Anchor the Pitch to the Exec's Incentives
Find the metric, OKR, or board pressure they own, then show how your idea moves it.
- Difficulty
- Moderate
- Time to result
- ~weeks to results
- Steps
- 4
- Confidence
- 90%
A method for making your proposal irresistible by tying it to what the executive is measured and pressured on. You first uncover their real success criteria (often via spicier questions than 'what's top of mind'), then explicitly connect your pitch, and even your routine roadmap and metrics, to that success. Use it whenever your and the exec's incentives should already align.
Origin
As Slack chief of staff, Fain saw almost no one ask what mattered most to the CPO before a review. She argues execs 'want to be successful, too' and that you should model your world to amplify their success, illustrated by asking her CEO 'Tell me what the board is pushing you on.'
Core principles
- 01Execs want to be good at their jobs; help them hit their metric, OKR, or board pressure and you both win.
- 02If your team's incentives don't align with the exec's, you're in misalignment from the start and should have that conversation.
- 03'What's top of mind' has become a neutralized trope; ask sharper questions to get the emotion and drive underneath.
- 04Alignment must ladder up: leading indicators your team can move should provably connect to the lagging business outcomes the exec owns (a theory of change).
How to run it
- 1
Extract real success criteria with spicier questions
Instead of 'what's top of mind,' ask 'what's the most urgent priority you're scared about messing up' or 'tell me what the board is pushing you on' to reach the emotion behind the priorities.
Pro tip Also ask the people around them (EA, chief of staff, peers who've pitched successfully) what the exec is worried about and what worked before.
Watch out Fain is 'not a big fan of the what's top of mind for you question'; it has lost its firepower.
- 2
Name the alignment explicitly
Spell out how the metric they're trying to move, the OKR they own, or the board pressure they're under is improved by what you're proposing, and how you get there together.
- 3
Embed the incentive into the whole roadmap
Go beyond the single pitch: understand how the OKRs and positioning came to be and inculcate that incentive structure into your team's culture and everyday priorities.
- 4
Make your metrics ladder up
Choose team metrics that provably connect (as leading indicators or a theory of change) to the lagging business outcomes the exec is accountable for, and get the exec to agree to that chain.
Watch out Your team often can't directly move enterprise revenue or conversion, so you must show the causal ladder from what you can move to what they own.
In the wild
Hearing leadership believed Slack had lost its product-craft mojo ('painting the insides of the cabinets'), Fain's core team paused engineering for two weeks; engineers picked what to fix, the only rule was you had to ship something good for users, capped by a fun exec-judged competition.
→ They shipped 65 improvements in the sprint, which mapped directly to what execs believed differentiated Slack in the market.
Common mistakes
Pitching in a vacuum
Proposing an idea without connecting it to conversion, enterprise growth, brand, or whatever outcome the exec is actually accountable for.
Leaning on the tired 'top of mind' question
Asking a generic question that returns a neutralized, uninteresting answer instead of the real fear or drive.
Is it for you?
Best for
Product leaders whose good ideas keep dying because they aren't visibly tied to what leadership is measured on.
Not ideal for
Situations where your team's incentives genuinely don't align with the exec's, which is a different (misalignment) conversation to have first.
From the transcript
“How is the metric that they're trying to move? The OKR they're responsible for the board pressure that they're under going to be improved by…”
“Tell me what the board is pushing you on because everyone's got a boss”
“excepts want to be successful, too. They want to be good at their jobs”
From the episode
The art of influence: The single most important skill that AI can’t replace
Jessica Fain (Webflow, ex-Slack)