incentives and metrics. Fain prefers asking what the board is pushing on to asking what is top of mind, which she calls a trope. Metrics should ladder up to company goals. Slack's customer love sprint, two weeks fixing rough edges, shipped 65 improvements.
Shrink the risk and build trust. Fain uses the book Switch to shrink a change, such as a one-week proof of concept that feels small enough to try. She also says killing or deprioritising work builds trust, as does responding quickly to the subtle threads executives leave.
AI makes influence the 10X skill. Fain says product management is entering a golden age, but as execution gets cheaper, influence and learning matter more. Faster decisions make mistakes compound faster. Rachitsky says taste and judgment stay human, and Fain says distribution is everything, pointing to Gemini.
Agents need onboarding like colleagues. Fain says everyone is now a director of work managing agents and must decide where to stay involved. Agents need onboarding in a team's product philosophy. Rachitsky notes Codex and Claude Code are good at generating ideas for what to build.
Meeting playbook for executives
Give context in the first 30 to 60 seconds, since a longer opening loses the executive.
Show the options considered. A product review with Rachel Wolan went badly until a new doc laid them all out. Teams can keep the full 15 in an appendix.
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On this episode 2
Show 1
Ask executives how they like to receive information. Rachitsky cites Barbara Minto's approach of leading with the recommendation, but Fain says preferences differ.
Run the PRD or pitch through GPT to anticipate pushback, as Webflow expects of its product managers.
Ask Slackbot what a leader has been posting about lately to learn what they think matters most.