The Ivory Tower Trap

Strategy execution fails in predictable ways. Over the last six weeks, I've explored six traps nested inside the larger Strategy Trap—patterns that consistently derail even well-designed strategies, and what to do about each one. This is the last one.

Part 6 of 6

The strategy is set. The kickoff went really well. But a few months later, the leader has moved on to the next thing, and the team is left navigating execution largely on their own.

A leader's job doesn't end when the strategy is handed off. It shifts. The planning phase requires strategic thinking. The execution phase requires coaching, which is the active, ongoing work of keeping teams focused, motivated, and moving forward as reality unfolds. That means helping people interpret the strategy as circumstances change, keeping them motivated, shaping the culture so the right behaviors get reinforced, and staying close enough to the work to catch strain before it derails things. Coaching is what connects the plan to the result.

Many leaders who land in the Ivory Tower Trap do so without realizing it. Setting direction seems like the main job, and once the plan is in place, the assumption is that a capable team could run with it. So attention shifts to the next challenge, and the ongoing coaching that execution needs never happens.

What It Looks Like in Practice

People are starting to act in ways that run against the strategy. A strategy sets direction, but the situations that come up while executing it are inevitably more specific than what got written down. Someone has to keep translating what the plan means for the problem in front of the team right now. When that translation stops, people either freeze or guess, and the decisions they make start pulling in directions the strategy never intended. Months later, the results don't match the plan, and no single decision explains why.

Motivation is fading even though the incentive plan is sound. Financial incentives usually get built into the plan up front and then mostly run themselves. The other two levers don't. Social incentives—recognition, feeling that the work is seen, peer accountability—and convenience incentives—removing the friction that makes the right thing harder than it should be—only work when someone is actively providing them week to week.

The team is pulling apart instead of pulling together. Danny Meyer's formula for culture is the sum of the wanted behaviors you celebrate minus the unwanted behaviors you tolerate. Both halves require someone paying attention on purpose. When no one is recognizing the people doing things well, or stopping the behaviors that shouldn't become normal, the small things that hold a team together stop getting reinforced. Collaboration gives way to people looking out for themselves, and that becomes just how the team operates. It isn't the team going bad on its own—it's what happens when no one is managing what gets reinforced.

People are burning out and tempers are flaring. A deadline gets missed. Someone snaps in a meeting in a way they normally wouldn't. A strong performer looks checked out for weeks at a stretch. Jon Ashton's research treats signals like these as data worth catching early, before strain compounds into burnout, turnover, and stalled work. In sports, a coach rests the gassed player before they pull a muscle. When no one is actively monitoring, the problem only becomes visible after it's already cost the team something.

A Few Questions Worth Considering

Are you connecting what your team is working on day-to-day back to where you're all trying to go, or has the strategy become something people remember from the kickoff rather than something guiding daily decisions?

When did you last give someone specific recognition for their work, or clear a piece of friction that was making the right move the harder one?

If you listed the behaviors you've recognized in the last month and the ones you've let slide, which list is longer? The team is learning what's acceptable from whichever one you're actually acting on.

Who on your team has seemed worn down, checked out, or shorter-tempered than usual lately?

Look at what you're asking of your team right now—the hours, the pace, the last-minute schedule changes. Is that a load people can sustain, or one that's grinding them down?

What to Do About It

Building a coaching practice into your leadership means creating regular opportunities to stay close to execution. It's having conversations that go beyond status updates and into what's harder than it should be, what's slowing people down, and how the strategy applies to the situations coming up right now, so people can make the right calls without veering from what the strategy intended.

It means keeping people motivated with more than the comp plan. Financial incentives get set once and mostly run themselves, but recognizing good work and clearing the friction that makes the right move harder than it should be are things you have to keep doing. It means paying attention to the culture taking shape by celebrating the behaviors you want more of and halting the ones that shouldn't become normal, because the team learns what's acceptable from whichever one you act on. And it means watching for strain in your team before it turns into burnout or turnover, which is partly about noticing the signals and partly about being honest regarding what you're asking of people in the first place.

Part of that is also protecting your own time to think rather than just reacting. A leader who is fully consumed by the day-to-day loses the perspective needed to see where a course correction is needed before things get harder to fix. That unscheduled thinking time—slop time as Dev Frohman calls it—is how you stay ahead of problems rather than behind them.

If you want to go deeper on how to build this into your leadership—including how to listen actively, ask better questions, clear obstacles without creating dependence, and sustain your own capacity to lead—I cover it in detail in The Strategy Trap.