“How can I learn to be a better manager? I have no idea what I’m doing.”
“I’m a tech lead, and responsible for shipping large projects, but all of my power is informal. How do I get people to listen to me and do what I need them to?”
“As a manager, I don’t feel safe talking to anyone about my work problems. What if it gets passed around as gossip?”
Leadership is such a weird thing. Leadership is something every one of us does more and more of as we get older and more experienced, but mostly you learn leadership lessons from trial and error and failing a lot. Which is too bad when you’re doing something you really care about, for the first time.
(Like starting a company.)
I’ve read books on leadership. I’ve been semi-consensually subjected to management training, I’ve had coaches, I’ve tried therapy and mentors. Most of this has been impressively (and expensively) unhelpful.
There’s only one thing that has reliably accelerated my development as a leader or manager, and that is forming bonds and swapping stories with my peers.
Stories are power tools.
A story is a tool. The more stories you have about how other people have solved a problem like yours, the more tools you have.
People are very complicated puzzles, and the more tools you have the more likely you are to find a tool that works.
Unlike management books which speak in abstractions and generalities, stories are real and specific. When you have the storyteller in front of you, you can drill down and find out more about how the situation was like your own or not, and what they wish they’d done in retrospect.
Details matter. Context matters.
Sometimes all you really need is a sympathetic ear to listen and make murmuring noises of encouragement while you work it out yourself out loud. Sometimes they have grappled with a similar situation and can tell you how it all worked out, what they wish they’d known. Sometimes they will cut you off and tell you to quit feeling sorry for yourself or sabotaging yourself.. if you’re lucky.
Peers?? Why not a ‘mentor’?
No insult meant to anyone who gets a lot out of mentoring, but it isn’t really my bag. I’ve always had.. let’s say issues with authority. Which is a nice way of saying “never met a power structure I didn’t simultaneously want to crush and invert”. So I prefer the framing of “peers” over even the relatively tame hierarchy of the mentor-mentee relationship.
I mean, one-way relationships are fucked up. Lots of my peers are more junior than me and some are more senior, yet somehow we all manage to be givers as well as takers. And if you’re both giving support and receiving it, then what the fuck do you need different roles like mentor and mentee?
I don’t want to be someone’s mentor. I want to be their friend and to sometimes be helpful. I don’t want to be someone’s “mentee” either, that makes me feel like their charity case (ha ha).
But friends and peers? Those just make my life better and awesomer.
From each according to their ability, to each according to their need.
The first year or two of honeycomb, I had a small list of friends who I got dinner or drinks with once a month like clockwork. Most of them were founders or execs or had been at one point, so they knew how depressed I was without needing to say so.
They listened to my stories (even though I was terrible company), and shared plenty of their own. They just kept showing up, reminding me to sleep, asking if they could help, not taking it personally whatever state I was in.
These friendships carried me through some dark times. When Christine’s role required her to level up at leadership skills, I encouraged her to get some peers too. And that’s when I began to realize some of the limitations of the 1×1 model: it’s very time consuming, and doesn’t scale well.
But hey! scaling problems are fun. 😀 I decided to pull together a peer group where people could come together and give and get support all at the same time.
(Actually two groups. One for me, one for Christine, so we could complain about each other in proper peace and privacy.)
Practicing vulnerability, establishing intimacy.
It took some time to assemble the right groups, but then we met weekly for 6 weeks straight, and after that roughly once a month for a year. The six starter weeks were intended to help us practice vulnerability and establish intimacy in a compressed time frame.
Last week was our one-year birthday.
There’s something sterile about management books and leadership material, something that makes it hard for me to emotionally connect my problems to the solutions they preach. I want advice from someone who knows me in all my strengths and weaknesses, who knows what advice I can take and perform authentically and what I can’t. Context matters. Who we are matters.
As word has started to get around about the group, sometimes people ask me about joining or how to form a group of their own. Turns out lots of people are hungry to get better at leadership, and there are precious few resources.
That’s why I decided to write up and publish my notes. Everything I learned along the way about how to run a tech leadership skill swap — the logistics, the facilitation, the homework, the ground rules. Who to invite. Recommended reading lists.
Here it is: https://github.com/charity/tech-leads-skill-share/. 
(It’s a little rough, but I positively cannot spare any more time.)
This shit is hard. You need a posse.
Would you like to run a tech leads skill swap? Please tell me if you do, I would love to know! I’m happy to help you get started with a phone call, if you want.
All I ask is that you try to pull together a posse that’s at least 50% women, queers, and other marginalized folks.
Good luck. ~charity
 I take a pretty expansive view of leadership. For example, an intern might exercise leadership in the vaunted area of database backups — just by volunteering to own backups, reliably performing said backups and serving as a point of coordination and education for how we do backups here at $corp.
If you have expertise and people rely on you for it, this is a legit form of influence and power … in other words, that’s leadership.
 A HUGE thanks to Rachel Chalmers for scribing a first draft of these notes, and to Kris for running the other group and contributing the homework sheet and stories of a related group at twitter.