A Tale of Two Leaders

When I first sat down to write this, I thought I’d be writing a “do’s and don’t’s” style article listing the characteristics of good and bad leaders, based on my many years of working with leaders or my own experience as a leader.

But what came out was a story. Two stories, actually.

Below are two stories of experiences I had with leaders. I’ve changed the names, but all of this really happened. I hope what follows may help you to feel great about being a good leader, perhaps become a better leader, or at least survive a bad leader.

What makes a good leader?

I’d been working with Ramon closely over the previous weeks to design a two day workshop for his team. Ramon was leading a team of around 35 people at a company that had just completed the acquisition of another, smaller company. As part of the acquisition, Ramon’s team had merged with another team . They had some serious pressure on them to deliver a series of cohesive products that would meet the needs of their health care customers. And they were just getting to know each other.

Some of the team members’ jobs were similar, and they were naturally concerned that they might lose their job due to redundancy. Some had been leaders and were now being asked to report to a new leader. There was no legitimate threat of layoffs. Those had happened already. But that wasn’t much of a comfort to people. They’d seen enough surprise layoffs in the news to remain on high alert.

Ramon and I, along with a few members of his leadership team, spent a lot of time together going through the possible inputs, the activities, and the desired outcomes for the upcoming workshop. We’d have to somehow help the team feel safe and supported while collaborating on what would end up being a key set of product decisions for the upcoming year.

I’ve led many workshops like this before, and I know that making critical product decisions can be incredibly difficult for even the most physiologically safe teams. Doing this with people who are unsure about their jobs is like climbing a mountain made up of mine fields.

But as we drew closer to the workshop, I felt more and more confident. Why? Because of Ramon. Ramon was IN IT from the beginning. He not only joined every meeting, but was actively engaged. I also saw how Ramon’s leadership team interacted with him. Nothing seemed fake. Everyone spoke directly. Agreement was voiced with the same tone as disagreement, respectfully. They laughed. But not the usual, let’s all laugh at the boss’s jokes kind of laughter. They laughed at themselves, each other, at the situation. Despite the tall task in front of them, they seemed to really be enjoying working through the tricky details with each other. I know I was enjoying it immensely.

This is exactly the kind of team I love to work with. And not just because of the laughter and respect. It’s because, time after time, that laughter and respect translates into results.

 Teams like this are like the most resilient of flowers. Plant them in a beautiful garden and they make the whole garden more beautiful without taking away from the beauty of the other flowers. Plant them in a shady alleyway, and they somehow find enough sunlight and water to thrive and brighten the entire space.

This kind of team doesn’t happen by accident. Great leaders usually have great teams. They get in the way when it’s needed — like providing cover from another leader or team so their team can remain focused on important work. They step aside when needed — like being OK not being involved in a big idea that the team clearly has a handle on.

Not surprisingly, all of this showed up when we got to the workshop. As the facilitator of these workshops, I often kick things off with a warm up and then give the leader an opportunity to say a few words before we dive in. If I don’t know what kind of leader they are by that point, this is the moment I find out. But I already knew. Ramon stood in front of the group and in just a few minutes:

• Acknowledged their fears about their jobs and how the acquisition might play out
• Let them know that he didn’t have all the answers and that we might not find them all in the next two days
• Made it clear that this was the most important thing on his plate right now. He would be there, in the trenches with them — this was the only thing on his calendar for the next two days

I watched shoulders soften, smiles develop, subtle nods exchanged.

The next two days were exhausting. We unpacked and established foundational norms, values and ways of working. These are steps I’ve seen some leaders push back against in workshops, feeling we should just “get to work”.

But it was worth it. I watched as the teams leaned on that foundation when we engaged in heated, respectful debates about what to prioritize, what might receive funding and resources. I watched as people let go of their attachment to the solutions, because they were aligned on what the problem was and why it needed attention. I watched as almost no one ever stepped out to take a call or check an email. They were there to be there. It was the most important thing.

In the weeks following the workshop, I checked in with Ramon and the news was exciting. The workshop had been the spark that lit the fuse that lit the rocket, and they were flying. Teams were focused on building out what they’d envisioned in the workshop. Engagement was high.

Each time I checked in, I missed them. I can’t wait to work with them again some day.

What makes a bad leader?

The first meeting seemed to go well. Travis, the leader of the team, excitedly introduced me to some of his leadership team. We discussed some of the logistics of the upcoming workshop — the who, the when, the where.

I learned that this team was newly created to be a hub for innovation. The members of the team had been sourced from five other teams inside the company. Some had worked together before, but most hadn’t. There would be some overlapping skill sets and hierarchy changes from what they’d experienced in their former teams.

Travis assured me that every member of this new team was excited for the mission and wasn’t concerned about things like hierarchies and reporting structures. His leadership team each took turns enthusiastically agreeing with this statement.

As the meeting was winding down, Travis let me know that he might not be able to join all of our upcoming meetings, but joked that he’d “just get in the way” of the smart people on his team. He assured me that they could decide on things in his absence and that he’d always be just a quick phone call away. 

I wondered about this. I’d heard it before.

In the weeks that followed, I met with Travis’s team multiple times. Travis rarely joined, but the team always wanted to wait for him, never sure if he planned to join or not. That generally ate up the first five minutes of every meeting. Usually one of the team leads would get a message from Travis’s admin saying he was tied up in another meeting and that we should go ahead without him. Then we’d get to work.

