The state of hiring an Engineering Manager in 2019

5 things I learned by spending four months job-hunting for a Software Engineering Manager role

Joe Greenheron
Practical Empathy
8 min readMay 24, 2019

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How to hire a bodyguard

Hiring knowledge-workers is difficult. People on a hiring-team get a few hours with a candidate, and then they’re forced to decide whether they want to spend 8–10 hours a day sitting next to this person, 5 days a week, for the next few years of their lives.

If I wanted to hire a bodyguard, the most important thing I’d need to know is whether they’d take a bullet for me. But I can’t determine that with certainty in a meeting room. And given 60 minutes together, it’s hard to even simulate a situation in which I could know for sure how a potential bodyguard would react in a life-or-death situation.

Most software development isn’t life-or-death but the analogy is apt. You have one most important thing you’re looking for in a candidate: it might be general like “do they fit with — and improve — our values?”, or specific like “we need to hire a subject matter expert in Foo.” You need to gauge their fit for this one thing with very limited data, over the course of a few hours.

For interviewing engineers, we (as an industry) have mostly moved from “can they write code on a whiteboard?” as the prevailing proxy, to a post-whiteboard-coding world where we’ve improved the realism of the process (e.g. with coding homework challenges and pair-programming interviews), at the expense of standardization (a great trade-off to make).

The 5½ things I learned

Management is a discipline that requires a referent: some outcome (e.g. a goal or project) or process (e.g. onboarding) to be managed. (“You manage things, you lead people”) This makes it even harder to evaluate in the sterile world of interview loops.

So when I decided to throw my hat into the Engineering Manager (EM) ring a few months ago, I had no idea what to expect. First off, this was my first time interviewing as an EM, since I grew into a management role at my former company (i.e. I interviewed there as a software developer, and transitioned to management).

Here’s what I learned (scroll to the end for the basic facts about # of interviews I did, etc.)…

1. I got more info about each company’s interview process than I imagined I would

One thing that’s drastically improving over time is the “information asymmetry” between the employer and job-seeker. In ancient interview experiences (circa 2013 and earlier), you’d get a date and a place to show up, and that’s about it unless you asked for more info.

This time, before almost every interview loop, I got lots of info about who was going to be interviewing me, and sometimes even what they’d be asking. I often got a list of the company values (most companies also post these publically on their websites).

Many companies offered a one-pager about “what to expect during your interview”, covering everything from what’s for lunch to what I should wear. It’s almost like every recruiter in the industry got tired of candidates asking “Will you please give me more info about what to expect?” and decided to preempt the question.

2. There isn’t a standard interview process

EM interview loops are still all over the place. Maybe that’s a good thing? Orgs can decide what they want to optimize for, and index for that in the interview process?

Props to Stripe for having the most fascinating EM loop by far. It was capped by a grueling full-day at their SF headquarters, but what was interesting was that the format kept changing throughout the day (I knew this ahead of time, See #1 above). The first couple hours were traditional behavioral/STAR questions (“Tell me about a time when…”).

And then shit got real. The next couple hours were role-plays, testing my leadership and managerial aptitude in the most realistic simulation possible. (I don’t want to give away too much here.)

The final two hours were split between a standard “how would you build a …?” architecture question (which was misleadingly billed as a collaborative “Design Discussion,” but my interviewer didn’t really collaborate with me so I did all the work myself!), and ended with me giving a presentation to a small panel about something I’d built in the past. (98point6 also does this.)

By the end of the day, I’d talked with 12 Stripe employees. When you add that to the recruiter and hiring-manager phone screens, and a mini-loop in their Seattle office, I had contact with 17 people from Stipe by the time they made their decision!

Overkill, perhaps, but if you want to de-risk a hiring decision, this is how you do it. (Read more about how Stripe approaches hiring)

3. Few firms over-indexed on vocational skills

I’ll leave this company anonymous, since I don’t think the following is their fault. They just didn’t know what they were looking for (they wanted a unicorn: an experienced EM with strong coding skills, who could spin up a new business-unit, and simultaneously open their new Seattle engineering office. If you know of someone who can do all this, I have a great company to connect you with).

After an hour with their CEO — who gave me one of the best product demos I’ve seen in a long time — I was subjected to two hours of deep technical questioning, stuff like CDNs and finding neighbors in a cartesian system.

This might be the exception that proves the rule. Most companies had the philosophy of “you need to be technical enough to add value to the work your team does, but we’re hiring you for your team-building skills” and the content of the interview reflected that.

Some companies had so little technical content in their process, I was a bit worried that the system might give false-positives to an experienced bullshit artist. Again, I won’t name names, though there was a company that did a full-day loop and only spent about 20 minutes on technical content (the standard architecture question, “How would you design a…?”)

4. Instead, it’s values Values VALUES (Advice nugget #1)

Instead of vocational skills, the zeitgeist in hiring right now (especially for management roles) is “values fit.” If I could give one suggestion to EM interview candidates, it’s to internalize the company’s values and work them into the discussion as much as possible.

If the values aren’t on the company’s website and the recruiter doesn’t send them to you, ASK! They’ll likely be all over the walls when you get to the office. Convoy even has them on laminated card in all of their meeting rooms. Shame I spent the entire evening before my interview there memorizing them :)

5. Focus on the value you’ll add (Advice nugget #2)

An alternate definition of “value” comes into play as well, and leads to my second second piece of advice (this isn’t anything new and it will always be good advice): find the BIGGEST problem the org is facing (the sooner the better, ideally in your first conversation with the recruiter), and position yourself as the person who will solve that problem.

When you think about it, there are really only three interview questions:

  1. Are your strengths a match for this job? (Can you do the job?)
  2. Is your motivation a match for this job? (Will you love the job?)
  3. Are you a fit for the org’s culture and values? (Can I work with you?)

Crafting your message around solving the org’s biggest problem answers the “Can you do the job?” question in a big way.

Although they come disguised as various unique issues, there are really a finite number of “biggest problem patterns” that an org faces (scaling, org structure, tech debt, product/market fit, etc). Once you find the problem, use their language when you talk about your experience solving it in the past.

Bonus: Remote loops are a thing

I interviewed for two remote roles: Healthify and 7 Cups. The former is based in NYC with about a 50/50 split between HQ and distributed. The latter is fully distributed. Both are awesome companies.

The “loop” for remote companies is a bit different, since you might interview with one person at a time, then get a follow-up with the recruiter, then schedule your interview with the next person, etc. This may spread the interview over the course of a couple weeks, making it harder to connect the dots between the answers to your questions (Advice nugget #3: think of some good questions to ask everybody you talk to, and triangulate your answers) or know how you’re performing.

The obvious benefit to this is that you spread out the energy-draining full day loop over a longer period of time.

Conclusion

I interviewed (in-person or via teleconference) at 8 companies over the course of four months. If you include companies where I did a phone-screen but didn’t proceed further, it was 14 companies in all. I ended up getting 2 offers (so far…)

This was accurate as of mid-2019, but with a discipline that’s as new and dynamic as Engineering Management, things are likely to change quickly (for the better, I hope). The only constant is change.

Hope this helps someone prepare for an EM interview. I’m happy to provide more information or details about particular companies that I didn’t feel comfortable telling to the entire internet.

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