A Leader’s Guide On How To Deal With Difficult Employees

Let’s face it: dealing with difficult employees isn’t fun.

But here’s the thing, it’s part of our job, and problematic behavior has to be dealt with before it affects morale and productivity of the whole team.

In this guide, I’m going to share what I’ve learned about dealing with difficult employees. We’ll explore practical steps that you can start using today. Whether you’re a seasoned pro or new to leadership, you’ll find something here to help you navigate these tricky waters.

Ready to become a pro at handling difficult employees?

Step 1: Recognize the Issue

As a leader, I’ve learned that spotting problems early is key to managing difficult employees. It’s like catching a small leak before it floods the whole room.

What Makes an Employee Difficult?

Sometimes, it’s about attitude. Maybe they’re always complaining or bringing others down.

Other times, it’s about work. They might miss deadlines or do sloppy work.

But here’s the thing: there’s usually more to the story. A  challenging employee isn’t trying to make trouble on purpose.

Often, they’re struggling with something we can’t see.

Maybe they’re dealing with:

  • Personal problems at home
  • Feeling overwhelmed by their work
  • Not understanding what’s expected of them
  • Health issues they haven’t shared

As leaders, it’s our job to dig deeper. We need to find out what’s really going on. Only then can we help them get back on track.

By understanding what’s behind the difficult behavior, we can solve problems better. Don’t think of it as trying to fix the employee, think of it more as working together to find a solution that improves the whole work environment.

Spot Problem Behaviors Early

I always keep my eyes open for changes in how my team acts. Maybe someone’s always late now, or they’re not playing well with others. These little things can be big red flags.

Here are some warning signs I’ve learned to watch out for:

  • Showing up late more often
  • Missing deadlines they used to meet
  • Avoiding team meetings or group work
  • Complaining more than usual
  • Doing the bare minimum instead of their best
  • Being rude to coworkers or customers
  • Making more mistakes in their work
  • Seeming distracted or uninterested
  • Not following instructions
  • Refusing to take on new tasks
  • Gossiping or stirring up drama

Don’t ignore these signs. They’re trying to tell you something’s up.

The sooner you notice, the easier it is to fix.

Trust Your Gut Feeling

You know that funny feeling you get when something’s not right?

Listen to it.

I’ve learned that my gut is often smarter than my head.

Don’t brush it off. Take a closer look and see what’s going on.

Step 2: Take a Step Back

When you spot a problem, it’s tempting to jump in and fix it right away.

But hold on a second.

Taking a step back can help you handle things better.

Breathe and Stay Calm

First things first: take a deep breath.

Seriously, do it right now. Feel better?

When we’re calm, we make better choices.

I like to count to ten or take a quick walk. Find what works for you.

The goal is to clear your head before you act.

Remember, It’s Not Personal

Here’s something I always tell myself: this isn’t about me. The employee isn’t trying to make my life hard on purpose, even though it may feel that way sometimes.

There’s usually more to the story.

Keeping this in mind helps me stay fair and kind.

Step 3: Talk to the Employee One-on-One

Now it’s time for the big talk. But don’t worry, you’ve got this.

Let’s break it down.

Set Up a Private Meeting

Nobody likes being called out in front of others. I always set up a private chat. It helps the employee feel safe to open up.

Send a quick message or catch them in person.

Say something like, “Hey, can we chat for a bit tomorrow?” Keep it casual but clear.

Choose a Neutral Location

Where you meet matters more than you might think.

Your office might feel too much like being sent to the principal. The break room is too public.

I like to pick a quiet corner or a small meeting room.

It should feel neutral and comfortable for both of you.

Over the next few steps, we’ll go over what to do in the meeting.

Step 4: Listen Actively

When it comes to solving problems, listening is your secret weapon.

It’s not just about hearing words; it’s about really understanding what’s being said.

Here’s how to do it right:

Let Them Share Their Side

When you’re dealing with a tricky situation, let your team member talk first. Give them the floor and really hear them out.

This could mean opening the conversation by thanking them for meeting with you and saying you’ve noticed how they’ve been showing up late more often and wanted to make sure everything was okay.

By phrasing it this way, the employee will begin to open up more often than not.

Don’t interrupt. Just listen. You might be surprised by what you learn.

Show You Care About Their Perspective

It’s not enough to just hear the words. You need to show that you truly care about their point of view.

You don’t have to completely agree with their side, but try to understand where they are coming from.

Put yourself in their shoes, even if you would handle the situation completely differently.

Step 5: Identify the Root Cause

Getting to the heart of the problem is like being a detective.

You need to look beyond what’s on the surface and find out what’s really going on. 

