The art of influence: The single most important skill left that AI can't replace

Source
executive-influencestakeholder-managementproduct-leadershipcareer-growthdecision-makingtrust-buildingai-product-management

Summary

Jessica Fain (product leader at Webflow, ex-Slack/Box) breaks down exactly how to influence executives - not through politics, but by treating stakeholders like users you need to deeply understand. The core argument: as AI commoditises execution, the ability to decide what to build and get organisational buy-in becomes the single highest-leverage skill. She provides a repeatable framework built from her time as chief of staff to Slack’s CPOs.

Key Insight

Executives are context-starved, not disagreeable. The #1 mistake is assuming execs have been thinking about your problem since the last meeting. Their calendar is a “strobe light” of unrelated crises. They haven’t gone to the bathroom, let alone reviewed your doc. The 30-second reset at the top of every meeting (why we’re here, where we left off, what we need today) is not optional - it’s the difference between engagement and a glazed-over phone check.

Influence is user research, applied to stakeholders. Stop asking “what’s top of mind?” (it’s become a dead phrase). Instead: “What is the board pushing you on?” / “What are you most scared of messing up?” / “What pressures are you facing right now?” These extract the real constraints that shape their decisions.

Tactical framework for pitching:

  1. Align with their incentive structure first. Find out how they’re measured, what success looks like for them. Map your pitch to their OKRs before presenting it. If you can’t connect your idea to their goals, either rethink the idea or rethink the timing.
  2. Lead with the recommendation, not the process (Minto Pyramid). Put all the research/evidence in an appendix. The baseline expectation is that you did your homework - proving it bores them.
  3. Show options, not a single plan. “Stuart plus two more” - present what was asked for, plus two alternatives. This pre-empts “did you consider X?” and creates a real discussion instead of a rubber-stamp meeting.
  4. Ask “How strongly do you feel about this?” Execs toss out ideas at high speed. Some are mandates, some are shower thoughts. If you don’t ask, you’ll either ignore something critical or derail your roadmap chasing a throwaway comment.
  5. Follow the breadcrumbs fast. When an exec drops a subtle hint (“I wonder if we should look at…”), the best people respond within hours, not weeks. By next week the exec has moved on and your window is closed.
  6. Kill things to build trust. Deprioritising your own work signals you think like a CPO. It’s the strongest trust-building move because it proves aligned incentives.
  7. Shrink the change. Big scary bets don’t get funded. One-week experiments do. Once you have signal, you earn the right to ask for the real investment.
  8. Use AI to simulate the exec. Train a GPT on transcripts from past reviews. Run your PRD through it to predict pushback before the meeting. One Webflow team does this as standard practice.

On AI and the future of PM: Execution complexity is plummeting. Everyone can build a V1 now. The scarce skills are: (1) deciding what to build, (2) judging if it’s good enough, (3) distribution. Strategy clarity becomes 10x more important because once you have it, you can fire off agents to build. PRDs aren’t dead - they’re more critical than ever as the anchor that keeps fast-moving teams aligned.

Career growth insight: The path to senior/exec PM is broadening your context beyond your feature. Think about the whole business. Talk about company metrics, not just your KR. The people who get promoted are the ones who show “product citizenship” - connecting dots across the organisation, not just shipping their backlog.