The Two Ways Leaders Fail

This series, Lessons From a Fictional Football Club, turns to Ted Lasso as an unlikely case study, treating it as a structural experiment in what actually holds an organization together under pressure, versus what was just one person's charisma wearing a disguise. Across this series, I will pull leadership lessons from specific scenes, ground them in research where it exists, and close with structural reads through the Loadmap framework.

Lasso time. Spoilers.

Scene: The most optimistic and improvisational coach in the league is on the floor of his office, and his heart is beating out his chest. Nothing obvious caused it. It wasn’t a loss or a scandal. Just the accumulated wear from the job he loves, arriving all at once, when he’s too strained to improvise.

Across town, at the same point in the story, West Ham is failing in the opposite direction. Its machine was built in advance and runs exactly to plan. A recruitment plan, the training plan, game plan... every part executes, and the whole thing drives into a wall that wasn’t part of the plan.

Last post covered what fear did to West Ham. This one is about the other thing its collapse shows us, because these two failures are a matched set. Leaders fail in the direction of their strength. Improvisers tend to burn out. Planners shatter.

An improvisational or instinctual leader keeps every decision open in the moment. Nothing surprises a team that never expected anything in particular. But every fresh response takes effort, and the job itself doesn’t refill the energy bar quickly. For Ted, there’s no single blow, which is what makes this one so hard to see coming. He was fine, then still fine, and then he's on the office floor, and everyone around him is shocked... because handling things was his... thing.

A plan-ahead leader builds the response before the situation arrives. Plans scale. Plans survive bad days and let teams move as one. But a plan assumes it knows the situation in advance, and when reality takes a turn, an unpracticed solution can’t just magically appear. It keeps executing as if the prediction was true. West Ham had the energy, but its prediction failed while the team kept running the same plan.

Each failure exposes something different. Ted’s improvisational club was unpredictable and driven: nobody knew what the next play or day would look like, and the club absorbed chaos daily without breaking. West Ham was predictable and brittle. Predictability and durability are different things, but I think most leaders build the first while assuming the second comes with it. And it doesn't.

To be clear, neither improvisational nor planned is the ‘good’ path. The improviser learns by doing. The planner learns before doing. Each carries its own weakness, and the show does a decent job showing that neither is always right or easy. West Ham’s owner earned his Vader-like ending with fear, and fear isn’t something that planning itself creates. Plenty of decent and friendly organizations plan. They still break. They just do it without the villain arc. 

Want something to practice? It’ll take ten-ish minutes and something to write on. Write down your last three workplace fires... the real ones. Then write down how you handled them. If you responded in-the-moment to most, draft the shock-absorber you’re missing: a checklist, a handoff. Create the written-down thing that would have made the second emergency easier to handle, and commit to trying it. If you usually executed a plan, write down what the plan missed. Then brainstorm options you could’ve tried in real time to deal with the unexpected. Both halves feel unnatural, because each is going against your natural strengths. The discomfort is a tell that it’s the right place to look.

We’re stuck with two options. Keep the decision open and pay for it with bursts of energy, or plan ahead and pay for it in missed predictions and wasted effort. Most leaders and orgs pick a lane, and the failure they can't manage is the one that hides in their strength. 

FWIW... Lasso had his balancing counterpart next to him the whole time. Coach Beard writes stuff down, plans training weeks ahead, and stresses about the stuff that happens after what’s next. Opposite inclinations, cooperating from day one. There's a whole post coming on why that works when it works.

Which way would you break?

Lessons from a Fictional Football Club is a series of unofficial analysis and commentary. It is not affiliated with, sponsored by, or endorsed by Apple, Warner Bros., or anyone connected with the television series Ted Lasso. Loadmap is the framework I think with in these posts. Loadmap, by Tate Linden, is offered exclusively by Stokefire. 

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