How to Deal with Difficult Employees as a New Manager
People are the hard part of management.
We all have little quirks that make us unique, but not everyone's quirks are fun to deal with, making people challenging to manage.
Difficult employees underperform and cause friction on the team, which can be hard to deal with, especially as a new manager.
But, as a manager, it is your responsibility to identify and handle difficult employees.
Dealing with these problematic employees is no easy task, which is why I've created a trusty guide for you to use as you navigate your management journey.

In this article you will learn:
👉 Four difficult personalities:
☑️ The Argumentative Employee
☑️ The Immature Employee
☑️ The Disengaged Employee
☑️ The Negative Employee
👉 How to identify these four different personalities and how to understand them.
👉 What each difficult personality needs to improve and how to coach them.
👉 Five coaching conversations you need to improve overall team performance.
Table of Contents:
4 Types of Difficult Employees
It's important to remember that when you're dealing with difficult employees that they're not always challenging on purpose.
Often when employees act out, there's something more at play.
Personal problems beyond work can cause employees to act out, but other times it's something to do with the environment at work that causes difficulties.
As the team manager, you must understand your team members individually to get to the bottom of what causes them to act out.
From the article, 4 Employee Personality Types: Understanding and Managing Different Personalities in the Workplace, you understand that there are four main personality types you will encounter in the workplace, a D personality, an I personality, an S and C.
The D personality is dominant and likes to take control and get things done.
An I personality is people-oriented and builds strong relationships with their team members.
An S personality is reliable and consistent; you can always count on them to get the job.
Finally, a C personality is highly detail-oriented. They're critical of their works and others and ensure everything is done perfectly.
Each of these personalities have their strengths that contribute to the team, but when these personality types are unsupported at work, they turn into difficult employees.
What Happens When the 4 Employee Personality Types are Unsupported at Work
Each personality needs different environments for success.
If these personalities don't get what they need, they'll act out.
When a D is stuck in a poor work environment, they're often reckless, rude, impatient, pushy and aggressive, all of which categorize an argumentative employee.
When an I acts out, they're emotional, impulsive, excited, and become the office gossip, just as you would characterize an immature employee to be.
An S in a hostile environment appears disengaged as when Ss are unsupported, they become indecisive, uncommunicative, slow, and lack initiative.
Finally, an unsupported C becomes a 'Negative Nancy' in a poor work environment as they become reclusive, revengeful, critical, self-centred, and moody.
Although these kinds of individuals are difficult to deal with, it's important to remember that you can turn each of these personalities around and help them become the team members you need for your startup's success with the right coaching and support.
The Three-Step Strategy for Dealing with Difficult Employees

Before we get into different coaching strategies for each difficult personality, let's first address an overall strategy you should take when dealing with difficult employees.
1. Gather Information
Before you jump to any conclusions; start by taking the time to understand your team member's situation.
As much as we are autonomous individuals, we are also victims of our environments. A team member's environment could be the root of the problem.
Gather the facts first before you judge your teammates. Ask other team members and co-workers about the problem employee and take the time to have a one-on-one conversation with the employee to hear their side of the story.
By taking the time to understand how your team members feel about the situation, you show your support and create a psychologically safe environment in the process.
2. Develop a Plan
Once you have a sense of what your team member is facing, it's time for the two of you to develop an action plan together.
Discuss how you see your current teammate's behaviours as problematic and what you think their ideal behavioural pattern would look like.
Next, ask your team members what obstacles they're facing preventing them from reaching the ideal behavioural pattern and what you can do as their manager to help them work past these obstacles.
After discussing what is causing the problem, work together with your teammate to develop a realistic solution. Identify steps you think the employee needs to take to improve and what feasible end goal would be.
SMART goals are an effective way to help your team members reach their goals as they ensure a specific and achievable outcome in a realistic time frame that holds people accountable as they move through the process of goals achievement.

3. Follow-up
Once you've set your employee on the right track, be sure to check in with them about their progress.