We had a lot to figure out and only a few weeks to do it. I’d asked to speak with members of the team that would be attending the workshop to gather some context, and I was growing concerned. Under the safety of anonymity more than a few team members expressed concerns with the new team structure. They weren’t sure where they fit in. Some were trying to stake their claim — to people, products, and resources. And the focus was less on innovation and more on job security.

I shared some of this information with the leadership team and was met with pained looks of worry. Occasionally, one or two would break character and drop an off-handed comment indicating they shared the same concerns. But as quickly as the crack in the wall would form, it would be just as quickly spackled over and painted. And they were back to repeating what Travis had said in that opening meeting.

I also started to notice a pattern. Decisions were piling up. Many of them weren’t even really decisions, just FYI’s. When designing a workshop, I take the task of deciding on things like team sizes, activities, timing and methods. It’s a big part of what I get paid to do. I don’t make these decisions arbitrarily. I make them based on what I believe will work best for that group and their situation. I inform the client of those decisions, but usually just to keep them in loop.

But this team seemed terrified to make any decision without Travis’s input. When I’d inform them of how I planned to structure a particular activity, they’d say “OK, that sounds great, Joe. I’ll grab some time with Travis to make sure he’s comfortable.” “With all due respect”, I told them, “Travis may not really have an opinion on this as it’s really in the weeds and… I assure you, I’ve thought this through.” “No, it’s OK.” they’d say, “I have a 1:1 with him later and I’ll just let him know.”

Then, at the next meeting, I’d learn that 1:1 with Travis got canceled because he was tied up, and we’d have to keep that item on the list. That list was growing and without telling them, I’d already moved on. I didn’t have time to wait. The workshop was fast approaching. Also, I’m pretty good at this. I was confident that what I was designing was the best path.

One area that Travis did end up weighing in on was a series of activities to help the team unpack and align on how they were feeling about the new team structure. I thought it was important to build a foundation of openness and trust in order to get to the other items on the agenda. Travis and his team were weary of this, feeling that time was short and we should use as much of it as possible to come up with ideas and solutions. I explained that this could backfire. Without the right environment, it’s hard for ideas to grow.

As a sort of compromise, Travis agreed to cover some of this in his opening remarks. That worried me. I’ve seen many teams get told how they feel and then quickly become disconnected if it doesn’t match reality.

I was able to keep some of the foundational work in, but I was still concerned.

Workshop day arrived.

I kicked off the day with a warm up and then offered the stage to Travis, to say a few words. I gritted my teeth as he began to address the group by letting them know:

• How excited he was about the newly formed team, especially how every single one of them was putting the innovation work first and not letting titles and hierarchies get in the way. (“Uh oh”, I thought. )
• His very clear list of priorities for the upcoming year — what was important and how he expected it to be done. (“Oh no….”)
• That this was his number one priority and that he couldn’t wait to get his hands dirty and work side by side with them for the day. (“OK, well that’s encouraging.”)

I watched shoulders stiffen, jaws clench, concerned glances shoot across the room.

I strapped myself in and got the workshop started. At first, Travis was true to his word. He was in the mix. But rather than following the steps in each workshop activity, he distracted others from them. The rules didn’t apply to him.

Every team he spent time with fell behind and fought to catch up when he moved on to his next victim. No one challenged him, seeming happy to get some rare face time with the boss. Jokes and shoulder pats, loud laughter that seemed mismatched with the jokes emanated from Travis’s traveling circle.

I approached Travis and encouraged him to engage in the steps in each activity, assuring him that they were really effective and if others saw him doing it, they would too. He thanked me for my candor, promised to follow my lead and quickly resumed the traveling circus. I’d seen this before and assigned one of my co-facilitators to “Travis duty.” Her job was to try to keep him from distracting everyone else. It was not going to be easy.

An hour or so in, Travis stepped out of the room. Everyone relaxed instantly and I hoped this was a permanent departure. Then I heard it. Travis was pacing, just outside the room, talking on the phone. Each time he paced past the open door, every head in the room turned. Then another person stepped out. We were in the middle of a workshop activity. “Maybe just a bathroom break” I thought. But then another, and another.

I asked one of Travis’s leaders if something was going on. Was there some sort of emergency? Should we take a break? No, they said, nothing out of the ordinary.

In the hours that followed, I watched the workshop devolve into a chaotic mess of people streaming in and out of the room, grabbing their laptops to catch up on email in the hallway. All the while, Travis continued to pace, taking phone call after phone call, even stepping into the room to occasionally pull someone out for a quick chat.

The people who resisted this chaos and remained in the room grew visibly frustrated. They’d cleared their schedule and were genuinely excited to get a lot of work done in the workshop. But they were now stuck playing the role of getting people “up to speed” every time they left the room and came back.

The results, unsurprisingly, weren’t good. The people who remained engaged consistently had to carry an unfair load. Despite this, they still made breakthroughs and generated some exciting new ideas, and they were looking forward to building those ideas out further after the workshop.

But that never happened. I checked in with the team a few times in the weeks that followed and it was like the workshop had never happened — erased from memory. The next day everything went back to the way it was. And team morale was low. A few people had already quit.

I was disappointed, but not surprised. I hoped that some of the team gained value from the day. I hoped that Travis was seeing more than he let on.

Two Leaders

Well, there you have it. The story of Ramon and Travis. Both well intentioned. Both nice people. Two drastically different outcomes.

If you have a story of your own or if any of this resonates with you, please share in the comments!