Jessica Fain, product leader at Webflow and ex-chief of staff to two Slack CPOs, argues that influence is the single highest-leverage skill for product managers — and that AI is only making it more important, not less. Most PMs do amazing work and then quietly run into a wall: their best ideas die on the vine. Fain's diagnosis is uncomfortable. When leaders don't buy in, the PM blames the leader. The right framing, borrowed from her first manager Annie Pearl, is: "It's not my fault, but it is my problem."
Her central observation from years sitting next to executives: PMs apply curiosity and empathy to their users, then forget those exact skills the moment they walk into an exec review. Instead of researching their executive, they show up centered on their own slide deck. Fain wants PMs to treat execs the way they treat users — with research. Ask the exec's chief of staff what's been on their plate. Ask the exec directly: "Tell me what the board is pushing you on." Skip the "what's top of mind" question, which surfaces nothing real.
She also reframes how exec calendars feel from the other side. A PM has been prepping for the product review for six weeks; the exec has been in a strobe light of finance, legal, hiring, and people problems and hasn't thought about the PM since. The single highest-leverage move is taking 30 seconds at the top to reset: why are we here, why does it matter to you, what happened last time.
The most counterintuitive lesson is on building trust: PMs build it by killing things, not by asking for more resources. Deprioritizing your own project signals you share the executive's incentives — company outcome, user outcome — not just your own headcount. That, Fain says, is what a CPO mindset looks like at any level.