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Understanding the Executive Calendar: A PM's Guide to Influence
Understanding the Executive Calendar: A PM's Guide to Influence
 ### Lenny Rachitsky@lennysan
People don't understand executive calendars.
I describe an executive's calendar as like a strobe light going off.
You wake up at 8AM, you've already got a huge list of urgent things going on.
You go from a meeting with finance on a budget, to an interview for another executive, to a people problem, to a legal problem, to a product review.
And the product manager coming to that product review, who's trying to make a pitch thinks I've been prepping for this meeting for two weeks.
But the executive coming into that session hasn't thought about you since.Show More
01:03
#### Lenny Rachitsky
@lennysan · 1d ago
Jessica Fain's best product ideas kept dying, and she couldn't figure out why.
So at eight and a half months pregnant, she pitched @SlackHQ's CPO @aunder on becoming her Chief of Staff. She wanted to see how executive decisions actually get made from the inside.
What she learned changed everything she knew about influencing execs.
People don't realize that an executive's calendar is like a strobe light going off. Budget meeting, a people problem, a legal issue—then your product review. You've been prepping for three weeks. They haven't thought about you since the last meeting. They may not have gone to the bathroom today.
And most people walk into that meeting chasing a quick yes.
Instead, she learned to treat execs like she treats her users—with the same curiosity and empathy.
Jessica has since led product teams at @SlackHQ, @Box, @brightwheel, and now @Webflow.
In our very tactical conversation, she shares:
🔸 The 60-second meeting opener most PMs skip
🔸 Why "that's so interesting, what led you to believe that?" can help you disarm an exec
🔸 How to align your pitch with what your exec is actually scared about
🔸 "Stewart plus two more"—her playbook for responding to a CEO's feedback
🔸 Why killing your own project is the ultimate trust-building move
Listen nyoutu.be/RP4vJeIb7WUiOEige Show More
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Mar 23, 2026, 7:07 PM View on X
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23.2K Views  Lenny Rachitsky @lennysan
One Sentence Summary
Lenny Rachitsky shares a mental model for navigating executive calendars, emphasizing the need for empathy and context when pitching product ideas.
Summary
This tweet offers a candid look at the chaotic reality of an executive's schedule, describing it as a 'strobe light' of disparate, high-pressure tasks. It highlights the disconnect between a product manager's weeks of preparation and an executive's lack of context. The content serves as a teaser for a podcast episode featuring Jessica Fain, which provides tactical advice on how to effectively influence executives by treating them with the same curiosity and empathy as users.
AI Score
86
Influence Score 22
Published At Today
Language
English
Tags
Product Management
Career Advice
Executive Influence
Podcast
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