Here’s how I do it:

Ask Open-Ended Questions

Getting to the heart of the problem takes some digging. Open-ended questions are your number 1 tool to get the employee to open up to you about their poor performance.

Here’s a chart you can use to help you ask better questions:

Direct QuestionsOpen-Ended Questions
Are you happy with your work?How do you feel about your current projects?
Did you meet your deadline?What challenges did you face with the last deadline?
Do you like your team?How would you describe your relationships with your coworkers?
Are you having problems at work?What’s been on your mind lately regarding your job?
Can you improve your performance?What areas do you think you could grow in?
Is your workload too much?How are you managing your tasks and responsibilities?
Do you understand your job duties?What parts of your role are you most confident about?

Remember, the goal is to get them talking.

When I use open-ended questions, I often hear things I never expected.

Look for Underlying Issues

Sometimes, what looks like a problem on the surface is just a symptom of something deeper.

Maybe they’re struggling with a task because they need more training. Or perhaps there’s a conflict with a coworker that’s causing stress.

I always try to look beyond the obvious.

Use the 5 Whys Technique

I’ve found the 5 Whys technique to be a powerful tool. It’s simple but effective. Here’s how it works:

  1. Start with the problem statement.
  2. Ask “Why?” five times.
  3. Each answer becomes the basis for the next question.

For example:

Problem: An employee is consistently late.

  1. Why? They’re stuck in traffic.
  2. Why? They leave home too late.
  3. Why? They’re rushing to get kids ready for school.
  4. Why? Their partner used to help but recently changed jobs.
  5. Why? The family is adjusting to a new schedule.

See how we got to the root cause? Now we can work on real solutions.

Try Other Root Cause Analysis Tools

I like to have a few tools in my leadership toolkit. Here are some others I use:

  1. Fishbone Diagram: This helps me visualize all possible causes of a problem.
  2. Pareto Analysis: It shows which factors have the biggest impact.
  3. Fault Tree Analysis: Great for complex issues with multiple factors.
  4. FMEA (Failure Mode and Effects Analysis): Helps prevent problems before they happen.
  5. Root Cause Mapping: A visual way to connect causes and effects.

Remember, the goal isn’t to place blame. It’s to understand the problem so we can fix it.

The key is to keep digging, keep asking questions, and always look for the real issue behind the problem.

When you find the root cause, you’re not just fixing a symptom, you’re solving the real problem.

Step 6: Set Clear Expectations

Once you understand the issue, it’s time to chart a course forward.

Here’s how to set expectations that work:

Be Specific About What Needs to Change

Once you understand the issue, it’s time to lay out a plan.

But here’s the trick: you need to be crystal clear about what needs to happen.

Don’t just say, “Do better.” Instead, try something like, “I need you to submit your reports by Friday each week.” The more specific, the better.

Explain Why It Matters

People are more likely to change when they understand why it’s important.

So, don’t just give orders. Explain the impact.

For example, “When you turn in your reports on time, it helps the whole team stay on track. It also shows clients that we’re reliable.”

By setting clear expectations, you’re helping your team member succeed. And that’s what great leadership is all about.

Step 7: Create an Action Plan Together

When it comes to solving problems, teamwork is key. I’ve found that the best solutions come when we work together. 

But how can we make this happen?

Involve the Employee in Finding Solutions

I always say, “Two heads are better than one.” When you’re tackling the problem, bring your problem employee into the process.

Ask them, “What do you think would help?” Their ideas might surprise you.

Plus, when people help create solutions, they’re more likely to stick with them.

Set Realistic Goals and Timelines

It’s great to aim high, but we need to keep things doable.

I like to break big goals into smaller steps.

For example, instead of saying “Improve customer service,” try “Respond to all customer emails within 24 hours.” It’s clear and you can measure it.

Step 8: Offer Support and Resources

As a leader, your job isn’t just to point out problems. You need to help your team overcome them.

Here’s how I make sure my team has what they need to succeed.

Provide Training if Needed

Sometimes, the best way to deal with a difficult employee is to teach new skills or enhance the skills they already have.

If your team member is struggling, ask yourself, “Could some training help?”

Maybe they need a course on time management or a workshop on communication skills.

Investing in your team’s growth is always worth it.

Connect Them with Mentors or Tools

You may not always be the best one to help your employee, and I can tell you from experience, you don’t have all the answers.

Sometimes, the best thing you can do is connect your team member with someone who’s been there before.

I often pair up team members who have complementary skills.

Or I might introduce them to a person who has had similar issues.

