So you want to start a tech leaders study group

Mazel tov! We did this in August of 2017. It was a great experience, and helped a lot of us brainstorm, problem-solve and level up in our careers. A lot of work went into making it the great experience it was. This document is designed to help you bootstrap a group of your own.

Mission statement

Leadership is not a spot on the org chart, or a role someone can assign you, or a set of facts you can memorize. Leadership is a muscle that every one of us has to exercise. It helps to have a set of peers you can be radically vulnerable with, who you can swap stories and experiences with and hold each other accountable.

The goal of this is not group therapy or support -- though there may be plenty of both -- the goal is to get better at our jobs by learning and practicing leadership skills in tech.

Checklist

So you want to start a tech leads group. Here is your list of things to consider, prepare, or do.

Invitations: Curate a well-balanced group of 6-10 interested people, with varying skill levels, roles, and diverse backgrounds.
Logistics: Set a start date/time and decide on a venue. Identify at least one facilitator. Create a mailing list or Facebook group for discussion, also make a recurring calendar invite.
Preparation: Establish the ground rules and code of conduct. Distribute the recurring homework assignment. Make sure everyone can commit to attending at least 4 of the 6 weeks. Ask everyone to write down an intention: how do they hope to level up in their career via this group?
Week 1: intros. And a facilitated discussion about areas of focus.
Week 2-6: for the next four weeks, send out the weekly theme on Thursday before the meeting. If needed, experiment with checkins or other pairwise social exercises to accelerate comfort level and progress on goals.
Last Week: wrap up. Take the pulse of the group: do they want to keep going? Discuss frequency and invite policy.

Invites

There are lots of things to keep in mind when choosing members. Some of these considerations will conflict with others; it is always a judgment call. The character of your group will be defined by who you gather, so this is perhaps the most important step of all. Here is a copy of the invitation email I sent out, which you are welcome to copy and modify.

You are curating a group, not inviting your best buds.
Our sweet spot was around eight people (we invited 10 to participate, had 6-9 in attendance each week). Less than five is not a good discussion. More than 9 and there isn't enough time for everyone to participate. If you ever have 10 show up, consider splitting into two random subgroups.
Confidentiality and high trustworthiness is absolutely critical. Gossip leaking to third parties would’ve killed our fragile vibe stone dead. We were explicit: if you leak, you get kicked out.
Don't invite people who work together.
Good to have: broad representation across race, age, orientation, gender, seniority, role. This contributed hugely to the richness of our discussions
If you want the flavor of your group to be for tech leaders, consider making your lower bound something like "senior engineer/tech lead".
I find mixed gender groups much more functional than all-women or all-men groups. But try balancing your group so that straight white dudes are a minority. (It's really good for them!)
What we could’ve done better: less-connected members took a while to figure out existing relationships. We should’ve started first meeting with introducing our connection to the group, eg: “I’m X, I’m here because Charity met me while standing in line for ice cream and convinced me to start my own aerospace company”

Logistics

We met from 4-5:30pm on Sunday afternoons at my home. A fair amount of thought went into this:
- The setting seemed to encourage more intimacy than an office setting,
- it did not take up a full weekend evening,
- we didn't have to try and muster up our most relaxed, vulnerable selves at the end of a long work day, and
- it let out before Game of Thrones started at 6.
We initially met for six consecutive weeks, and required everyone to commit to at least four of them. This was to create vulnerability and trust and get to know each other better as quickly as possible.
Have a facilitator.
- I started out reluctant to explicitly facilitate, but found it went much better with a firmer hand on the wheel.

Preparation

Homework: using the below diagram, we discussed where we were at in three broad areas: work, family and self. This turned out to be such an enormously effective icebreaker and meeting opener, we’re keeping it as we move to informal meetings.
Send around the reading list and resources (see bottom), and your code of conduct.
Ask people to get there a few minutes early. It's really disruptive to have people arrive late.
Your facilitator should prep an outline of the 90 minutes, and keep everyone roughly on time.
Ask everyone to write down an intention for the next 6 weeks. How do you want to level up in your career?
Share the ground rules:
- Put your phone away (exceptions made for on call or babysitters)
- Be fully present
- Do your homework before you get there. Set aside some time to reflect, don't scribble it in haste.
- Show up early: we start on time
- You will be kicked out for repeating anything shared in confidence
- Use nonviolent communication ("I feel ...")
- Dig deep. Listen hard. Don't dominate the conversation. This is not a social club, let's make the time meaningful and valuable.
No booze. (at least that's how we preferred it)

