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Lenny's Knowledge Sketch

Silicon Valley's
Missing Etiquette

Sam Lessin
Partner, Slow Ventures; former VP Product, Facebook
JAN 15 2026
The Frame

Show Up in the Room
With a Low Heart Rate

CALMGIVETRUST
"Etiquette is a skill for how to show up in a room with a low heart rate."
  • Come in with a mindset not of scarcity but of abundance
  • Give more than you take, build a relationship, not collect business cards
  • If you show up like a little energizer bunny, you're going to scare one off
  • This is not your one shot, this is not the entire story
Framework

Entering the Room

EARLYGIVETRUST
  • Be early, but not half an hour early, just enough to take a beat
  • Strong handshake, firm, don't crush the person's hand
  • Repeat names back: "Hey, Lenny, it's great to meet you"
  • If you're with your partner, introduce them first
Sam's rule"What matters in some ways is the signaling of the effort as much as the actual thing."
Situation Rules

Dress, Dining, Meetings

  • Dress: Dress one level up, not two, not three. Fit is everything, a well-fitting $20 shirt beats a misfitting $500 one.
  • Dining: Don't order the most expensive thing on the menu. Don't order first, let someone else set the tone.
  • Tipping: 20% feels like the minimum. You don't want your tip to be memorable.
  • Meetings: Be 10 to 15 minutes early. Camera on for video calls, and close your closet.
Etiquette gets out of the way

"The point about etiquette is that it gets out of the way. It shouldn't be memorable."

What throws it off

Racing in late with a high heart rate. The energizer bunny who scares people off. Overdressing or underdressing so far that the room notices.

Playbook

The Everyday Rules

  • If you're the less senior person, let the other person tell you when they're free and make it work on your end
  • Owe at least a quick acknowledgement to any email you receive. Keep it short and to the point, no emojis
  • Respect EAs and PAs. Say thank you, follow up with them, treat them as part of the team
  • Stand up when people leave the table. Send thank-you notes after meetings, short, not ridiculous
Sam's TL;DR"The goal of all etiquette is essentially building trust and projecting genuine confidence. Always maintain an abundance mindset. Keep your heart rate low."
Contrarian

SV Social Myths

✗Show up like an energizer bunny to signal driveINSTEAD →✓ Show up with the calm of abundance. It's not your one shot, you'll have other opportunities.
✗Skip the small talk, get right to businessINSTEAD →✓ Start with weather or "how was your weekend?" It cuts the air, then you flip into business.
✗Send a Calendly link when someone senior wants to meetINSTEAD →✓ You're asking for something, you do the work. Let them tell you when they're free.
✗Ask lots of questions to seem interestedINSTEAD →✓ A conversation is ping pong, not the inquisition. Give as much as you get.
Based on Sam Lessin's episode on Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTubeFollow @lessin on X
GO DEEPER IN THE EPISODE
04:18 The role of etiquette in business success09:30 Introductions and entering a room16:20 Engaging conversations and building relationships23:55 Hygiene and dress code essentials33:42 Dining etiquette37:15 Tipping etiquette41:36 The “B&D trick”43:05 Humor in social settings45:18 Self-deprecating humor47:42 Winding down conversations49:20 Scheduling etiquette55:23 Communication and email etiquette01:02:28 Meeting etiquette tips01:04:03 Virtual meeting best practices01:05:15 The importance of cleaning up after yourself01:05:58 Exiting and follow-up etiquette01:07:24 Final thoughts01:09:20 AI corner01:11:13 Contrarian corner01:16:25 Lightning round
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