Addressing an Underperforming Employee Without Micromanaging

Last week I sent out a request to help me train the spam filters that I’m not spam.

The solution was simple.
Reply to this prompt:

“What difficult conversation are you not having?”

I’m grateful for the responses.

And I think we may have stumbled into something more than a workaround.
This might be a new way to build community here.

Today, I want to respond to one of those challenges.

And going forward, I’m going to end each newsletter with that same request.

You get to move the conversation you’ve been avoiding from your head to paper. That’s the first step in AGENT. Becoming aware of the conflict.

And I get to write about something that matters to you.
Which fuels my passion to help.

That feels like a win-win.

1. THE SITUATION

Maggie, a manager at a local nonprofit, wrote back.

“I’m having a hard time addressing issues with someone I supervise.”

Maggie leads a small team built on trust. Flexible schedules. No clock-watching. No hovering.

That wasn’t accidental. It reflects how she wants to work and how she believes people do their best work.

But one relationship has started to feel different.

One of her direct reports, someone older, with a different lived experience, and possibly navigating ADHD, has not been getting work done.

Weekly check-ins come and go.
Updates feel vague.
Progress feels unclear.

“I don’t want to micromanage,” Maggie wrote.
“But I don’t know if she’s even working a full week sometimes.”

That was the entire exchange.

Just a leader naming the conflict she is not addressing.

2. THE TURN

On the surface, this is the tension Maggie is navigating.
Step in more and risk micromanaging.
Step back and risk the work not getting done.

But that is rarely where the difficulty actually lives.

For most managers, the hesitation is not about what to say.
It is about what might happen next.

If Maggie raises this directly, will the relationship shift?
Will it feel awkward, strained, or less trusting?

Will her employee experience this as support, or as a judgment of competence?

And if the conversation does not go well, what then?

If the employee disengages or leaves, Maggie inherits the problem.
More work.
More pressure.
A gap that needs to be filled.

So the calculation becomes quiet but powerful.

Tolerate what is happening now,
or risk something that could make things worse.

And so, without deciding to, Maggie begins to turtle.

She steps back.
Waits.
Hopes it resolves itself.

The kind of move that protects the moment,
but not the outcome.

(If that sounds familiar, it’s one of the most common conflict instincts I talk about in my TEDx talk.)

There is also something more personal underneath it.

Many managers do not see themselves as disciplinarians.
They see themselves as supportive, fair, and human.

So the conversation starts to feel like a violation of that identity,
instead of an extension of it.

And then there is HEART.

Will her employee feel Heard?
Will her sense of Esteem stay intact?
Will she still feel Autonomy over her work?
Will there be clarity about her Role and what success requires?
Will Trust between them hold?

No wonder it is easier to wait.

3. THE SHIFT

Reading Maggie’s note, something becomes clearer.

This is not just a question of what to say.

There are two things that make this conversation hard.

Clarity and confidence.

Clarity about what is actually not working.
Not a general sense that something is off, but specific expectations that are not being met.

And confidence about what happens if nothing changes.
Her BATNA (best alternative to a negotiated agreement).

Without those, the conversation feels risky.
With them, it becomes a choice.

There is also a deeper shift available.

This may not be a discipline problem.
It may be a clarity problem.

If expectations have not been fully defined, or not fully understood,
then the conversation is not about catching someone doing something wrong.

It is about getting aligned on what success actually looks like.

Seen this way, the goal changes.

Not to confront.
Not to control.

But to create the conditions where both people can succeed.

That is what opens the door to a win-win conversation.

4. AGENT IN ACTION

To the best of my knowledge, Maggie hasn’t had the conversation yet.

But I’ve had many of these.

And this is how I’ve learned to approach them over time.

It usually starts the same way.

A sense that something isn’t working.
A hesitation to address it.
A quiet hope that it might resolve itself.

And if I’m honest, some frustration.

Frustration with the person that put me in this situation.
Frustration because I have so many other things to focus on.
Frustration that this is now mine to deal with.

The first shift is becoming Aware of the conflict.
Not pushing it aside. Not explaining it away.
Just naming it clearly.

From there, I’ve had to get Grounded.

That means getting clear on what is actually happening.
Not the story in my head, but what I’m observing.
What’s getting done. What’s not. What I’ve said out loud. What I haven’t.

And sometimes it means admitting something uncomfortable.

I may not be fully clear what I actually need from this person.

I was hoping they would take the initiative to figure it out.
And now that they haven’t, that responsibility comes back to me.

Which can feel like one more burden on top of everything else.

It also means acknowledging what I’m feeling.

Because frustration, left unchecked, has a way of showing up in the conversation in ways that don’t help.

But Ground requires something even harder.

Getting honest with myself about my options.

If this doesn’t improve, am I willing to keep this person in the role?
What happens if nothing changes?
What action am I prepared to take?

In other words, what is my BATNA (best alternative to a negotiated agreement)?

Not the ideal outcome.
The real one I am willing to follow through on.

Because without that clarity, it’s easy to enter the conversation hoping instead of leading.

Then comes the harder part.

Taking time to Empathize.
To consider what might be going on for the other person.
Not to lower the bar, but to understand how they are experiencing the situation and how the conversation is likely to land.

Only after that does the conversation itself start to take shape.

This is where we begin to Negotiate.

Not as a correction.
More as a conversation about what success looks like and how to get there.

What does success look like here?
What support is needed?
What needs to change?

What this can sound like in practice:

“I care about you being successful here, and I think we may not be fully aligned on expectations. Can we take some time to walk through that together?”

It’s not perfect.

But it does a few important things.

It shows care.
It names the issue.
And it opens the door to a conversation that can move toward a win-win.

And when that part goes well, it leads to something simple and powerful.

We Tie it together.

Clearer agreements.
Shared expectations.
A way forward that works for both of us.

That’s the AGENT framework in practice.

Not something abstract.
Something you can do.

And when it works, it doesn’t just resolve the conflict.

It creates the conditions for a win-win.

5. PRACTICE FOR THE READER 🛠

Try This Before Your Next Conflict

• What difficult conversation am I not having right now?

• What feels at risk if I address it directly?

• What am I tolerating today because the alternative feels uncertain?

6. CLOSING REFLECTION

Avoiding a conversation often feels like the safer choice.

Until you realize it is still a choice.

And it is shaping the outcome, one week at a time.

See you in the win-win moments this week!
Sam