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How To Have THAT Difficult Conversation With An Employee


As I’ve coached leaders around the world, I’ve listened carefully to countless challenges. Difficult boards, drifting away from strategic plans and frustrations with time and task management.


However, there’s one challenge that comes up more than anything else. I’d estimate 50% of my coaching sessions have been some variation of this challenge:


How to deal well with a difficult employee.


Sometimes they’re difficult because they’re… different. Other times they’re difficult because they’re literally crazy. And everything in between.


What’s inevitable for every leader is you WILL have difficult employees.

And therefore, no matter how much you hate conflict, no matter how much a ‘gentle little lamby’ you are and no matter how much you close your eyes and wish it ain’t so…


You WILL have to have difficult conversations.

So if difficult conversations are inevitable, why not learn how to master them?


As I’ll explain later, difficult conversations are like regular exercise. Uncomfortable? Yes. But your team and organization will thank you later.


Here’s how to have THAT difficult conversation with an employee:


Before we jump in, I have a FREE DOWNLOAD for you: Click here to download The Leader's Guide To Difficult Conversations.


1. Expectations First!


Are your expectations crystal clear? I mean, crystal. Clear? If not, go back and have an expectations conversation first. If you don’t, you are setting yourself up for failure.


2. Be Open To The Employee’s Perspective


You’re now at a point where you need to have THAT difficult conversation with an employee. I’m going to assume you’ve clarified expectations. To set yourself up for success, focus on having an open hand and an open heart.


Seek to truly listen in this conversation. The more your employee feels heard by you in this conversation, the better things will go short-term and long-term.


3. Welcome Feedback


This is a difficult conversation. Not a difficult presentation. Prepare and know what you’re going to say. But be equally open to welcoming feedback. Go into this conversation clear on what you want to communicate.


Communicate clearly once, twice and more if needed. Don’t be afraid to overcommunicate. But that’s unlikely. What’s likely is you’ll need to listen and listen well. Once you’ve communicated your points, listen by pausing, repeating back and summarizing back.


4. Be Respectful And Stay Calm


One of my favourite leadership ideas is the thermostat vs thermometer. If you are a thermometer in this difficult conversation, you’ll reflect your employee’s temperature. Don’t do that.


Stay calm and be respectful. Be a thermostat no matter how hard it is on the inside. Practice makes perfect. Don’t be a robot, but do set a temperature of respect and calm.


5. Give Direct Feedback


It's important to give clear feedback. Before you have this difficult conversation, run through what you’re going to say with a confidential coach, mentor or friend outside of the context (if appropriate).


Explain to them what you’re going to say and ask, ‘Is there any way I could make that clearer?’


6. Set the meeting agenda


If this difficult conversation is a planned meeting, consider setting a meeting agenda. I recommend having difficult conversations in the hallway whenever possible. Why? Because you automatically know you’ll need to address specific and recent behaviour!


If you’re setting a meeting agenda, you want the employee to be 110% clear on what you’ll be discussing and why it’s at this point. If I was to sit down with that employee privately and ask them, ‘Why is this meeting happening between you and your boss?’ You want them to be able to give me a clear answer.


Unfortunately, if their answer to me is, ‘I have no idea!’ then you’re probably setting yourself up for a tough time.


7. Show Empathy And Genuine Care


Be kind and show that you really care. Don’t be a robot. Stay clear with your communication. But remember this is a human being. Put them first in every way possible. As you have this difficult conversation, remember what Brené Brown says: Clear is kind, unclear is unkind.


8. Work With The Employee To Come Up With A Solution


This conversation is an opportunity for the two of you to find a way to solve the problem. Listen to their ideas and come up with a plan that works for both of you. Leave your assumptions at the door.


9. Avoid Getting Caught Up In Arguments With Them


Sometimes the employee will get upset. That’s okay. Focus on staying calm. Prepare well by avoiding surprises wherever possible. Then, instead of arguing with your employee, articulate and overcommunicate your points clearly.


I like Simon Sinek’s FBI method: Feelings, Behaviour, Implication. As Sinek shares, conflict is improved when we communicate all three. And it’s often necessary to repeat them again and again. Don’t do this in a hurtful way. But make sure you’re as clear as possible.


