How to lead 'difficult' employees?

Apr 06, 2023

Leading employees who are labeled as 'difficult' or 'challenging' can be a challenging task for many leaders. However, with the right approach and understanding, it is possible to create a win-win situation for everyone involved.

In this article, we will provide you with a step-by-step formula for dealing with difficult employees, as well as an understanding of why people may exhibit challenging behaviors.


Part 1: Who are Difficult Employees?

The term 'difficult employees' is often used in several scenarios. For instance, you may perceive someone as difficult simply because they have a different personality, approach, or way of thinking from you. In this case, building trust and developing relationships with diverse personalities can be challenging, but it is necessary. Also, bringing awareness of different personality styles (like DiSC) might be very beneficial for you to understand & communicate effectively.

Alternatively, you may be leading a person who is perceived as difficult by others, and their behavior affects the team's performance. There are at least six types of difficult employees:

  1. The complainer: This employee is never satisfied and always finds something to complain about, regardless of how trivial it may be.
  2. The procrastinator: This employee consistently misses deadlines and puts off tasks until the last minute, causing stress and delays for others.
  3. The micromanager: This employee is overly controlling and insists on being involved in every detail of a project, making it difficult for others to work independently.
  4. The gossip: This employee spreads rumors and talks behind others' backs, causing tension and mistrust in the workplace.
  5. The aggressive employee: This employee is confrontational, and argumentative, and may even resort to bullying or intimidation tactics a person who always thinks he/she is right
  6. The resistor - A person who simply resists embracing a new way of doing, and does not respect the agreements or commitments that have been agreed upon in a team or individually and stays in a way.

Do you have any of those employees on your team?

If yes, you need to take action soonest possible. Living it unaddressed will lead to conflicts, and lower engagement, and affect the performance and the overall well-being of a team.


Part 2. Why do people behave that way?

Before delving into how to deal with difficult employees, it is important to understand why people behave in certain ways. Most often, people are not inherently difficult, but their behaviors may stem from unresolved past traumas or personal struggles.

They may also be trapped in patterns and behaviors that do not serve them well.

(Ex. procrastination, micromanagement, emotional regulation, blaming, and judging - are examples of mind sabotage. It's not a personality trait.)

If you as a leader are not aware of it and have not done the work on yourself to identify and work on your behaviors, you will be limited in how you can help the other person.

As a leader, seek help from a coach to understand how to help employees who may be struggling with certain behaviors. This understanding can help you avoid judging employees and instead focus on finding solutions.


Part 3. How did you contribute to the situation?

Before having a conversation with a difficult employee, it is important to evaluate how you may have contributed to the situation.

For example, you may have avoided providing effective feedback or neglected small behaviors that could have helped improve the situation.

You may have also not spent time to understand the person and build trust & relationships to understand what are these person's needs and motivators.

By evaluating these points, you can identify where you may have fallen short and take steps to restore trust and build stronger relationships with your team.


Part 4. How to move forward and create a win-win?

So, after checking point 3, now is the time to prepare for an honest conversation with your employee, because this is what you need.

I will give you a step-by-step formula on what to do before, during, and after such a discussion.

STEP 1 - things to do before the conversation:

  • Evaluate your contribution (see point 3)
  • List down what behaviors are not acceptable and you want to address - be factual. List the impact on you and the team.
  • Look at the person from an empathy lens - Put yourself in the shoe of your employee to see/feel/observe from his/her perspective what is going on.
  • Set an intention for the conversation - What do you want with this relationship? What behaviors you would like the person to change? What do you want from this meeting?
  • Embrace a positive lens - what gift/opportunity this conversation can create? - ex.: align the understanding of the situation, understand better the other person's needs and deeper motivations, and create new ways of working together, define the relationships, and verify the match.
  • Create a structure - how you want to start and set the tone, what you want to say that aligns with an intention, how you want to create a safe space for this conversation, and what open-ended questions you want to ask.
  • Check-in your emotions - difficult conversations carry triggers - so if you have not done work on yourself review what might trigger you and how you want to keep your emotions to neutral


STEP 2: How to lead the conversation - ensure the following are included:

  1. Open the conversation with a clear intention

State why you have the conversation, and what the expected outcome of the conversation is.

2. Create psychological safety - it's critical to bring mutual openness. Show your vulnerability - ex. if it's a difficult conversation for you - say it. Ensure you listen and not only talk, but also verbalize what you appreciate in the relationship and person, and summarize what you hear to ensure understanding.

3. Share YOUR factual observations & Impact

Use 'I' language: 'I see, I observe, I feel, I hear.....'. 'When you do impacts me', it impacts others .....

AVOID using a You language, labeling, and assumptions - it causes a defense. (Ex. YOU are not reliable. YOU are a complainer. You do not care about the job etc)

4. Seek to understand- Ask the other person for the person's view on the situation, impact, feelings, needs etc.

Give space. Listen. Do not Interrupt. Take Notes. Keep your Emotions - breathe!. Summarize what you hear - to ensure the understanding - I heard that...What I'm seeing now is....Thank you for sharing it.

5. If you can not manage your emotions - take time off.

You will never achieve a good resolution when you are emotionally hijacked. (You will benefit from working on your emotional agility)

6. Brainstorm solutions- after gaining mutual clarity of a situation, co-create the solution or vision and ideas on how to get there

7. Agree to the next steps & the way to follow up - choose the key idea from the brainstorming, agree on clear next steps and when exactly you will follow up and on what, how will you mutually measure the progress, and how the person wants to be helped to stay accountable

8. Offer support - many behavioral issues need support from a professional - coaching or therapies might be a very supportive way here.


STEP 3 - What to do after the conversation:

  • Summarize the agreements or ask the person to do it
  • Set up a periodical follow-up call to check in a progress and offer a feedback
  • Reach out to organize support


Finally, what to do when the conversation did not bring a positive outcome:

  • If you follow all from above and showed up with a helpful and open attitude and the person was in resistance -> it's time to consider an expert help or seek HR guidance/support to take other measures
  • If you as a leader notice that dealing with difficult conversations is challenging - get a coach to elevate your skills & break through what holds you back from handling it effectively.


Dealing with difficult employees requires patience, empathy, and understanding. It is important to remember that people are complex, and everyone has their own struggles and challenges. The ultimate goal is to create a win-win situation that benefits both the employee and the team.

Provide regular constructive feedback when it happens, set clear expectations, invest in building relationships with your employees & understanding their needs, and partner for solutions. Do not wait to do it when you have time, because that time may never come.

Put priority on building relationships, empowering & developing people - it will help you grow your business and take care of customers.


Want to be more effective in leading people and creating an engaged culture? - connect with me.

#theextraordinaryleadership #conflictsmanagement #difficultemployees #leadershipdevelopment


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