Letter to Engineering Manager Candidates

Created By
Bo (COO)
Last updated
August 14, 2021
Reading time
5 mins

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Context: We write a lot, partially because we’re a 200+ person team in 20+ countries in 10+ time zones, and partially because we think “writing is thinking” and clear thinking is better communicated in prose (and unclear thinking harder to hide in prose). As a side benefit, we have almost no PowerPoint, and very few meetings for a team our size. This letter reflects our culture of writing that communicates deep thinking.

Welcome to the Engineering Manager Final Interview

Welcome! We’re excited to get to know you. We’re a bit of an unusual place, so we wrote you a letter. If you think about it, there are a bunch of reasons why we think a letter to candidates is helpful before an interview:

  1. We write a lot, partially because we’re a 200+ person team in 20+ countries in 10+ time zones, and partially because we think “writing is thinking” and clear thinking is better communicated in prose (and unclear thinking harder to hide in prose). As a side benefit, we have almost no PowerPoint, and very few meetings for a team our size. This letter reflects our culture of writing that communicates deep thinking.
  2. We think from first principles to look for: how can we get closest to the ideal but impossible outcome? In interviewing, the ideal but impossible outcome is if you and I shared the exact same context: you knew everything I knew and I knew everything you knew. Well, what’s the best way to communicate context? Thoughtful introspective writing. Is it a bit weird? Yes. Do we care? No. We do what we think best accomplishes the mission, not what’s “not weird”. I hope you hold this letter to that standard and reflect back to me any improvements you think I should make to this letter for future candidates as you go through this (relatively fast) interview process with us. (As an aside, in the packet you get when you start is, you guessed it - letters from others who’ve started before you written to future Clipboarders like you to help you onboard).
  3. We think hiring is the most important thing we do. Thus, we embrace hiring as if it were a core ops workflow for the company, because it is. Hiring is the root of success, or the root of failure, and explains so much in human endeavor. Our team is far more important than our codebase, so we’re going to be maniacal about improving the team even more than the codebase. Like Matt Damon’s character in the movie The Martian (the book is even better in my opinion), we are going to science the heck out of it. :)

What to Expect & What We’re Looking For

As a candidate, you’re often left wondering “what are they going to ask? Why are they asking me this? What are they looking for? What’s important to them?” so let me just straight out tell you. I’ll be asking you exactly these questions (as a starting point for our discussion) during our interview:

  • How do you measure your team? How should I (as a stakeholder) measure your team?
  • What traits define the best engineers on your team? How specifically do you assess a candidate for these traits during hiring?
  • Tell me the most recent time you had to manage an under-performer. As a retrospective, what if anything will you do differently going forward?
  • Imagine I’m an individual contributor engineer being promoted into engineering management for the first time in my career. I ask you “what makes a good engineering manager, and very specifically what should I do in my first 30 and 90 days to be a great one? How specifically do I measure myself as an engineering manager 90 days in?”
  • What does your team most depend on you to do in your role as an engineering manager? When you’re in the interview loop assessing a candidate for engineering management (i.e. hiring a peer to you running another team), how specifically do you assess if the candidate is good at this?

Feel free to send over any written thoughts on this, or examples of existing writing (even if emails from day-to-day work that would help us sync our minds - per the Ideal Impossible above).

You see, this is not a guessing game where you win by guessing what we’re looking for: this is a show (not tell) how you work, and we’re on your side! We’re really excited and optimistic that you’ll do great as part of this team, and our time together is designed so that you can show off your craft. We are looking for...

  • We’re looking for you to have specific, nuanced, and sharply defined strong opinions that are weakly held. We’re looking for you to communicate them concisely and precisely.
  • We are dedicated to our customers and our craft. For example, one leader’s craft may be designing great products, hiring, and managing managers. We think a lot about our craft and hope you do too, and we hope you teach us things that expand or refine (in a sharp, specific way) our worldview and mental models about your craft.
  • We’re doers, not recommenders. We value coming up with an actual specific implementable solution and lessons learned from implementing them in reality, not “asking the right questions” (though that’s necessarily on the path).
  • We’re good at math. No seriously, this is a very math-heavy business, multiple leaders here have competed or won math & science competitions at the state/national/international level, and we run the business accordingly. We are unafraid to dive as deeply into the math as necessary; indeed our Series B data room contained a multi-page methodologies PDF full of equations.

Though an unusual practice, I hope this letter helps you succeed in our upcoming interview. Remember, we’re on your side, and are really looking forward to hopefully working with you to advance the mission of lifting as many people up the socioeconomic ladder as possible. -Bo

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