Transitioning to Management: Part One

One question I get from engineers more often than any other is “Should I become a manager?”. It’s easy to provide a quick answer (“Yes!”, “No!”, “It depends!”) that is often dismissive of the underlying aspirations and concerns that the engineer may have. Actually, “It depends” is probably the most accurate answer, but the important part of the conversation is an exploration of what factors – those intrinsic to the engineer, and those pertaining to the company and the team – the answer depends on and how to collapse the ambiguity into a clear answer.

Below are some of my observations helping engineers answer that question. Keep in mind that there aren’t a lot of universally true statements when it comes to the management track and one’s fit in it. When you think about your own path and ask yourself if you should become a manager, read the below less like a blueprint and more like a set of guiding questions, some of which may not apply to you or your circumstances.

Ask Yourself Some Initial Questions

To figure out if you should transition to management, it helps to adopt a mindset of thinking in the long term. Management (and especially getting good at management) requires an attitude, skills and abilities that are often wildly different from those that make you an accomplished individual contributor, and it’s a path that takes a lot of time to master. If you want to move to a management track, you should ideally want to stay in it for an extended period of time, even after you leave your current company.

Now that you think in terms of long time horizons, ask yourself where the impetus for moving to management is coming from. There could be a number of reasons – but we’re not always honest with ourselves about the real ones. What I often hear is a combination of:

I want to have more impact
I’m already doing a lot of the “management” work and want to formalize the path
I want to grow professionally

But what I often get to, after some probing, is often a combination of:

I believe that it’s the easiest / most likely / only way to make more money
I don’t see myself being able (or willing) to grow into a very senior engineer and I’m thinking about a way to “pivot” my career (“might as well try being a manager”)
I would like to have more authority (making decisions at a higher level / without asking for permission / telling people what to do)
I don’t like that I work late nights and would like to have a healthier work-life balance

I strongly believe that there is nothing wrong with these “private” reasons. As much as companies value a growth mindset, pursuit of excellence, and low ego, we are driven by a number of forces and it would be unhealthy if none of them were either “selfish” or “pragmatic” or otherwise “unpopular”. But having a clear set of reasons will help you navigate this decision better, so be honest – at least with yourself. Then spend a large amount of time questioning these assumptions and generating data points in their support. Most of the unhappy or unfulfilled managers I know haven’t informed themselves enough before deciding to jump into management. Depending on your comfort level with your manager, try to share all the reasons with them – it may require some vulnerability but if you have a good relationship, it may could be a good opportunity to get some targeted advice. For example, your manager may be able to tell you candidly if assumptions you are making about possible future compensation or work hours are true.

The toughest part of getting informed is the fact that the answers will vary from company to company, and often even from team to team within the same company. For example, some companies do pay managers significantly more than similarly-tenured individual contributors. Others, on the other hand, tend to value impact coming from senior ICs more than the managers. Your understanding of how valid the assumptions you uncovered above are will be tinted by the specific company you are looking at. However, your criteria should be long-term and should go beyond any individual company. To address this contradiction, talk to friends who work in other companies, or ask colleagues and managers about their prior companies, to extrapolate better.

As you reflect on a possible shift to management, there are a few other questions that are helpful for you to discover answers to. You could know these answers already, or have some idea, but the best thing to do is to talk to people you trust, people who know you well, and people who are managers (not just at your company) to arrive at satisfying answers that feel right. Doing this helps you surface assumptions (and biases) or constraints on the path to management, even if the actual answers end up being completely different from what you initially think.

What do I think a manager does? Try to see if you have any misconceptions or stereotypes about the role that may not necessarily be true (e.g. “managers add value mostly by setting up meetings”). What does your manager do? If you talk to a specific person, ask both about the day-to-day, as well as the high level responsibilities. What are success criteria for managers?
What does a manager not do? Specifically, what are the aspects of an individual contributor’s job that shouldn’t be done by the manager? (either because they don’t scale, or because they don’t empower the team)
What have I done in the past that offers data points in favor of me being a good manager?
Do I think I can be a better manager (relative to other managers) than I can be an individual contributor (relative to other ICs)?
What do I think I will struggle with the most?

Consider These General Themes

While everyone’s situation will differ, here are some general themes I’ve collected around the answers I encountered to the above questions. If your answers are very different, think about whether the difference warrants a deeper exploration.

