Over my career, I’ve had the opportunity of being a manager from time to time.
In my late teens and early 20s, I worked at Toys’R’Us. I stocked shelves, hopped on cash, built bikes, and unloaded trucks. It was retail but it was a job and it paid the bills. Barely. Kind of.
The hierarchy within a given store is the store manager, the assistant manager, the department heads, and then everybody else. At one point, I was promoted to department head. As a department head, there was no pay raise but you were given the added responsibility of managing a section of the store. There was no training for the role.
On a busy day, I remember trying to delegate some work to someone else so that I could help another customer. The employee said no. Huh. Well, um, that’s … uh, not helpful. As a department head, I had no authority. There wasn’t anything I could do. I soon realized that responsibility without authority leads to frustration.
In my mid 20s, now in my career as a web developer, I took on the role of project manager. Break down a project into its constituent parts and delegate.
I think I did an okay job as a project manager. I learned how to budget time for projects (take any estimates and double them; the salesperson would then take my estimates and double them again). I delegated to the people I had available.
Sometimes, though, I got frustrated when things took longer to finish than I thought they should. I remember a couple devs trying to get a SQL Server up and running. After 2 days, they were no further ahead. I jumped in and had it running in a couple hours. I started doing more and more of the work myself. I realized that maybe I’m not that great at delegating.
In my early 30s, I worked as a freelancer. Nobody to manage, nobody to delegate to. I had a fairly successful career as a freelancer (albeit with the usual ups and downs in cashflow). Sometimes things would get busy and I’d think about bringing someone on to handle the overflow of work.
I subcontracted from time to time but could never muster the courage to hire someone full time. Knowing my history as a manager, I didn’t feel that I could handle it. And so I didn’t.
In my late 30s, I worked on a small team, all of which worked in an office while I worked remotely. When my manager quit, I was given the opportunity to lead the team.
It’s difficult to have much oversight working remotely with a team that’s not set up well to do so. Communication broke down and the role moved to someone in the office.
I realized that I work well autonomously—something that doesn’t work well when you’re the go-between for multiple teams.
In my early 40s, I advocated for a new team to exist and I was asked to lead the team. I resisted but eventually said yes.
I read books on management. I read books on building performant teams. I did 1-on–1s and tried to mentor the people on my team as best I could.
At the same time, I had a product roadmap set out and delegated to the team to move the product forward. Everybody on the team did fantastic work.
When I left there, I felt like I had finally done a decent job of being a manager. On my way out, I worked to find someone to replace me. I tried to find another me.
What I didn’t do, though, was to ask my team what they needed in a manager. I assumed I knew what the team needed and what the company needed. (I have a habit of assuming I’m always right.)
I’m back to working by myself, for myself. I still have a long career ahead of me and I suspect I will again be in the position of managing a team.
In recent discussions with friends, we’ve talked about working for bad managers. I’ve worked for them, too. To which I said, “maybe one day, I’ll run my own company. I’ll be the bad manager, everybody will quit, they’ll run their own company, and the cycle will be complete.”
Management is a very uncomfortable role for me. It doesn’t come naturally. If and when I find myself in that position again, I hope I’ll be better. (And maybe realize that I don’t have all the answers.)