To Manage or Not to Manage.

May 3

So you’ve officially reached the part of your career where you’re wondering if management is right for you. Where do you go from here? In this article, we’ll first walk through questions to ask yourself to make sure you’re going into management for the right reasons. Then from there I’ll give concrete advice on how to increase your chances of successfully transitioning into management.

Questions to ponder:

Why do you want to go into Management?

When I ask some folks this, their answer is centered around power. The ability to make decisions and have things done their way...if your primary answer is anything similar to these responses, I’m going to advise you not to go into management. While you are technically in charge when you’re a manager, the best leaders realize that they have their team for a reason. Your team was hired because they bring value to the company. While you guide them as their leader, you should also heed their expertise. For example, as an Engineering Manager, your team will be much more in the coding weeds than you are. They’ll know the code base more intimately than you and likely be able to point out pitfalls that you may not be privy to. Managers can make the final call, but they should do so with their team’s input taken into consideration.

Collaborating with your team on technical decisions not only avoids pitfalls, it increases the team’s psychological safety and the likelihood that the team will care about the decisions that are being made within the team since they know their opinions are important and valued when added. Occasionally, I’ll experience a team that is leaned out in technical team discussions and when I dig a little deeper, I realize it’s because they’ve been shown that their opinions and thoughts don’t matter. So they opt to save their breath and energy.

I decided to go into management because I love creating psychologically safe spaces people can thrive in and also helping them plan a career that will bring them joy. I knew what it was like to have a manager that didn’t do either of these things so I wanted to do my part to create a space where someone else could avoid that experience.

What type of manager do you want to be?

This question can be interpreted two ways: 1) the level of technical engagement you’ll have as a manager and 2) what managerial values would you like to lead by as a manager?

Level of technical engagement – Some Engineering Managers (EMs) don’t code at all while others split their time between management and technical tasks. As a first time manager, I recommend starting without the expectation that you will be coding. Mainly because management can be unpredictable and a lot to manage (no pun intended). As you settle into the saddle, it would be nice to not have you blocking the flow of work and/or having coding tasks drag on because you’re spending the majority of your time learning to manage. Even once you have some EM experience under your belt, I’d suggest you minimize your technical involvement. Instead of picking up tasks that have to do with core functionality, consider yourself an enhancer. What tasks can you take on that won’t block other important work, but will make your team’s life easier? Shoring up monitoring and error handling? Cleaning out some tech debt? Whatever it is, when you have an itch to lend a technical hand, favor this work first.

Being technically sharp is an advantage, but you also need to be mindful of the power imbalance within your team since you’re a manager. Your word will carry more weight in these technical discussions and potentially influence how your team interacts with and around you. Team members may be less likely to give critical PR feedback if the PR owner is someone that decides their next raise. This may sound a little dramatic to some, but egos can be fragile. When in technical discussions with your team, be mindful to not take up too much air.

In addition to this, it’s also important to give your more senior engineers space to lead and make decisions. Many senior engineers care deeply about their voices being heard within their team so you don’t want to crowd them out. Give them room to spread their wings and also be leaders within the team.

Managerial values – Who do you want to be as a manager? If you don’t know, I want you to think about the managers you weren’t particularly fond of and then think about the managers you’d follow anywhere. If you haven’t had managers that fit into either bucket, think of what a manager would have to do to fall into either of those buckets and use these answers to craft the type of manager you’d like to be.

These guidelines will be your managerial compass. Yet, even still, make sure you acknowledge that every person on your team will likely be different. So if you’re up for it, ask your team members how they like to be managed and do your best to manage them how they like to be managed. For example, when I push my team members on stretch goals, some like soft nudges while others ask me to push hard on them or else they know they won’t do it haha (for this, I know it’s a fine line because people should be able to motivate themselves, but even hard workers sometimes need a push).

Will you have support?

Once you’ve identified opportunities where you could potentially start your EM career, check with those roles to see if you’ll have support in these roles. Meaning, will you have a mentor and the space to ease into this new role? As a first time EM, support is absolutely essential. Humans are complex and as alluded to above, every individual on your team is different. Making the role of being a good manager very difficult. Having support as you slide into this role will make that transition much more tolerable.

