Every workplace has those employees that many will label “difficult”.   Dealing with these unique humans isn’t an easy task and one of the biggest frustrations for many, especially leaders who are responsible for creating and maintaining a strong, healthy work environment.   The most frantic calls I receive from my mentorship clients are often around how to deal with these employees and here’s the secret to success:  “Difficult” people don’t exist. No one ever wakes up in the morning and decides to make life difficult for others.  They just don’t…so change the label and the context and keep reading.

There are people that will challenge us and here’s the thing about leadership that you must remember during these challenging times: You must lead all of your people! Not just the employees who make your life all rainbows and roses, but also the ones who add a little fire to your life!   We need to change the context from seeing these people as being a thorn in our side to being our greatest gift.   Leaders are always ready to accept any challenge and these wonderful humans teach us so much about acceptance, diversity of opinions, empathy, teamwork and patience.   They also challenge us to think outside of ourselves and understand the magic that different personalities, opinions, ideas and solutions bring to any work environment.   You just need to know how to lead, empower and nurture them just like you do all your rainbow and roses. 

Fortunately there are simple ways that you can create a positive work relationship with even your most challenging employees (and an easier life for you).  

Name your feelings

My work and experience with leading these challenging employees has taught me the importance of naming the feeling that this person stirs within me.  Not only naming it, but then creating a game plan on how to appropriately lead this person while keeping myself in check.   Perhaps this person triggers certain feelings in you OR perhaps they have figured out your buttons and will push them.   Whatever it is, you need to accept it and not let these feelings shape your relationship with this person moving forward.  

Listen Carefully

Challenging employees are often misunderstood, shrugged off as difficult and dismissed.   Take an opportunity to truly listen to them.   What is their intention?  What are they truly trying to tell you?    It’s amazing what you can learn about someone and the way they function by just simply listening. 

Be adaptable

Leadership is never about making your employees adapt to your needs.   You need to learn each person’s communication preference and personality traits and adapt your leadership style to approach and meet their needs.   If you don’t know what they need, simply ask them.   They will appreciate that you care enough to ask and it will make your life so much easier. 

 Don’t avoid

I worked for an employer early in my career that would simply avoid the challenging employees.   The avoidance created a horribly toxic environment where the challengers controlled the employer and the rest of us suffered.   It may take some extra time in the beginning to work through scenarios with these employees, but will save a lot of time and headaches in the end.  Trust me! 

Know when enough is enough

When a challenging employee starts causing a ripple effect within the team, you need to recognize when it’s time to end the working relationship.  Even the greatest leaders know when they’ve done everything in the their power to make it work and it just won’t (I like to say that we’re all miracle workers, but this isn’t the case).    No one wants to let anyone go, but unfortunately this is also the reality of being a leader in a management role.   Having said this, it still doesn’t make them “difficult”.  It may just be that they weren’t a good fit for your organization but will be a great fit for another.   Everyone fits in somewhere and everyone deserves a fair chance.  

So, if you truly take the time to understand each and every one of your employees, what makes them tick and how they need you to show up for them, you will be pleasantly surprised.   Change the context from them being our biggest challenge to our biggest gift and see what happens.  


  • Carrie McEachran

    Executive Director, Mentorship Coach

    Sarnia-Lambton Rebound, The Female Revolution

    Carrie is the Executive Director of Sarnia-Lambton Rebound, an award winning non-profit organization in Sarnia, Ontario that supports and empowers children and youth.   Her passion for supporting and empowering others also carries over into her work with up and coming women leaders through her mentorship community, F.Revolution (Fearless Female Leadership).   Carrie lives in Mooretown, Ontario with her husband, 5 kids, 3 ducks, 5 chickens and Mabel the lab retriever.