Manager having a private, supportive conversation with an employee at work.

When an Employee Is Struggling: What Good Leaders Do Next

⏱ 17 min read

Something has changed.

Maybe an employee who used to be dependable has started missing deadlines. Maybe someone who normally participates in meetings has gone quiet. Or perhaps there’s tension between team members, and you can’t quite figure out where it’s coming from.

You notice it. Other people may notice it, too.

But what are you supposed to do?

You don’t have a large HR department. You may not have an employee assistance program (EAP). And you certainly don’t have the time—or the qualifications—to figure out whether someone is dealing with depression, anxiety, burnout, or something else entirely.

Nor should you have to.

Your responsibility isn’t to figure out what’s happening inside someone’s mind. It’s to respond thoughtfully to what’s happening in the workplace.

That sounds simple until you’re sitting across from an employee who says everything is fine, even though their work tells a different story.

Or someone starts crying during what was supposed to be a routine conversation about missed deadlines.

Or you realize that while you’ve been trying to give one employee some breathing room, three other people have quietly taken on additional work.

Now you’re dealing with more than one person’s difficulty. You’re trying to balance compassion, privacy, fairness, and the responsibilities of running a business.

And there’s no perfect script for that.

But there is a way to approach these situations without becoming someone’s therapist, ignoring what you see, or treating a struggling employee like a problem to get rid of.

It starts with understanding what belongs to you as a leader—and what doesn’t.

Something Feels Off. Is It Your Place to Say Anything?

Let’s establish something important.

Not every change in an employee’s behavior means they’re struggling with their mental health.

People get tired. They have difficult weeks. They experience family problems, financial pressures, workplace conflicts, and ordinary frustrations.

Sometimes an employee isn’t overwhelmed by life. They’re overwhelmed by an unreasonable workload.

Sometimes the problem isn’t the employee at all.

That’s why you need to separate what you’ve observed from what you’ve assumed.

For example, you may notice:

  • Deadlines that used to be met are now repeatedly missed.

  • Work quality has changed.

  • Communication has become inconsistent.

  • An employee is having recurring conflicts with coworkers.

  • Important responsibilities are being left unfinished.

Those are workplace observations.

“They must be depressed” is an assumption.

“They don’t care anymore” is an interpretation.

“They’re probably having problems at home” is a story you’ve created without enough information.

And stories have a way of becoming dangerous when leaders start treating them like facts.

Look for patterns, not personality changes

A naturally quiet employee isn’t necessarily disengaged. Someone who gets emotional during a conversation isn’t automatically unstable. A person who questions your decision isn’t necessarily being difficult.

What matters is whether there’s a meaningful workplace issue that needs attention.

Ask yourself:

What specifically has changed? How long has it been happening? What impact is it having? And have I considered whether the work environment itself might be contributing?

That last question matters.

If three employees are missing deadlines after you’ve doubled everyone’s responsibilities, you might not have three employees with personal problems.

You might have a workload problem.

Your role is to understand the situation well enough to lead—not to diagnose the people involved.

Why avoidance isn’t compassion

Most leaders don’t ignore difficult situations because they don’t care.

They ignore them because they don’t want to make things worse.

They tell themselves it’s personal. They wait for the employee to say something. Or they quietly redistribute responsibilities, hoping everything will eventually settle down.

It feels kind. It feels patient. It even feels professional.

But sometimes it creates a bigger problem.

The employee doesn’t get clarity. Coworkers don’t understand why expectations seem to have changed. Work gets uneven, and resentment begins building in places no one wants to acknowledge.

Avoidance creates ambiguity.

Ambiguity creates tension.

And tension spreads.

Compassion doesn’t require you to ignore what’s happening. It requires you to address it without stripping someone of their dignity.

How Do You Talk to an Employee Without Playing Therapist?

This is where many leaders freeze.

They rehearse the conversation. They worry about saying the wrong thing. They wonder whether asking a question will make the employee uncomfortable.

And sometimes they avoid the conversation altogether.

You don’t need a perfect script.

You need a clear, grounded entry point.

Start with what you actually know

Imagine an employee named Jordan.

Jordan has missed two important deadlines, and another team member has had to step in to finish the work.

You could approach the conversation this way:

“Jordan, I’ve noticed the last two project deadlines were missed, and we’ve had to reassign some of the work. That’s different from how things usually go. I wanted to check in and hear your perspective.”

Notice what you didn’t say.

You didn’t ask whether Jordan was depressed.

You didn’t accuse Jordan of being lazy.