Offer additional support they need and encourage their success.
How to Coach an Argumentative Employee
Do you have a team member who likes to argue just for the sake of it? Sure some people debate ideas and opinions, but others argue simply out of habit. They make a fuss out of the most trivial things to cause conflict.
However, the argumentative person is often a result of defence mechanisms from dealing with a hostile environment.
For example, Ds in a poor environment react argumentatively. They become rude, impatient, pushy, and aggressive.
Someone's argumentativeness comes from something personal, and the root of the problem is much deeper than the surface anger they show.
But there are ways you can deal with a difficult person as a manager without feeling like their therapist.
Below I have collected three strategies from a study by Takebe & co. to help you manage an argumentative employee.
1. Have a one-on-one meeting.
One of the firsts steps when dealing with any difficult person is to hear their side of the story.
According to Takebe & co., when people allow their anger to ruminate, it only makes it worse (Takebe & co, 2016), and it often surfaces in other ways, such as lashing out or arguing with others.
Show your team member your support by acting like someone they can talk it out with.
Have a calm and professional meeting with your team members, expressing concern for their well-being and work actions.
When you're talking about the employee's problematic behaviours at work, be sure to comment on the action itself and not their character.
Additionally, you're going to want to come prepared with documentation of these problematic behaviours.
By sharing specific examples with your teammate, you may help them open their eyes to problematic behaviours they were participating in without realizing it.
2. Don’t take things personally.
When dealing with argumentative individuals, the most important thing to remember is not to take things personally.
Argumentative people are often just looking for a fight as they want to express their anger somewhere.
The main point you have to keep in mind is that it's not you, it's them, and you don't have to get angry in return.
You'll remain neutral in your conversation with that employee by avoiding taking things personally, which is essential to getting to the root of a problem and creating an action plan.
3. Avoid getting caught up in arguments with them.
Argumentative individuals don't just make things up out of thin air. They pick something out about what you've done or said and use it against you in an aggressive way.
Instead of acting defensively against what they've said, remind yourself they want to argue and let their attack go by giving up the need to be right.
When it comes to arguing with an argumentative person, you're never going to be right, even if you're correct.
Instead, shift your perspective and try to understand theirs rather than trying to prove your point.
After hearing their perspective, you can ask to offer them constructive feedback.
By asking to give them feedback, you're making it their idea, making them more open to the feedback you share.
These are three tactful and scientifically proven ways you can successfully coach your argumentative teammate.
Article Reference: Takebe, M., Takahashi, F., & Sato, H. (2016). Anger rumination as a risk factor for trait anger and anger-in: A longitudinal study. Personality and Individual Differences, 101, 451-455.
How to Coach an Immature Employee
As a professional, it can be tough to deal with an immature individual.
All you want to do is tell them to 'grow up.' But you and I both know that this isn't going to help.
Instead, you need to develop a professional way to deal with this immaturity in the workplace.
Below I share four strategies to help you deal with your immature teammate in a calm and collected manner. Keep reading to find out. 👇
1. Show them the impact of their work on the business.

Frequently employees don't understand how they fit into the bigger picture.
When this happens, they tend to feel like their work doesn't matter. If someone's work is only seen by 30 people and has no direct impact on anyone's lives, who cares, right? 🤷♂️
That's why you must show your employees that their work matters. Connect their work to the bigger picture and show them their impact on the business's functions.
When employees understand that their work plays a role in the bigger picture, they'll start to care about their work and start acting professionally about it.
👉 To learn what you can do to help your employees feel valued at work, read Here’s How to Make Your Employees Feel Valued at Work.
2. Reinforce excellence and demand accountability.
If you don't expect high-level work from your team members, guess what? They won't give it to you.
A critical step to having a professional team is to demand professionalism and excellence from them.
When your team realizes you don't kid around, neither will they.
A good way of reinforcing excellence in your team member's work is to reward, highlight, and applaud great work.
