• Jason St-Cyr

Becoming a Leader – Letting it go

In this series, I’ll be writing about some of the challenges of transitioning to being a leader within the team you are in. In this article, I’ll cover delegation and letting go of your previous responsibilities.

When you first transition to go from being a member of the team to leading that same team, usually it is because you demonstrated some sort of expertise. Some sort of “leadership quality“, maybe. Others see it. Whatever it is, people see that you have “it“. Now they want you to take this on.

Then your teammates start calling you “boss”.

Now the first challenge I wanted to talk about is delegation. When I speak with my colleagues and other managers, a lot of us have had the same experience. In general, it seems to be very hard when you’re inside of a team, and transition to leading it, to give up some of those tasks that you used to be doing. This was definitely true for me!

To delegate, or not to delegate

The first management role I took over, I was in a small product company, leading the R&D group. Smart team, really great people. I found I was doing a lot of development work, even though I was supposed to be managing the team.

Now I look back at it, and, I guess what happened is, that I gave myself a choice. I said to myself:

  • Hey, you could throw away almost a decade of experience and everything you’re good at and really focus on this management job

  • Or, you could do two jobs really poorly,

  • Or, you could do both jobs and try to do both well!

So of course I went with that option, right? I learned so much: I learned about SWOT analysis, I learned about product management, release management… and how to burn out in under a year.

It was super tough to give up those tasks that I was used to doing. I knew I could do them, I knew it would take time for me to get somebody else to do it. Not only that, everybody’s plate is super full, so if I’m giving this to somebody else, something’s going to drop.

How do I need to handle this?

Eventually, I burnt out, I left that job, and then somebody had to pick up those tasks anyway. Except now I wasn’t there to help or guide them through it. And you know what? They did great! I was the only one preventing that team from going forward. That was a big learning moment for me.

Am I holding the reins, or pulling the sleigh?

Now I’ve had this scenario repeat a few times, where I’ve done this transition into leading the team, and it was hard to let it go. I knew I needed to delegate, I knew I had tasks I shouldn’t be doing. Even just recently I started training somebody up on how to upload videos into our portal. This is probably something I probably shouldn’t have been doing for years!

I needed to get better at looking at my tasks and seeing what type of things were they. Are they strategic, driving tasks? Or are these tasks more at the execution level, more independent contributor tasks?

If a task is strategic, driving the team type of task, that’s probably something, as a leader, I should be working on.

Is it something that requires absolutely no expertise? If literally anybody could pick this up with some basic access and instructions, that’s definitely the first thing I should get off my plate.

The hard one is the learned expertise. Meaning that I could help somebody else learn it, but I’m probably the only one who knows how to do the tasks and it would take significant time and effort to get someone to up to the level where they can take over the task. Those are the tough ones to let go.

In the subtitle here, I refer to the concept of holding the reins and pulling the sleigh: the sled driver and the sled pulling team. As a team, the sled needs to get somewhere. Someone is doing the really hard work of making sure that sled is moving. The driver needs to be able to take a look, give nudges and guidance to make sure the sled gets to where it’s supposed to go. Together, you succeed. And you can’t effectively do both at the same time.

What did I learn?

So what did I learn? Well, I definitely learned the “Don’t do two jobs at once” thing. That did not work for me. I also learned something that I didn’t know then, but I see now: that I was blocking the team from growing. I was keeping them from expanding their own capabilities. And from doing it better than I could.

I learned that a part of me delegating, aside from me lightening my load, was making sure the right work was going to the right people who had the right expertise. Trying to do it all meant that tasks were not getting picked up by anybody else. I was a bottleneck and I was not providing growth opportunities. The job is not getting done right!

I had to learn to trust my team. I needed to be able to say “This is not in my ballpark, this should be somebody else’s work”. And I’m not going to say that I’ve solved this completely today, this is an ongoing challenge, but I like to think that over time we get better and better at this. Better and better at being able to give away work that somebody else could probably help us with.

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