10. Don’t Lose Your Temper


No matter what happens, don't get angry or yell at your employee. That’s inappropriate. If you feel like you’re losing control of your emotions, find a way to end the meeting. If you feel your employee is losing control of their emotions, find a way to end the meeting.


Then, once you’ve cooled down or given them time to cool down (at least 2 hours), take steps to reconvene so it doesn’t just get swept under the rug.


11. Apologize If Necessary


As leaders, we know what we need to do in these conversations. I agree that being clear is a priority. But don’t be afraid to be human. I prefer to lean on the side of humility rather than legal and HR.


If you have a legal team and HR team, then sure, keep them in the loop. But if you’ve dropped the ball in some way, share that with your employee! If you could have done better in communicating expectations months ago, then apologize!


Humility and clarity go hand in hand.


12. Speak to Your Difficult Employee Privately


There are many occasions where a hallway conversation works well. Or, in a high-performing team, where accountability conversations can happen in a team environment. However, if it’s a sensitive topic or you’ve taken lots of small steps and nothing has been resolved, then talking privately is the answer.


13. Recognize The Fact That Some People Won’t Change


As I’ve mentioned elsewhere, remember the saying, ‘You can’t wake people up.’ As you prepare for this difficult conversation, imagine your employee chooses not to change. Or chooses not to listen. Or chooses to purposefully undermine you after this meeting.


That’s all out of your control. You are not responsible for your employee’s response. Your job is to be as clear and helpful as possible from your position. The rest is up to them. Take your ‘rescuer’ hat off and leave it outside of the room before the conversation.


14. Set A Specific Timeline For Improvement


Be clear in your feedback. Then, be clear in how long it should take the person to improve their behavior. Give them a timeline and let them know when you will check in on their progress.


This difficult conversation is not a one-off and then you go back to artificial harmony. Set yourself up to have more difficult conversations if needed. You’ll find the conversations are still uncomfortable, but less difficult as time goes by.


15. Aim For Behavioural Awareness, Not ‘Fixing’ Them


When helping your employee, focus on teaching them what to do instead of trying to "fix" them. You are not their mum or dad. You are not responsible for their behaviour.


This is also helpful to keep in mind so we stay away from any character assassination. Be specific and focus on recent behaviour. Make sure it’s clear this isn’t about who they are, but about their behaviour.


16. Schedule The One-on-one


Plan a time to meet with a difficult employee alone if needed (as mentioned above). Don’t put this difficult conversation off! The bigger and bigger the meeting needs to be, the worse it’s likely to end up.


Clear and early is the key. The smaller and more regular the battles are, the less likely you are to experience a horror show.


17. Explain Why The Employee’s Behavior Is Inappropriate.


It is important to be clear and direct when telling someone why their behavior is not okay. People want clear feedback. Don’t beat around the bush. Prepare in advance so you’re clear and articulate. Be direct but polite. Explain why they are wrong and what they should do differently.


18. Reject Excuses


When dealing with difficult employees, don't accept excuses. Follow the tip above about avoiding arguments. Instead, if you hear an excuse, make sure they feel heard. Then repeat back to them the FBI to make it clear that excuse doesn’t change anything.


Make sure they understand that they must be accountable for their actions and cannot make excuses in future.


19. De-personalize The Conversation


When talking to someone, try not to make it about the person. Instead, talk about the behavior and how it can be improved. Don't say anything mean or insulting, but be honest and respectful. Show that you care by listening to their ideas and offering help.


20. Discuss Actions With a Difficult Employee


When dealing with a difficult employee, talk to them and be respectful of their opinions. Listen to what they have to say and thank them for it. Act quickly but don't make decisions until you have all the facts. Ask questions and offer support to help motivate them.


21. Discuss Performance, Not Personality


When talking about work, it's important to focus on what someone does and not who they are. Talk about their behavior and what can be done to improve it. Avoid saying anything negative about who they are and their personality.


Instead, focus on the actions they’ve taken. The more specific you can be and the more recent the actions have been the better. For example, it’s never a good idea to say something like, ‘For the past couple of years, your performance hasn’t been great.’


Replace it with something like, ‘Six weeks ago I spoke to you about the Dartmouth County submission. I explained the case studies needed to be expanded. Two weeks after that you made the submission but the case studies hadn’t been expanded.’


