Your Team Can't Execute What They Don’t Know

Recently, I was preparing for a leadership offsite with a new executive team. The original request was straightforward: help the group become better storytellers.

Before designing the session, I interviewed several members of the leadership team.

A pattern emerged almost immediately.

The issue wasn't that they struggled to communicate. It was that they hadn't yet aligned on what they were trying to communicate.

Each leader could explain their own priorities, but there wasn't a shared narrative about where the organization was headed or why that direction mattered. Before anyone could tell the story well, they first needed to agree on the story itself.

I shared my observations with the executive sponsor, we’ll call her Maya, and recommended we redesign the day. Rather than focusing on presentation techniques, we'd spend our time aligning around the organization's strategy, identifying the messages that mattered most, and creating a narrative the entire leadership team could consistently carry forward.

She agreed. Enthusiastically.

Throughout the offsite, we adjusted the conversations together as new themes emerged, and Maya continued offering positive feedback.

The discussions were thoughtful. The team made meaningful progress. By the end of the day, they had far more clarity about their direction than when they walked into the room.

Then, a week after the session, she shared something in our debrief that caught me off guard: She had hoped we would have spent more time teaching presentation skills.

It would have been easy to dismiss the moment as a simple misunderstanding.

Instead, it made me curious.

Not about the workshop. About leadership.

Somewhere between our planning conversations and the day itself, something got lost.

Not because anyone was intentionally hiding information. Not because either of us was unwilling to adapt.

Because one important expectation never became explicit.

Maya was moving quickly, juggling competing priorities, and assumed we were aligned because the overall direction felt right.

She never paused to test whether the picture in her head matched the one I was carrying into the room.

That's a remarkably common leadership habit.

The more senior you become, the easier it is to assume everyone else can see your leadership vision.

They can't.

Your team hears your priorities. They don't automatically understand the thinking behind them.

They hear your goals. They can't see the picture you're using to judge success.

So they do what capable people always do: They make reasonable decisions based on the information they have.

Then, weeks later, you find yourself saying, "That's not quite what I meant."

By then, everyone is frustrated.

Not because people weren't working hard, but because they were solving a different problem than the one you thought you had assigned.

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When Expectations Stay Invisible

This is one of the hidden traps of senior leadership.

As your scope grows, your conversations naturally become more strategic. You spend more time discussing outcomes than execution. That's appropriate.

Sometimes withholding feedback is exactly the right call. You don't want to derail the meeting or undermine someone in the moment.

Other times, the reason you aren't giving direction is simpler: you haven't fully worked through your own thinking yet. You know something feels off. You know what you don't want. But you haven't yet clarified what you do want well enough to explain it to someone else. ‍

The problem is when silence becomes the default. ‍

Your team can't execute against expectations that only exist as half-formed ideas in your own head.

Some leaders assume everyone else fills in the same blanks they do. They won't.

And sometimes your ego reinforces that assumption. Once the picture in your head feels obvious, it's easy to believe everyone else sees it too. We become attached to the outcome instead of staying curious about how others are interpreting the work.

Later, Maya shared that her own leader had observed something similar. ‍

Her team, he said, "keeps trying again because she stays too high-level."

It isn't a capability problem. It's a timing problem. ‍

Her signal simply arrived too late. ‍

Acknowledging that requires a certain amount of humility. ‍

It's tempting to assume people should "just know" what we mean, especially when we've been carrying the strategy around in our own heads for months. But leadership isn't about protecting the image of being clear. It's about being clear enough that others can execute well.

A leader’s job isn't simply to evaluate finished work. Their job is to make their expectations visible while the work is still taking shape.

That doesn't mean having every answer. It means externalizing your thought process before people commit to the wrong work.

Share the assumptions you're making. Name the tradeoffs you're weighing. Explain what success looks like before everyone starts filling in the blanks themselves.

Instead of saying: "Looks good."

Try saying: "The one thing I'm still hoping to see is..." ‍

Instead of waiting until the final presentation to explain what feels off, surface your feedback while there's still time to adjust. ‍

The earlier your team understands how you're thinking, the less likely they are to spend weeks solving the wrong problem.

The strongest leaders don't wait until their feedback is perfectly formed. ‍

They externalize their thinking while it can still change the outcome.