Treat the Executive as Your Key User
Run stakeholder conversations as discovery interviews, not approval requests.
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 4
- Confidence
- 93%
A mental model that redirects the empathy and curiosity you already use on customers toward the executive you're trying to influence. Instead of walking into a meeting to get a plan approved, you walk in to learn what the exec sees, believes, and is pressured by, then use that to strengthen the plan. Use it whenever you need buy-in from someone more senior.
Origin
Jessica Fain developed this as chief of staff to April Underwood and Tamar Yehoshua at Slack, after watching PMs center their own ideas instead of the executive's world. She frames the exec as 'our key user here' and cites the failure mode of going in 'just looking for approval for your plan.'
Core principles
- 01Product managers' best skills are curiosity and empathy, but they abandon them the moment they talk to an executive.
- 02Influence is increasing the odds your good ideas survive; politics is manipulating outcomes for your own gain.
- 03If you don't respect the person or believe they know something you don't, you should quit, not manage them.
- 04It's not your fault the leader didn't buy in, but it is your problem to solve.
How to run it
- 1
Reframe the goal from approval to learning
Enter the meeting asking 'how can I learn, how can I strengthen this plan' rather than 'how do I get a yes.' Going in just looking for approval is the disastrous default.
Pro tip Treating a review like a rubber stamp is a failure state that executives actively dislike.
Watch out This does NOT mean being a yes-man. You get paid to be a domain expert and have an opinion.
- 2
Apply customer-discovery curiosity to the exec
Direct your user-research instincts at the executive: what are their incentives, what pressure are they under, how has their day been. Treat their perspective as data you're trying to extract.
- 3
Disarm disagreement with a genuine question
When an exec says something that seems wrong, don't argue and don't cave. Ask 'That's so interesting. What led you to believe that?' to surface the experience or board pressure behind the belief.
Pro tip This co-creates with the person who offered the opinion, so the better solution feels jointly owned.
Watch out Execs are trained to seem certain because they make fast decisions with little information; certainty is not the same as being right.
- 4
Respond with your expertise, then converge
Once you understand what's behind their belief, bring your domain data and insight to bear so the two of you reach a better solution together rather than one side winning.
Pro tip Keep a running notebook of things you learn from leaders (as Noah Weiss did with Stewart Butterfield) for genuine growth, not for showing off.
In the wild
A member of Fain's team, on hearing something that flew in the face of his data, would respond 'That's so interesting. What led you to believe that?' instead of dismissing it, then unpack the reasoning before responding with his own expertise.
→ The exchange co-creates a better answer and makes the exec feel they built the product alongside you.
Common mistakes
Centering yourself
Focusing on your own desires, motivations, and slice of the world instead of understanding where the exec is coming from, which hurts both your career and the product.
Dismissing the leader as clueless
Saying 'they just don't get it, they're not in my meetings.' If you truly believe that and don't respect them, the honest move is to leave, not to resent them.
Is it for you?
Best for
ICs and mid-level product leaders who believe great work should speak for itself and keep getting passed over for buy-in.
Not ideal for
Solo founders or sole decision-makers who don't need to convince anyone above them.
From the transcript
“Influence is about increasing the odds that your good ideas survive.”
“That's so interesting. What led you to believe that?”
“it's your fault if the leaders didn't buy into your idea”
“one of the most disastrous things you can do is going into a meeting just looking for approval for your plan”
From the episode
The art of influence: The single most important skill that AI can’t replace
Jessica Fain (Webflow, ex-Slack)