Dealing With Difficult Employees as the CEO

Difficult Employee in the Workplace Graphic

Dealing with tough employees is a tough job for any CEO. Managing different personalities in the workplace can be tricky, and is one of the challenges that separates an average leader from a great one.

Here are some ways to deal with tough employees, and advice on turning problems into opportunities for growth and productivity in your team.

Signs and Behavior of a Difficult Employee

A difficult employee is a big problem for any CEO or business owner. Their behavior can affect employee morale and overall performance in the workplace. But how can you spot these problematic team members before things get out of hand?

Type #1: The Underperformer

They don’t do their job properly, not living up to their potential despite having the ability to.

Type #2: The Negative Nelly 

They’re always complaining, and spreading negativity which undermines leaders and team members alike. Their attitude directly affects productivity and creates a toxic work environment that could lead to higher staff turnover if not addressed soon.

Type #3: The Know-It-All

They think they know more or are better than everyone else around them. They ignore input from colleagues and demoralize other team members in the organization.

Management of Difficult Employees

One obvious solution to dealing with your toughest employees is to fire them. But let’s assume you have a good reason not to fire them yet. Maybe you think you can coach them to turn around or you need them until you can find their replacement.

Assuming you are going to manage them, here are the steps you can take.

Identify the Problem

The first step in managing tough employees is for you to identify the problem. Bad attitudes and poor performance are often symptoms of underlying issues.

A troublemaker might be struggling with personal issues, lack of skills required for the role or feeling overwhelmed with responsibilities. In some cases, your employee won’t do their job because of misunderstanding of expectations or poor communication from leadership.

To identify these root causes you need to observe your team members closely and have open conversations with them. Open communication (done well) allows employees who exhibit difficult behavior to express their concerns without fear of retribution.

This will help you find out if there’s a management style issue within your organization that is affecting employee performance negatively.

Establish Boundaries

Dealing with difficult employees involves setting clear expectations. This is key to managing problematic behavior and for your hard-working employees to know their place in the team. To ensure an employee succeeds you need to set and communicate expectations for acceptable behavior.

If an employee doesn’t meet their obligations or performance is sub-par you need to establish consequences.

  • Create a Code of Conduct: This document outlines expected behaviour and what happens if those standards aren’t met.
  • Promote Open Communication: Encourage direct reports to speak up without fear of retribution, build trust between leaders and team members.
  • Maintain Consistency: Apply the rules across all levels of staff; this prevents favouritism which can lead to higher staff turnover.

Remember, boundaries are not about control but creating an environment where everyone feels respected and valued.

Communicate Effectively

Effective communication is key. This is more than just delivering clear instructions or setting expectations, you need to create an environment where open and respectful conversation can happen.

Research shows poor communication often leads to misunderstandings that exacerbate issues like bad attitudes, difficult employee behavior, and even disruption of employee morale.

  • Create Clear Expectations: Make sure each team member knows their job; this reduces the chance of poor performance due to confusion.
  • Provide Honest Feedback: Constructive criticism helps the employee improve while addressing the behavior directly. Remember: It’s not a personal attack but a way to grow.
  • Establish Frequent Check-ins: Don’t wait until annual reviews to discuss the underlying issues affecting the employee’s behavior.

Be consistent in your message – direct but understanding of their concerns. This helps with managing difficult employees and fostering team harmony.

Listen Carefully

You need to learn to listen. This means more than just hearing what they say, but understanding what’s really behind the behavior. A bad attitude or poor performance can often stem from feeling unheard or unvalued at work.

Leaders who listen actively build stronger teams and better environments.

The Art of Active Listening

To effectively manage problematic employees, you need specific skills required for active listening:

  • Show empathy: Let your team members know you get it.
  • Maintain eye contact: This non-verbal cue shows you’re paying attention to what they are saying.
  • Nod occasionally: This simple gesture shows you agree or understand what’s being said without interrupting the flow.

Remember communication is not just about getting your point across, it’s also about understanding theirs.

Be Flexible

Managing difficult employees requires a balance of firmness and flexibility.

The trick is to be flexible not just for the benefit of the difficult employee but also for your whole team.

For example, if you have an employee who is working incredibly hard but exhibiting difficult behavior due to stress or burnout, offering flexible hours or remote work options might help take the pressure off and keep their value to the team.

This can turn a bad attitude into a more cooperative team member. It shows as leaders we’re willing to meet them halfway – we acknowledge the underlying issues affecting their performance rather than just focusing on punishment for poor performance.

Just remember; being flexible doesn’t mean you tolerate negative behavior that disrupts the team forever. There should still be clear boundaries set from the start on what is acceptable behavior in your organization so no one person can create a toxic environment and drive up turnover.

Take Action

If an employee’s behavior is still impacting others and dragging down your team’s morale then it may be time for more serious steps such as written warnings or even dismissal.

Always consult with HR before taking any drastic action against a troublesome employee to make sure you’re following company policy and the law.

This isn’t easy but remember one person’s bad behavior shouldn’t bring down leaders or create a toxic work environment and higher staff turnover or poor customer relations.

