Treating Engineering Teams Like Adults, Part 2 with Jacob Kaplan-Moss

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On today’s episode of Scaling Software Teams, we’re airing part two of our interview with veteran software leader and co-creator of the python web framework, Django, Jacob Kaplan-Moss.

In part one of our conversation, we discussed how Jacob helps rapid-growth software companies navigate change using the Satir Change Model, and how prioritizing the emotional well-being of contributors is the key to weathering whatever storm comes your way. [Listen to part one here]

Today’s interview touches on two things that every startup leader should be thinking about as they grow their team: how to craft company policies that are equitable and accessible to all, and how to document those policies so they have an equitable impact.

You can listen to the full episode here

Here are a few of the key lessons we picked up from Jacob:

Manager READMEs Can Be Valuable, But It Takes Work

Late last year, tech management leader Camille Fournier wrote a piece about why Manager READMEs are an ineffective means of communicating a leader’s needs to their team..

It’s the perfect jumping off point for our discussion with Jacob, who believes that while Manager READMEs can be more useful than Fournier gives them credit for… they are effective only so long as the manager works to ensure that they’re a clear, self-aware articulation of written and established policies.

If your Manager README is a self-serving document used to bludgeon your team, or justify bad work habits of your own, however, you’re not doing your job as a manager.

“It’s one thing to say ‘this is how I work.’ It’s another to use [a README] as an excuse not to not do your job,” Jacob tells us. “There’s a lot of stuff you have to learn about your boss that no one writes down. I want that stuff to be written down.”

If It’s Not Written Down, It Doesn’t Count

Many progressive software startups pride themselves on a lack of internal policies - believing that unlimited PTO or work remote capabilities will lead to happier, more productive teams.

But as Jacob points out, it’s impossible to have zero policies; the only choice is between documented and undocumented policies, and the latter can become a sticking point in your organization that privileges few, while confusing everyone else.

Reasoned and informed written policies allow teams to do their best work by setting defaults and universal understanding within your organization.

Incentivize The Behaviors You Want

Finally, when making policy decisions, leaders need to make a conscious effort to incentivize the behaviors that they want to see in their organization.

Jacob spoke with us about an organization he worked with whose unlimited PTO policy had resulted in employees taking fewer vacation days. What’s more, it led to giant racial and gender disparities between who felt comfortable asking for time off. This could have been prevented, Jacob says, with more clearly articulated policy and incentive structure.

After all, it’s not about what benefits you offer your team, it’s about how your benefits package is used, and if no one feels comfortable taking time off, the incurred PTO is far from “unlimited.”

This show is brought to you by Woven. At Woven, we help software teams screen engineering candidates so they can spend less time on bad interviews, uncover hidden gems, and back their hiring decisions with evidence. If you want to learn more about how Woven could help you scale your software team, you can check us out here.

Our team is excited to help you build your perfect software team, and we are always looking for your feedback about how to make the show better. If you have anyone you think we should interview, tweet us at @woven_teams and our team will reach out.

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Tim Hickle