Engineering Management Distilled: Transitioning from IC to management

Chris Chiu
Jan 30 · 7 min read

Word: manager

Definition: a person responsible for controlling or administering all or part of an organization.

Origin: from Italian maneggiare “to handle, touch,” from Latin noun manus “hand”.

Example usage: I hate my manager.

This article is the first of many (hopefully) in the Engineering Management Distilled Series.

The Good

You are feeling excited. Maybe you’ve been working towards this gig for a while, or, if you’re like me, you were thrust into it by your boss. Either way, you’ve been promoted to an engineering manager! You’re unsure of all the implications but you already notice some differences. Your sphere of ownership has grown significantly and has ventured into new directions. The company just put you in charge of a team, and more importantly, its people. You are a boss — literally. You realize you have some newfound powers like the authority to hire and fire people and to approve expenses or vacation days (some powers are more glamorous than others). You’re also now in charge of setting the team’s direction for the quarter or introduce that one process you think the team so desperately needs. Glancing at your calendar, you are surprised to find invitations to closed-door meetings like leadership offsite and engineering staff meetings. Other teams want to set up time with you and have you make decisions on behalf of your team. And finally, you look up the career ladder and find that there are clear steps from you all the way to the very top. This is the chance you’ve been waiting for; to show the world what you’re made of and you’re gonna take full advantage of it!

But, I’m here to give you some bad news. It’s not all rainbows and butterflies.

The Bad

Your day is no longer your own, and your calendar is filled with other people’s meetings and they always need something from you. You start noticing that those hours of focused heads-down time that made you feel like a 10x engineer aren’t happening as often, if at all. Stress levels are noticeably higher and it doesn’t turn off after the workday is done. You realize that now, the buck stops with you. You’re responsible for the volume, content, and quality of the team’s output. You’re also responsible for your team’s motivation, retention, and morale. It’s no longer enough for you to identify and flag problems on the team. It’s now your job to fix them. From the company’s perspective, they’ve equipped you with everything necessary for success, and therefore, they retain the right to blame you for any failure.

A good friend of mine once said this about the transition from engineering into management:

The highs are not as high, the lows are much lower, and it swings wildly back and forth in the span of the day. — Tim Rodriguez

The Ugly

And what’s at stake?

From the company’s perspective, they’ve taken a huge gamble on you. Depending on your team size and seniority, you’re managing anywhere from $500k to $2M of yearly personnel expense. They’re also very aware that if you fail, it won’t happen elegantly. Because managers (unintentionally) tend to drag morale and employee retention down with them as they crash.

If the company is betting big on you, then your direct reports are all in! Ironically, they likely didn’t get much of a say in having you as their manager but now you’re one of the most impactful people in their day-to-day lives. Studies show that work ranks higher than family responsibilities and health concerns as a form of stress in the American psyche. Additionally, 75% of people say the most stressful part of their job is their immediate manager. That’s why the saying goes: People don’t leave bad jobs, they leave bad bosses.

The failure modes are many. Managers can:

  • Be overly-prescriptive and micromanage.
  • Be underly-prescriptive and detached.
  • Be neglectful of the individuals on their teams and their growth.
  • Steer into the wrong product direction and fail to launch.
  • Steer into the wrong architectural direction and create tech debt.
  • Be self-serving and put their career growth over the team’s success.
  • Fail to gain the respect of their peers and the executives.
  • Be rude in the name of directness.
  • Be too uncritical and fail to keep people accountable.
  • Contribute to the gossip of the company.
  • Be too strategic and fail to execute.
  • Be too tactical and fail to form a vision.
  • Be a bad information conduit.
  • Not be technical enough to gain the respect of the team.
  • Fail to follow through and see initiatives to their completion.

The list goes on and on.

Now that I have you sufficiently sober, let’s start.

The Start

Management is not the next iteration of your old job, it’s a brand new one. This reality can be challenging to internalize. Firstly, because not a lot seems to have changed. You are still at the same company, office, team, code-base, and project. You still have the same boss and you’re surrounded by the same people. But don’t let that lull you into a false sense of stasis. Secondly, in all of your previous promotions, you were likely performing at the higher level for months before receiving the title. However this time, the transition is immediate. From 0 to 1 in the span of a week.

Here are three starting principles to help you through the transition.

Embrace discomfort: Like trying to learn to write with your left hand (or right hand — I’m not biased against left-handed people), management mechanics can initially feel unnatural. Your preference will be to fall back to old instincts that made you successful in the first place. Don’t. Embrace the discomfort and work at the new. It’s different for everyone but here’s some of the familiar cast:

  • Become more organized and take notes.
  • Practice and enforce good development lifecycle hygiene.
  • Spend time planning and prioritizing your day.
  • Delegate (completely) the important technical parts to someone else.
  • Spend more time writing docs.
  • Take in opposite opinions and respectfully consider them.
  • Do 1:1s with everyone (including all your former peers).
  • Give hard feedback to someone as their boss.
  • Get hard feedback from someone as their boss.
  • Be more responsive and over communicate.

Focus on the things that make you uncomfortable because they’re likely your biggest levers for experiential growth.

Hit the books: When learning a new technology, it’s often easiest to download it and play around with it. Management, unfortunately, doesn’t have an equivalent to the “side project”. However, what it does have is decades of written wisdom in the form of management books. These books can range from very instructive to more inspirational. Both are good. They can also range from career-defining to a complete waste of time. The following books I’m suggesting are optimized for industry relevance (tech), practicality (prescriptive), and ease of reading (engaging).

  1. The Manager’s Path by Camille Fournier (more prescriptive)
  2. Managing Humans by Michael Lopp (more inspirational)
  3. High Output Management by Andrew Grove (both)

Outside of hands-on experience, reading is the fastest ways to grow as a manager. And unlike experience, you can accelerate the rate of learning by reading more.

Warren Buffet once said this while addressing 165 students at Columbia Business School:

Read 500 pages like this every day. That’s how knowledge works. It builds up, like compound interest. All of you can do it, but I guarantee not many of you will do it.

Bias towards conservatism: It’s tempting to want to enact changes right away. After all, as a former member of the team, you have many opinions about how things should be done. However, it’s best to adopt a conservative mindset for the first few months and avoid the type of changes that are “high risk, high reward”. Learn and listen before acting. The reasons are:

  1. The team is already trying to adjust to new leadership.
  2. You may be wrong, and time will give you more context.
  3. With time, you’ll be better skilled at driving changes successfully.
  4. You don’t have a proven track-record to buffer a large failure yet.

The End

You’re now equipped with an appropriate appreciation of the task at hand and a few rudimentary tools at your disposal. Success is just a matter of thought, intention, training, and a lot of humility. Because to be a good manager, you don’t have to always hit the bullseye, just don’t miss the board.


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Chris Chiu

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Engineering Manager @ Flexport.