Please Don’t Go: How to Retain Employees (and Supervisors) on the Verge of Quitting
Let’s be honest.
You can feel it coming.
The shift in tone. The subtle detachment. The increased "sick days." The slightly-too-fast response when someone mentions a job lead.
You know something’s off. But instead of acting, perhaps you’ve done what many leaders do: you wait. Not because you don’t care—but because:
You’re exhausted.
You’re down three people already.
And let’s face it… the idea of one more person quitting makes your stomach do somersaults.
So you delay the conversation. You hope things will smooth out. Maybe you even convince yourself, “They’re probably just going through a phase.”
But when a good employee—or an even better supervisor—is pulling away, avoidance is not your friend. Early action is.
Let’s talk about what to do when someone great is almost gone… and how you might still win them back.
1. Misplaced Compassion Can Keep You Stuck
When someone’s been loyal, overworked, or clearly struggling, it’s natural to feel for them. You might think:
“They’ve been through so much—maybe I should just give them whatever they’re asking.”
“They’re burned out… I get it. I don’t want to push them.”
“Maybe this is my fault for not doing more.”
Compassion is a leadership strength—but misaligned compassion? That’s a recipe for resentment and confusion.
Here’s the trap: fear and empathy can cloud our judgment and make us tolerate performance or behavior that we would never accept from someone new.
Sometimes, you already know the answer—you just don’t want to face it:
This person has been checked out for months.
Their behavior is disrupting the team.
They’re not showing any willingness to re-engage.
The first retention question isn’t “How do I get them to stay?” It’s “Do I really want them to stay?”
2. Start a Real Conversation (Not a Pep Talk)
If they’re someone worth keeping, you’ve got to open the door before they walk through the exit.
This isn’t a motivational speech. This is a sit-down, face-to-face, “Let’s talk about what’s been hard.”
Here’s how you start:
“I’ve noticed some things have been heavy lately, and I want to check in. If you’re open to it, I’d like to hear what’s been frustrating or wearing you down lately.”
Not “How are you?” (Too easy to dodge.)
Not “You’re not quitting, are you?” (Yikes.)
Keep it concrete. Use observations, not assumptions:
“I noticed you’ve been picking up fewer shifts than usual.”
“You seemed a little checked out in the staff meeting last week.”
“I know things have been rough with coverage lately.”
Then… pause. Let them fill the space. Because often, what you’ll hear isn’t petty. It’s real.
They’re tired of being the go-to for coverage. They feel like their feedback is ignored. They’re not sure they matter anymore.
And now you have something you can work with.
3. Own Your Part, Validate the Pain, Then Offer a Reset
Let’s be clear—this isn’t just about letting them vent. It’s about creating a moment of connection that lays the groundwork for change.
But first, you have to own your side of the street.
“You’re right—we haven’t handled that as well as we should have. I didn’t realize how much that was weighing on you. That’s on me.”
Then, validate the feeling:
“It makes total sense you’d feel frustrated. You’ve been showing up in big ways, and it hasn’t always felt like anyone noticed.”
This isn’t weakness. This is leadership. And if you’ve truly made them feel seen and heard, then you can move into the reset:
“If you’re open to it, I’d like to hit reset and make this better—with your help.”
But don’t skip ahead. If you don’t slow down and fully acknowledge their pain, the reset will feel insincere, and might drive them towards resignation even faster.
4. Let Them Help Design the Fix
Here’s a powerful way to re-engage someone on the verge of quitting: involve them in building the solution.
It’s not about dumping the problem on them. It’s about asking:
“What ideas do you have for making this better?”
“If we could change one thing that would help right away, what would it be?”
“Would you be open to helping shape how we solve this?”
From a behavioral science perspective, this is powerful. Giving someone some control and choice over how things improve increases both buy-in and follow-through.
Even small fixes—like adjusting shift communication, tweaking onboarding, or piloting a new task support system—can go a long way when they help create them.
They don’t need to rebuild the system. They just need to feel like their voice matters in shaping it.
5. Over-Communicate (Yes, Even More Than That)
This is where most leaders fall short—and it’s so easy to accidentally let this happen.
You hold one good meeting, share your plan, make a few tweaks... Then things get quiet. Life moves on. The crisis passes.
But the employee? They’re still watching. They’re waiting to see if this change is real, or just another round of “We value you” with no follow-through.
So don’t just communicate—over-communicate.
Follow up weekly (even with a 5-10 minute check-in).
Celebrate small wins. (“Hey, I noticed the schedule got finalized on time this week. Thank you!”)
Revisit the fix and ask: “Is this helping?”
Because silence will almost always be interpreted as indifference.
6. Common Stuck Spots (And How to Break Through Them)
Let’s address a few common traps human services leaders fall into—and how to avoid them:
Stuck Spot 1: “This isn’t fair to everyone else.”
You’re afraid that adjusting for one person will create a domino effect.
Solution:
Fair doesn’t mean equal. It means responsive. If someone has taken on more, carried more, or been in a tough spot longer—of course the response should be different.
Equity is the new equality.
Stuck Spot 2: “I can’t fix all of this.”
Maybe the person brings up real issues—understaffing, poor onboarding, scheduling chaos—but you can’t fix them all overnight.
Solution:
Don’t promise everything. Instead, say:
“Here’s what I can fix now. Here’s what I’ll advocate for. And here’s what I’ll check back on in two weeks.”
Small wins create momentum.
Stuck Spot 3: “They’re still quiet... is it working?”
You make changes, but the person isn’t gushing gratitude. Now you’re unsure if they’re still halfway out the door.
Solution:
Ask. Don’t guess. Use a simple script:
“How are things feeling this week—lighter, heavier, about the same?”
Track it. Adjust accordingly.
7. The Bigger Picture: Stop Playing Whack-a-Mole with Retention
The best way to retain great people isn’t just to rescue them at the last minute. It’s to build a workplace they don’t want to leave in the first place.
Here’s how:
Design an amazing onboarding experience (not just paperwork—real connection).
Create a performance-based recognition system that rewards behavior, not just tenure.
Train supervisors to lead people, not just schedules. (You can read more about training supervisors here.)
Fix what’s frustrating before it turns into burnout.
Because the most effective retention strategy is to build something people feel proud to be part of—on the hard days, not just the good ones.
Final Word
If you’ve got a good person slipping away, don’t assume it’s too late. And don’t assume it’s all on you to fix.
Sometimes what they need most isn’t a new role, a raise, or a rewards program. It’s a moment of honesty. A reset. A little less silence—and a little more listening.
And maybe most important of all—an invitation to help make things better.
When people help build the solution, they’re far more likely to stay for the long haul…
and be proud of what they’re helping create.
