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Sam Lessin: recommendation

15 Jan 2026 Lenny's Podcast How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin

“If you're the less senior person, if you are the less busy person, you should let the other person tell you when they're free and then make it work on your end, is what I would say.”

— Sam Lessin

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Speaker
Sam Lessin
Attribution
Verified speaker
Claim type
recommendation
Recorded
15 Jan 2026
Publisher
Lenny's Podcast

Transcript context

…Wow. No bad press. No bad press and no bad tweets. Yeah. So I think, look, there's a few obvious ones. Make sure you have availability. If you ask someone to schedule with you, it's not always wrong to be like, "Here's my availability or here's a link." But make it real. You have to give them real options. I really strongly believe the default should not be Calendly. The default in most situations, especially if you recognize the power hierarchy or the busyness hierarchy. If you're the less senior person, if you are the less busy person, you should let the other person tell you when they're free and then make it work on your end, is what I would say. And it's fine if the first thought doesn't work, but one of the first three really needs to. So I think that in some ways that it's important to respect that. It's better to ask what they can do and then move your schedule. If you really can't and you're going to use a scheduling agent or something, it just needs to actually have real options is basically, I think that comes up all the time. Look, rescheduling happens when you do it, give notice as much as possible. Once you're asking for rescheduling, you need to be even more accepting of what the other person can do, I think is really important. If you're asking to reschedule, you basically within reason need to make it work for them, is what I would say. And then look, I think there's obvious stuff that people should know and sometimes forget. Time zones are really tricky. People screw them up all the time. Check. It's worth the extra check to make sure you're not both scheduling, you're getting the numbers right, but then also really importantly, scheduling at reasonable times. Sometimes people are like, "I want to meet at this time." You're on EST, you're aware, that's like 4:00 in the morning for me. And so I think being respectful of that and just asking, I think is super important. It's not rocket science because it's important. Last point I make, which we make in the book is you really need to respect EAs and PAs and the whole people. The number one way to look extremely classless is to not respect people who are helping the other person. This is the number one thing. Now you don't need to be so over the top exuberant. You don't want to overdo it, but there should be this deep well of respect for anyone who's helping you, whether that's a server or a PA or an EA or whatever. This needs to come with an extra gesture of respect. That means saying thank you when they schedule and follow up with them and things like that. I'll tell a story when we were selling our company to Airbnb, we had this guy helping us sell the company and he made it a big point to build a good relationship with the EA and office manager at Airbnb because if they like you, it helps. It helps you get the thing.…

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