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Before you take any action to confront a difficult employee, I recommend you ask yourself these 10 questions:

  1. Is toxic leadership to blame for difficult employees acting out?

It is important to ask if toxic leadership might be causing difficult employees to act out. This way, you can find out why the employee might be behaving the way they are and how best to help them. The best way to do this is to have a conversation with the difficult employee about expectations. If you are open and aren’t defensive, you may learn something that proves to be a game-changer in this situation.

  1. Are you the problem?

Don’t close the page! The truth is ALL of us as leaders can grow. Look back at your ‘wake’. Henry Cloud describes the water behind a boat as an analogy for our leadership integrity. Is the ‘wake’ behind you choppy and full of corpses and wrecks? Or are there smooth areas with continued relationship? If it’s the former, consider that you might be the problem. The good news is, if that’s the case, you can 100% change, grow and become a great leader.

  1. What if the poor behavior is related to company culture?

Is this person’s difficult behavior related to company culture? Are there other teams where their behavior is normal or even encouraged? Be tough on yourself: is their behavior normal in your team? If so, consider they may not even realize their behavior is inappropriate. Consider a more lenient approach.

  1. What if the problem is your management style?

I’ve seen it time and time again: one person loved their leader. Another person found the same leader challenging to follow. How is your management style contributing to this person’s behavior? If they struggle with feedback and your ‘normal’ is to provide an avalanche of feedback, that is part of the problem. If they like direct and regular confrontational feedback and you prefer to smile and encourage, then part of the solution could be for you to grow in giving direct feedback.

  1. How do I ensure confidentiality?

Before you move forward in dealing with a difficult employee, think carefully about confidentiality. I love peer-to-peer accountability (see Patrick Lencioni’s The Five Dysfunctions of a Team) where accountability takes place in a team setting. But sometimes the behavior needs to be addressed one-on-one and includes confidential discussions. If so, honor the confidentiality of the other person and shut down any attempts to draw out additional information.

  1. Is there not enough incentive to perform?

If you were in this difficult employee’s shoes, would you be incentivized to perform? Rewards through compensation and more soft-touch strategies like private and public recognition have an impact on employee culture and behavior. Pay close attention to rewards around high-value behaviors. Do they exist in your team and organization? If not, what might that look like?

  1. Is there something going on in their personal life?

Don’t be nosy but do pay attention. Is there anything happening in their personal life you glossed over or don’t know about? Sometimes finding out someone has lost a loved one, is going through a separation or has a stressful situation in another area of their life helps difficult behavior to make sense. It’s also always helpful to walk in with empathy and listening.

  1. Does the employee feel that there’s no way to develop their career?

Some people need to see career progression and next steps to be motivated in their current role. For others, this doesn’t factor in at all. Find out which one is true for this person. If they need career progression then think creatively about how to link opening doors with high-level behaviors.

  1. Does the employee feel that they’re not being challenged enough?

Leadership is a lot like parenting. Some kids misbehave when they’re bored. Some people need to be challenged in their role to be fulfilled and love their work. Are you providing healthy challenge for the people you lead?

  1. Does this difficult employee have too much work on their plate?

In my experience, when you confront poor behavior there’s often some level of overwhelm involved. This isn’t always the case, but you should expect it. Think beforehand about this person’s role. Is their job description doable? If you fired them would you have to hire multiple people to replace them? If yes, get ahead and find a way to reduce their workload.


About the Author:

Jonno white

Jonno White is the Founder of Clarity. He helps leaders build high-performance teams and grow organizations that impact more people’s lives. Jonno is the Author of Step Up or Step Out with more than 10,000 sales worldwide. He also hosts The Leadership Conversations Podcast with listeners in more than 100 countries.