Common traps when hiring your company’s first engineering manager

If you’re looking to hire your company’s first engineering manager, how can you make sure they’re right for the role?

As a consultant for engineering companies, I’ve recently run into a number of organizations that are thinking about hiring their first engineering manager. While there’s a lot that’s been written for first-time managers, there isn’t a whole lot out there for folks trying to hire a manager for the first time. So, I thought I’d assemble some of the common mistakes I’ve seen:

1. ‘We don’t need managers’

In my experience, the places that claim to not need managers are the ones that need them the most. These organizations tend to be marked by difficulties with focus and prioritization, low investment in technical strategy, and organic and reactive organizational structures. These difficulties lead to tangible problems like high rates of burnout, high-failure rates when attempting to deliver on large or complex tracts of work, and an inability to pivot or align on business needs.

One new hire isn’t going to solve all these problems, but it’s your first step towards establishing an engineering management capability that will one day be able to help you make significant strides in each of these problem areas.

2. Turning your best engineers into managers

Don’t. Just, don’t. No matter how many times it’s been written or said, I still come across companies that are doing this. Listen, I get it. At some point in a company’s early history, this was the logical way forward. Back when it was just a scrappy founding team, the technical co-founder was both the best engineer and the best manager. But being the best on a small team doesn’t equate to being good.  And if your company makes it to the next round of funding, you owe it to everyone involved to provide an improved level of management.

3. The player-coach

This model is where an employee spends part of their time managing and part of their time coding. On the surface, this sounds really quite appealing. From the leadership point of view, you get a little bit of management while only losing half of someone’s coding time. From the employee perspective, you get to dabble in management while still being able to do the thing you came to do (ship code). It’s a win-win. In fact, this is how I was lured into management. (Narrator: he did not, in fact, ever ship code again…)

First, it should be noted that there are a few ways in which this model could be viable. If your team remains small (less than five engineers) or if you don’t have to manage a lot of change (e.g. if you have low attrition, a stable long-term strategy, and a strong financial position) you can hang out here for a while and be okay. However, for growing companies, this is a transitory state, not a stable one. It’s a pitstop on the way to more advanced and mature organizational infrastructure.

So, how does this get tricky for first-time managers? First, the most damning evidence comes from the professional sports world. Think about it: there’s currently no person employed to both coach and play on a team. This is true for the top folks in the game, never mind for first-time coaches. It tells us something that a group of people obsessed with performance don’t back this model.

Going deeper, learning how to manage is hard. Like learning any new skill, it requires spending a lot of time in your discomfort zone. Similar to how the fastest way to learn a new language is by immersing yourself in it, the fastest way to get spun up on management is to do it full time. With the player-coach model, you’re looking at a very unstructured part-time immersion program where it’s far too easy to spend most of your time coding than managing because the former is easy and the latter hard. Additionally, while on paper you end up with half an engineer and half an engineering manager, in reality, you’re only getting about a quarter to a third of each due to the amount of context switching.

4. Hiring internally vs. externally

‘Do we give an internal candidate a shot or should we hire someone externally?’ This is usually the first question I hear from companies. More often than not, my answer is to hire externally for your first manager hire.

This is a moderate-risk, high-reward recommendation. Especially if your company is predominantly made up of first-timers, you’ll likely lack the experience to know what good management looks like or how to hire for it. Hiring an experienced, qualified manager gives you the best chance of not only getting your team the management support it needs but also improving the level of management at the company as a whole. It deepens your talent pool, and that’s super important. Winning the organizational growth game means bringing in people at every level who are more skilled and capable in their specific role than you are or ever will be.

Of course, there’s nuance to this advice. While there are many successful companies that can get away with only hiring senior or experienced talent, transitioning one of your engineers into a manager might make sense for a number of reasons. The first is budgetary; in this market, hiring talent is an expensive investment that not every company can afford. Second, every manager has to start somewhere, and starting from a place where you already have a deep understanding of the technical systems can be a real advantage. Finally, providing career opportunities for your employees is a worthwhile endeavor. Just go into it knowing that it takes a very particular type of person to be successful in this scenario. And, if possible, hold off on transitioning internal folks until you have a more established management practice in place.

5. Hiring a first-time manager

When it comes to hiring externally, a common mistake I see is a willingness to hire a first-time manager. There’s a time and a place for giving folks a chance and growing them in-house, but this isn’t it.

From an organization-building perspective, this is a missed opportunity to improve your company’s position. It’s also a move that’s somewhat more fraught than turning a current engineer into a manager. Not only will this person need to learn how to become a manager, they’ll also need to simultaneously learn about your technology stack, which is a very difficult position to be in. And while this is happening, very little progress is going to be made on your management problems – the reason you hired this person in the first place.

What if you’re unable to avoid all these traps?

While I’ve described all these scenarios as non-ideal, sometimes running a startup feels like a series of non-ideal situations. It could be that your only option is to hire a first-time manager internally. So what can you do to improve the odds of success?

First, find someone who’s genuinely curious about the role. Conscripting someone into management against their will is cruel to all parties involved. Not only will you suck the living joy out of a high-performing engineer, but you’ll also be doing a disservice to their reports. This is a situation that’s likely to end poorly. Where you once had a missing manager problem, you now might have an entire team that’s a flight risk in three to six months.

Second, look for folks with a variety of work experience. That doesn’t have to be strictly software development. It could be a work history in an entirely different industry. What you’re seeking here is someone who has been exposed to different managers and management styles in the hope that they’ll have a healthy set of archetypes to emulate while they figure out the job.  

Third, put support systems in place. Find them a coach, get them enrolled in management training, and find or provide them with a cohort or community where they can seek help. You don’t want your manager feeling like they’re on an island. Putting these support systems in place will not only help your first engineering manager, but also every manager you hire from here on out.

Reflections

If you’re looking to hire your first manager, congratulations! It likely means your company is growing and you’re preparing to lead your team into a new phase. Avoiding these common mistakes is a great way to maximize this opportunity and set your team up for success.