You didn’t begin listing everything you think might be wrong.

You named the work issue and opened the conversation.

That is leadership.

Ask, but don’t corner

After you’ve explained what you’ve observed, give the employee an opportunity to respond.

You might ask:

“What has been making these deadlines difficult to meet?”

Or:

“Is there something about the workload or expectations that we need to look at?”

Then listen.

And don’t rush to fill the silence.

The employee may explain that the priorities have been unclear. They may tell you that a family situation has made scheduling difficult. They may raise a health-related concern.

Or they may say nothing is wrong.

You don’t have to force a deeper conversation.

Your job isn’t to extract a personal confession. Your job is to understand and address the work-related concern.

And if the employee doesn’t want to discuss their personal life, respect that.

You can still talk about deadlines, communication, responsibilities, and what needs to happen next.

What If the Employee Cries, Gets Defensive, or Says Everything Is Fine?

Here’s where the situation becomes uncomfortable.

You’re prepared to discuss a missed deadline.

Instead, the employee starts crying.

Or they become defensive and insist you’re being unfair.

Or they tell you everything is fine while refusing to discuss the work problems.

Now what?

If they become emotional

You don’t need to panic because someone is crying.

Give them a moment.

You might say:

“We can take a few minutes. I can see this is difficult.”

Then pause.

You don’t have to rush into reassurance, offer personal advice, or ask for the details of what they’re experiencing.

If they want to share something, listen respectfully. But remember that hearing someone’s personal story doesn’t make you responsible for solving it.

You can care without taking over.

If they become defensive

Stay with the facts.

“I’m not questioning your worth or everything you’ve contributed here. We still need to address the missed deadlines and figure out what happens next.”

This is especially important when you feel yourself becoming defensive, too.

A leader who interprets every difficult response as disrespect may turn an ordinary work conversation into a battle over authority.

And a leader who cannot tolerate someone else’s discomfort may rush to withdraw perfectly reasonable expectations.

Neither response is particularly helpful.

If criticism or disagreement tends to unsettle you, I’ve written more about why criticism can trigger such a strong emotional response. Those reactions are worth understanding in yourself rather than projecting onto the employee sitting across from you.

If they say, “I’m fine”

Accept that they may not want to share personal information.

Then return to the work.

“Okay. We don’t need to discuss anything personal. What we do need to talk about is how to get the current projects back on track.”

This isn’t cold.

It’s respectful.

You are allowing the employee privacy without pretending the work problem has disappeared.

If they disclose a medical condition or ask for an adjustment

Now the conversation may require a different process.

If an employee says they need a scheduling change, leave, or another workplace adjustment because of a medical condition, don’t dismiss it as an excuse or treat it as an ordinary favor.

Depending on the situation and applicable law, it may be a request for reasonable accommodation or protected leave.

You don’t need to decide that on the spot.

A responsible response is to acknowledge the request, explain that you’ll review the appropriate process, and seek qualified HR or employment-law guidance when needed.

Respecting boundaries doesn’t mean ignoring legal responsibilities.

What Can You Actually Offer Without an EAP or Large HR Department?

Let’s talk about the reality many smaller organizations face.

You may have six employees, not six hundred.

You may handle payroll, customer concerns, staffing, and operations yourself.

You don’t have an HR specialist sitting down the hall. You don’t have a comprehensive wellness program. And you can’t spend hours researching every mental health nonprofit because someone on your team is having a difficult time.

So what does meaningful support look like?

Often, it’s less elaborate than people think.

Start with the working conditions you control

Before assuming an employee needs outside help, look at what is happening inside the organization.

Maybe the employee is juggling five priorities, all of which you’ve described as urgent.

Maybe two managers keep giving conflicting instructions.

Maybe their responsibilities have expanded without anyone acknowledging the additional workload.

Or maybe the work itself is perfectly reasonable, but an employee needs more clarity about what success looks like.

You can address those issues directly.

For example:

  • Identify the most important tasks and clarify their deadlines.

  • Break a complicated project into smaller deliverables.

  • Discuss available scheduling flexibility.

  • Review whether responsibilities have been distributed fairly.

  • Establish a regular check-in instead of leaving everyone guessing.

These adjustments don’t require a large budget.

They require attention and sound judgment.

But don’t make promises you cannot sustain.

If you offer flexibility, be clear about what you’re offering and how you’ll evaluate whether it’s helping. And remember that legally required accommodations are not simply discretionary favors; they need to be handled through the appropriate process.

What if the employee needs professional help?

