Should You Become a Manager?

Advice for high performers in any company

Cap Watkins
Aug 21, 2018 · 5 min read
Photo by Steven Lelham on Unsplash

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Since starting my own business as a leadership coach, I’ve spoken with a lot of folks who are at a crossroads in their careers. Should they become a manager, or should they continue to pursue excellence in their craft? Are those paths mutually exclusive? If not, how can they do both?

For many, this can be a very nebulous, stressful decision. There are only a few people I’ve spoken with who’ve known without a shadow of a doubt which path they wanted to take (I was not one of them, surprisingly).

After hearing from so many struggling with this decision, I’ve told each of them the same few things.

Management is like starting over completely

People nod when they hear this, but I still see so many new managers get really surprised by just how incompetent and unsure of themselves they are at first. For instance, being someone’s manager in a 1:1 is much different than being the person venting to their manager in a 1:1. Learning the ins and outs of an organization — what motivates different people, who really makes decisions on a team, who you can ally with on certain things, which team members tend to be blockers, and how to navigate them — is a huge shift from delivering a wireframe or some code. Coming up with processes for tasks like recruiting, instead of simply participating in other people’s processes, can be tough. Finally, learning that everything you do and say is being scrutinized more carefully than ever can be incredibly daunting.

Being a manager is not a higher-level version of the job you had before — it’s an entirely new job and an entirely new way of working.

Not becoming a manager limits your upward mobility

Whenever I hear a company claim that they’ve figured out how to parallelize the manager and contributor (non-manager) tracks, I raise an eyebrow. It mostly turns out to be bullshit.

Sure, a lot of companies nowadays do have some parallelization in their tracks. But ask them to name a VP or director-level equivalent who is not a manager, and I’ll bet cash money that 99.9% of the time that person or role does not exist (and is probably not even defined).

Even if it is defined, moving up in your capacity as an individual contributor is, at least for now, exponentially harder than moving up as a manager. This is primarily because creating new senior management roles is a need-based activity. As companies grow, they need more managers, and then even more managers to manage them, and the list goes on. Eventually, you’ll have a team with 10 directors managing 40 senior managers who manage a few managers each.

And how many director-level contributors are there? Maybe one, probably zero.

This may change someday. But right now, if anyone tells you that you can achieve the same level of pay and authority while remaining an expert craftsperson in your own right, don’t believe it. This isn’t a reason to become a manager by itself, but it’s definitely something to consider.

Consider whether you want to become accountable

This is the core piece of advice I give to those considering management (and anyone who wants to rise past certain points as contributors). Becoming a manager or a very senior contributor means being accountable for the work of others.

Looking back on my career choices, the driving force for me was a desire to become more accountable. When I became a manager, it was because I’d been a member of poorly run teams and wanted to be in a position where I could fix things — and where I knew that, if things weren’t working, I’d be on the hook. I wanted to be responsible for an entire design organization. Now, I’m looking for work that lets me influence and work across many departments and functions.

Even for those who are already managers, it’s important to carefully consider whether you really want the new responsibilities that come with a promotion to Director, VP, or something else. Just like moving from contributor to manager, each level of management contains the potential to be vastly different than the one before it.

The Peter Principle states that people in a structure tend to rise through promotions until they reach their level of incompetence. This happens when people assume roles for which they don’t actually want to be accountable. Many people end up underperforming as managers because they never really wanted to be a manager in the first place — as a consequence, they don’t put in the time to learn how it’s done. They never learn how to be truly accountable.

No one is ever ‘ready’

Many of my clients are uneasy about stepping into management. They don’t feel ‘ready.’ They worry that they just won’t do a good job, and they talk about trying to get more management experience in their current role somehow, before going for it full-time.

If you feel this way, here’s my advice: take the leap. The fact that you care so much about doing a good job is a strong indicator that you will, in fact, do pretty well. The best new managers are those who sweat the details, those who ask themselves if they’re doing right by their team, their department, and their company. These are the leaders who are most open to feedback, who examine problems from all sides, and who learn the most the fastest.

No amount of preparation will fully prepare you for the reality of managing people. As with pretty much everything, the best experience is direct experience.

You can always go back

When I first started managing others, I had my first 1:1 with my own manager, Randy. He asked me how things were going and I told him, “To be honest, I could be really bad at this, or I might learn that I don’t like it, so I’m kind of nervous.”

My manager thought about it for a moment and said something that stuck with me ever since: “That’s okay. Let’s just keep talking about it. If it turns out you’re not good at it, or hate it, that’s okay. You can always swap back to being a designer.”

That was when I realized becoming a manager wasn’t a life sentence or an irreversible career choice. Since then, I’ve seen quite a few people I know move into management, only to move back into design or engineering or product. Sometimes you just have to try if you want to know whether something’s right. And trying something new doesn’t mean you’ll lose all your past expertise and experience. Check in with yourself regularly. Be honest with yourself and others, and you’ll find your path.

Cap Watkins

Written by

Leadership coach and organizational consultant at @practical_works. Prev: VP of Design@BuzzFeed. Also worked at Etsy, Amazon, and a bunch of failed startups :)

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Notes on leveling up your professional life, selected by Medium’s editors.

Notes on leveling up your professional life, selected by Medium’s editors.

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