By rewarding team members' best work, you are extrinsically motivating them to be the best they can be. An example of such motivation could include a Christmas bonus for everyone who reaches X amount of sales.
3. Give them opportunities to develop.
People tend to rise to the occasion. As Shakespeare told us, some have greatness thrust upon them, so allow your teammates to achieve it.
I'm not saying to put your worst employee on the most important sales call of the year, but allow your employees to develop.
Progress happens best with baby steps, so start by slowly increasing the employee's responsibility until they can take on more responsibility.
As they reach greater and greater heights within their roles and the company, your team members will begin to feel empowered. An employee who's empowered will improve their overall performance, including their maturity level.
Once they understand that you trust them, they won't want to let you down.
👉 For more information about helping your team members go from good to great, read Three Ways to Empower Employees to Do Their Best Work.

4. Set clear boundaries.
The best way to demand maturity from your teammates is to set clear expectations and boundaries.
If a team member acts out during a meeting, penalize their behaviour by calling them out on it. For example, if an employee makes an immature joke, tell them it was inappropriate and explain why.
Meanwhile, ensure you reward mature behaviour.
By encouraging mature behaviour and condemning immature behaviour, you help your team members learn the type of behaviour you want to see in the workplace.
Reinforcement makes it more likely that you will see the desired behaviour again, while punishment makes it less likely.
The type of learning you are installing in your employees is what psychologists call operant conditioning (a method of learning that employees reward and punish for behaviour).
To learn more about the concept of operant conditioning, check out the TEDx video below. 👇
How to Coach a Disengaged Employee
Gallup's study shows that 85% of the world's employees are disengaged at work, which costs your businesses hundreds of thousands, if not millions, of dollars in revenue each year.
Disengaged employees often don't connect to their work and feel disconnected from the organization they work for.
More often than not, these employees actively look for another job and leave their current position when a better situation presents itself.
When we talk about an engaged employee, we want a team member who's enthusiastically involved and committed to their work and organization.
The best way to actively engage team members is to ensure they have meaningful goals at work, encourage them to solve problems, and set clear and attainable work goals.
1. Ensure employee goals are meaningful.
Nobody likes to put effort behind something they don't care about. Ensuring employees connect to your organization at a greater level shows them how their work contributes to the business's goals.
When employees realize how important their work is to achieve the organization's mission, they feel connected to something bigger than themselves.
They are connecting to a bigger mission that aligns with their values impacts team members to do their best work by inspiring motivation.
2. Encourage problem-solving.
By encouraging individual problem solving, you are helping team members gain greater autonomy in their work.
When team members experience greater independence, they feel free to work on tasks that they do best.
By allowing individuals to work to their strengths, you're helping team members achieve their goals, but you also ensure your organization's goals are reached.
Allowing teammates to work to their strengths encourages them to develop their skills and encourages greater creativity, essential for innovation.
3. Set clear expectations.
To do their best work, team members need to understand what it is that they're doing.
Team members need to understand what role they play within the organization. They also need to have a thorough understanding of what the expectations and tasks are of their position.
For employees to be effectively engaged in the work, they must have role clarity.
When team members fully understand their team's role, they set attainable goals for their work and reach these goals efficiently and effectively.

The best way to engage team members in their work is to remind them of its importance.
When team members realize the impact their work makes, they are happy to ensure their work is done to the best of their ability because it becomes something to be proud of.
How to Coach a Negative Employee
While it is beneficial to have a critical thinker on your team, too much critical thinking, aka negativity, brings the whole team down, slowing down everyone's productivity and effectiveness.
Hostile team members can be incredibly hard to work with because they tend to drain the joy and positivity out of everything you do.
Additionally, team members who offer up problems with no solutions are not being helpful to anyone.
So, how do you coach a Negative Nancy to be a Happy Hailey? 🤔 Keep reading below for my top three tips for managing a negative employee. 👇
1. Help Them Realize Their Moods Affect Others.
Sometimes people don't realize how much they're bringing others down.
