How to Have a Difficult Conversation With a Difficult Employee

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A few weeks into a new job, I was asked to fire someone. Told really. We did not have any type of HR so I was expected to do it on my own and was uncomfortable for several reasons outside of the obvious legal implications. I did not agree with the reasons this person was being fired and of course had limited insight into the situation. I was uncomfortable because it seemed unethical and went against my values.

At the same job, months later, I had a recurring situation with one of my staff whose performance was not meeting expectations. It was a difficult conversation with a person I found difficult. I did not want to have this conversation because it was going to be difficult and unpleasant. I was uncomfortable not due to ethics or values but simply because it was going to be hard.

DECIDING WHETHER TO HAVE A DIFFICULT CONVERSATION WITH A DIFFICULT EMPLOYEE

There is a difference between being uncomfortable because of something that violates your values or ethics and not wanting to do something because it will be difficult. When it comes to addressing difficult workplace conversations, it is important to distinguish between the two. Ask yourself, am I choosing not to have this conversation because it goes against my values or do I simply not want to do it because it is hard?

Another consideration when deciding whether to engage a difficult conversation is the purpose. What is the desired outcome? Are you trying to help this person grow or are you merely trying to get them to adapt to something you want? Is what you are asking reasonable? Feasible? What is the value in engaging this conversation? What is the harm?

These considerations hold true for most conversations with most people, difficult or otherwise, employee or colleague. There are all sorts of tricky situations that arise in the workplace and learning how to confront them will be invaluable to your career. The information in this piece will focus on having a difficult performance conversation with an employee but the principles will apply to many other challenging conversations you will encounter. 

PREPARING FOR A DIFFICULT CONVERSATION WITH A DIFFICULT EMPLOYEE

Once you determine that this is a difficult conversation you should have, spend as much time- if not more so- on the preparation for it as you do on the having of it. Where will you hold the meeting? What day and time? How long will you schedule it? What information will you share ahead of time? What will you put on the agenda? Who else (if anyone) should be there?

The answers to all these questions have implications, so be thoughtful about each one. If you have an HR department, involve them if it is helpful and/or if there are potential legal implications, but be cautious about being too heavy-handed if the situation does not warrant it. You are trying to create an environment that is conducive to working through something that is challenging and including people who should not be there can be as harmful as excluding people who should. 

It may also be helpful to prepare with another person who is ethically privy to the situation. Consider discussing it with your own supervisor, your coach or a trusted colleague. You may benefit from role playing or simply talking through your concerns. Whatever you do, be thoughtful about it. These conversations can have serious repercussions.  

LEADING A DIFFICULT CONVERSATION WITH A DIFFICULT EMPLOYEE

There is nuance to all situations and relationships, and you know the specifics of your own stuff better than anyone else. Be flexible in adjusting to these specifics. There is no system, framework or suggestion that is going to be equally effective in all situations. It can be difficult to know ahead of time what the best one is, so make the best choice you can based on what you know. Sometimes you will get it right and other times you will realize you should have taken a different approach. This will happen no matter how thoughtful you are so do the best you can and adjust accordingly for the next time. 

Taking these nuances into account, there is a framework you can use in all of your difficult conversations to help guide you through them. You can use this framework with any employee regardless of how difficult you may find them. You can use it when you are addressing performance or when you are broaching a conversation about a delicate subject. You can use it when you are confronting a colleague or asking something of your own supervisor. The steps and the premise remain the same and they remain effective. It is important that you go through each of these steps instead of diving right into the issue which is what most people do. That rarely works. Here is what does.

* Start with appreciation. The person on the other side of that table- proverbial or otherwise- may or may not want to be there. They may or may not have a legitimate choice to be there. Whatever the case, you want to show gratitude for their presence. Few people enjoy these difficult conversations and acknowledgement of their willingness to engage in them is important. You can say something as simple as, “Thank you for agreeing to talk with me today.” Depending on the situation, you may want to acknowledge the awkwardness or discomfort, saying something like, “I know this is not an easy conversation to have.”

In addition to this acknowledgement at the beginning of your meeting, there is a great opportunity and benefit to sharing something you appreciate about this person. If possible, share something related to the topic you are about to address. You want to set up the conversation to be respectful and this can help relieve some of that initial tension. Of course, you want to be sincere here and not just check the box of saying something nice. Think about this ahead of time and come prepared to share.  

* Proceed with purpose. After sharing your gratitude and appreciation, be clear about the purpose of the meeting. In most cases, you should have shared this ahead of time so the other person does not feel blindsided. If there are additional details to add, do so upfront. Give as much information as is helpful and make sure you are both in agreement about why you are there. 

