On Safe Spaces (in One-on-Ones)

I’m spending more time on Twitter these days (I know, *gasp*) and I had a bit of a tweetstorm (not really) about the power and importance of 1-on-1’s in an organization:

1/ as a startup founder / CEO, my most IMPORTANT meetings are my 1-on-1’s.

it’s an opp to hear what’s REALLY going on in my organization… and not just the what but also how folks FEEL about it all.

it’s the most challenging, rewarding, and hope-filled moments of the week.

2/ and some of the ABSOLUTE best moments are when a new-ish employee FINALLY pushes back or surfaces something that ultimately challenges me in a serious way.

for instance:

them: hey, you’ve been working more than 40 hours this week… what’s up with that?

me: … fuck.

love it!

3/ my singular goal for 1-on-1’s is to create a SAFE / TRUSTED space for my staff to talk about #thereallyreal — the hard truths about our work and our struggle to make it all make some sort of sense. vulnerability is never easy nor fun. but, it’s necessary for growth.

4/

i describe some of our process here in our #opensource #handbook 1-on-1’s start the first week of an employee’s time in my co… and it’s an uncompromisable part of our culture.

if you don’t think these are important than you’ll never work for me.


Creating a safe place for conversation is hard. It’s difficult because it requires an incredible amount of self-control to just sit there and listen — the majority of the time.

Being comfortable with awkward silences is a useful skill if you have it (and if you don’t, then, you’ll have to practice.

Remember: It’s good to disagree. People are not software. And building trust takes time (and small deposits).

Don’t give up too early.