Management does provide an opportunity for greater impact, but only if the manager is adding value. It is not the case that just by the virtue of your role your impact gains a multiplier. In fact, at first you will likely provide less value than you did as an individual contributor who likely led projects and leveraged deep context. Similarly, a manager has the potential to destroy value by damaging the team’s morale, creating too much process, or hiring poorly
It is true that many companies prioritize the management track over the non-management one. The answer isn’t necessarily to become a manager – it may be that another company would value your contributions more highly
Some engineers who don’t think they can grow (or who look around and don’t see themselves as technically strong as the strongest other team members) are probably not getting enough coaching – technical and otherwise. To grow as a technologist, you should grow not just your technical muscle, but also your product and customer mindset, team collaboration, and your ability to deliver, which requires strong communication and planning skills. Many engineers just look at the technical growth and don’t see themselves as “up to date” on new technologies, or as competent architects, and mistakenly think that they will thus never be able to grow into Staff or Principal engineers
Managers can have more visible authority in that they often divvy up work and delegate work to others, but they are also exposed to a lot more inner workings of the organization where many feel much less empowered
On average, managers work longer hours and don’t feel they can “unplug” as much as engineers – especially very senior engineers, who leverage the context they have and their technical intuitions and abilities as well as the teams they are working on projects with. Per unit of time, a senior engineer may add more value by doing a 30-minute code review than a junior engineer who spends four days writing the code in the first place.
Junior managers often add value over longer periods of time (e.g. by working with junior engineers on their growth plans) or in ways that are speculative (e.g. trying different things to improve the team’s morale). If you are uncomfortable with the speculative and long-term nature of the value added you provide, this is something to think about
Managers themselves wear many hats. They are ultimately responsible for their team, that is: the output the team generates today; the ability of the team to generate output in the future (viz. tech debt); the growth of their team members; morale; team size and composition; inter-team effectiveness and collaboration with other teams. They primarily meet these responsibilities by growing and structuring teams, defining the responsibilities and jobs for others on the team, providing the team with resource, holding the team accountable, being an information conduit for the team, and executing on growth plans for their reports. But managers also need to flex to whatever the role requires, often dealing with situations they have never seen before
New managers bring up three activities that they find most uncomfortable or frustrating: performance reviews, negative feedback conversations, and dealing with conflict on the team. How do you feel about these? They are one of the most important ways in which managers add value. If you’re not sure, try to create circumstances on the team today where you get some practice. For example, you probably already do 360 feedback, so put in more effort as if you were the person’s manager (and if you don’t do 360 feedback, do it!). If you’re coaching someone, give them negative feedback – but even if you’re not, give feedback to someone on your team based on your observation. And volunteer to have difficult conversations, lead retrospectives or other similar instances where conflict may appear
Most engineers who transition to management struggle with creating leverage for themselves. Their intuition is to do things themselves because it will be done better and faster. And that is true, but the idea behind good management is to empower the team to ultimately do these same things just as fast and well (if not better) than you would do them. Think about the last time you created leverage for yourself – did you delegate a part of the project? Did you put in place a tool to save the team’s time? Did you teach someone “to fish”? Did it come easily? How can you do more of it?

Reflect, Seek Feedback, Change

By far the single most important characteristic of all managers, but especially entry-level ones is what I would call the “self-improvement loop”:

The self-awareness and input-seeking to understand your gaps in the role
The ability to diagnose these gaps to root causes
The execution ability to address these gaps

A valuable litmus test for whether you would be an effective manager is therefore your ability to figure out how you might shine as a manager and where you’ll struggle, understand where these strengths and weaknesses come from, have a plan for addressing the weaknesses / playing to the strength, and your ability to actually change yourself accordingly. Most people find it hard to do either of these critical things. The latter is the toughest – I have met multitudes of people who are very self-aware and have intellectualized what they need to get better at, and maybe even have a plan, but can’t change their habits and grow their abilities to internalize these reflections.

This doesn’t require a psychoanalyst’s level of introspection. The best way to get a rich picture of the gaps and often also the root causes and even the plan is to seek feedback often and transparently. The best managers create an environment where they get frequent and candid feedback (even if only in private) so that they can accelerate the self-improvement loop.

Similarly, by applying the same process to the team itself, a manager creates a continuous improvement loop (identify gaps on the team, diagnose them, suggest a plan for improvement, and execute on the plan – or coordinate the execution if the manager is not the one executing). The good news is that it is not exclusively the manager’s responsibility. This means that you can introduce these loops right now to assess how well you do it.

