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Becoming A Leader In Your Team

One of the most difficult transitions to make is from being a member of the team, to owning your former teammates performance reviews. It is awkward. It is stressful. And you can do it! In this session, we'll take a look at the challenges of making this transition and how you can face them head on. Leveraging the years of experience I've built up, you can learn from my healthy backlog of failures, poor decisions, and generally bad ideas. These mistakes were what helped me to learn, and now you can too!

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Thanks very much. Well, everybody, welcome to stepping up, becoming a leader in your team. I am Jason, as mentioned. I come from Ottawa, Canada, so you might hear a little bit of the Canadian accent coming through. One of the things that I like to do as part of this talk is talk about all the failures that I have done as a person who has tried to do this multiple times.

So I'm here to talk to you about what did I do wrong so you won't have to make the same types of mistakes and learn something from what I've done. I've talked about there is an awkward moment when you're that member of the team, and then suddenly you go to leading the team. And you know, you first make this transition, and it feels a little strange. Somebody saw something in you. You're good working up and down chain and maybe you can collect teams from different departments together, or you did a project, whatever it is. Somebody saw that you have "it", and they want you to take this on. This leadership quality is great, but awkward when your team-mates are calling you boss, and you are in charge of their performance reviews. And it can be hard when you're transitioning to let go of all that stuff you used to be doing. S

trategic work is a very different type of work. You might be used to the you take your task, get it done, and now you're doing stuff that takes quarters or years before you see success. I will go over four main areas before first, talking about delegation. How do you balance out the independent stuff you're used to doing with now this new manager role? How do we switch our mindset? Go away from being a subject matter expert to more of a coach behind the scenes. And then there is the fun part of middle management which has been stuck in the middle. We will get into that, and finally, an important section on mental health, how to prevent burn-out, just a few tips and stuff from this type of a transition.

Now, you may have noticed a little bit of a theme with these pictures. A lot of toys. I have three daughters, young, and we use stories to try to teach and have something resonate because stories have an emotional connection, allowing us to recall something. If you're, say, a Star Wars fan, if I said "Let the Wookie win" you would be transported to that point in time in the movie. How do we take the stories of what we've done and fin the recall moments, the point where something important was learned so that we remember and can go back to that? And you're making your own stories out there, just like I have, and hopefully we can find a way to bring those stories together and crease note learning moments.

Now the first challenge I mentioned I want to talk about was something I've talked to a lot of managers and colleagues about, and this is a whole delegation business. When you're an independent contributor, stuff gets brought to you, and you get it done.

Now that you go into being a manager, now you have to find a way to take things and bring them to other people. And it can be hard when you're used to being inside the team to start transitioning stuff to other people. I know this was hard for me. When I first became a manager, my very first time, I was at a small product team, and I started leading the R&D group. It was a small team but great people, loved it there. But I was doing a lot of development work when I was supposed to be managing the team. And I didn't know it at the time.

It took some time removed from the position before I was able to look at it and go oh, I guess I gave myself some choices. I could, one, throw away a decade of experience doing what I did, everything I was good at, and then try to figure out this new job, or I could kind of do some of the other stuff that I knew, and then not really do the new job great, or, and this is the one I went with, completely redo the old job I was doing, and then pour myself into learning this new management role and doing it really well. That seems like the win-win option, right?

I learned a lot. I learned about swat analysis, I learned about product management, release management, all kinds stuff. I also learned how to burn out in under a year. Which was not fun. It was super tough for me when I made that transition to give away all that stuff I was doing. I mean, I knew I could do them, and it was going to take me a bunch of effort to get somebody else to learn it. But not only that, now as the manager of the team, I can see what everybody else is working on.

If I'm giving my stuff down, that means something on their plate has to drop. I don't want that. How was I going to handle that? The approach I chose seemed to work well for a while, but ultimately, it didn't work for me, and I wasn't able to handle it, and I burned out, and I left that job. So guess what happened? My task got picked up by other people on the team. And they did fine. They prioritised. They figured it out. The only person in the room who was having problem with it was me.