What to Do if The Difficult Employee Has Created a Toxic Work Environment

If you have a challenging employee who has created an unhealthy work environment, you need to act quickly and firmly. As we’ve discussed a negative culture can lead to higher staff turnover, poor customer relations, and disrupts employee morale.

Firstly, acknowledge the issue. Ignoring an employee’s behavior only makes it worse.

Open Communication:

  • Talk openly with your team members about what they are experiencing. This will help identify underlying issues that may be causing this negative atmosphere.
  • Poor communication fuels bad behavior so make sure everyone feels heard.
  • Set clear rules of conduct for all employees, including consequences for bad attitude or any other form of misconduct.
  • Invest time into teaching managers the skills required to deal with difficult employees in the future.

FAQs in Relation to Managing Difficult Employees

What is the best way to deal with difficult employees?

The best way is to identify the problem, set clear boundaries, open communication, listen to concerns, offer support and resources, be flexible when needed, and take action if required.

What are 8 types of disruptive employees?

The eight types include: The Know-It-Alls, The Slackers, The Drama Queens/Kings, The Loners, The Gossip or Rumor Spreaders, The Negativity Spreader, The Overly Ambitious, and finally those who Resist Change.

How do you deal with a disruptive employee?

Addressing disruption requires direct communication about the problematic behavior. Set clear expectations for improvement while providing supportive resources. If the issues persist, consider disciplinary actions.

Disruption requires direct communication about the behavior. Set clear expectations for improvement and provide supportive resources. If the issues persist then disciplinary action.

How do you deal with an aggressive employee?

Dealing with aggression means an assertive but respectful conversation about their behavior. Set firm boundaries and suggest they do professional development programs that promote emotional intelligence in the workplace.

Conclusion

Dealing with difficult employees doesn’t have to be a CEO’s nightmare, but by using the proper techniques, you may be able to turn them around.

Contact an Experienced CEO Coach

My name is Glenn Gow, CEO Coach. I love coaching CEOs and want to help make you an even better CEO. Let’s decide if we are a fit for each other. Schedule a time to talk with me at calendly.com/glenngow. I look forward to speaking with you soon.

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Janice Raises Over $100M for Her Company

Janice Raises Over $100M for Her Company

As one of the founders, Janice had created the perfect solution in an exploding market. As her CEO Coach, we worked very hard to create a scalable business model that significantly accelerated revenue growth. This model included geographic expansion, the addition of new product offerings, and stickiness to create repeat business.

This triple revenue-acceleration model not only worked but it attracted the interest of growth investors.

But a growth model wasn't enough. We needed to help Janice become a better CEO. Specifically, we worked on how to manage her board, so their faith in her as the CEO grew as time went on.

For some CEOs, the board can be intimidating. At first, it was for Janice as well. We worked on how to manage the board and get the most out of the board. Ultimately, we turned the board into a strong set of advisors and advocates for Janice as the CEO.

The support and confidence of the existing board was a critical factor in enabling her to raise well over $100M in the next round, increasing the valuation by more than $600M.

Darren Raises His First $3 Million

Darren Raises His First $3 Million

My CEO client (Darren) was starting a company in a new category. He was focused on raising capital for his business and wanted help crafting his story. Darren is a brilliant CEO, yet he realized he could produce a better story with help from someone who has created successful fundraising stories many times.

When we started working together, his story was overly complex, difficult for investors to understand, and not as strong as it could have been. Together we built a story about the tremendous value the company was creating. We used historical precedent to bolster the vision and mission. We gave investors confidence in the founders. We proved that the company could scale.

Investors are pattern-matchers. They look for the patterns that tell them this opportunity is like other opportunities they’ve seen, giving them a strong belief in the potential ROI. Together, Darren and I constructed a winning story that helped key investors see the patterns of success.

According to Darren, “Glenn gave me the perspective and confidence I needed to succeed.” Darren raised $3 million for his startup company in his first round. Darren has continued to successfully raise money in later rounds as well.

Meilin Creates A Scaling Organization

Meilin Creates A Scaling Organization

Meilin was always asking, "How can I help my company grow faster?" She was successful by most measures but had higher growth ambitions.

As her CEO Coach, I helped focus her efforts and energies on an often-overlooked area for many CEOs. This area enables scaling and enables the CEO to manage their team more effectively -- values.

Most CEOs have corporate values but don't use them as the ultimate way to install a belief system - a way for every employee to focus on the most critical issues for the company.

Meilin and I worked on making the values core to the thinking and speaking of the management team. Once the management team adopted these values and started speaking about them in their regular communications, we knew that we were on our way to ensuring that every employee “lived” the values.

While values are not the only thing a company needs to grow fast, they are critical to its success. Meilin's company is now growing over 100%.

Sean Gets It All Done

Sean Gets It All Done

As CEO, Sean had no work-life balance, and he was struggling with the overwhelming responsibilities of being a CEO. One of the biggest challenges of any CEO is to get everything done. The list of critical items seems to grow every day.

As his CEO coach (and as a former CEO), I recognized the stress he was under. That level of stress is no fun. To help Sean become a better CEO, I focused him on delegation, talent development, and balance.