Do you see how much harder it is to argue with that latter example? This is why have difficult conversations as soon as possible is so important. The further away and the bigger problems get, the more subjective they become.


22. Provide Behavioural Guidelines With Consequences


If someone does something wrong, it is important to give them guidelines of how to act and what will happen if they make the same mistake again. Don’t be horrible about this. Be direct but polite. Be clear.


For example, you might have a team member who is keen for a promotion. Their job isn’t at stake, sure. But they are regularly late with deadlines. You could explain to them clearly the next time they miss a deadline how this behaviour affects their likelihood to be promoted.


Remember to be clear. You could say, ‘If you miss deadlines like this in coming months, you won’t receive a promotion. So if you want to be promoted, one thing you need to do is to stop missing deadlines.’


23. Practice What You’re Going To Say, And How


Practicing what you say and how you say it can help you remember what to say and make sure you sound confident. Think about what words you want to use, rehearse it out loud, and be ready for any questions. There aren’t many things in life more challenging or important than crucial conversations with employees. It’s worth taking the time to practice and get feedback from a coach or mentor.


24. Give The Employee The Benefit Of The Doubt


Guess what? You’re wrong. Maybe not about this whole situation, but there’s always something we don’t know or don’t know the full details about! Wear your Sherlock Holmes hat into this difficult conversation.


Instead of taking a defensive posture, be clear but curious. What information don’t you know? Have an open hand and an open heart and assume the best.


25. Get To The Root Of The Problem


20 minutes into the difficult conversation… you get an inkling. It’s the elephant in the room. Do you go there or do you avoid it because elephants are heavy and they can squish you? In my experience, elephants get heavier and more dangerous the longer they’re left unaddressed.


If you get an inkling, go there if appropriate. These difficult conversations are always uncomfortable (sorry!) so if it’s uncomfortable, that’s just part of the process. I like to remind leaders that you may be the FIRST person in your employee’s life who has had the courage to give them constructive feedback.


It’s hard. It’s tiring. And you’ll question, ‘Why do I bother?’ sometimes. But so many leaders I know tell stories of the worst conversations they’ve had and then 20 years later that person seeks them out and says, ‘You know what? Thank you for what you told me 20 years ago. I needed to hear that even though it took me another 10 years to deal with it!’


26. Gain An Understanding Of The Problem


Gaining an understanding of a problem means learning more about it. Ask questions and listen to what your employee says. Try to figure out why the problem exists and what can be done to fix it. Don’t walk into this conversation as a closed book. Go in seeking to communicate clearly and to understand more deeply.


27. Don’t Sandwich Negative Feedback Between Positive Reinforcement


This is a myth! Don’t be robot Bob who sandwiches all his negative feedback. Rip the bandaid off. What’s worse? Ripping a bandaid off a small wound? Or ripping a cast off a fractured femur? The key here is to have the difficult conversation when it’s a little wound before the whole leg breaks!


Make your difficult conversations clear and early. Give specific feedback and be as recent as possible. Be direct but polite. Yes it will be uncomfortable. But in the long-term you’re setting you, your employee, your team and your organization up for a win.


Last of all, I want you to think of your difficult conversation like exercise. Is going for a run painful? Yes. Are we sore afterwards? Yes. But the alternative is to sit on the couch and choose not to do any exercise because it’s too hard.


If you choose to sit on the couch and sit, and sit, and sit, there’ll come a point where your body tells you something’s wrong. You go in to see a doctor and you’re 200 kilos overweight. Your joints are seizing up because nothing’s moved in years.


What would happen if you just tried to run a marathon at that point? Your body wouldn’t cope. Joints would spasm and your heart would be under stress it wasn’t prepared for. Worse case scenario, you could die.


I want to challenge you to put on your running shoes, press start on your watch and hit the pavement. Start having difficult conversations as often as you exercise.


It will be uncomfortable, but when your team and organization is running marathons in years to come, you’ll thank me.


Are you dealing with a difficult employee, right now?


If you found this blog helpful, you'll love my book Step Up or Step Out: How to deal with difficult people, even if you hate conflict.


In the book, you'll discover the system for dealing with difficult people that REALLY works.


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