I made a mess of managing a project which was being delivered by a new employee. Why it all went wrong is pretty obvious to me now. But in the moment, I made an assumption about what good management looks like — an assumption I now know to be completely false. I assumed that the type of management I like is the type of management that everyone likes. Allow me to explain.
Builders and Drivers
Something I love about working at a tech startup is the get-shit-done culture that is rewarded and encouraged, especially in the early days. What I mean is the attitude that if I don’t figure this out, it’s not going to happen, and the fire that it lights under you to get something done. It’s the sense of urgency that draws five people from across the office to one computer screen to solve a client’s problem together — because if we don’t fix it, no one will, and the client will churn.
That attitude is imperative in the business’ early days. A startup is built by people who have a willingness to be the first person to do something with very little guidance or instruction, people who risk complete failure in order to make something better for the next person who attempts the feat. I call these people “builders” and consider myself one of them. We are inspired by ambiguity, motivated by new challenges, and take pride in “figuring it out.” We thrive when we’re trusted and given space to problem solve.
A business can’t only be made of builders, however. That level of urgency must be tempered over time in order for the business to succeed. Eventually, the company needs to reach a level of stability where the builders have laid the foundation for growth, and it’s time to hire folks who can execute on the systems and processes that the builders have put in place. They’re more like drivers, who have autonomy to execute, and range in their ability to self-navigate based on their experience in the driver’s seat.
The profile of these newer hires is different. For starters, they tend to be more risk averse. This makes sense because the business at this point is more established, probably venture-backed, and has a much longer runway. These newer folks want to be part of a growing business but also value having systems and processes that set them up for success. They are equally as important as builders because they stress-test the systems put in place and optimize them over time, allowing the business to scale.
Learning Moment
So let’s go back to my mismanagement story. I was a builder who moved into my first management position as the company grew. I had learned from previous managers what I did and didn’t like. I was determined to emulate the people who I felt were great managers — people who had given me tons of latitude and trusted me to figure things out. But that’s what worked for me, a builder. Micromanagement is our equivalent of nails on a chalkboard, and is the most effective way to demotivate us. (What I might celebrate as “space to operate” could be defined by someone else as “a total lack of guidance and support,” however.)
I was a newly minted manager with a recently hired employee who was earlier in their career. I assigned this new employee the task of developing a case study with one of our strategic accounts. Without question this was going to be an important asset, one that we would pump through our marketing campaigns for 6-12 months. It was a high visibility project, something I thought would give this person an opportunity to shine and make them feel valued. I offered some high level guidance, and sent them on their way to execute.
The project didn’t make a ton of progress. I was frustrated with the pace — the project timeline was slipping leading up to the holidays. But I didn’t change my tactics. Instead, I left this person to their own devices and kept giving them the space I would have wanted.
My report shared their work-in-progress with me the day before our office closed for the holiday break. Needless to say, I wasn’t satisfied with the outcome. The project was already far behind. We had intended to send a version to the client for review before the holidays, and that was certainly not going to happen.
I went into all-out builder mode. I felt I needed to take matters into my own hands. I didn’t share any feedback with my report, and I rewrote the piece over the holidays. When the office reopened, I shared the news with my report. It did not go well. They felt I had set them up to fail, and that rewriting the piece myself had demonstrated my lack of faith in their ability to deliver.
Management Styles
Unfortunately, what I missed was that this person needed a very different kind of management to succeed. “Good management” for this person would have involved me setting clear expectations of the structure and content of the final piece, a mutually-developed workback plan they could commit to, and pre-scheduled check-ins on progress so they wouldn’t need to feel self-conscious about asking for help, for example.
Ask for Guidance
Everyone on your team will have different needs of you as their manager. If it’s not obvious to you what these differences are, ask! Especially if it’s early in the relationship. Let people tell you about what good management looks like for them.
Ask for regular feedback on your management style. It can be scary for a direct report (new or otherwise) to proactively tell you what’s not working for them. Asking for feedback proactively makes it less awkward, and much more likely that you’ll be keeping your managerial relationships on track. Just make sure you actually do something with that feedback you receive, or you may not receive honest feedback in the future.
The Buck Stops With Me. What Can I Do Better?
What I learned from this experience is that if someone on my team is not delivering, the first place I should look to understand why is my own management. Now, there might be a skills gap at play, and in fact there should be a skills gap if I am giving my team the opportunity to stretch and try new things. But even still, my job as a manager is to help bridge that gap and support people as they take on new challenges. It’s on me as a manager to figure out what I am doing that isn’t setting that person up for success.
If something’s not working, take a minute to reflect on how you might be contributing to the problem. If you can’t come up with anything, that’s a good signal that it’s time to get some feedback from your peers and/or direct reports. Take it from me. When the project was going off-track, I did not stop to ask my direct report what I could be doing differently to help. I know now that if I had stopped and course-corrected with feedback, I could have avoided the rewrite-over-the-holidays-and-lose-trust debacle. The mistake still stings, but I learned from it. I’m a better manager now because of it.
