Quandary Mat: Individual performance vs culture work with Gen Z

Dear Hunter,

I’m stuck. And frustrated.

One of my employees is smart, thoughtful, and deeply committed to our mission in health care. But there are parts of her work that just… don’t happen. Deadlines slip. Details get missed.

Every time I bring it up—when I try to talk about performance or expectations—she turns the focus to what she needs from me or from the organization. Her workload is too heavy. She’s anxious. She needs more support.

And I get it. I want to be a good boss. I listen. I offer suggestions. I point her to the EAP when our check-ins start to sound like therapy. We talk about time management and how to flag problems early.

But nothing changes.

It feels like we’re talking past each other. Maybe it’s generational—me as Gen X, her as an older Millennial or younger Gen Z. I am supportive. But the work still has to get done.

What do you think?

Thanks,
Not a Mean Boss

Dear Not a Mean Boss,

Oh, I know this dance. You’re both trying so hard to be good people in a system that makes it hard to be both kind and clear.

The question you’re circling is one I hear all the time:
Where’s the line between supporting someone and holding them accountable?

Here’s the thing: there isn’t one. Support and accountability aren’t opposites—they’re partners. The best kind of support includes accountability, because clarity and follow-through are some of the kindest things we can offer each other at work.

You’re right that there’s a generational twist here. Younger workers often have a sharper radar for what’s healthy and fair. They’re more likely to say, “Hey, this workload isn’t sustainable,” or “This dynamic doesn’t feel right.” And that’s a good thing—it challenges us all to work with more humanity.

But where it gets tricky is when every conversation about performance gets swept up in a bigger one about support, culture, or workload. Those conversations matter, but not if they keep you from talking about the work itself.

So what can you do?

Start by naming what’s happening.
You might say, “I’ve noticed that when I give feedback, we often end up talking about workload or support. Those are real issues, but it means we don’t get back to what needs to change in the work itself.”

You’re not scolding—you’re simply putting words to a pattern you both can see. Once something is named, you can work with it together.

Then, make space for both kinds of talk—just not at the same time.
You could agree that feedback about specific tasks or deadlines stays focused on the work itself, and that broader topics—workload, wellbeing, team culture—get their own space in regular check-ins.

If she starts blending the two, you can gently say, “I think we’re shifting into a support conversation—let’s finish this part first.” That’s not being harsh; that’s being clear. And clarity is kindness.

Also, check your own assumptions.
It’s possible that her push for support feels like deflection because you’re trying to fix a performance problem she sees as a structural one. Sometimes people who ask for help aren’t avoiding accountability—they’re describing what keeps them from meeting it.

You don’t have to agree with her take, but it helps to show curiosity before redirecting. A simple “Say more about that” can open space for honesty—and then you can still return to expectations.

**And about that generational piece—**let it inform, not define.

Yes, there are differences in how we were raised to think about work. Many Gen Xers learned that being dependable meant working through anything. Many Millennials and Gen Zers learned that burning out isn’t noble. Somewhere in between is the sweet spot: care and competence, compassion and results.

That’s what you’re both trying to find.

When you separate the conversations and keep both moving—“what I give the job” and “what the job gives me”—you help each other stay grounded in reality and kindness.

You’re not a mean boss. You’re a boss who’s paying attention. The fact that you’re asking this question tells me you’re already doing the most important part of leadership: seeing your people as people.

Now, your work is to help this employee meet you halfway. Keep the expectations clear, keep the support real, and when the two start to blur, help bring them back into focus.

You can do that with empathy and firmness, both at once.

Because that’s what good leaders do—they hold the whole picture.

Let me know how it goes. 

Best of luck, 

Hunter