Ask HN: Engineering managers, how do you “upskill” your team?

I usually stick with this approach:

* Two sit-downs anually with each team member to figure out long term and short term goals.

* Fridays are for fun, almost as mini-hackathons, if the calendar allows for it; use it to get rid of technical debt, try something new etc.

* 3-4 hackathons, each 3 days long, each year.

* Conference budget per team member of their choice. Should allow for at least one conference anywhere in the world per year.

* Don't micro-manage; engineers are best when they are allowed a lot of freedom.

* Work from anywhere, anytime, but try to keep a core schedule from 9 to 15.

I liked to do an "Eng Weekly" meet where we took a deeper dive on some technical thing. Might involve someone doing some research and showing off something they learned, or doing a deep dive on some tech we used or looking at data structures or design patterns in our code base that could be improved in some non-obvious way.

Anything was fair game as long as it was technical and interesting. My main goal was to level-up the team a bit, show them how fun actually building stuff was vs adding a dependency of some 3rd party service or library, and have some fun just nerding out a bit on what other stuff was going on in OSS or the community at large.

Start by creating a career ladder for the main roles in your org. Do periodic evaluations of where each person each. Have them do a self evaluation. See where the evaluations are alike and where they differ. Decide what skills the person would like to focus on either to more fully show up at their level, or work toward the next level. Make a plan of action to improve those s skills. The person drives the initiatives, and you monitor, enable, and motivate them via regular checkins.

If you would like to chat about this, DM me — see profile.

At Promyze, we have an engineering team of 6. We hold a 1-hour, bi-weekly meeting to share and review key learnings and best practices. We dogfood our own tool to log those best coding practices and get suggestions in the IDE.