How to nab the role:

Look within your current company – at your current company you’ve (hopefully) built up some trust already and they want to retain you. Chat with your manager to see how feasible it would be for you to slide into an EM role. If they agree it’s feasible, set up a plan on how to make it happen. Getting the initial experience in a new role is the hardest part so if you can get it at a place you’ve already created trust, it can make the transition easier. Once you have that initial experience, finding additional EM roles down the line will be less cumbersome. If you can’t assume the title of EM, see if there are responsibilities you can take on that will help you show future potential employers that you have demonstrated EM skills even if you haven’t held the title.
Seek roles for first time managers – it won’t always be stated in the job description, but lean on your network to help you find roles that are intended for first time managers. These will have more realistic expectations and increase your chances of success.
Tailor your resume – even if you haven’t held the title of Engineering Manager, something you’ve done in your past likely aligns with what it would take to be an Engineering Manager. Make sure your resume highlights this clearly.
Utilize your network – you should do this regardless of what job you’re seeking when interviewing, but always use your network. Don’t apply cold, get a warm introduction to increase your chances of getting your foot through the door.

Side note: this is a loving reminder to keep up with your network so you don’t become the person that only reaches out when they need something. Wish people happy holidays, check in to see how they’re doing, do random coffee chats if they’re someone you enjoy. It pays off.

How to increase your chances of success:

Go where you’ll have support – we touched on this in the “Questions to ponder” section, but it’s important enough to repeat. As an EM you will be managing humans (at least until AI takes over the world) and humans are complex. Given this, I can guarantee you’ll be hit by some unexpected development during your initial journey into management. This fact coupled with it being difficult to juggle tasks in a high paced environment make it nice to have a quality support system to help you through the transition. If you won’t have support on your immediate team, have a mentor you can lean on.
Know your triggers – As a manager you’ll be responsible for all kinds of different types of personalities and people. Potentially people you’d generally try to avoid in your personal life. You’ll also be responsible for setting the tone within your team. So these two things make it imperative that you take some time to become acquainted with your triggers. Do you hate being wrong? Get particularly agitated with people who talk over others? Hate when people openly lie? Struggle to admit when you’re wrong? Whatever the things are that “get you going”, reflect on them and have a plan on how to deal with them if they arise while you’re managing. The plan can be as simple as getting some initial space from the issue to give you time to think and come up with a more acceptable response. And while you want to coach people who do things like talk over teammates and lie, (if they’re lying, try to dig into why. They could feel a lack of psychological safety that makes them want to cover up mistakes) you also want to make sure you’re minimizing bias against them as their manager.
Be intentional about setting the culture – When you join the team, don’t be the EM that comes in and starts changing everything because you think you know best.

1 on 1s –

For the initial 1 on 1, ask them questions about what has negatively impacted their work efficiency, what things they think you should focus on improving as their new leader, what goals they have that they’d like your support in achieving, how they like to receive feedback, and how often they’d like your recurring 1 on 1 to be (ie: weekly or bi-weekly).
For your recurring 1 on 1s, remember that these 1 on 1s are their time. Create a running doc that they can add topics to and allow them the space to talk about what’s on their mind. 1 on 1s are not a time for you to get work status updates from them. If they bring it up, it’s okay to talk about, but don’t eat their time up with these discussions. Be sure to prioritize these 1 on 1s and not consistently cancel them. Especially in a remote world where you have less touch points with your team. Use the time to connect with your engineers on the things that are on their mind and provide coaching where it makes sense.

I occasionally make an exception to this rule in cases where urgent coaching is needed, but that’s something that’s very rare unless the engineer has had prolonged performance issues.

Set the tone – Have an initial team meeting to introduce yourself. Let the team know what kind of EM you’re aiming to be, let them know you know it’ll take time to build trust, but assure them you’re here to listen to them and improve the things that will make their jobs easier (within reason, of course). Also let them know that you’re open to feedback when they see ways you can improve as a leader. It’s a small thing, but having feedback be a two way street is a great way to build trust within a team and ensure everyone is operating at their best.
Know when to be flexible, know when to be rigid – As humans, we’re going to make mistakes. When your team makes mistakes, be mindful of when to be flexible and when to be rigid. As long as the behavior isn’t a pattern, doesn’t threaten the team’s psychological safety, and isn’t malicious, I try to be flexible and give grace. Mistakes are going to happen and the team seeing you’re willing to extend grace to them goes a long way in fostering psychological safety. But if you’re seeing behavior that threatens psychological safety, I’d encourage you to be rigid. For example, seeing one person on the team belittle or repeatedly talk over another. These are things you cannot let slide and should address directly.

There’s so much that can be said about the best way to decide if you should manage or not and I hope this overview will get you one step closer on your journey. Good luck!

Taylor poindexter