Stepping Up - Becoming a leader in your team

Stepping up - Becoming a leader in your team

Hi there, welcome to Stepping up: Becoming a leader in your team.

When you transition from being a member of the team to being the leader of the team, it’s usually because of your demonstrated expertise and some unknown “leadership quality” that others see. Maybe you are willing to be opinionated. Maybe you are passionate about what you believe in. Maybe you are comfortable talking up and down the chain and across departments. Whatever it is, people see that you have “it” and want you to take it on.

And now your teammates start calling you “boss”.

My name is Jason St-Cyr, and I lead the team of Tech Evangelists over at Sitecore. Today I want to talk to you about the times in my career when I’ve made that transition from being a part of the team to leading that team, and hopefully how that can help you.

Agenda

We’re going to look at a few challenges over the course of this session:

1. How do you learn to delegate, and balance those independent contributor and manager roles?
2. How do you switch your mindset from being the subject matter expert, to being the coach of a team of experts?
3. How do you deal with the “in the middle” part of being in middle management?
4. And finally, how do you keep yourself for burning out in this process?

Letting it go.

So the first topic I wanted to tackle was delegation. Funnily enough, while trying to capture my thoughts for this talk, I was having conversations on this with some colleagues. It’s not easy to let go when you are transitioning from a task-oriented, independent contributor role into a leadership role, especially in the same team.

To delegate, or not to delegate

The first management role I took on was within a small product company, leading the R&D team. Smart team, great people. But I found I was still doing a lot of developer tasks while doing that management. When I look back on it, really, when I started taking on that role, I had a choice for myself to make:

1. Drop everything I had been doing for years and focus only on this new management role
2. Do the old job badly, and focus on the new leadership thing, and still not do it great
3. Do the old job and also do the new job

Of course I went with that option. So I learned a lot: SWOT analysis, product management, release management, and how to burn yourself out in under a year.

It was really tough to give up those tasks. I knew I could do them, and I knew it would take time to get somebody else to do it. Not only that, everybody on the team already had a full plate, so if I added my stuff to their plate, what was going to drop?

But guess what, when I burnt out and left that job, somebody had to pick up those tasks anyway, but now they didn’t have me as part of the team to help with it and guide folks. And you know what? They did great. I was in my own way. I was the only one stopping that from happening. So that was a big learning moment for me.

What did I learn?

So what did I learn? You can’t do two jobs well for any length of time without leading to burnout, and we’re going to talk about burnout later. Also, what I didn’t know then, but I understand now, by me holding onto these tasks, was that I was also blocking the team from growing their own capabilities. Part of me delegating, sharing that load, also meant being able to look at work tasks and determine what type of task it was.

Trying to do it all also meant that those tasks I was doing were not getting picked up by anybody else. I was still a bottleneck and was preventing learning and growth opportunities. When I stopped doing things, other people had better ideas on how to get the job done.

Learning to trust your team and delegate is an ongoing challenge, I’m not going to say I’ve solved this today, but I like to think I’ve learnt how to let it go just a little bit and give room for my colleagues to do their thing.

I work alone.

The next challenge we’ll look at is the challenge of switching from that expert mode into being the “boss“, leading a team. A lot of times, we are the experts on the team. We rise through demonstrated excellence at our craft. We show the ability to execute. We can get it done. But when you make switch from being the expert to leading that same team of experts, it can feel like you are starting over. Instead of all the skills you’ve built over the years, now your core focus is expected to be things like coaching, mentoring, project management, strategic thinking. But these are now what are expected to be your main focus.

When I first made that move to being a leader, I very much felt that I had no idea what I was doing. I was used to knowing what I was doing, leveraging my experience. I knew how to work on my stuff, and work with others, but delegating to others and leading in that way? That was all going to be new. Putting aside that expert hat was a big challenge.

Use your Spidey-senses

A lot of my expertise was also still very applicable, especially early on after the transition. Knowing what the team is doing in depth makes it really difficult to stop providing expertise.

On a call with one of my reports, they were asking me a question. With my head in ‘expert’ mode, I attempted to answer the question, doing heavy direction and going into a long-winded response of various things they could look into.

At one point, thankfully, they interrupted and explained that they understood the details, but what they needed was to see if I supported with them going with a particular approach. They didn’t need the ideas, they had that part.

My need in that instance was to be more careful of paying attention to cues as to whether somebody was in a situation where they needed heavy direction or support, or if they were looking for coaching, maybe less direction.

I needed to put aside that ‘expert’ hat and realize that now, people needed me for a different reason. It wasn’t always to get an answer. I needed to have more awareness of what the situation was.

What did I learn?

Ultimately, what did I learn from moving away from being the expert? I learned that my new role was not to be the expert at all the things the team is doing. I didn’t have to know more than they did about everything that was happening. And I didn’t need to have years of management expertise to do the role.

A lot of what I needed was about listening, coaching, reacting to the situation, and identifying what is needed in a situation. In some cases, my previous expertise could help with empathy as I could more likely understand the situation they were in and how that might be affecting them, but the real job was listening and changing the focus to them.

This is definitely one of the biggest things I still struggle with. It’s not an easy part of the job, and needs constant focused practice to slowly get better at it. I try to get better at it every day, and continuously evolve.

Caught in the middle.

One topic I want to talk about is the middle. Specifically, the fun role of middle management.

When you become the leader in your team, you start delivering pressures in multiple directions, and receiving it from multiple directions. Sometimes it feels like everybody is pushing on you, and it takes time to adjust to that. Sometimes it’s just too much, no amount of adjusting is going to help. In the end, we’re stuck in that middle and we have to choose where to push back.