Week 1

Sample agenda:
- 5 min, Facilitator kicks off by welcoming everyone, acknowledging that this is gonna feel hella awkward for the first week or two, talks about the point of the group: this is not therapy, this is because we all want to level up at our careers and support each other in leveling up too.
- 20-25 min, Go around the room in a circle doing introductions (~2-3 min/person, allow time for some detail. explain how you are connected to the organizer(s).)
- 30-45 min, Go around the room (or have facilitator call on folks at random, ~4-5 min/person and have them share two of the 6 homework answers they wrote down. Whichever two are calling out to them the most. Give any other useful context about how this relates to what's going on in your life right now and why you are here. Then share your intention -- what do you hope to get out of the next 6 weeks? How do you hope to level up in your life and/or career? What surprises are you most open to?
- 10-15 min, Gather topics and themes. What in particular is this group interested in learning about, or what are they particularly equipped to teach on? Take notes, facilitator, and coalesce into four topic areas for the next 4 weeks.
  - Note: the most successful topics were very personal (e.g. "coping strategies and self-care" we could have done four weeks on that!). the least successful topics were impersonal (e.g. "how to run a meeting")

Week 2-6

Send out the topic on Thursday before the Sunday meeting.
Encourage everyone to keep it in the back of their minds and jot down any useful stories that come to mind, any questions, any challenges they have now or in the past that relate even loosely to the theme.
Facilitator should come up with a loose outline beforehand and keep the meeting on track for 90 minutes total. Can't make anyone late for game of thrones.
Sample agenda 1:
- 10 min, homework circle
- 70 min, facilitated discussion
- 10 min, closing and wrap-up
Sample agenda 2:
- 10 min, homework circle
- 10 min, gather scenarios for role play
- 30 min, role play in pairs
- 40 min, discuss and re-enact, give and get feedback
Sample agenda 3:
- 15 min, homework circle
- 45 min, split into two smaller groups to workshop different questions
- 30 min, come back together and discuss findings (15 min each)
Topics that came up for us
- Engineering management, including interviewing
- Running and facilitating meetings
- How to run technical projects with delegation, playing to strengths, etc
- Founder trauma
- Coping strategies/self care
- Recruiting
- Assertiveness
Exercises we tried
- Homework: using the below diagram, we discussed where we were at in three broad areas: work, family and self. This turned out to be such an enormously effective icebreaker and meeting opener, we’re keeping it as we move to informal meetings.
- Role playing: we workshopped interviews by role-playing difficult candidates. Always a stimulating experience
- Asking peers about coping strategies: a lot of times, family and friends saw things very differently
- Accountability buddies: we paired off to work on specific personal challenges, and checked in with one another mid-week. A lot of us got huge tasks accomplished by virtue of this
- At the last meeting, our homework included extra questions: What did I learn? Where do I want to be in a year?
Mid-week checkins?
- How are things feeling after week 2? getting less awkward? Ours still felt spotty, so we decided to randomly pair up and get together once during the week for tea or a cocktail. This was really instrumental in helping the less-connected people feel closer to the group.
- We also experimented with accountability buddies. After the self-care session, each of us set an intention to improve one unit of self-care. We checked in with our buddy throughout the week to see if having someone check in affected our ability to meet our commitments.

Last week

Leave at least the last 30 minutes to discuss what impact the group has had on each person (~4-5 minutes apiece).
At the end, discuss whether the group wants to keep going or not, keep requiring homework or not (some folks adopted it as a personal habit after this), or wants the group email list/FB group to live on instead of in-person meetings, etc. Our group opted to keep going but less frequently; we have settled into a rhythm of around monthly, and the list gets occasionally used for questions.
Someone please let me know how it went for you!

In conclusion

What worked

Candor, honesty, presence. Getting offline/silencing phones. Respect for the space. Meeting in a member’s home contributed to this, as did Charity’s care in selecting group members who would engage in this way
Sharing perspectives across very different experience sets
Asking questions rather than giving advice
Giving each other the benefit of the doubt and assuming good faith
Bringing home-cooked snacks

Where we faced significant challenges

Scheduling - everyone’s calendars were a nightmare, and one meeting fizzled because only 2-3 people showed up
Less technical people felt a little self-conscious
Less connected-with-the-group people felt very self-conscious, and we could have done a much better job of including them from the outset

Resources

”The Artist’s Way”, by Julia Cameron
Headspace app
"The Hard Thing About Hard Things", by Ben Horowitz
"The Manager's Path", by Camille Fournier
"First, Break All The Rules", by Marcus Buckingham
"Radical Candor", by Kim Scott
TED talk or "The Checklist Manifesto", by Atul Gawande
Forum, a peer group developed at Twitter