Why You Keep Cleaning Up Manager Messes

Good managers don’t fail because they lack talent.
They fail because they are guessing.

When expectations are not clear, the senior leader ends up doing the cleanup.

You’ve seen this pattern more than once: a manager steps into a bigger role. They want to prove they can handle it, so they avoid asking clarifying questions. They don’t want to be the leader who “needs too much” from you. They rely on assumptions instead of confirmation. They build plans on a shaky foundation.

The outcome is predictable: more friction than necessary. Extra meetings. Decisions that get revisited. Escalations that shouldn’t be escalations. Rework that burns everyone’s time.

The problem isn’t capability.
It’s that they’re operating without a complete leadership system.

When clarity is missing, they guess.
When alignment is missing, they work in the wrong direction.
When ownership is unclear, they hesitate.

And when any piece is missing, the weight shifts upward.
The senior leader becomes the interpreter, the safety net, and the absorber of noise.

This letter looks at one slice of that larger pattern: why managers guess, and how to help them stop.

Guessing Isn’t Incompetence

It’s the natural response of someone who has never been taught a structured way to align with their leader.

Most managers grow up in environments where expectations are only halfway defined, priorities shift without context, and alignment happens informally. They assume this is normal. They assume asking for clarity signals weakness. They assume silence means “you’re fine.”

Senior leaders can unintentionally reinforce this.
You move quickly. You share what you can in the moment. You expect capable people to fill in the blanks. And most of the time, they do, until their scope expands and assumptions multiply.

When expectations aren’t aligned early, managers work hard on the wrong things, and senior leaders spend time correcting issues that could have been prevented.

What looks like a performance problem is usually a clarity problem that started at the beginning.

Clear expectations are not extra work. They are the work.
They prevent the confusion, rework, and repeated clarifications that show up when smart managers try to interpret what matters instead of confirming it.

A Simple Way to Help Managers Stop Guessing

1️⃣ Bring clarity before execution begins
Managers guess when success sounds broad. Replace high-level direction with a concrete picture of “good.”
Clarity on the front end saves ten conversations on the back end.

2️⃣ Establish alignment through explicit confirmation
Don’t leave space for interpretation. Ask managers to reflect back their understanding of priorities and outcomes.
This isn’t micromanagement, it’s how professionals prevent confusion before it spreads.

Alignment is real only when both people confirm the same picture of success.

3️⃣ Create ownership by defining what the manager is truly accountable for
Ownership is the antidote to unnecessary escalation. Help managers clearly state:
• What they own
• How they’re approaching it
• When you can expect updates

Strong ownership keeps problems at the right level, theirs, not yours.

Senior leaders will always carry pressure, that comes with the role.
But the preventable load drops quickly when managers stop guessing and start aligning.

Expectations are only one part of the leadership system managers need as they grow.
When any piece is missing, you feel it.
When each piece strengthens, your job gets lighter, and the organization moves faster.

If you could strengthen one alignment habit across every manager you lead, which one would you choose?

Cheers,

Jeff