You can acknowledge that professional support may be useful without acting as if you know what diagnosis or treatment they need.

If your organization offers health coverage, the employee may be able to look for behavioral health services through their insurance provider.

If they need help finding treatment, you can share a resource such as FindTreatment.gov, a federal treatment locator maintained through the Substance Abuse and Mental Health Services Administration.

You don’t need to research providers for them.

You don’t need to select a therapist.

And you don’t need to keep checking whether they followed your recommendation.

You can make information available without taking ownership of another adult’s healthcare decisions.

If someone appears to be in immediate danger, expresses an urgent intent to harm themselves or someone else, or presents an immediate safety threat, that’s different from a routine performance conversation. Follow your workplace emergency procedures and contact appropriate emergency services. In the United States, the 988 Suicide & Crisis Lifeline is also available by call or text for crisis support.

You can be supportive without becoming the support system.

That’s an important distinction for a small-business leader.

What about employee rights?

You also need to know when a situation has moved beyond your ordinary discretion.

The federal Americans with Disabilities Act generally applies to employers with 15 or more employees, while the federal Family and Medical Leave Act has different coverage and eligibility requirements. State and local protections may also apply, including to smaller employers.

And a medical-related adjustment doesn’t become optional just because your organization lacks an HR department.

You can begin with the EEOC’s guidance for small employers on reasonable accommodation rather than trying to interpret every employment law yourself.

When the circumstances are complicated, get qualified guidance before making a decision that could affect someone’s job or rights.

That’s not overcomplicating leadership.

It’s recognizing where your responsibility includes knowing when to seek expertise.

How Do You Support One Employee Without Overburdening Everyone Else?

Here’s a situation that doesn’t get discussed enough.

You’re trying to support Jordan.

You’ve adjusted a few deadlines. You’ve offered additional check-ins. You’ve given Jordan some breathing room.

But now another employee is staying late to finish the work.

Someone else has stopped volunteering for projects because they expect unfinished tasks to land on their desk.

And you can feel the tension building.

This is where leaders sometimes confuse compassion with making everyone else absorb the consequences of a situation they haven’t addressed clearly.

Support for one person should not mean forgetting the rest of the team.

But the answer isn’t to share Jordan’s private circumstances.

You can redistribute work thoughtfully, review overall capacity, or change priorities without explaining another employee’s personal situation.

You might tell the team:

“We’re reviewing the current workload and adjusting priorities so responsibilities are manageable. I’ll clarify who’s handling what and when.”

That’s enough.

Your employees don’t need access to someone else’s medical information to understand their own assignments.

Don’t confuse fairness with identical treatment

This distinction matters.

Fairness doesn’t always mean everyone receives exactly the same arrangements.

Someone may need a legally required accommodation. Another employee may be working a different schedule because of their role. Someone else may be taking approved leave.

Those differences aren’t automatically evidence of favoritism.

What matters is whether you are managing work responsibly, respecting applicable rights, and communicating expectations clearly.

You can protect privacy and still protect the functioning of your business.

You can support an employee and still take the rest of the team’s experience seriously.

You need both.

What Happens After the Conversation?

One thoughtful conversation is not a leadership strategy.

You still need a way forward.

Before ending the discussion, make sure both of you understand what has been agreed upon.

What needs to be completed?

What priorities have changed?

What support or adjustments are being considered?

When will you check in again?

For ordinary performance concerns, a brief written follow-up might say:

“Thanks for meeting today. As discussed, the client report is now the first priority, with a revised deadline of Thursday. We’ll review progress on Tuesday and identify any remaining obstacles.”

No dramatic language.

No lengthy analysis of the employee’s emotional state.

Just clarity.

Keep routine performance notes factual and limit access appropriately. If medical information is disclosed or accommodation documentation is involved, follow the applicable confidentiality and recordkeeping requirements rather than mixing sensitive details into ordinary personnel notes.

Watch for drift

Sometimes a temporary change becomes an indefinite arrangement simply because no one revisits it.

Deadlines stay unclear.

Assignments are quietly transferred.

Check-ins stop happening.

And nobody knows whether the original problem has improved.

That’s not a good outcome for anyone.

With ordinary, discretionary work arrangements, review what is and isn’t helping. Where a formal accommodation or protected leave is involved, follow the required process before changing an arrangement.

The point is not to pressure someone into a quick recovery.

It’s to keep the workplace from operating on assumptions.

What if nothing improves?

Then you need to evaluate the situation based on the actual work requirements, the support already provided, and any applicable accommodation or leave obligations.

