The Art of Herding Cats: Mastering the Leadership of Challenging Individuals

Leadership coaching for managing difficult people effectively.

Let’s say you are a leader at a company you like working at and are doing great! Then a shift in personnel happens, and you end up with a few of the MOST DIFFICULT EMPLOYEES IN THE ORGANIZATION!

You are in a panic! You and your team have worked so hard to reach their current superior level of performance. So, what do you do now?

Not to worry, I will break it down for you here. Most of the time, people just need to be heard or misunderstood, and a discussion will usually fix the problem. But there is something I need to caveat this guidance with…you need to answer two questions about the difficult person:

  • Can they change? This deals with ability.
  • Will they change? This deals with attitude. 

For this to succeed, you need the answer to both questions to be a YES. If they aren’t, you, as the leader, must be honest with yourself and the employee in question and make the call to decide if they should remain in your organization. Too many leaders don’t want to make this difficult choice and leave the poor-performing/poor-attitude employee in place for too long. This causes strife among the rest of your people, promotes mediocrity, and it’s just not fair to all involved.

Hopefully, the answer to both of those questions was yes, so we can move on to how to lead these people to success.

Here’s what you will learn from this post:

  • The steps to leading the difficult person(s)
  • Ways to approach the difficult person(s)
  • How to remain flexible…there’s not a one-size-fits-all answer

Important points to always remember, particularly if the conversation gets heated:

  • You can’t reason with an unreasonable person, but there are proven strategies to deal with these dubious situations.
  • Verbal de-escalation guidelines include listening, staying calm, and looking for their hidden needs.
  • Remember that one response does not fit every situation; you will need to remain adaptable.

Are you ready to get this problem under control?? Let’s do it! 

According to John Maxwell, a well-known expert in leadership, there are five steps to addressing a difficult employee: 

  1. Meet privately ASAP to discuss their behavior. Don’t wait too long to address the behavior. Meet privately, and don’t be vague. Use specifics of the situation, and don’t use secondhand reports as proof. Go into the meeting with a positive attitude and give them the benefit of the doubt. You want a positive resolution.
  2. Ask for their side of the story. You never know what’s going on in their life. They might have been having a bad day and need help or someone who understands.
  3. Try to come to a place of agreement. You need to find out if they agree with you. Admitting wrongdoing can be humbling, but it opens them up to change, which is best…you can help someone with that attitude and an open mind.
  4. Set out a future course of action with a deadline. No matter if they agree with you or not, you have to lay out a specific plan of action for them to take. Put it in writing if you deem it necessary, this ensures you are both on the same page, and the discussion actually happened.
  5. Validate the value of the person and express your commitment to them. Before you end your meeting, let them know you care about them and want a positive resolution. There is a strong chance you will have to let them go. If you are having a difficult time making the decision, ask yourself if you know what you know, would you still hire them? If it’s yes, keep them. If it’s no, let them go. If you aren’t sure, wait 3 months and reevaluate. If you still don’t know, then the answer is really no.

As we have already established, leading difficult people can be challenging; but you can navigate the situation more effectively with the right approach. In general, here are several things to take into consideration:

