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Killing your own initiatives loudly is the highest-trust move with executives

By Jessica Fain · VP Product, Webflow; ex-Brightwheel; ex-chief of staff at Slack · 2026-04-28 · podcast · How to influence executives (and why it's not politics)

Tier A · TL;DR
Killing your own initiatives loudly is the highest-trust move with executives

Claim

The single highest-leverage trust-building move with executives is killing or de-prioritising your own initiatives publicly when they underperform. Most operators pitch wins-only stories; an operator who shows what they killed and why signals that they share the executive's incentive — to spend the org's time on what actually works.

Mechanism

Wins-only narratives raise executive suspicion: nothing the team tries ever fails? Either the bar is too low or the operator is hiding the misses. A loudly-killed initiative converts the operator's credibility from "promoter" to "steward." It also gives the executive concrete evidence that the operator's bar is high and that the next bet is not theatre. Trust compounds — the next pitch lands because the prior kill earned the runway.

Conditions

Holds when:

Fails when:

Evidence

"One of the biggest things you can do to build trust is kill things, deprioritize things. That is a very, very senior way of thinking, and it shows that you have the same aligned incentives as the executive."

— Jessica Fain on Lenny's Podcast, 2026-04-28

Signals

Counter-evidence

In some cultures (especially boards under pressure or politically anxious orgs), visible kills are read as failure. The operator pays a credibility cost rather than gaining one. The discipline is conditional on executive culture.

Cross-references

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