Possible Resources to Help Difficult Employees

  1. Online Learning Platforms
    I’ve found great success with sites like Coursera or LinkedIn Learning. They offer courses on everything from time management to conflict resolution.
  2. Company Knowledge Base
    Don’t overlook what’s right under your nose. I always make sure my team knows how to use our internal resources.
  3. Professional Coaching
    Sometimes, a one-on-one approach works best. I’ve seen amazing turnarounds when employees work with professional coaches.
  4. Peer Support Groups
    I love setting up small groups where team members can share challenges and solutions. It builds community and problem-solving skills.
  5. Time Management Apps
    For those struggling with deadlines, apps like Trello or Asana can be game-changers. I use them myself!
  6. Communication Workshops
    I’ve sent team members to workshops on active listening and clear communication. The results are often immediate and impressive.
  7. Mindfulness Resources
    Stress can make anyone difficult. I encourage my team to try mindfulness apps or local meditation classes.
  8. Employee Assistance Programs (EAP)
    Many companies offer these, but employees forget about them. I make sure my team knows about our EAP for personal or work-related issues.

Remember, every person is unique. What works for one might not work for another.

The key is to keep trying and to show your team member that you believe in their ability to grow and improve.

I’ve seen some of my most difficult employees become my strongest team members with the right support and resources.

It takes time and patience, but helping someone find their path to success is one of the most rewarding parts of leadership.

Step 9: Follow Up Regularly with the Difficult Employee

Your job isn’t done once you’ve made a plan. The real magic happens in the follow-through.

Here’s how I make sure we stay on track.

Schedule Check-ins

I always put check-ins on the calendar.

It shows your team member that you care about their progress.

These don’t have to be long meetings. Even a quick 15-minute chat can make a big difference.

Celebrate Progress and Address Setbacks

When things are going well, shout it from the rooftops!

I love to celebrate wins, big and small.

But if there are setbacks, don’t ignore them. Talk about what went wrong and how to fix it.

Remember, every setback is a chance to learn and grow.

Step 10: Document Everything

I can’t stress this enough: keeping good records is crucial. It’s not just about covering your bases. It’s about making sure everyone’s on the same page.

Keep Records of Meetings and Agreements

After every meeting, I jot down the main points.

What did we discuss? What did we agree on?

I find it helpful to send a quick email recap to the employee.

This way, there’s no confusion about what we decided.

Protect Yourself and the Employee

Good documentation isn’t about playing “gotcha.” It’s about clarity and fairness.

Don’t just document the negative behaviors; make sure you document anything positive as well.

If you keep clear records, you’re protecting everyone involved and keeping the full story straight. 

Step 11: Know When to Escalate

Sometimes, despite our best efforts, we need to bring in reinforcements.

That’s okay.

It’s part of being a good leader.

Understand Your Company’s Policies

I always make sure I know my company’s rules inside and out. This way, I can make informed decisions about when to take things to the next level.

Don’t be afraid to review these policies regularly.

They’re there to guide you.

Involve HR if Necessary

HR isn’t the enemy. They’re there to help.

If you’re feeling stuck or unsure, reach out to them.

This may mean just talking to them to get guidance and clarification on how to handle the situation. 

I’ve found that involving HR early can often prevent bigger problems down the road.

Step 12: Learn and Grow from the Experience

Every challenge is a chance to become better. As leaders, we should always be learning and growing.

Reflect on What You’ve Learned

After each performance improvement plan, I take some time to think.

What worked well? What could I have done differently?

Don’t be too hard on yourself. Remember, you’re learning too.

Use These Lessons to Become a Better Leader

The lessons you learn from one employee can help you with others.

Maybe you discovered a new way to explain tasks clearly. Or perhaps you learned the importance of more frequent check-ins.

I always try to apply what I’ve learned to my leadership style.

This way, I’m constantly improving, just like I ask my team to do.

Remember, great leaders aren’t born. They’re made through experiences like these. So embrace the challenge and grow from it.

Conclusion

Dealing with difficult employees isn’t easy, but it’s a skill you can master. Remember, every challenge is a chance to grow as a leader and help your team improve.

I’ve used these steps time and time again, and they work. But don’t just take my word for it, try them out yourself. Adapt them to fit your style and your team’s needs.

Now go out there and lead with purpose. Your team is counting on you!

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About The Author

With over 22 years of leadership experience in both military and civilian contexts, I founded Growth Tactics out of a commitment to personal and professional development. My extensive journey as a manager and leader has equipped me with invaluable insights and experiences, which I am eager to share. This platform also serves as an avenue for me to enhance my own skills. My ultimate aim is to empower others to unleash their full potential. Join me on this path of continuous improvement and let’s grow together.

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