Stepping Up - Becoming a leader in your team

Welcome to Stepping up – Becoming a leader in your team

Hello everyone and welcome to the teaser for the session on becoming a leader in your team. My name is Jason, and I hail from the town of Ottawa, in Canada. I lead our Developer Relations efforts over at Sitecore.

Today, I want to chat with you about that awkward moment when you go from being just another one of the team, to then leading that team.

When you first transition to go from 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. Maybe you are really opinionated. Maybe you are really passionate about something you believe in. Maybe you’ve shown you can really work up and down the ladder and across departments. Whatever it is, people see that you have “it“. Now they want you to take this on.

Then your teammates start calling you “boss”.

But while you’re doing this it can be tough to give away being the hero, building the thing, saving the day, being that expert. There’s a dopamine hit you get every time you push a task to done. And taking on strategic work, it could take months, it could take quarters, it could take years before you see success from your efforts. So it can be hard to let that go of that other side of the world.

I want to talk to you about the times where I’ve had to go through this transition myself, and hopefully how you can learn from what I went through.

Agenda

In the full version of this session, I cover five key challenges:

First, how do we learn to delegate, and kind of balance our independent and manager roles? Secondly, how do we go about doing a different style of decision making. You know, when you’re not sure how things are really going to turn out? Next, why don’t we take a look at how we switch your mindset away from not being the subject matter expert anymore, not being the hero, and instead being the coach? We also want to take a look at that “in the middle” part of middle management And finally wrap up with a little bit about mental health and trying to prevent burnout

Today, we’re going to take a look at the first one: Letting it go.

The power of stories

You might have noticed a little bit of a theme around toys. This talk is a lot about stories, and what we learn from them. Now as a dad, I’m finding that stories are a great way to use toys and teach my kids about something and have it resonate.

Stories allow for us to create an emotional connection. It also allows us to have an easy recall for something. So, for example, if you’re into Star Wars, I might say something like “Let the Wookie win” and you’d know exactly what point in that story I’m referring to and you’d be transported back to it.

So, we’re going to go through a lot of stories today, and hopefully you are going to be able to use those stories to come back to a learning moment. And for those of you out there creating your own stories right now, make sure that as you’re learning, you are creating those recall moments that you can come back to.

Now let’s get started!

Letting it go.

This challenge is all about 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, 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 in 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.I wanted to have it all, no priority decisions, no dropped tasks.

Eventually, I burnt out, I left that job, 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 a 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.

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So what did I learn? Well, I learned the “Don’t do two jobs at once” thing. That didn’t 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 to stop being the bottleneck and making sure the right work was going to the right people who had the right expertise

Ultimately, I had to learn to trust my team. 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.

Thank you!

Now, I only have time today to go through the first part of these stories, but I’d love to have you join me at the end of July for the full session and we can go through some other challenges like moving to new ways of decision making, taking off the SME hat, middle management, and mental health.

How are you handling the transformation? How can I help?

I think we have a little bit of time now, so let’s move on to see if we have any questions from the audience!