Becoming a Leader: From Title to Trust

It used to be that whenever anyone asked me what I wanted to do in my career, I said that I wanted to run a support team. I wanted to manage. But over the course of the past few years, that has shifted. Now I want to lead. Let me tell you: it’s easy to say “I want to lead. I want to be a leader.” Almost as easy as it is to say “I want to manage.”

But what do those things mean? How do we get from managing to leading? Well, let me start from the beginning.

I’ve been working in support on and off for the past 15 years. Those of you that know me or have heard me talk know that I took a break for a few years there to work in coffee and just generally enjoy some prolonged adolescence. This time, I’ve been working in support for 7 years. I was a Customer Champion at Wistia, then started conducting 1:1s in a leadership capacity sans title; then I moved to Campaign Monitor where I was an integrations manager for a team of 1. Next, I moved to Trello as a Support Engineer, became a team lead, and eventually, head of support.

A lot of these roles were things I was doing before I had a title—I was leading prior to managing. But I built additional trust with my fellow team members and got their buy-in with each new step I took. And that’s what I’m going to teach you how to do today. Keep in mind, some of the things in this talk might not resonate with you, or maybe you’ve never wanted to be in management. That’s okay! There are other opportunities besides management, but most of the lessons here are going to be most applicable to that job path.

First off: management is different from leadership. When you lead, you inspire the people around you and lift them up to do greater things and take steps towards a larger team vision on their own. When you manage, you make sure that they are doing all the shit that they need to do to get to that same vision, but do not give them the freedom to chart their own path. Notice the language that you use to describe what you do: do you say “I run the team” or “I’m the support team manager” or “I lead the support team”? How you talk about things says a lot about how you perceive them, so try to notice how you talk about what your role in the team is and how you might shift it.

I read a book a little while ago called The 5 Levels of Leadership, and it changed the way that I perceive management and leadership by proxy.

There are a five levels of leadership, and they build on top of one another:

  • Level 1: You’re a leader because you’ve been given the title

  • Level 2: You’re a leader because people CHOOSE to follow you

  • Level 3: You’re a leader because you get shit done and motivate those around you.

  • Level 4: You’re a leader because you are developing other people to be leaders

  • Level 5: You’re a leader because the leaders you developed are going through the same steps (it’s a little bit like an MLM).

As a seasoned gamer, when I learned that there were levels the first thing that I wanted to do was know how to beat them, right? We all want to get to the final boss. But, with leadership, as with all challenges, you need to start from the beginning.

Level 1

When I was at Wistia, I only had any management privileges because my manager gave them to me. I hadn’t earned them through any particular leadership except via individual contribution to the queue. You do not need any trust cultivated to become a level 1 leader, as it is wholly title-related. This is often times how managers get started: they’re on a team, and they get selected out of the group to manage when someone steps down or a role opens up. It was no different for me. I hadn’t done much except for a bit of strategizing and totally slaying the queue.

Did that mean that I didn’t deserve the title? No. But what it does mean is that I wasn’t a leader by any means I had visibly earned. The team was only following me because the title deemed it, and our leadership said they had to. This is a great example of a Level 1 leader. I never got out of Level 1 at Wistia, and at Campaign Monitor I never had people to lead, so I never got out of it there either.

To be clear, being a level 1 manager isn’t necessarily a bad thing. My team was doing just fine, I was doing just fine; we were meeting all of our metrics and people were generally happy. But, if I stayed as a level 1 manager, I never would have been able to advance in my career, or start working strategically on advancing a team forward. It was time to do more.

Level 2

When I went to Trello, I was given the role of Support Engineer. It wasn’t exactly what I wanted: as I said earlier, I wanted to be running a team. But Ben, the then-manager, told me that there was opportunity for growth, and so I came aboard. After a few months, Ben shifted my role to team lead. I was nervous, there were other people on the team who had more historical context at Trello than I did, and I wondered how they would take it.

The work that I did while I was a Support Engineer helped. Unlike at Wistia, I had served as a support to the people of the team in a leadership capacity already without the title. I had helped to bolster and get to know their needs, and then support them through it. When I was given the title, it was just a secondary affirmation of the role that I’d already been performing.

In order to build that trust, I had to get to know them. I could never have moved from Level 1 to Level 2 without the team putting their trust in me. I couldn’t just passively wait for them to get to know me. I had to learn. What was their dog’s name? What did they do for their girlfriend’s birthday? Know whether they like Star Trek or Star Wars better. What were their professional goals, and how could I help to get them there. Without that focus and mutual understanding, the team never would have supported me in the shift, especially because I was so fresh to the team.

This is a common issue for people that are new to a team, especially managers just coming in to a company without any previous experience. To shift from Level 1, where people just follow you because they know they have to, to Level 2, where people follow you because they choose to, you need to get to know them, and let them get to know you. Be vulnerable. Welcome feedback. Let them know that you are like them and you are on their level.

Other than just conversing about personal stuff with them, one of the best ways that I know to do this is to be in the shit. When the queue gets bad, they’ll notice whether you are there with them or not. Don’t break that trust that you are beside them.

Level 3

When you manage, it can be easy to let go of the day to day drive to accomplish things. Instead of your own merit being what deems you a “good worker” it is the merit of those you lead. With that, it can be easy to fall into a trap of “just” people managing, without continuing to develop yourself or develop the team.

After a few months of being the team lead, Ben left Trello and I became the temporary manager of the team. Temporary. It frustrated me that I wasn’t just being given the title, and instead had to conduct interviews and evaluate people that were champing at the bit for what I perceived as being rightfully be my job. I fell right back into the old habits from Level 1, and I could have stayed there. I was upset to do the work without getting the recognition.