First, we focused on developing Sean's delegation skills. Delegation is the "8th wonder of the world." When you make it work, your workload diminishes, and the company performs at a higher level. As Sean became better at delegating, he also began to see strengths and weaknesses in his leadership team from a different perspective.

The next step was to refresh his leadership team. We created a plan to either develop the ones that could step it up and perform better or find new leadership team members for those that couldn't help the company grow.

Finally, we worked on creating a way of living for Sean that provided him some balance. I tell my CEOs to "put their oxygen mask on first." If a CEO wants to perform at the highest level, they need to take care of themselves first.

Now that Sean has a much better leadership team, he has become a master delegator. By delegating many of the activities he had taken on before, he now has much more time to take care of himself.

Sean's company has now entered a new growth phase. More importantly, he is enjoying his work a lot more and his life a lot more.

Viraj Fires His “Best” Employee

Viraj Fires His “Best” Employee

As a CEO, Viraj was focused on employee retention. He recognized the value of keeping high-performing employees and the high cost of turnover.

One of Viraj's direct reports was one of his "best" employees. This person consistently out-performed against their targets. Within their function, they were a rock star.

However, this same person was toxic to the rest of the organization. They constantly argued with others, and they made most others feel bad about themselves. Viraj found he was spending a great deal of time managing around the toxicity created by this employee.

Viraj valued this person's contributions within their function, and he also really hated the idea of employee turnover. As a result, Viraj put up with this person and continued to work around the toxicity issue.

As Viraj's CEO Coach, I helped him understand that team alignment and team cohesion are critical factors to help the company grow. We agreed that preventing employee turnover is a good goal, but not at the expense of creating a well-functioning team.

Viraj wanted to become a better CEO, and he knew what he had to do. While it was difficult, he decided to fire the person he once thought was his "best" employee.

The first thing he heard from the rest of his direct reports was, "What took you so long?"

Olivia Finds Product-Market Fit

Olivia Finds Product-Market Fit

Olivia, my CEO client, is a product genius. She is highly creative, an excellent problem-solver, and knows how to get products out the door on time.

Olivia raised a great deal of money based on her product ideas and some early successes. The challenge was that her company wasn't growing fast enough. The pressure from the investors was building, and she was worried.

Raising a lot of money early is a blessing and a curse. The curse is that Olivia delivered her product too quickly. She delivered it, making too many assumptions about the market she was serving. When the product was released, it was a good fit but not a great fit.

Olivia was concerned about the time and dollars it would take to conduct research and test product-market fit in multiple market segments. We created a partnering strategy that enabled us to test multiple new market segments in a short time.

Olivia has found multiple market segments that are a fit for the product. Now that she has achieved product-market fit, the strategy is to "go big" on the go-to-market. And her company is taking off.

Wilson Turns the Board Around

Wilson Turns the Board Around

Wilson was a first-time CEO. The company was doing well, but not quite as well as the board had hoped. Wilson found himself uncomfortable as a minority shareholder working with a board that could fire him if he didn't perform.

Wilson wanted to know how to manage a Board of Directors. The first step was to acknowledge that a board has different measures of success than the CEO. That means there will naturally be tension. The second step was to dig in to deeply understand what the key drivers are for each board member.

Based on this information, Wilson can now address his needs, the company's needs, and the board's needs. That was the first breakthrough.

Once he knew how to address the needs of the board, we turned to address his needs. As Wilson's CEO Coach, I helped him realize that the board is an incredible asset to leverage.

Wilson began to build relationships with the board members individually to understand better how they could be of service to him and the company.

When Wilson works with the board, he is fully aware of their needs and addresses them appropriately. More importantly, he now tells the board what he is doing and relies on their insight and experience for feedback on how to help the company perform at a higher level.

Wilson is no longer concerned about the board and now gets more out of them than ever before.

Darius Solved His Crisis

Darius Solved His Crisis

I got the call at 10 PM on a Thursday. Darius, a CEO client, reached out to me just as I was about to end the day. "Glenn, my Chief Revenue Officer, just resigned, and I'm not sure what to do."

Darius was running a rapidly-growing business that was highly dependent on a well-run sales organization. He had delegated sales responsibility to his Chief Revenue Officer so Darius could focus on engineering and product.

The good news is that Darius didn't relinquish oversight or reporting of sales, just sales execution. It's also true that Darius wasn't in a panic, and we had worked on a plan for the departure of each of his direct reports.

At the moment, though, Darius and I needed to review that plan to ensure it was our best option. We checked whether or not the interim head of sales could genuinely step into the role. We discussed which accounts Darius should immediately nurture relationships with. We agreed that the recruiter we would need was still the right recruiter.

We quickly put together a communication plan on how to bring this news to the leadership team and the rest of the company. We worked on the exact next steps to interact with the interim head of sales, the director of sales operations, and HR.

Darius felt he didn't know what to do, but in actuality, he did. We had prepared for this, and he just needed to talk it through in the heat of the moment so he could execute against the plan immediately.

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