Becoming an engineering director

What does stepping into this role really look like?

I was promoted to director less than a year after becoming a manager. In the movie version of my life, getting promoted was a recognition of years of hard work and undeniable, innate leadership ability. The truth is probably closer to me being the available warm body to throw at the problem.

To set the scene, it had been about eight months since I had switched tracks from individual contributor (IC) to manager. I walked into a meeting with the VP of Engineering for what I thought would be a compensation adjustment to go along with the change in my role. Instead, I got a hearty handshake and a ‘Congratulations, you’re the new Director of Infrastructure. Keep doing what you’re doing.’ And, mustering as much fake confidence as I could, I smiled, mewled a quick thank you, and walked out the door.

I remember wishing to know exactly what it was that I should continue doing.

Comparatively, as a manager, I had a vague idea. I had been a manager before. I had been managed. From those experiences, I had formed opinions that guided my management practice. But, ‘engineering director’ was a new machine. In my career to date, I had rarely interacted with directors in my personal or professional life. I had neither any exposure to the role nor anyone in my network who I could ask. When I look back on that time, I realize I spent the first 18 months in my new position being just useful enough to not get fired. To save you some of that hardship, here are a few things I learned about operating as an engineering director.

Context

Since titles mean different things at different places, it’s very possible that the role I’m describing goes by another name at your company. In order to help contextualize, here’s what my situation looked like: I became a director at a company that was then around 300 employees with about 80 engineers. Within 5 years, that company would grow to over 1,000 employees with 360 engineers, with my org growing from 13 to about 85 engineers across a dozen teams. It was a time of rapid change. I reported directly to the VP of Engineering who shared engineering leadership with our CTO, and my primary responsibility was to oversee everything that was not product development or systems operations. 

Goodbye manager support

While the bar for management in our industry is pretty low, when you are an IC or front line manager there is usually at least the guise of having a manager to provide support, mentorship, and aide. At the Director level, or pretty much any level that reports to a VP or C-suite executive, that pretense is non-existent. Generally, you’ll alternate between being left completely alone when things are going well or being called into a multitude of emergency meetings when things are not. It may not be articulated, but the expectation is that you are able to self-manage.

Of course, the idea and the reality of self-management are two different things. But at this level, the onus is on you to find the support you need. I highly recommend taking advantage of whatever programs your company offers, such as a professional development stipend, internal management training, or getting time with any advisors the company has retained. We all need help of some kind, and this is definitely the time to build out your support network if you haven’t already done so. Find a coach, develop relationships with your peers at work, and start reaching out to leaders at other organizations. This can feel uncomfortable, but once you have those things in place, your only regret will be not doing it sooner. 

Uncertainty and ambiguity

There’s often a misguided belief that as you climb the org chart, you become privy to more information with which to make decisions. This turns out to not be entirely true. Chances are you’ll be added to one or two more meetings, email lists, or Slack channels. Those email lists and Slack channels will be relatively low trafficked and the meetings neither productive nor expressly relevant to your work. You’re going to be left with a feeling of ‘is this it?’

While it might feel like you haven’t gained elevated access to useful information, the reality is that you actually do have access to more information. It’s just not the information you think it will be. This information you gain comes from the new teams that now fall under your purview. It’s information you’d find useful if you were managing that team. And if your only job was to ensure that your teams ran well, it would be enough. But running high-performing teams is only part of your job. The other part is deciding in what direction they should be running. And this is the information that you thought you’d get access to that remains elusive – the type of information that would help you make directional decisions. That information doesn’t exist because it is now your job to manifest it. (However, don’t forget to collect the information you do have access to.) And doing that well means not only manifesting this information but also doing it in a way that attaches your team’s work to the company’s needs. 

How do you navigate through this misty haze? Think about your job as turning uncertainty and ambiguity into clarity. Two really helpful tools for doing this are storytelling and decision-making.

Storytelling

The interesting thing about living through history is that it rarely feels historic in the moment. When they say history is written by the victors, your job is to think about your eventual success, what you want the historical record to say, and articulate those notable events and circumstances as they are happening. While this may sound simple, it’s not as easy as you think. As leaders, we sit on information all the time. We have a tendency to self-isolate, and oftentimes forget that we have only been talking to ourselves. A former colleague of mine is fond of saying that all actors in a system are behaving rationally for their given context. It’s a reminder of the effects of information asymmetry. You’ll find a lot of value in externalizing your inner monologue. Find ways to shape and convey context on a regular basis through various communication channels such as 1:1s, team meetings, a week in review, or town halls. I have a general rule of pushing any given piece of communication in at least three different channels. In a world in which change happens quickly and our collective memories have become extremely short, repetition is more important now than ever.

Making decisions

The first thing to know about decisions at this level is that if you don’t make a decision, someone or something else will make it for you. That’s not necessarily a bad thing, but knowing this can help you prioritize what set of things you want a direct impact on. The second thing to know is that the majority of decisions you make will represent some trade-off that will be difficult to quantify, with a low likelihood that all parties involved will come out happy. This can be paralyzing. 

There are a few ways to get through this morass. The first is to ask if what you’re trying to decide can be broken down into smaller parts. For example, if you’re trying to decide whether you should underwrite a two-year platform migration, start with just deciding how you would investigate such a migration. From there, you might discover you need to decide what the criteria are for moving forward. As you continue down this path, you’ll find that one set of decisions will flow from another, and reasoning about these smaller decisions will be far easier. Breaking these decisions down helps you understand if what you’re trying to do is complex or complicated, difficult or easy. 

Second, there will be a set of decisions that you are just not going to feel very confident in making. And for these, I find solace in understanding the Dunning-Kruger effect. The Dunning-Kruger is mostly known for mapping people’s confidence to their ability. The study demonstrated that people in the lower quartile of ability tend to overestimate their performance while people in the highest quartile of ability tend to underestimate their performance. But what’s less discussed is that folks with average performance have the smallest gap between their perceived ability and their actual ability, and by definition, most of us are average. So, if you feel like you only have 60-70% confidence in a decision, while it might not feel great, it is actually likely to be accurate and will probably be your new normal for a while. That is okay. Expectation management is part of management. It is more desirable to say you have middling confidence and deliver middling results, than to feign high confidence and deliver well below expectations.

Finally, there are times where we sit on decisions because we are afraid of upsetting folks – of creating winners and losers. This is, perhaps, one of the more corrosive forms of leadership. Ultimately, if a decision could have been adjudicated before reaching your desk, it would have been. You’re sitting with it explicitly because your team is seeking clarity for which they have been unable to derive for themselves. Abdicating your responsibility here prevents all parties from moving forward and allows context and narrative to splinter as you leave individual parties to continue on divergent paths and build up expectations that they will win out. For this, I’ll say that in all my years, I have found that people much prefer knowing if they are winners or losers to being left in a state of limbo and ambiguity. 

Conclusion

Personally, the transition from manager to director was markedly more difficult than moving from an individual contributor role into management. I had to establish a new support system, learn a brand new skillset, and get comfortable with occupying a seat of power (that’s an article unto itself). But once I understood the role as transforming ambiguity and uncertainty into context and clarity, I found the work incredibly rewarding. I got to set and execute strategy, establish new norms and practices, and invest in the next generation of leaders in my organization. 

Eighteen months is a long time to struggle with not knowing how to do your job. I do not recommend it to anyone. It took me this long partly because I’m a slow learner, partly because I was too caught up in reacting to daily events, and partly because it was a different time and the engineering management community was far less developed than it is today. So for anyone who’s looking to make the jump from manager to director, or struggling in ways similar to what I experienced, I hope this illuminates some of the journey ahead.