Learn about the three steps to having, managing, & dealing with tough, difficult & challenging conversations with your employees & staff at work or in the workplace.If there is one topic that new and seasoned leaders ask about the most, it is how to have difficult conversations. The reason for the conversation varies: performance issues, personality conflicts, behavioral concerns and even the most dreaded conversation of all, body odor. I find that one of the ways I spend at least part of my day, every day is coaching leaders through a difficult conversation.

The topic of how to have difficult conversations will be one of the first we roll out with our learning management system coming next year, but until then, I thought I would give three tips for preparing for and having even the most difficult of conversations.


I think one of the biggest mistakes made in having these conversations is that the leader goes into it without preparing. They want to get it over with so they bring the person in and just start talking. Because they haven’t thought it through ahead of time, they may not use the right words or be as direct as they need to be. For the employee it can feel as though the leader vomited a bunch of words on them that really don’t mean anything. A conversation where the employee leaves the room unsure of what was just shared or of what they are expected to do next is not going to fix anything.

While conversations should happen in a timely manner, it is ok for a leader to take some time to prepare. Sitting down and writing out key points that you want to cover, being specific about the exact problem and what you are expecting the employee to do after the conversation will help you stay on point later.

Potentially a more important part of preparation is thinking about the employee themselves and how best something like this should be communicated in a way they can hear it. What specific words does this employee need to hear? How direct can you be without shutting them down? Some employees need a bit more of a tender touch while others want no fluff. What type of employee is this? If your business has done any kind of personality workshops, like Myers Briggs, and you know the employee’s personality type, this is a great time to review how they like to be communicated to and use that in your discussion.

I firmly believe that when we communicate we should mimic the style of the person we are speaking too rather than expect them to adapt to our own. We need them to be able to hear our message in a way that it sinks in. Our normal style may not be able to accomplish that.

Focus, Specific and Action:

These are the three words I ask every leader to remember during the conversation. Tough conversations can get derailed very easily. Especially if emotions start to run high. Our natural defense when someone is giving us negative feedback is to deflect and start blaming other things. For this reason, a leader has to be able to focus and manage the conversation again and again. They have to be able to not start going down the rabbit hole of all the other things that may be brought up and remember to stick to the topic at hand. The employee isn’t going to do this so it is the leader’s job to bring the conversation back as many times as necessary.

Another pitfall that happens in these conversations is that the leader is not specific about the issue. They dance around or try to downplay the severity in an effort to save hard feelings. Indirect feedback rarely accomplishes anything. Employees need to be clear on what happened that is not acceptable. A leader should check for understanding several times throughout the conversation. If they feel the employee may not be getting the point, they should try to explain it in a different way until they are sure the employee understands the problem.

Finally the conversation has to included actionable items the employee can and should do to correct the problem. We shouldn’t always assume that the employee knows how to correct the behavior or that their way of correcting it is what we would prefer. We as leaders, must lay it out for them in a way that makes it clear what we expect.

Follow Up:

The reality is that no matter how much you prepare and follow the tips above, difficult conversations may still be very difficult. Emotions can get the best of employee and leader. Harsh words that shouldn’t have been said, can be. Desired outcomes may have not been as clear as needed. Both parties can leave the conversation angry and exhausted.

For this reason I suggest leaders wait a day or two and then follow up with the employee. Let emotions die down a bit and then do a quick check to see if the employee understood and knows what they need to do going forward. This isn’t the time to rehash everything and in the end, the employee doesn’t have to agree with the feedback, but they do have to understand it and be willing to work towards a solution.

Then of course, there should be additional follow up throughout the following weeks and months to make sure the employee is on track with the changes that needed to be made. This follow up should be full of praise when changes are made and slight course corrections so that the end outcome is highly positive.

In the training that will come out next year, we will walk through each of these steps in detail and give suggestions for what to say and do during each phase. For now, this simple guideline should put you on the path to better conversations, even when what you are saying is hard to hear. I don’t think anyone ever gets to the point of liking difficult conversations, but we can get to the point where we are comfortable having them. Like anything, it takes practice and experience. Experience that we don’t want to have, but helps us tremendously in the long run.


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