Use specific examples to show them the negative behaviour they're exhibiting.
If you observe them acting negatively in meetings, be direct and tell them how this brings down others' moods and optimism. Explain how their moods hurt the team performance.
Show them an alternative they can do to this behaviour, such as sharing that they're not having the best day but only going into detail when asked.
2. Create positive interactions.
It's crucial to your team's entire well-being that they all have positive interactions with each other.
You can help your opposing teammate create more positive interactions in their workday by reinforcing a positive statement or contribution you hear from them.
Remind your employee that positive interactions don't have to be complicated and can be as simple as a friendly greeting in their daily meetings.
3. Get to the root of the problem.
Many times hostile teammates are focused solely on problems without offering an alternative or solution.
When a negative teammate brings up a problem, ask them to provide more details.
Use open-ended questions as this will cause them to provide a more thorough answer than 'yes' or 'no.'
For example, if they express dislike for a design, ask them what they specifically don't like about the design.
You can then work on the solution by getting to the root of the problem as you poke for more details.
It's essential to find a solution when working with a negative employee. Having a solution-based mindset keeps the team focused instead of spiralling into a black hole of negativity.
With these three steps listed, your workplace should start feeling more upbeat in no time! 😄
5 Coaching Conversations that Improve Employee Performance
Now that you understand how to coach each difficult personality uniquely, you also understand the importance of regular coaching and feedback in your team members' work lives.
Without effective coaching from the manager, the success of any goals and performance metrics of the team and its members is left to chance.
One of the biggest priorities of any team manager is to become an effective coach.
Effective coaches know how to develop their people, hold them accountable, and raise their standards.
To become more effective coaches for all of your team members, follow these five steps below. 👇
1. Focus on providing role clarity and understanding strengths.
The first step to being a great coach is understanding your team’s strengths and weaknesses.
A culture of leadership is established based on the strengths of each team member.
A good manager knows each team member on a more personable level and can understand where their strengths lie and what tasks best fit those strengths—this where leadership truly becomes about leading each person differently.
By allowing a team member to work to their strengths within a role, you give them greater autonomy and show the other team members that they can rely on one another based on their strengths, which creates interdependence throughout the team.
2. Establish routine conversations that provide a connection between manager and employee.
Employees hate feeling ignored.
That means that ongoing conversations with the team and its members are essential for best management practices.
It's important to remember that ongoing conversations should be based on employee strength to create more engagement.
These one-on-one interactions don’t need to belong, only about 10 minutes, but should happen at least once a week.
These quick and regular conversations help employees understand they’re on the right track.
3. Check-in with your employees regularly about their performance.
Check-in conversations help both employees and managers review success and barriers to their performance and align and reset expectations with the company’s overall goals.
These conversations should take place once to twice a month and should be about 45 minutes to 1 hour.
Check-ins require planning as they will be a discussion of expectations, workload, goals, and needs.
4. Coach them through career development.
Understanding your team members’ goals and aspirations helps you properly encourage employee growth within the organization.
The most effective way to host this conversation is to know the employee well and understand their unique personality.
Keep in mind that the purpose of this conversation is to give your team members advice, support, and direction in their developmental opportunities.
5. Take ‘The Coach Approach’ to create and deliver a productive performance review.
Performance needs will change throughout the year, which is why year-end performance reviews are so essential.
These meetings will review performance progress and reset expectations as performance needs change.
Performance reviews should focus on celebrating success, setting standards of future objectives, and planning for development and growth opportunities.
These meetings should happen at least twice a year (if not four, for quarterly reviews) and should last from one to three hours.
Remember, the dialogue in these conversations need to be consistent with the feedback from the steps above.
This article has given you a clear direction on how to identify difficult employees and how to deal with them individually.
You now have effective strategies to coach argumentative, immature, disengaged, and negative employees.
Additionally, you also have five different coaching strategies that you can use to help all of your teammates, difficult or not.