Your Guide to Dealing with Difficult Employees

Dealing with difficult employees is a topic that often comes up around our TAB boards.

Whether it’s managing a team split between home and the office, or addressing underperformance, people challenges are part and parcel of running a business.

Managing people is one of the toughest parts of leadership, especially when someone’s behaviour starts affecting the wider team.

According to Inc.com, a difficult employee is someone who fails to act responsibly or professionally in the workplace. That definition might sound simple, but the reality is rarely straightforward.

Many business owners avoid tackling the issue head-on, and that’s understandable. But left unchecked, a difficult employee can quickly have a negative impact on morale, productivity, and even company culture.

Understanding the Impact of Difficult Employees

Affecting Team Dynamics

One of the most common concerns we hear from business owners is how a single difficult employee can impact the wider team.

Disruptive behaviour doesn’t just affect performance, it can leave colleagues feeling uncomfortable, undermined or even bullied. And when someone regularly voices negative views about the business, that mindset can spread.

Before long, one difficult employee can start to chip away at your company culture.

As we often say at TAB, company culture isn’t just a ‘nice to have’. It directly affects your ability to retain good people and drive the business forward. If culture suffers, performance and morale will likely follow.

Impeding Business Performance

When an employee consistently misses targets or pushes back against leadership, it’s more than just frustrating. It can work directly against your company’s vision.

If your team isn’t aligned, productivity and momentum suffer. And if that individual is in a customer-facing role, the stakes are even higher. Unprofessional behaviour or a failure to follow protocol can damage your reputation and put client or supplier relationships at risk.

At that point, it’s not just an internal issue, it’s a business-wide problem.

Drain on Management Time

As a business owner, time is one of your most valuable resources.

Dealing with a difficult employee can be draining, especially when you'd rather be focusing on strategy, growth, and the bigger picture. The more time you spend managing disruptive behaviour, the less time you have to move the business forward.

And over time, that distraction can take its toll.

Not All Difficult Employees Are a Lost Cause

It’s also worth recognising that employees labelled as ‘difficult’ aren’t always a negative force.

As some of our TAB facilitators have pointed out, these individuals can sometimes be the catalyst for positive change. They might challenge the status quo, highlight flaws in existing processes, or force you to examine what’s really going on.

That doesn’t mean disruptive behaviour should be tolerated, but it does mean understanding what’s driving it can often be valuable.

With that in mind, let’s explore how to address the issue constructively.

Strategies for Managing Difficult Employees

Act Early

One of the most consistent pieces of advice we hear from TAB facilitators is simple—don’t let things fester.

If something doesn’t feel right, deal with it early. Delaying the conversation rarely helps and often gives the issue time to grow. Left unchecked, minor problems can quickly escalate into bigger ones that affect the whole team.

So the key is to act promptly and professionally. But how you do that matters, too.

Understand the Facts

Before jumping to conclusions, take a step back.

Speak to everyone involved and take the time to understand what’s really going on. Getting the whole picture will help you decide the right course of action.

Sometimes, what looks like difficult behaviour is actually a simple misunderstanding, and in those cases, a quick, informal conversation can go much further than a formal intervention.

The aim here is to respond proportionately and avoid escalating something unnecessarily.

Take the Conversation Out of the Day-to-Day

If you need to have a difficult conversation, try to step away from the usual work environment.

Whether it’s meeting in a quiet room or arranging a face-to-face catch-up with a remote worker, removing the day-to-day distractions can help both sides feel more at ease.

A change of setting often leads to a more open, honest discussion and gives the conversation the space and focus it deserves.

Keep Emotion Out of It

We’ve worked with hundreds of business owners, and one common challenge is letting emotion take over, especially when it comes to conflict.

But when you’re dealing with a problematic employee, staying calm and objective is essential. Don’t take sides, and don’t let frustration cloud your judgment. Your team will be watching how you handle it, and your response can either build or undermine trust.

As TAB York facilitator Elliot Rich puts it, “Treat the situation how you would want to be treated yourself.” That usually means staying mature, measured and focused on resolution, not reacting to emotion with more emotion.

Be Brave

Let’s face it, not many people enjoy confrontation. But avoiding it often makes things worse.

As TAB facilitator Jonathan Smith says, “It just takes 20 seconds of bravery to raise the issue, and it’ll probably lead to resolution. If you don’t take those 20 seconds, it could cost you a lot more in the long run.”

Sometimes the hardest step is starting the conversation, but it’s also the most important one.

When You Personally Find Someone Difficult

Sometimes, it’s not about performance or open conflict; it’s simply that you find someone hard to work with.

So, how do you handle that as a leader?

Check Yourself First

Start by taking a moment to reflect. Could the issue lie in your own reaction or working style? Sometimes a clash stems more from how we’re wired than from anything the other person is doing wrong.

TAB Thames Valley West facilitator David Abbott recommends a quick sanity check by speaking to a trusted colleague or peer, not to vent or complain, but to get a balanced perspective.

If it turns out the issue is more about your response than their behaviour, there’s often something you can shift in your approach to ease the tension.

Try to Understand

Before jumping to conclusions, take a step back and try to understand the behaviour you’re finding difficult.

At TAB, we regularly use DiSC behavioural profiles to help business owners better understand their teams. Knowing someone’s natural style—how they communicate, make decisions, and respond under pressure—can make a big difference.

When you look at things from their perspective, what once felt frustrating can start to make more sense. And that understanding can often be the first step towards a more productive working relationship.

Find Common Ground

Start by having an open conversation. Try to find a level where you can communicate clearly and respectfully.

As TAB facilitator Jonathan O’Shea suggests, focus on the business's purpose. What are you both here to achieve?

Finding shared goals, however small, can help shift the dynamic. When progress is made together, mutual respect tends to follow.

Are They the Right Fit?

If you’ve done the groundwork—reflected, communicated, and tried to find common ground—but the issue remains the same, it might be time to ask a tougher question.

Is this person the right fit for your business and its values?

That’s why getting hiring right from the start is so important. At TAB, we regularly support business owners in making confident decisions about their teams, whether it’s improving fit or moving people on when needed.

If you’re currently grappling with this, you might find value in this short read: Getting the Right People in the Right Seats, a chapter from Timeless Principles of Exceptional Businesses.

Should ‘Difficult’ Employees Exist?

We’ll leave you with one final insight from TAB facilitator Jonathan Smith:

“Don’t label people ‘difficult’. The chances are, someone finds you difficult—just ask your partner or spouse. Instead, focus on building constructive relationships with everyone.”

It’s a helpful reminder that leadership is rarely black and white. Strong leaders take the time to understand others, challenge their own assumptions, and approach conversations with clarity and respect.

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If you’re dealing with a situation like this or simply want a sounding board to discuss it, you don’t have to do it alone.

At The Alternative Board, we help business owners navigate people challenges through peer board support and one-to-one coaching. Sometimes, just having the space to talk it out with others who’ve been there makes all the difference.

Find your local TAB board or get in touch with us to see how we can support you.