So that was a learning moment that I came out of that, that this can always get done, and people will always get the highest priority stuff, will get done next, so that was a key piece that I had to learn. I repeated the scenario a few times, and I've never done it perfectly, like even this last time when I became, went up from being a Developer Advocate to a developer advocacy lead, I was still uploading videos to YouTube and things like that, for years, without — that was a task that easily should have been done by somebody else. I knew I had to get better at looking at tasks, what type of tasks, OKRs, that are looking at the whole team, strategy, those are clear.

I could figure out that stuff that I should be having on my plate. Things that literally anybody could do with a little instruction, and some access, those are easy. Get those on to somebody else's plate. Those don't need to be on mine. The hard one, though, is the learned expertise. That stuff that maybe I'm the only one who knows how to do it, or it would take a really long time for somebody to be able to learn how to do this. There is a huge investment there to get someone to take that on, and it can be hard to give that stuff away.

I mentioned over here in the slide that the concept of the sleigh, somebody's got the reins, somebody is pulling. In that metaphor you've got a team getting — you need to have a driver looking at the what are the obstacles in the way? Are we going in the right direction and try keeping us on course? And you need both. And it is really hard to effectively do both at the same time. So you need the whole team to be able to get where you need to go.

So what I learned from this, first of all, I should not do two jobs at once, it doesn't help for me mental health-wise, so avoiding that. I learned was that I needed to share. I needed to stop blocking the team from growing. They could probably do this better than me if I gave them the opportunity, and that was one of the roles as a manager how do I give opportunities to other people so that they can succeed?

My role was not to try to get it done. And also, even when I was trying to get it done, now I'm the blocker. I've got other pulls on my time too, and that is no good for the team anyway. I had to learn to trust my team, learn to be able to say okay this is not what I should be doing, let's get the right people on it so the right work goes to the right people at the right time.

The next section I found hard was turning off the expert mode. You build up this years of experience, you really are good at something, and then you become a manager, either for the first or second time, and, "I don't know what I'm doing here." Like for me, I was used to working in a mode where I knew what I was doing. I had built up years of experience doing it, and suddenly now I didn't know how do I do this next piece? How do I do the new task? I'm starting to learn all over again.

And so you have a confidence issue there. And a lot of the skill sets that you use to become a great independent contributor can translate a little, but I felt it was a little bit like imposter syndrome, and, along with that, how do I get my team to trust I'm going to make the right decisions? How do I get them by and how do I get them involved in this? How are they going to look at me and say, yes, this is going to work, right, when I clearly don't know what I'm doing? My team-mates may never have felt this. That's how I felt going into that transition, making that change, so I eventually learned from others how to get some of this done, and one of them was the concept of an early win.

This actually works whenever you're doing work for a customer, or working on any project, have something with your new team, in the new model, succeeds. It can be big or small. If you win early, then that becomes the normal. And then when something wrong happens later, that becomes the thing that is unusual, because everyone in their mind has already said, of course this is going to work, that must have been the aberration. So that is a tip that was given to me.

Second, how to be more empathic and think about other members of the team. As an independent contributor, you're focused in how do you do well, and how do you succeed in your career? I have to think more about how do I make them succeed? What are their challenges? By doing that, and having the conversations, that helps them trust you more because you have a better idea of what they're going through.

But in that first, I think the one that helped the most was honesty, and we talked about this just before the call was how do we be more honest and more transparent? How does that build trust? The saying things like this is going to be new for me, I'm going to need your help along the way as we adjust to this new model with right, or you're being open about the fact maybe there's going to be bumps along the way, and that helps build that trust.

Now one other thing that is in this kind of area that I encountered was the concept of being able to know what people are coming to you for. I'm used to, as an independent contributor, as an expert in something, being the subject matter expert, and they come to me and they want my expertise.

