Crowdsourcing CTO/VPE learning circles.

February 11, 2020. Filed under management 99

As part of moving into a CTO role, I wanted to take a stab at putting together learning circles for folks in CTO, VP Engineering and Staff+ Engineer roles. This is the sort of thing I’ve done internally within a company before, but most companies only have one CTO or function-leading VP Engineering, so this sort of learning circle needed to happen beyond the scope of a single company.

I’ve been playing around with the idea that you can use a sufficiently-large Twitter community to unlock operating online in the same way that you would within a company, and so I decided to try to put together learning circles over Twitter, much as I would have in a several thousand person company.

This culminated in a tweet, an Airtable form, some notes on running learning circles, eighty-six folks who filled out the form, and three learning circles containing nine folks apiece. One of the circles had its first meeting last week, and the other two are in the process of scheduling. This left about sixty folks without learning groups.

Composing circles

Once I had a bunch of names, I went through and cleaned the location data to make it easier to filter down to appropriate groups. Folks showed a lot of creativity in various fields, but ultimately it was pretty quick, maybe thirty minutes of data cleaning.

Airtable schema for name, etc

Next, I put together some pivots to figure out where we had the most chronological and physical density. There were good numbers near Montgomary St BART and the SF Caltrain station, and a long-tail of other locations in the East Bay, South Bay, and across the US: New York, Boston, etc.

Airtable schema for name, etc

I've always learned the most within diverse groups, so I started with that as a priority, but ran into the classic challenge of the lazy organizer: building strong representation within a community takes real work, and isn't the sort of thing you can accomplish with a Twitter broadcast.

About one in ten of applicants self-identified as women, and after chatting with several folks, I decided that the best way to make the groups useful and safe for those folks was to form two groups with balanced gender representation that they would participate in. With this approach and limited colocation of applicants, I ended up with one well-balanced circle in San Francisco, and the second well-balanced circle over video conferencing. If I had collected additional identification data, I would have extended this approach further.

Other dimensions of building a good group were easier: each group got a good mix of very senior engineeers, folks operating as CTOs, and folks leading large groups within large companies.

Altogether, I was able to spend about two hours and compose three solid groups, and decided to stop there. I could have "finished" by haphazardly grouping the remaining folks into circles of eight, but I don't think that approach would have worked, so it seemed better to pause.

There is a real challenge here around mass-group formation, and I suspect my approach isn't quite right. Maybe a more scalable approach would be having a signup form for folks to join a Google Group or Slack channel, and then a mechanism for folks to self-organize from there.

Group initiation

Once I established the group members, I emailed each of the folks individually with

  1. the proposed time and location for the learning circle,
  2. a short code of conduct I pulled together for the learning circles, and
  3. the initials, company and pronouns of the other folks in their group.

The email ended by asking their permission to add them to a Google group for coordination purposes.

Once folks gave permission, I added them to a group, and we moved to scheduling the initial meeting.

Folks doing similar stuff

There are a bunch of folks out there doing similar things on a more full-time and less ad-hoc basis. Maia Bittner pointed me towards Jordana Stein, who is the CEO of Enrich and doing something quite similar. Likewise, Jerry Li was doing something very similar with SFELC. I’d even say that Plato is doing something similar albeit on a more one-to-one basis.

Doing this well really is a full-time job, so I hope these companies work out.

What’s next?

Given the overhead of running these sorts of programs, and the added friction of doing them externally, my guess is that these sorts of groups will continue to mostly occur informally for groups of folks who already know each other, as well as within the halls of large companies. I do think there will always be a small – but healthy – business run by companies who specialize in fostering these groups, but ultimately I believe groups like this are so prone to dissolving over time that it’ll be a tricky business to scale.

Personally, the learning circle I joined met last week and had a delightful discussion. We'll have our second meeting in early March, and I hope it lasts for six months or so before it fizzles out. Either way, I've already gotten to meet and learn from some great folks.