  1. Understand their perspective and validate their feelings: Take the time to understand their motivations, fears, and concerns. Put yourself in their shoes and try to see the situation from their point of view. This can help you develop empathy and find common ground. Acknowledge their emotions and let them know that you understand their perspective. Validating their feelings does not mean you agree with everything they say but shows that you respect their experiences and concerns.
  2. Communicate clearly, openly, and honestly: Be direct and transparent. Clearly state your expectations and provide specific feedback. Avoid vague or ambiguous instructions that could lead to misunderstandings. Listen actively to their concerns and address them constructively. Keep them informed about relevant updates, changes, or decisions that may impact them. Clear and honest communication can help alleviate their distrust and address any misinformation.
  3. Stay calm and composed: Difficult people may try to provoke or frustrate you. It’s essential to stay calm and composed in such situations. Take deep breaths, practice mindfulness, and respond rather than react. Your calm demeanor can help defuse tense situations and set a positive tone.
  4. Listen actively: Take the time to listen to their grievances and concerns without interrupting or getting defensive. Show genuine empathy and let them express their frustrations. Active listening demonstrates that you value their opinions and can help build trust.
  5. Focus on solutions, not blame: Instead of dwelling on past mistakes or assigning blame, shift the focus to finding solutions. Encourage them to contribute ideas and collaborate on problem-solving. You can help create a more productive environment by redirecting their energy toward positive outcomes.
  6. Seek common ground: Find areas where you can find agreement or common goals. Finding shared objectives can help align their interests with the organization’s objectives and create a sense of collaboration. Emphasize the bigger picture and how their contributions can make a difference.
  7. Set clear boundaries: Establish clear boundaries and expectations for behavior, and make it known what is acceptable and what isn’t. Be consistent in enforcing these boundaries and open to discussions and negotiations when appropriate.
  8. Build relationships and rapport: Invest time in building relationships with these individuals. Find common interests or topics that can help you connect personally. Developing a rapport can make it easier to address difficult situations and foster a more cooperative atmosphere.
  9. Provide support and resources: Some difficult people may act out due to frustration or a lack of necessary resources. Identify any support or resources they might need to perform their tasks more effectively. Helping can help alleviate their difficulties and improve their attitude. Identify any underlying issues causing their dissatisfaction and work towards resolving them. Offer support, resources, or training to help address any skill gaps or challenges they may face. Collaboratively explore potential solutions to their concerns and involve them in decision-making whenever possible.
  10. Lead by example: Demonstrate the behaviors and attitudes you expect from others. Be a role model by showing professionalism, respect, and integrity. When difficult people see your consistent behavior, they may be more inclined to emulate it.
  11. Seek mediation if necessary: Consider involving a neutral third party to mediate conflicts in challenging situations. A mediator can provide an unbiased perspective and help facilitate a constructive dialogue between you and the difficult person.
  12. Self-care and self-reflection: Leading difficult people can be emotionally draining. Take care of your own well-being by practicing self-care techniques such as exercise, mindfulness, and maintaining a healthy work-life balance. Reflect on your own reactions and behaviors to identify areas for personal growth.
  13. Lead with empathy and patience: Leading difficult people requires patience and understanding. Approach each interaction empathetically and remember that their dissatisfaction may stem from valid concerns. Be patient in addressing their issues and give them time to adjust and engage positively.

In conclusion, there are several ways to lead and deal with difficult people. Over the years of being a leader, I have recognized that most “difficult people” just don’t know how to be heard, so they behave in difficult ways to get the attention they believe they need in order to be heard. This is where empathy comes in and goes a very long way. If you can empathize with people, no matter what their background, work history, etc., you will make headway. I have been able to connect with extremely challenging employees through empathy, and we were able to turn things around. It just takes patience and understanding where they are coming from. Good luck leading difficult people and people in general; it’s a wonderful thing! 

If you think a leadership coach would be helpful in your life, please contact me at, or 805-265-3275 for a no-obligation, free strategy session to determine if we are a good fit or just have some questions. Thanks for reading. Have a fantastic day!

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Nikki Gianni

The Leadership Architect™, Leadership Coach Nikki Gianni, was born & raised in Queens, New York. She has lived all over the country, currently living in Southern California with her 19-year-old son. Nikki spent 25 years with the Department of Defense in acquisition as an active-duty member and a civil servant. She was an award-winning executive-level leader for over 15 years and transformed organizations from zeros to heroes in record time, resulting in outstanding retention and performance. Nikki became a leadership coach and mentor to share her love of leading and to support new leaders reach their full potential as quickly as possible by providing them with the knowledge, training, and coaching they need to perform successfully with the decisive confidence every great leader needs.