I was on a call last year, maybe two years ago, one of my reports came to me, and they asked a question, and I went into expert mode right away. Here are all the options, the pros and cons. I'm going through the stuff, and they, thankfully, stopped me and said, "Jason, I know about the options, I already have put together a plan, I've gone through that stuff. What I need to know is can you support this plan? Do you see any issues with us bringing this to upper management," right?

This was a lightbulb moment for me that I was totally coming at this thing the wrong way, not identifying what somebody was coming to. I was used to being the expert. Now I've got the expert coming to me who is looking to me for the stuff I have access to as a manager. The stuff that is outside our team. And trying to get me to buy in. But sometimes, because I've been an expert, people will come to me and they do want my expertise because I've done something a lot of times and they have me mentor them through it.

One of the things I had to learn was how do I situationally figure out and sometimes the, like, hey, what kind of feedback are you looking for on this? What is the situation here? Which hat do I have to put on? And all of this, what it came down to was a lot of listening.

I know everybody talks about you've got to listen more, really deep listening, and all this stuff. It's really key to being able to know which part of you needs to come to the table, and how do you build trust, how do you connect with the team, and switch the focus? Because it's not about you any more. Now it's about them. How do you make them the focus of everything you're working on? Now, I'm not going to day say I'm an expert at this. Day-to-day, I have to work on this.

If we get better and better saying I have expertise in this area, but what do you think? And that allows us just to build up a better team, connect a little bit better, transition a little more into that leadership side.

Next topic. I wanted to such on was the fun part of middle management, oh, when you take that step up, and you first just see how many directions it can pull you at once.

You also get your own team pushing up at you different requests, and they need stuff from you, your management needs stuff done, you've got other teams in the organisations who are coming in at you, and sometimes you manage to juggle it all, and it seems like it's good.

But then all of a sudden, it all comes in at once. And now you've got to start pushing back, and that can be tough. There was one time several years ago I was on implementation agency, essentially working in a team lead as a group that delivered projects for customers.

It was probably THE most extreme scenario I have had of being pushed in on all angles where there was, you know, a high risk in it. I definitely was not paying enough time to pay attention to what my team needed. Because my team was struggling with the project. And this project was not going well. Like if something could go wrong, it went wrong.

If we had a timeline, it's out the window, it's not going to happen. So, I was looking at it, and we were too late now, I'm going to my team, and they're like we need more time. The timeline has to change. We can't get it done. But the customer had these real-world dates. There was nothing we could do about it. It was out of their control. It wasn't like they could say go and do a new date. That wasn't going to happen. Go to my management. No, the if you get is fixed, we cannot afford any more people, any more time on this.

If you're familiar with the concept of the iron triangle of resource management, it was — oh, definitely the most strict iron triangle I've been stuck in. I'm in problem-solving mode. How do we overlap? I had pitched a plan. Everybody was like okay, that could work, and then, of course, everything goes wrong, given how everything had gone so far. But we did it. We did it by having the team pull a ridiculous amount of overtime, super high stress, we got it out the door, big celebration, and then the whole thing starts unravelling, because now we are over budget, so my management's not happy, and the customer's not happy, because one of them is going to have to pay for it.

The customer was stressed out the whole time not sure we were going to make the deadlines. Down to the wire. They're not happy about the situation. My team, I've made them do weeks and weeks of really stressful high-risk, lots of work, they're not happy. So we go into this massive retrospective, what went wrong, and there was a lot. Right, refilled a whole lot. But with the one thing, the one thing that I took out of all of that was at no point in an entire process did I say, "No, it's not happening." I was always in, "How do we make it happen?" Which was great from a problem-solving perspective but not great from a leadership perspective. I didn't stand up for my team, and I regret that.