Flavors of Management

A helpful framing of “should you be a manager?” is a more specific “what kind of a manager would you be?”. There are a number of different manager archetypes that reflect management styles, superpowers, focus areas and mandates. Just like there are multiple dimensions of professional growth, there are multiple manifestations of good management. Some helpful archetypes are:

A “Tech Lead” – a hybrid between a people manager and a technical responsible party. Many managers start as tech leads, having built deep context of the technology and becoming the ultimate decider and point of escalation for technical decisions within a team. They also mentor new/junior team members and help divvy up and coordinate work. It’s the most “Jack of all trades” role that is very close to the team and the technology and is appealing because of its direct impact, but it scales less well: a common failure mode is that a tech lead neither provides the management their team needs, nor has enough mindshare and context to make optimal technical directions. Another is that a tech lead is too slow to empower others on their team in their own technical decision making.
A “Delivery Manager” – someone responsible for making sure the team delivers what they are supposed to deliver, on time. Many tech leads are de facto delivery managers, but sometimes that role is played by a product manager or a project manager/scrum master. The not-so-secret truth is that most executive teams care about delivery management more than any other hat, so good delivery managers are valued in organizations. Doing this well requires a basket of abilities, including some technical depth, but this is a role that many former engineers often feel least stretched technically in.
A “People Manager” – someone who is responsible for the growth and healthy functioning of the team. This is a role with a good deal of authority (HR managers are usually in charge of budgets, and are the “representatives” of teams) and often leads to further growth (people managers grow naturally into managers or managers without having to alter their job descriptions that much), but it comes with the most process and interaction with support organizations (such as HR). Most engineers, when they think about downsides of management, often imagine activities that are important in a People Manager role. It is also the role requiring dealing with challenging situations (dealing with conflict, letting people go) and a great deal of EQ.
A “Team Builder” – someone tasked with hiring people, getting them onboarded and effective, and ensuring the team includes the right people, in the right roles. It’s highly empowering and a very visible role (you get to entice engineers to join) but also a high-stakes one that affords little feedback and often feels least in your control. It’s a role that requires substantial salesmanship.

Actual managers are some combination of these, and they often flex from one type to another over time. For example, many “most senior engineers” on a team turn into tech leads, who flex into delivery management and later into team building as the need for a larger team emerges. It’s important to note that each of these archetypes has the potential for great impact; how much actual impact you would have playing one of these roles depends on what the company values and requires, and on how well you perform in your role.

Think about what other archetypes you’ve come across. Which archetype appeals to you the most? Also: which archetype are you currently closest to? The two answers may not be the same – in which case, it’s important that you think about whether you can (and want to) shift from what you naturally gravitate towards to what you aspire to.

Talk to people who embody the archetype you’d like to be. There are probably managers in your company who fall in this category. Be honest with yourself around what your gaps are, and around whether you are comfortable taking on the not-so-glamorous aspects of the role. For example, for a People Manager role, a large part of your job will be doing performance reviews well. If you hate performance reviews with all your might, it might not be the best type of manager to grow into.

Companies need managers across the spectrum, not just a single archetype. I found it to be more effective for engineers to use a realistic archetype (one that they already exhibit some aspects of, or have a strong desire to be) as a north star and find an area within a company that values that archetype, rather than to try to fill a need that isn’t a natural fit.

How to put all this together? The above could form a basis for, say, a three-month plan that would allow you to answer fairly confidently if you should switch to a management track. First, acknowledge that this is a long-term journey (and think about the implications of it). Then ask yourself why you want to be a manager, and question your assumptions and preconceived notions – ideally with data. Talk to a lot of managers, in your company and others, to understand what it is really like. Figure out what kind of manager you would ideally like to be. Work on the self-improvement loop as well as the continuous improvement loop for your team.

Then spend the time trying out activities that managers are usually responsible for, that you can try in a low-risk way without requiring authority: mentoring junior engineers, being involved in hiring and even selling candidates, more substantial 360 feedback, giving feedback, leading retrospectives, creating leverage without having the authority to tell people what to do.

Finally, have an open, honest conversation with your manager – not just during your performance review, and not just a one-time chat. Come up with a plan together to figure out if you should aim for the management track. You don’t have to have a timeline for the actual transition (many managers may be uncomfortable committing – even implicitly – to a transition), but you should have a good sense of how long it might take you and your manager to figure out whether you should become a manager in the future.

Now that we covered the topic of how to figure out whether you should transition to management, an obvious next step is to ask how exactly you could do the transition. That’s the topic for the next installment in the series.