Don’t assume the employee isn’t trying.

Don’t assume that struggling means they cannot do the job.

And don’t assume that because you’ve been compassionate, you’re prohibited from addressing performance.

Sometimes the next step is clearer training or supervision.

Sometimes it’s a different workload arrangement.

Sometimes it requires specialized HR or legal guidance.

And sometimes, after the appropriate processes have been followed, a difficult employment decision may still be necessary.

What matters is that you reach that point through a fair and informed process—not frustration, resentment, or an emotional reaction.

The Emotional Work Leaders Need to Do Themselves

We’ve talked about the struggling employee.

Now let’s talk about you.

Because how you respond to another person’s difficulty may reveal something about your own relationship with discomfort.

Some leaders learned that caring means solving everyone’s problems.

So when an employee struggles, they overfunction. They take on extra work. They make themselves available at all hours. They quietly become responsible for keeping another adult emotionally steady.

Other leaders learned that emotions create trouble.

So they avoid difficult conversations until problems become impossible to ignore.

And some leaders learned that authority means always being in control.

When someone cries, challenges them, or doesn’t respond as expected, they feel the need to shut the conversation down.

These responses may feel like personality.

But sometimes they’re familiar patterns playing out in a leadership role.

This is part of what I explore through my Emotional Pattern Framework: how earlier emotional lessons and survival strategies can shape the way we lead, relate, and respond as adults.

The framework isn’t something you use to analyze your employees.

It’s a way to become more aware of yourself.

Because the employee’s situation isn’t an invitation for you to play therapist.

But it may be an opportunity to notice how you handle uncertainty, conflict, boundaries, and responsibility.

Do you need everyone to be okay before you can feel okay?

Do you avoid necessary conversations because you don’t want someone to dislike you?

Do you mistake giving more of yourself for being a better leader?

Those questions matter.

And you can work on them without making an employee responsible for your growth.

Support is not rescue. Boundaries are not punishment.

I want you to remember those two distinctions.

Supporting someone doesn’t mean taking responsibility for everything they’re experiencing.

And maintaining a boundary doesn’t mean you lack compassion.

You can listen without taking over.

You can make appropriate adjustments without abandoning standards.

You can acknowledge an employee’s humanity without requiring them to explain their private life.

You can recognize when professional support is needed without pretending you’re qualified to provide it.

And you can admit that a situation is difficult without assuming you’re failing as a leader.

That’s emotional maturity in practice.

Not perfection.

Not having all the answers.

Just the willingness to recognize what belongs to you, respond thoughtfully, and stop carrying what was never yours to hold.

You Don’t Have to Know Everything to Lead Well

At some point, you’ll encounter an employee whose behavior or work has changed, and you won’t know why.

You may never know why.

They might be dealing with something personal. There might be a medical concern. They could be overwhelmed by work. Or the problem may be entirely different from what you initially imagined.

Your job isn’t to solve that mystery.

Your job is to pay attention to what’s happening, have the necessary conversations, respect the person’s privacy, consider the support and obligations that apply, and make responsible decisions about the work.

You don’t need a large EAP program to begin.

You don’t need to become a mental health expert.

And you certainly don’t need to make yourself responsible for another adult’s emotional life.

But you do need to lead.

Sometimes that means speaking up when you’d rather avoid discomfort.

Sometimes it means giving someone room to explain.

Sometimes it means recognizing that the work environment needs to change.

And sometimes it means holding a boundary even when doing so feels uncomfortable.

Good leadership isn’t about choosing between compassion and accountability. It’s about understanding how to practice both responsibly.

You can create a workplace where people are allowed to be human without losing the clarity, fairness, and structure everyone needs.

And you can do it without losing yourself in the process.


When Your Leadership Patterns Need Attention, Too

If you’re trying to lead without overfunctioning—without rescuing, avoiding, controlling, or carrying what isn’t yours—that’s part of the work I do.

My six-month coaching program, The Path, helps leaders examine the emotional patterns influencing their decisions, boundaries, relationships, and leadership.

It isn’t mental health treatment or an employee-management service. It’s an opportunity to understand yourself more deeply and make different choices about how you lead.

If that speaks to where you are now, you can explore the program and decide whether it’s the right fit.

👉 Explore The Path Coaching Program

Keep Following the Pattern

Disclaimer:
Everything on DeniseGLee.com is for educational and informational use only.

I’m not your doctor, therapist, lawyer, or emergency contact — I’m a healing and leadership coach.

If you’re in crisis, please reach out to qualified professionals or local emergency services immediately.