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Q&A With Rands

We asked Michael Lopp (Keynote speaker at the inaugural Developer First conference) to share his thoughts on some commonly asked questions from new leaders in tech. Check out his responses below!


What was your biggest challenge when you first start managing humans? My biggest challenge was that no one and I mean no one set my expectations nor prepared me for the job. I was learning on the job every single day. This is disappointing because I was mistaken that because I was chosen to be manager somehow implied I was instantly qualified to do the job. I wasn't. It took years to figure out the job. What is the biggest challenge you face in your current role? During rapid growth, systems you build that have been performing well for years suddenly break without warning. I'm talking about technological and sociological processes equally. Why? Each human who walks in the building brings equal parts additional productivity and complexity. This means while each new human does give you the ability to get more done, they also make everything more complicated. These complications are the reasons things start to break.

What is the best piece of advice you have received? When you get a new role, it takes three years - minimum - to learn the job. What is the most common mistake you see new leaders make? Failure to delegate the work they love to do. Delegation is one of the most effective habits a leader can deploy to both scale the team and build trust.

What qualities do you look for when promoting an individual contributor into a management role? The health of their current team and their relationship with those they work with tells me a lot about the current state of the individual's soft skills. How do they communicate with different humans on the team? How are they trusted and respected? An individual contributor who has some natural ability relative to the soft skills is an excellent leading indicator that they'll have initial success as a leader.

(Sidebar: It is ironic that the term soft skills describes some of the hardest work of leadership.)


As a leader, how do you balance giving your team guidance vs allowing them to make mistakes and learn along the way?

This is one of those it depends questions where so much of my answer depends on the situation. A simple way to view is this is via a risk/reward perspective. What is the risk of this project failing? While mistakes are a great way to learn, if a project is more mission critical to the team or company than mistakes, bad mistakes, on this project could be a risk to the team or the company. In this case, I am providing a lot of guidance. For a less riskier project, I’ll give a team a lot more room to work. Again, situational.

What is your favorite book?

I’m currently loving The Overstory by Richard Powers. It’s about nine people’s experiences with trees and how they are brought together to address the destruction of forests. I love trees.




Michael Lopp is a veteran Silicon Valley-based engineering leader who builds both people and product at historic companies such as Slack, Borland, Netscape, Palantir, Pinterest, and Apple. While he's not deeply worrying about staying relevant, he writes about backpacks, bridges, people, leadership, and werewolves at the popular weblog, Rands in Repose.

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