And another example of when you get into this pressure of like balancing different things as loyalties to different people, you probably heard the phrase "HR is not your friend" and apologies if you have any HR professionals listening here, this is not just HR that that is about, right? In general, at larger companies, processes are designed for managers and leaders to protect and enhance the company. That's their goal. It's not about the individual.

Sometimes these pro he accesses align, and what is good for the company is good for the individual. Some examples could be managers getting software for your team, for example. You might have to go through a procurement process to evaluate different vendors, that type of thing. Or you might be hiring a contractor that might be a specific way that you do SOWs to protect everything legally. You could be acquire another company, and then certain people of leadership are pulled into that, and there are certain things that you can talk about, and certain things that you can't. There are certain rules around that.

The one that is hardest for me is having to let somebody go. When it comes to saying goodbye to a team member, oh, this is really a case where the process is not your friend. There are tons of great management people out there, tons of great HR people who work to advocate for employees all the time, but if you look at the role of what an HR system is, it is about the people around the company, it's not about an individual necessarily. It becomes a tough situation when you're looking at letting someone go because that's about the individual.

There are emotions, careers get involved, and you as the middle manager are between the corporate process and your team member. This becomes a difficult situation for you. If you've got a good people team, they've probably got FAQs, guide, a script to help you with this, you know what to say.

Sometimes, you may be told not to deviate from the script because there's specific wording that's been picked because there might be legal issues or you're supposed to have minimum information shared, or you just are supposed in general to control the situation from an emotional perspective.

Now, when you're a people leader, if you act like I am, I have that instinctive reaction to reject that, because I'm trying to listen. I'm trying to be empathic, trying to do what is right for my team member. And reading some robotic script doesn't align with that. Now I'm feeling this pressure of who do I listen to? If you want a responsibility to my employer. I need to respect that. I have a responsibility to the continuation of the rest of the team, but I also have a responsibility to my team member.

And the tricky part is balancing both. I think if you're put in this situation, my advice would be to push back and do what is right for your employer. Not everybody's in the situation where you can push back and maybe those are times when you can remember like the little tag line here, the process is not your friend.

Sometimes doing what is good for the company is not going to be what is good for that individual. And for me, in this situation, that is when I have to make a cull of how much do I follow my instinct, and how much do I follow the process? Are there things that I can do to change it up? Kind of play both sides? Are there ways I can personalise the message to acknowledge the connection we have had as a team member? Ways that I can help? Maybe there's a way I can help them find their next position using my network. How do I capture the right tone? How do I give them the feeling that this matters?

And all the while, this is really hard. Like how much do you push back? You probably should not go and blast your company on Twitter, for example. There are certain lines you should not cross. So you have to show respect to the organisation, but in the end remember, careers are really long. You're going to work with other people. Your reputation follows you, so I think the Agile manifesto got it right here. People over processes.

All this comes back from different — my role as a leader is to say no, to push for my team. Every time I try to make everybody happy at the expense of my team, it backfired on me. How do I make sure that I am pushing back and doing what is necessary so that my team is as strong as possible? But that is hard too because I'm a people pleaser.

I'm one of those individuals who really want to help you. I want to be helpful. I want to see you succeed, and saying no to you is hard. I found it is easier when you're doing it upwards rather than going down or sideways, so you can hold those nose for things coming on top, that can be helpful. Sometimes saying no doesn't work. You push back, and you're told, do it anyway. That's tough. At least you can hold on to you did your best, fought what you pleased in, and you did everything you could. The last section I want to talk to you about is really important to me and this is around mental health.

It can be really tough when you make this transition to balance everything out and avoid burn-out. I think that people in the position of being in a team, and then immediately leaving that team have a lot of pressures and pulls on them that can put us in an awkward position. There are a billion things out there about work-life balance self-care. I want to pull out a few things that I thought were important for elements that you can watch out for.

One of them is whether or not you are balancing everything on your plate early. I talked about it earlier as the product R&D lead and burned out in a year. I was not doing well mental health-wise pip certainly felt like I had been going full out way too much for that time. And at one point, I leave, and my thought process out there was that I'm not right for management.

