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Providing Leadership Advice

A couple of weeks ago, I was invited to participate in a panel of engineering managers and directors to chat about a few of the details and nuances of our jobs. It was set up by Plato, a startup that latched onto this idea that people management is hard, and that there aren’t that many resources available for those transitioning1 into the role for the first time. Our topic focused around identifying software engineers who’d make good managers; you can view it in full here:

The event made me realize a few things:

  1. Engineers and engineering managers, as a group, are terrible at public speaking and engaging with an audience. There are notable exceptions, but the gaiting awkwardness portrayed in shows like Silicon Valley is rooted in reality.
  2. Per my wife, I really should not try to wear medium-sized T-shirts anymore.
  3. There is real demand for mentorship and coaching for people management.

Given the general lack of excellence in management and folks’ propensity to quit their bosses, it’s unfortunate that there isn’t more support for folks who want to get into management or have just made the move. In fact, the descriptor, “middle management”, is itself almost derogatory: not grounded enough to do the actual work, but not skilled and experienced enough to claim an executive position. Being caught in the middle makes for an ambiguous, exhausting position.

Of course, most people in this position are smart and self-aware enough to know to look for advice. Big companies solve this problem via management training classes2 and using their own set of senior leaders to guide the up-and-comers. Smaller companies, however, don’t have the same luxury, and in many cases the lack of an established framework is even worse: the new manager is expected to help develop the management standards which will carry the organization through its next stages of growth. Startups implode when they can’t navigate this transition.

All of this prompted me to start offering to simply chat with folks who are thinking about moving into management, or who have already jumped into the fray. I already take calls as a mentor via Plato weekly, and I’m set up via Clarity for more randomized conversations. I’ve also refocused this blog to enable easier contact and reaching out, and will spend more time writing about management-specific topics3. That said, engineering management is a relatively niche role, and I recognize that my own expertise and experiences are only helpful to a subset of this group.

But—It only takes a few connections, a few managers helped, to make this worth the time.


  1. Watch the video to see why it’s “transition” and not “promoted”.

  2. I think I’ve taken the same introduction to management class 3–4 times now, across different companies.

  3. Amidst the rest of the other things I enjoy, of course.

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