Maybe the team needs a check-up

Several years ago, I was leading a group at an implementation agency. It’s probably one of the most extreme scenarios where I really felt pushed from all angles, and I didn’t really handle it well. And I wasn’t paying enough attention to how the team was doing and what they needed.

My team was struggling, trying really hard to get a project done but it seemed like everything was going wrong. Every initial estimate and timeline we had was thrown out the window. But of course, the customer had real world dates that could not be moved.

My team needed changes to the timeline made so they could be successful. My management wanted us to stay on budget. The customer needed the functionality live on specific dates because of business needs. I really felt the pressure of all these demands.

So I came up with a plan: We would do a gradual roll out of the functionality so that we could incrementally deliver to production. This would allow us to hit the various production requirements of the customer, but not have to get everything done all before the first deadline. We prioritized with the customer what was needed first, and it all seemed right in my head.

Except for the part where it was completely wrong.To make it happen, my team needed to work horrible overtime hours, going all out for each deliverable, just to make things happen. We were over budget. And barely making timelines. The customer wasn’t happy. The team wasn’t happy. My management wasn’t happy.

The whole thing ended in a massive “what went wrong” retrospective. There were a lot of things that went wrong. But I remember that moment of trying to make a decision and not fighting for “no” as an answer. I regret that.

What did I learn?

Saying no is hard, but I know it’s my job as the leader to say no. I need to push back on behalf of my team to say “This is not happening, this is not a reasonable situation”. Trying to make everybody happy at the expense of the team just doesn’t pay off, and ultimately eats away at my own credibility as a leader.

But I still struggle with No. It’s built into my core to try to support and help others, and I hate not being able to do that. However, others will usually understand. They are struggling with the same lack of time and resources as everybody else.

Saying No doesn’t always work. Sometimes you say No, and the response is “Do it anyway”. I learned that one. But in those cases when that happens, at least I can look back and say that I did the right thing for my team. I made sure I fought for what they needed.

Avoiding burnout.

Now the final topic I want to take on is very important to me. It’s about mental health. There must be a billion things written about burnout out there, most of which talk about work/life balance and self-care. I don’t want to rehash all of that, but I think that folks like us who are doing that transition between being a member of a team into leading a team face an unusually high percentage chance of burnout.

It’s a lot to take on, and it’s hard to pass off what we’ve been doing previously. There are built-up expectations of what you do, and now new expectations of what you will do.

Maybe I need a break?

Earlier, I spoke about the first time I went from being a developer on a team to managing that R&D team. I was not doing well, and it certainly felt like I had been working two jobs at the time. At one point, I had nothing left in the tank and started looking around for something different. Something NOT management. I put the blame squarely on the management job and my inability to do it.

I felt like I needed to be able to focus on something. Simpler task-based working. No strategy. Just getting the thing done. At least, I thought that was the solution.About 3 months into the new job, I was trying to lead groups, joining tiger teams, pushing for process changes. I couldn’t help myself. Yet, somehow I was feeling better? I wasn’t feeling as burnt out, but I was probably doing more strategic stuff in that role than I had been previously. What was going on?

Here’s a hint: it was the doing two jobs thing. I put the blame on my fit for management. Really, it was my inability to transition to the job, and not doing some of the things needed to make that jump.

What did I learn?

So what did I learn from this? In a lot of situations we are supposed to deal with burnout ourselves. Go off, take a vacation, you’ll feel better. But it doesn’t tend to fix the underlying issues. It’s just a temporary fix, but then you return to a systemic issue. Without resolving the systemic issue, you can’t solve the long game.The biggest thing that helped me was learning how to recognize my burnout symptoms. Monitoring your own mental health is one of the most difficult things to do. You also can’t just solve it with a short vacation, and you can’t always solve it by balancing work responsibilities.Sometimes it’s about saying no to some things, sometimes it means having a recharge outlet like a hobby. For me, 30 minutes of playing some video games on the Xbox allows me to recharge and focus in on something. Sometimes it’s about shifting between different task types (procedural and strategic) to help yourself not get overloaded mentally.

It’s a very long game we are playing in, and that means rationing ourselves over a long period of time.

Recap

When we started, I mentioned we would be looking at specific challenges in making the transition to being a leader in you team. We covered these 4 topics to see some examples of the challenges you can face.

And, from those stories, we took away some key lessons you can use as building blocks.

Lessons learned

1. First, Make sure to share your load, delegate those tasks you used to, and start getting used to taking on a more strategic role in the team.
2. Second, Listening is one of the biggest ones. You aren’t the hero anymore, and a lot of your leadership success is going to be driven on how well you can improve your listening skills.
3. Next, learning to say no is a hard, but necessary, step. Fighting for your team will help you out in a lot of ways, even if it feels uncomfortable to do so.
4. Finally, working on monitoring your mental health and balancing everything in your life will help you be ready for the long game.

Hopefully some of those stories of my own switch to leadership resonated with you. There was a bunch that we didn’t go into today, but I think if you use these basic building blocks you’ll be able to be ready for those other things when they come up.

Thank you!

You’ve got this!

Make sure to connect with me and let me know your thoughts on what you heard, I’d love to hear about the types of challenges you have been facing.

I know this is a continuous learning path for me, so hopefully we’ll see each other out there learning together.

Questions?

This is the fun part of the talk where we get to chat about what you’re dealing with, what your transformation scenario is. What hard lessons have you learned?