Like caveats? Try writing about leading teams!

It’s tricky to write about leading software teams. Herein, reflections, not complaints, on pursuing higher software leadership truths. Many of which are riffs on 4 Reasons Writing About Software is Hard:

Writing is actually an incredibly relevant skill for engineering leadership (and engineering in general), but it’s still hard. You can have all the insights in the world, and still struggle to convey your message or find the right audience.

First off, writing is hard so writing about software is hard too. Developing our thoughts beyond “that sounded nice in the shower” is hard but rewarding work.

It’s difficult to translate “this worked” out of the system of people, circumstances, and goals. As noted above, at one scale everything works, at another basically nothing works.

No advice on software development is universal. From the smallest coding details to how we structure our multi-person/week projects, there are no best practices. There’s only “this worked/failed for us when building this particular project”.

Writing about software leadership ends up being a lot of describing the people and scenarios that led to a successful approach. The trick is that getting down to particulars about people and scenarios is either too personal to share on the internet or too specific/proprietary to make sense outside a specific organization. It’s hard to write high-quality leadership ideas without drowning in setup, hedging, or over-generic characters.

It’s tempting but insufficient to suggest “act as a good person would and most things will work out”. Merely acting as a good person does will not get me out of situations where individual best intentions created bad outcomes. Perhaps specifying what a good person does with enough clarity that another person can apply and/or emulate it is a laudable step.

In practice, it seems better to say “act as a good person 95% of the time but do the minimally jerk-y thing 5% of the time to cut Gordian knots created by good intention”. I’m not happy with that trade-off, but it does seem like a necessary part of leading people. I build context so I can trade accumulated trust for impact when the situation requires it. (Hopefully! I often don’t know if I was spending from a surplus or deficit of trust until much later.)