No Regrets: My Time in Management Wasn’t Wasted

As I’ve previously written, I spent a brief stint as a manager before ultimately deciding that management really isn’t for me and I moved back to the individual contributor track. When I’m talking to people, one of the common follow up questions people ask me is if I regret spending time as a manager. Do I regret the decision I made to go into management in the first place? Despite the fact that I really strongly believe that management is not for me and have been super vocal about that, I actually really don’t regret my time spent as a manager.

I learned about myself and what I like. There’s definitely a lot I learned on a deeper level about myself and what drives me, but I think the most valuable thing is that I now know for sure that I don’t like management. When I was trying to decide whether to enter management or not, I suspected that I might not like it, but I wasn’t sure. I spent a long time waffling over the decision. I spent a lot of energy trying to think through what being a manager would mean and trying to think through every aspect. If I hadn’t tried it, I would probably still be wondering about that choice. Should I try out management now? Did I make the wrong decision previously by not trying it? As it stands now, I know for sure that I don’t like it. I won’t say that I would never consider going back into management in the future, but I definitely don’t see it in the short term and I don’t have to spend any energy thinking or wondering about that.

Being a manager was not a setback on the individual contributor track. Growing up, I was always really driven, how do I get ahead as much as possible early? Get into the honors classes, skip some levels, get into the best school. A lot of it was about finding the most efficient ways to get to where I was going. It was natural for that drive to transition with me into the working world. How do I most efficiently get to the top of my chosen career track? How do I get to the next rung of the ladder? From that perspective, it felt like if I picked the wrong track, I would be totally wasting a few years, which at best would leave me where I started and at worst actually cause me to forget some things. I had heard people say that a career is a lattice, not a ladder, but it’s hard not to assume that even if it is a lattice, there are some paths that are more efficient for getting to the top than others. I wanted to be efficient. In all of this drive, I overlooked a few key points.

A career is long. A year or two is not that long when you’re talking about a 40+ year career. Even if I did get set back, over the course of the rest of my career, I have more than enough time to make that up to the point where it will barely make a difference, if at all. I’ve recently been listening to Michelle Obama’s book, Becoming, where she also talks about trying to climb the ladder as fast as possible and it made me realize that exploring early to get a sense for your options and what you like may actually be more efficient than trying to climb up the first ladder you find. Instead of spending a lot of time climbing one ladder only to find it was the wrong one, it’s actually more efficient to explore a few ladders and find the one you really like.

You don’t actually forget that much in a couple of years. Even though I wasn’t coding and really not even reading code by the end of managing, I found that the year or two was still short enough that I moved right back into coding very easily. I’m sure that if instead of a couple of years, it had been many years, my experience may have been a little different, but it’s also not like I was working a job in an entirely different field either. Even though I wasn’t coding, I was still working in engineering. I still knew what problems my team was working on and what technologies they were using. I still had one foot in the door and quite honestly, I wasn’t really even trying to stay current. If I had tried harder, I could have stayed even more in touch with the technical side.

You can overcome the changes in technology. I’ve heard people worry over the fast pace of technology and whether you can still be relevant when you come back. I’ve long believed that software is first and foremost about solving problems and everything else is just the tools to get there. I’m currently strongest in PHP and Java, but I have no doubt that given a couple of months, I could be nearly as effective in any number of other languages. It really is less about the specific language or technology and more about how to problem solve and approach new things. Interestingly, this area is one where belief in your abilities is almost more important than anything else. I’ve found that the times I’ve been unsure or thought that I didn’t know a language very well, I’ve been overly cautious or thought that there was a bigger knowledge gap than there actually was. Meanwhile, when I forged ahead assuming I knew everything, I made a few mistakes but generally did pretty well. All of this is to say that even though technology moves quickly, if you know your fundamentals, it’s easy to learn the latest trends and languages and none of this should be feared.

Management skills can still be leveraged as an individual contributor. Management is definitely different than coding, but some of the skills required to be a good manager still apply on the individual contributor track — especially at the higher levels. While it would take me forever to enumerate everything I learned (and I talk a bit more about that in this post), a few highlights include:

• Gaining understanding of a large variety of people in terms of what motivates them and how they view the world. I’d heard that everyone is motivated in different ways, but I didn’t truly internalize it until I was working with all of my own direct reports. I was able to see how what worked for one person might not work for someone else. By gaining this understanding and empathy, I am now able to better align incentives and work effectively with everyone around me now.
• Better understanding how our company works. Even at a company that tries not to play games, there are still politics. There are particular ways that decisions are made and things get done. As a manager, I got to see the cogs that make our company tick and gained a better understanding of how a lot of these things work. This allows me to better leverage the system now.
• Getting better at motivating, convincing and leading a team. This is obviously important for a manager, but as a senior person on the individual contributor track, you’re also seen as an engineering leader. At our upper levels, we expect our senior leaders to be able to lead large projects from a technical aspect, get other people on board with their decisions and convince people why something is important. We also expect them to be able to mentor more junior engineers and generally raise the abilities of everyone around them. While all of these have a more technical nuance on the individual contributor track, these are still directly things we expect of our managers.
• Better understanding my own managers and what issues/problems/challenges that they’re contenting with. I gained insight into how a manager thinks and what things can actually be more difficult. It’s also made me see my managers as peers. Both of these things are to say that I have a better understanding for how to get what I need out of my relationship with my manager. I have a better understanding for how to make certain things easier for them (for example, asking for very specific feedback will more often yield helpful responses than just generally asking ‘do you have any feedback for me?’).

It was easy to switch back. I know that in this aspect I was a little bit lucky in that my company let me switch back to being an individual contributor and even better, it’s not viewed as a demotion here. However, when I made the decision to try management, at some point I realized that right now in the valley, software engineers are in high demand. I felt confident that with a few weeks (or less) of studying, I could get myself into strong interviewing shape for a software position. As it turned out, my company let me switch back without this, but I felt confident that even if they didn’t, I would be able to easily leave management by switching jobs if needed. As I’ve come to realize since then too, there are actually a large number of software people who have moved back and forth between the individual contributor and management tracks over the course of their careers. Even though it seemed like this crazy divide to me, it’s not actually nearly as separate as I had assumed.

I obviously can’t make the decision for anyone else of whether they should go into management or not. I know that managing was definitely the wrong choice for me. I also know that despite the fact I ultimately ended up hating it, I don’t actually regret the time I spent managing. Never trying management can be the right decision. Going into management and loving it can also be the right decision. Trying out management even if you aren’t quite sure you’ll like it can also be the right decision.

Interested in joining Box? Check out our open positions.