Dylan Etkin, Co-Founder and CEO, Sleuth

August 7, 2023

8 Min Read
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Konstantin Mironov via Alamy Stock

Getting hired as an engineering manager for the first time means you’ve already shown you have the right mix of technical experience and people skills. But there are certain things to keep in mind that will help you start on the right foot and avoid some pitfalls of management. Here are five to get you going.

#1: Figure out what kind of organizer you are

Why it’s important: Knowing your organizational preferences will determine how successful you are at leading a group of people to get things done in a set amount of time (in other words, your job).

Ask yourself how much organization you need to be comfortable with your team. How organized do you need your team and its processes to be in order to be confident your team can achieve its goals?

Take sprint planning, for example. Will you run that loosely or tightly? I've worked with folks who were way more organized than I am, and their sprint planning was driven off of the Jira board. Everything was story pointed, and they knew they would do A, B, C, all the way through to Z.

I’ve also worked with looser approaches. These managers approach sprint planning with, “What are we getting done this week? What's going to come out the other side?” They might know the functionality it’ll have and a general sense of how to break down the work, and that’s enough for them to feel confident in getting the work done.

They’re very different styles, and both can work.

The point is, I haven’t seen many managers succeed in adopting something that doesn't fit their natural tendencies. More often than not, they fail when they're trying to emulate somebody or a process that doesn’t align with their preferred working style.

The engineering manager is the one taking on the responsibility to organize a group of people to get things delivered. As the new person coming in, you have to figure out what works for you and your team.

All this is going to determine your satisfaction and confidence in the way your team works. It’s your team, and you need to be comfortable with how they operate so you’re not second-guessing things. You need a process that allows you and your team to thrive.

#2: Figure out what kind of manager you'll be working for

Why it’s important: Your manager judges your success on what information you give them and how you present it.

Whereas the first tip is about your working style and interactions with those who work below you, this tip is about acknowledging your manager’s working style and how you’ll conform to it while maintaining your own.

Figure out how much reporting up your manager wants -- are they a details person, a big-picture person, or (hopefully not) a micro-manager?

The reality is, their style might be very different from yours. You might be very organized, but your manager is very loose. You might show them the sprint board, but they only want to know how it’s all going, what you’re delivering, and where you are in the process.

Your level of organization will likely be able to produce that information; you just need to present it differently. If your organizational approach doesn’t easily produce the information your manager needs, you need to adjust your process -- but you can still do that in your own way.

I've had direct reports who were more organized than I was, and I had to tell them that their sprint board didn’t mean anything to me. I could tell the team did a lot of work, but I wanted them to zoom out, give me a sense of where they were at, and if there was risk involved in that project.

Here’s a reality check, though. You'll switch managers, and all of a sudden you have a totally different universe.

For example, I reported to a very hands-off, trusting manager at Bitbucket. I was enjoying the autonomy, until my manager changed, and then I hated my job. The new manager was a micromanager who wanted to know details 10 layers in.

I was on top of all of those things, but he was stressed because he didn’t know the answer to everything. It meant I spent more time documenting what I knew so that he could know them too. If I didn't do it, my life was going to be even more unenjoyable than it already was reporting to this guy.

Coming from an individual contributor role, you might not be used to reporting up much. Understanding who you work for is hugely important. Even if you don't like them much, you have to figure out how to work with them. They're your boss.

#3: Understand what your organization expects of an engineering manager

Why it’s important: The expectations will create the landscape of your job, and you have to be able to meet them.

Every company does things differently, but the lowest common denominator typically is that engineering managers have responsibility for both the personal and technical sides of things -- but the emphasis can be quite different.

There's a big debate in the industry about whether engineering managers should code or not. I think EMs should focus on doing impactful, useful things. Coding is a distraction. But some organizations want EMs to spend a percentage of their time coding, which creates a very different job layout.

This ties into how technical you’re expected to be. I've worked at places where they wanted EMs to have a nuanced understanding of how to build and grow teams, make them efficient, and use the roles on the team, while also having enough technical acumen to know what’s BS and what’s legit, but not necessarily have to answer technical questions.

At other places, they want you to be able to do the technical work if you had to and have technical conversations. Likely, you’ll know this before getting hired into an EM role, but it’s important to know what mix of expectations will make you satisfied in your job.

#4: Become an expert at hiring

Why it’s important: Getting hiring wrong is hugely expensive, time consuming, and frustrating.

I entered management not realizing that hiring can be 50% or more of the job, and not understanding what it meant to be good at it.

I went through a phase where I figured the organization would ultimately handle hiring. Only after messing it up for many years did I realize that not taking it more seriously led to big problems.

Even if you work for a giant organization that has a robust hiring process, if it's not doing what you need it to do, you’re not going to get a great squad.

So, figure out what you and your team need to do to hire well. This means many things:

  • What interviews to run and what you want to get out of each

  • What skills are must-haves and what skills can you teach

  • What your minimum bar is for what makes a candidate worth considering

  • How you’ll decide as a team who can be additive

Own your candidate pool and hiring processes such that your team can be successful.

I never really wanted to know how to hire well, but when I realized I wasn’t very good at it, I thought, “How do I get better?” I read some books, took ideas I liked, and came up with a structure for what to test for in interviews.

If your team says a candidate seemed good but nobody was really thrilled with them, then you don't hire them, because you’ve agreed you're the type of team that's looking to be thrilled.

Understand the hiring expectation, too. Is your team growing? What’s the right configuration of who you have and what you need? Determine what skills you’re missing and what skills would augment the team.

I've interviewed people who were brilliant, but I’d never hire them because they weren’t team players and they’d destroy the team's cohesiveness.

I was interviewing a manager who seemed great to all of my other managers. But our most senior engineer, who is the nicest guy on the planet, had nothing good to say about the candidate because of the way he asked about things. That told me something wasn’t right with this candidate.

So, be intentional about hiring. You might think there’s some degree of trial and error -- you hire someone who checked all the boxes but they end up not performing well -- but that’s an expensive experiment.

You're hiring because you're behind, and you need somebody to help you get ahead. If you mis-hire, now instead of having somebody who's helping you get more done, you have somebody who’s a problem and takes up 50 percent of your week. You want to be fair, so you spend time meeting with them more often, trying to help them succeed.

But often it doesn’t work out. So bulletproof your hiring process.

#5: Be open to learning on the job

Why it’s important: It’s the best way to improve and be effective.

You can keep all of these tips in mind as you start your new role. But the best advice is to jump in and do the work. Get your hands dirty. Make mistakes and learn from them and make fewer mistakes next time. The worst thing you can do is aim for perfection -- the enemy of good.

Run an experiment for a process change. If your team shows up to the retro and says the system you came up with is garbage, change it again.

Set a goal to change something at least once a month to zero in on what’s working and what isn't. Even if everything seems to be working, there's always one thing to do to be a little bit better.

If all the devs complain about something that you don't think is a big deal, but it's affecting their morale, shake up the process and see what works better. The best managers who have worked under me do this in real time, all the time.

As with any role, it’ll take time to figure out what processes and dynamics work for you and your team. But for engineering managers in particular, the faster you do this the sooner your team will run efficiently, be happy, and be a source of your satisfaction.

About the Author(s)

Dylan Etkin

Co-Founder and CEO, Sleuth, Sleuth

Dylan Etkin is CEO and co-founder of Sleuth, the leading deployment-based metrics tracker. As one of the first 20 employees at Atlassian, Dylan was a founding engineer and the first architect of Jira. He has led engineering for products at scale at Bitbucket and Statuspage. He has a master’s degree in computer science from ASU.

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