* Get on the same page. Next, you want to get on the same page about what you want the outcome of the meeting to be with as much specificity as possible. At the end of the meeting, you want it to be objectively clear to both of you if you reached that goal or not. If it is an issue you anticipate needing more than one meeting to work through, set a realistic goal for what you hope to accomplish in the session and then plan for a follow up. Spend as much time as needed on determining the goal. In some cases, this may take the majority of the meeting. That is perfectly fine. It is essential that you are both working toward the same outcome for the conversation to be successful. Ensuring a mutually agreed upon outcome is what is going to determine whether that meeting is successful.

* Dive into the issue. Once you have done all of that, then and only then you can dive into the issue. As the leader of the conversation, you will set the tone and facilitate the process, but it is important to remember that this is not a sermon or a lecture. Whether it is a conversation between supervisor and supervisee or colleagues, whether it is about performance or something else, you are engaging in this conversation as two professional adults. You should be talking and listening and working together to get to the outcome you have both chosen. As facilitator, it will be important for you to bring the conversation back to that shared goal again and again. That is why you are there and you want to keep the conversation on track.

Make sure both of you have an opportunity to share what you have been experiencing and how it has affected you. Ask and answer questions to ensure you understand one another. Be very clear about what that issue is from both of your perspectives before you start trying to fix it. Be prepared that your perceptions and experiences may be quite different. Listen to understand, avoid judgments, and take ownership of your own reactions.

* Start fixing it. Once you have both had the chance to share your experiences with the issue at hand, decide together when you are ready to get to the fixing part. Then, once again, create space for both of you to share ideas and suggestions on how to reach the goal you have agreed on. Be open to ideas that are different than your own and keep the focus on getting to that shared desired outcome. 

* Check in. Make sure you do not go over the time you have set for the meeting. When you are getting toward the end of that time, check in to see if you have reached the goal you have set out to reach. Make sure you agree on whether this has happened. If it has, celebrate that. If it has not, acknowledge the work that has been done and make a plan for the next meeting. In either case, be sure to follow up to capture what occurred and put into place whatever you have agreed to do next.

* Be clear about next steps. There is no need to editorialize. In your follow up, stick to the facts that have already been agreed upon, and share them with the other person in a form like,

“Yesterday we discussed ________________. We decided to ____________________. As a next step, I am going to _______________ and you are going to__________________. We will meet again on ____________________ to check in on our progress.”

* Express your gratitude. Before closing out completely, express your gratitude and appreciation once again. Recognize the work that has been done and thank the other person for their willingness to do it. If it was a tough experience, you do not need to gloss over that and pretend otherwise. The gratitude is simply for the combined effort to work through this, not only if it ended up being easier than you thought. You can say something as simple as, “Thank you again for working with me on this. I appreciate you.”

THINGS TO REMEMBER WHEN HAVING A DIFFICULT CONVERSATION WITH A DIFFICULT EMPLOYEE

A common tactic used by people in challenging conversations is to do what they can to get through it quickly or avoid it altogether. They might shut down or on the other end of that spectrum, lash out. Some may exhibit both at different times throughout the same conversation. Do not let this derail you. Acknowledge it and work through it. Make it clear that this conversation needs to happen. I had a staff respond at the beginning of one such meeting with folded arms and a stern, “I guess we’ll just agree to disagree.” In this particular situation, we needed to come to an agreement and I let them know as much. They were not happy in the moment, but I did my job and ultimately, we got to an outcome that worked for both of us. 

You can never control someone else’s reaction and you only have so much control over the outcome. Too often, we avoid difficult conversations because of what we anticipate the other person’s reaction to be. Whether this anticipation proves to be true is irrelevant. People are responsible for their own reactions and your best guess of what it might be is not reason enough to avoid it.

Similarly, when it comes to outcomes of the meeting and the behavior that is being addressed, you cannot control what the other person chooses to do. If it is an extreme situation where they must do X or they will be fired, they have every right to make the choice for themselves whether they do it. Your role is to give them everything they need to meet their goals and the goals of the organization.

Remember during the entire process to be a human being. Exhibit empathy and respect, and access your strongest communication skills throughout. Do not pretend that you have all the answers or assume that your side is the one and only right one. The main reason conflict arises in the first place is not that one person is right and one is wrong but instead when two people have conflicting ideas about what is right and wrong. Honor other perspectives and appreciate that often the decision is not the only one that can be made.

Finally, keep in mind that a difficult conversation with an employee you consider difficult is not much different than a difficult conversation with anyone else, including people you do not supervise like a colleague or your own supervisor. With some adjustment, the same principles shared above apply, and the same strategies will be successful.

 

 

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