However, after the initial month of so of sulking about not being just given the title, I realized that the best way to show that I deserved it was to earn it. Ben and I, prior to his leaving, had worked on an OKR program to try to drive forward initiatives within the support team outside of the inbox. We’d never done anything like it, and it was a radical idea. We were effectively giving responsibilities that would have normally fallen to a manager to our team to champion, like evaluating and managing the switch to a new help desk, or pioneering a proactive support methodology. We were believing in them to be able to do things far out of the scope of their normal day-to-day. Not only to do those things, but to excel at them.

The team was freaked out about the idea of taking so much time out of the queue, especially when, up until this point, it was their primary method of measurement. But, after the first round and seeing exactly how much they were able to accomplish, they were in. They trusted the process, but most importantly they trusted me to lead them through it.

Ultimately, Trello decided that I was the best fit for the role over the other external candidates that they’d interviewed.

To move from level 2 to level 3, you need to prove to your team that you have the chutzpa to take the things that you know about them and use that to direct them forward. If I had waited that whole time to get started on strategizing and leading the team, I would have lost all of the trust that I’d built and probably wouldn’t have been able to drive the initiatives forward that I did.

I knew, from conversations with my team, that it was important to them to do more and have more impact than working in the queue could provide. Ben and I built the OKR program to address that, and then had the faith in them to be able to do the more self-directed work it took to make it happen.

I could have easily just let myself fester over the anger of being appointed “interim manager.” Had I done that, I would have remained at level 2 with my team until I was given another opportunity to drive them towards larger goals and get shit done. The best way to get to level 3 from level 2 is to show your team that you hear what they are looking to do, then find a way to align it with company goals and get that shit done. Knowing that you are acting with their best interests in mind and that you care what they think about the future of the team helps them to trust you more.

Level 4

Getting shit done is all well and good until you can’t anymore. During this whole thing, I was very pregnant and knew that, at some point, I would have to go on maternity leave. I did as best I could: I made a list of all of my responsibilities and then delegated them out, I prepped the team with a list of everyone they would need to reach out to if anything went awry. I developed a schedule of 1:1s with the person that I reported to so that everyone would have their voice heard. Then, the acquisition happened.

Oh fuck.

The person that was supposed to be conducting my 1:1s left the company, and I was a mom fresh into baby-having-dom. I came back part-time to try to make sure that the team had 1:1s and felt that they were being advocated for during this scary time, but otherwise was absent.

It wasn’t ideal.

I had my feet both in the boat and in the ocean, and wasn’t paying very much attention to either. I needed to pick one. I picked my baby. But what did that mean for the team?

I’d been working to cultivate leadership skills amongst the members of the team, having them participate in interviews, work as mentors when people first came on board, and I knew that there were a few people who had leadership on their list of long term development goals. So, we did it.

I had one of my employees serve as the team lead while I was out on maternity. I gave him all of my trust and believed that he would make the right choices to get it done. Trust had evolved: it was not just him that was putting his trust in me as his leader, but me putting my trust in him to continue leading in my stead. And he did awesome.

You are able to move from level 3 to level 4 in your leadership when you start trusting people enough to let them be leaders on their own, and when they trust you enough to start making the big steps to get there. Mike, the person who I’d appointed to as lead in my absence, had to do a lot of extra things to make the role work, but he knew that I and the rest of the team had his back. Subsequently, the rest of the team seeing this, knew that they could trust me enough to tell me if they, too, were interested in leadership, and believe that I’d do all I could to get them where they needed to go.

Level 5

I haven’t made it to level 5 yet. I have been lucky enough to start in young organizations that do not have so many levels of leadership to allow me to be a leader of leaders who are then going on through the levels themselves. But, it is my goal to get there. Eventually, I hope that the Trello Support team will be large enough that I will allow the people that I developed on Level 4 to truly take the reins and run things--I hope that I will be there to see them.

But, for a great example of a Level 5 leader, I’d recommend taking a look at Mat Patto’s career and what he’s doing in his life right now. Not only did he manage the support team at Campaign Monitor (which was HUGE and multinational), but now he writes and builds documentation for HelpScout’s customer base to make them even better leaders. His net is so wide it’s ridiculous.

All of this is not to say “hey, it’s easy. If I can do it, you can too.” The picture that I’ve painted is definitely much cleaner than it was in the moment, and it took me some time to figure it out. Furthermore, the level that you are on differs with the person you are talking to. Just recently I was speaking with one of my team members, and he said that he didn’t see me as an “inspirational leader” but instead someone that he could come to with his problems and that would support him.

This boggled my mind. I’d never heard anything like it before. I had assumed that I knew where I was at with this person, but I’d never asked. The best way to find out how people perceive you is to ask. I did this by building a survey and sending it out to my team. Here's a version of the survey you can copy and use for yourself:

The responses that I got reassured me, but also let me know where I needed to be doing better. Each section corresponds with a leadership level. I was all “Yes” up until Level 4, where it started to diverge. I need to be developing people more readily and providing them with outlets to grow. I know this to still be an opportunity for me, but it was validating to see it confirmed by my team’s assessment. I’d recommend trying it for yourself just as a gut check.

Leadership is never easy, and there will never be a sure fire way to know how to do everything right. Hell, maybe even the path that I’ve taken isn’t right. Maybe the 5 levels of leadership are a total crock. But, to me, they are a useful map that is sketched out with a gist of kind of where I want to go. That’s what’s so fun about it: it’s a journey. There is not final boss, or way to beat the game, you just have to keep always playing, always striving to get better. So, no matter what you do, keep striving, be humble (as Kendrick Lamar says), and most of all trust others so that they may trust you.