I'm not like these other people who are up here doing, they all seem to be doing great. It must be something about me. I should go and do something else that is not management. So when I went and got the next job, I went and got something that was supposed to be more technical, more in the trench, like, more task-orientated. And then within a few notes, I was suggesting process changes, leaving groups, trying to get into tiger teams. I couldn't help myself. That's what I wanted to do. And suddenly I realised it doesn't feel the same. I'm not feeling the same pressure I was before. So what was different?

The difference was when I went into this new position, I now had control over my expectations, because there were no expectations on me. The difficulty in the previous position didn't matter when I was fit for management or not, the fact of the matter is win didn't transition out of my old role. So a key piece here is to look for that: are you transitioning? Because if you don't transition, you can get stuck trying to do too much. And on that topic of going and doing too much, it's not just about doing too much work, it can also be about when life starts getting too much.

So a couple of years back, it's been almost three years now, since March 2020, a lot of people have been having challenging times. And it takes a toll. Now, for me, before the pandemic hit, I was a remote worker, globally distributed team. My work didn't seem really to change. If anything, I couldn't do events any more and travel like that, so it was getting easier, but I felt like I was hitting a limit. Why? I recognised some of the burn-out feelings. What didn't occur to me was I wasn't balancing life into my equation. I was trying to avoid the problem I had before — that I had too much work. I was looking at my work tasks: am I balancing my work tasks properly? It didn't occur to me that life needed more from me and I had to reduce what I was doing at work.

That is one thing that kind of pulls on you. Another element is when you lose a loved one. In July of 2019, my mother-in-law, Pat, was diagnosed with pancreatic cancer. We were trying to do everything we could, then in summer of 2021, things got really bad. My family really needed me. Not just during off hours, like all the time.

We had, like, it was hard to say, like there are these great projects, I'm not going to be a part of it, but also hard to keep a straight face and pretend like quarterly reports mattered at all to me at all right now. It didn't seem important. I realised that part of what I needed to do was to be able to step away. And do that.

And then it occurred to me that my management was letting me do this. They recognised something maybe I hadn't done up until then was, when give your team-mates space to do what they need to in that I life, you will get back better. If you push them through it, it's ultimately not going to work.

I recognised what I needed in that time is what my management gave me. How was I going to bring that to my team, ask right questions to ask how they were doing, support them when something went wrong for them? How do I give them that space so give them what they need for their mental health. It's a heavy burden to carry when you have loss, and sometimes you need help. And sometimes as a manager, you're going to be that help for someone else. You're going to be able to make them get through it.

And all of this came down to balancing, balancing everything. The whole look and seeing what goes right. Sometimes, that's about doing less. Sometimes, it's about doing the right thing. Different work tasks have different stress levels.

Maybe there are tasks you can do that are fun and give you a break. You want to look for recharge moments. I play XBox for 30 minute, whatever, just helps me get into a different head space. And those types of things, maybe for you, it's learning a new code piece, or make a fun video on TikTok, or something like that. Whatever it does that does it for you, those help with balancing, sometimes, it's adding.

Over the course of this session, I went through a bunch of stuff. Mainly these four topics. We talked about how do we let things go and share it with the team? How do we listen more and know that it is not about our expertise, it's more about the team that we've got to be in that coach mode? Talked also about pushing back, being able to protect your team and fight for them, and also how do we balance things, because we need to be there for the long run.

A bunch of stuff I didn't get into today, and you've got a bunch of stuff on your plate too, but thank you so much for spending the time here. I know you got this. I want you to connect over on my website be you can find links to all my socials. Connect with me. I want to know what you're going through and what challenges you're seeing. How did you solve it? For me, I'm on a continuous learning path. I want to hear from you. Thank you very much for your time. Do we have time for some questions?