Scheduling by Deference
The one asking does the work: let the busier person set the time, and give real options.
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 3
- Confidence
- 88%
A rule set for respectful scheduling that inverts the default 'here's my Calendarly' behavior. The core principle is that the less senior or less busy party absorbs the friction, and anyone who reschedules owes even more accommodation. Use it whenever you're requesting time from someone more senior or busier than you.
Origin
Lessin, famously an anti-Calendarly crusader (he claims his rant drove a meaningful chunk of Calendly's monthly growth), lays out how to schedule without offloading work onto the more important person.
Core principles
- 01If you're asking for something, you do the work.
- 02If you're less senior or less busy, let the other person say when they're free and make it work on your end.
- 03Calendarly should not be the default; if you use a scheduler, it must offer real options.
- 04Whoever reschedules must, within reason, make it work for the other person.
- 05Extend deep, extra respect to EAs and PAs; disrespecting them reads as extremely classless.
How to run it
- 1
Let the busier party set the time
Recognize the power/busyness hierarchy. If you're the junior or less busy person, ask when the other person is free and then bend your own schedule to fit, rather than sending a link.
Pro tip You can still offer your Calendarly as a fallback in parentheses ('here's my link in case it's easier'), as long as the default is you doing the work.
Watch out Don't make the more important person do the work of fitting into your grid.
- 2
Give real options, not a wall
If you must use a scheduling tool, ensure it presents genuine, workable times, not a facade. One of the first three offered slots really needs to work, and double-check time zones and pick humane hours.
Pro tip It's worth an extra check on time zones; scheduling someone into 4am their time is a classic disrespect.
- 3
Over-accommodate on reschedules and respect the staff
When you reschedule, give as much notice as possible and become even more accepting of whatever the other side can do. Throughout, thank and follow up with the EAs/PAs who make it happen.
Watch out Don't overdo the gatekeeper courting either; showing up with flowers for the EA becomes too transactional unless you're very confident in what you're doing.
In the wild
When selling their company to Airbnb, the banker helping them made a point of building a good relationship with Airbnb's EA and office manager, on the logic that if they like you, it helps the deal.
→ Cultivating the support staff smoothed the path toward getting the deal done.
Common mistakes
Defaulting to 'here's my Calendarly'
Sending a link to a more senior person offloads your work onto them and reads as disrespectful of the hierarchy.
Disrespecting EAs and PAs
Treating the people who help someone as unimportant is, per Lessin, the number-one way to look extremely classless.
Is it for you?
Best for
Founders and junior operators requesting meetings from busier, more senior people and their assistants.
Not ideal for
Flat peer relationships where rigidly deferring on time slots just adds friction; and Lessin concedes very senior people's calendars legitimately move more.
From the transcript
“I really strongly believe the default should not be calendarly.”
“you're asking for something, you do the work is the upshot”
From the episode
How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook
Sam Lessin