Leadership Lessons from Ted Lasso

Happy Saturday, everyone! I wanted to share some leadership thoughts I had after watching this week's episode of Ted Lasso. Aside from the triumphant return of favorites like Roy Kent, Coach Beard, and Mae, it had some moments that really got me thinking about recognition and retention.

Season 4, episode 2 starts with Coach Alice Chilton, the assistant coach of Richmond's women's team, passed over for the head coach job and handing Rebecca her resignation. On her way out, she asks one question: was a woman ever even considered for the position?

She doesn't get the answer she deserves. Nobody fights to keep her. Rebecca tells her that "I'm here if you need anything," which we all know isn't particularly helpful now that she's already resigned.

Over the course of the episode, Coach Chilton ultimately decides to stay. It's not about a stay bonus or getting the next title. Ted finds a way to retain an excellent assistant coach through observation, advocacy, and acknowledgement. His empathy enables him to achieve this.

The stay conversation started a week early

Ted arrives excited to meet Coach Chilton, particularly because of the detailed dossier she wrote on the team and its individual players. He makes specific mention of her work on this both to her and to Rebecca when Coach Chilton isn't in the room. This is a move many leaders skip: he noticed the unglamorous work and thanked the person who did it, acknowledging the impact of the work since it's been extremely helpful in his transition.

Then, he spends the week demonstrating a willingness to learn. He recognizes that she knows this team far better than he does, and he includes her every chance he gets: he asks her to join him at the press conference, not as a courtesy, but because she's the more knowledgeable person in the building. He watches how she interacts with the team. He pays attention to how the women's team is treated compared to the men's.

One of the things I love about Ted in this episode is that he doesn't spend his time telling the team what he's going to do to support them. For example, he's unimpressed with the women's locker rooms (they have only one shower while the men have eight, and they aren't always allowed to keep their toiletries in their cubbies). He quietly makes their new locker room happen, in coordination with Keeley, within the week. He shows through action that he's willing to advocate for the team — and that their conditions were urgent enough to act on now.

Anyone who has raised an issue at work and been told "we hear you," then watched months pass with no action, knows exactly why that lands. Ted knew that actions spoke louder than words, and he demonstrated his care for the team quickly.

"Difficult" is often devotion you haven't decoded yet

In the beginning of the episode, Coach Chilton reads as prickly and cold. Blunt, sour, hard to be around. It would be easy for a leader to file her under "attitude problem."

Ted takes a different approach. Instead, he sees her turn protective the instant a player goes down injured. However, I think he picks up on her care for the team earlier in the episode, after the press conference: he sees the locker room, hears a room full of reporters ask the women's team's coach only about the men's side, and suddenly her worldview makes sense. It was never rudeness. It comes from her frustration with how her players are treated. The "difficulty" was devotion, worn down.

I've been in that very same seat. I recall a very specific HR team meeting I was in this year. I raised an issue on behalf of the frontline Operations leaders I supported: our hiring process was cumbersome and frustrating for leaders, with three different checklists they needed to follow just to get someone in the door. The response from our Operations VP, HR, in front of my peers, was "let's remember to be collaborative." Not an answer to the problem or even concern about the experience for our Operations leaders. Instead, I got a correction of my tone.

That was one of the clearest moments in my decision to leave. I wasn't willing to work on an HR team where advocating for the leaders I supported was treated as poor team play. I resigned a few months after that meeting.

That's what the "attitude problem" label costs. It rarely sticks to the people who've checked out. It sticks to the people who care the most, right up until they leave.

Fix the thing that benefits them

Notice what the locker room is: it's something that benefits the players themselves. Not the club's standings, not the fans. The speed communicated three things no speech could: he took the concern seriously, he felt ownership for the outcome, and he saw it through in partnership with Keeley. He wasn't willing to let his team live with those conditions for one day longer than necessary.

Every workplace has a locker room, or specific conditions that are pain points to their employees and leaders. It might be development opportunities — investment that helps that employee grow, not more work they can absorb on behalf of the team. At a small business it might be as concrete as the break room. The question to ask is simple: what are your employees' specific pain points that hit them personally, on a regular basis? And how long have they been living with them? Are you doing anything about it? Or worse — have you said you're going to do something about it without following through?

Empathy is a superpower

Ted also spends his first week learning his players individually — enough to pick up which of the bickering twins is the older one. That's not trivia. Knowing people at that level tells you what drives them, what their triggers are, and how they're likely to react before you make a decision that affects them.

At an organization I worked for, Empathy was considered one of the nine Leader Capabilities, or qualities that every leader was expected to demonstrate. However, in my experience, it was probably the most downplayed capability. I worked with a senior leader at this organization who would caution her peers about overemphasizing empathy. While this leader and I largely agreed on things, her take on empathy didn't resonate with me at all, and this episode of Ted Lasso reinforced this further. The most effective leaders I've known are extremely empathetic — not because they always make the popular choice, but because they understand the dynamics of their team and the personal and emotional weight of the business decisions they make. Empathy doesn't soften the decision, and leaders will always need to appropriately balance business need — but it is a people and sentiment forecasting tool. The most empathetic leaders can anticipate the reactions of their team, while leaders without empathy will always be reactive to the emotional and personal responses from their team.

Which brings us to the conversation at the end of the episode. When Ted finally sits down with Coach Chilton, he doesn't get defensive, and he never tries to make her feel small or replaceable. He does the opposite: he has the humility to acknowledge that he needs her and that he will simply be more successful with her. Then, he sets his pride aside to say it out loud.

That conversation with Coach Chilton cost Ted nothing but time and effort. Compare that to the cost of replacing her.

Monday morning

If you lead a team and you take any lessons from a fictional football coach, take these:

Thank the squeaky wheel. As Higgins reminds us with his mother's line — strong women stand up for themselves; stronger women stand up for others. Don't put people down for standing up for the needs of someone else. They're your early-warning system and the strongest advocates for your employees, not your problem. Be more concerned about the folks on your team with nothing to say.

Find the pain points. Do you actually know what they are? Have they been open issues for months? Make time to fix one in a visible and quick way. If there are pain points that you're aware of and haven't addressed for a month plus, fix them and apologize to your team for your delayed action.

Learn one new thing about each person on your team this week. It may tell you more than you realize.

And lastly, I cannot say enough good things about Ted Lasso — tune in on Apple TV!