Keys to Having Difficult Conversations

One of the most stressful jobs for any school administrator is the supervision of employees, especially during difficult situations. Sitting face to face with a subordinate who is struggling with poor performance or in trouble for serious wrongdoing is always a daunting task. I served a total of 22 years in school administration, 14 of those specifically as an assistant and then deputy superintendent for human resources in a school district with over 3,000 employees. As is the case with many district office leadership positions, it was also my responsibility to supervise and mentor building and department leaders and help them be successful at managing their employees. I quickly learned that navigating the waters of adult supervision took some special finesse. Over the years, I watched colleagues who seemed to have the right balance of accountability and support. I listened to effective leaders talk about how they successfully worked with their staff in difficult situations. I also facilitated hundreds of difficult personnel conversations with employees and as I did so, I developed a set of guidelines that helped me in virtually every situation. I used these guidelines to support other leaders as well. Over the years, what I found was that when a situation went south, it was likely because I failed to implement one of my own guiding principles. So I committed the following to memory, and when I found myself sitting with a troubled employee, I had a protocol that usually proved to be successful.

Guiding Principle #1: Be Prepared

Even when you are caught off-guard and find yourself dealing with a difficult situation with little or no warning, you must (at a minimum) take a few minutes to think about what you’re doing before you do it. Before you enter into a conversation with a staff member, especially when there is a problem, it is important to have a plan. You are more likely to accomplish something if you have a goal in mind. It might simply be to hear what the employee has to say. Maybe it’s to inform the employee of something. Perhaps you are going into an interview during a planned investigation. As much as possible, have a conclusion for that meeting in mind so that during the meeting, you can keep your eyes on the outcome. This will aid in avoiding the temptation to walk into a situation and make statements or decisions before you have all the information.

If you go into a meeting with an outcome in mind, you are more likely to stick with that objective, and not overstep by saying or doing something you regret later. Example: an employee makes an appointment with you to share what they deem as serious concerns about another employee, but provides you with no additional information. In that case, I would focus on outcomes that look something like this: 1) Understand what the employee wants me to know by listening carefully and asking clarifying questions. 2) Have good notes for future reference and documentation. 3) If during the meeting I find the situation warrants immediate action, take a break in the meeting to step out and review the facts, and talk to a suitable team member or supervisor to verify my thoughts and refine my plan of action. 5) Inform the employee of the action and my next steps (i.e. investigation, other communication, etc.). If immediate action is not needed, I will inform the employee that I will look into the situation, or consider the information and get back to him/her. Be sure to give the person some kind of timeline. Having this plan in mind may help you from making a hasty decision “in the moment.”

Guiding Principle #2: Ask Questions

This one is more appropriate for those times you have a planned meeting. Think about some leading questions you can ask the employee to get the difficult conversation started. Prepare for this, because

you don’t want to ask questions that may mislead the employee or complicate the conversation. In other words, if you are going into a meeting about an employee’s misconduct and subsequent discipline, you should start off with a question that is sincere and serious-minded, like “How are you doing” rather than something more light-hearted like, “Did you see that Cardinals game last night?” Beyond that initial ice-breaker questions, I found that by asking a few questions at the beginning of a difficult meeting, it gave me the opportunity to do three things. 1) I could understand the feelings and intent of the employee. Were they remorseful? Were they confused? Were they angry? Were they struggling with other issues that resulted in misconduct? Had they been working hard to improve the situation? By asking questions like, “What is your understanding of the reason we are here?” or “Tell me your assessment of how things have been going with regard to your work,” it allowed me to gain a lot of information about the employee. 2) Being able to listen gave me time to breathe. Serious conversations must be met with a professional demeanor and by inviting the other person to talk, it gave me time to listen, reflect and make sure I displayed the proper disposition for the meeting. 3) Asking questions (followed by active listening) sends the message that you care about the person and that you care about what they have to say. On many occasions, an employee has said to me, “We may not always agree, but I know you always want to hear what I have to say.”

Guiding Principle #3: Listen

To listen sounds simple, but it is not; and can be especially difficult when you’re the boss. This became even more evident to me when I became the “boss of other bosses” as a district administrator. Employees want supervisors who care about them and who listen to them. They want to have voice and they want to feel important. Listening builds trust and positive relationships so that when difficult conversations occur, your staff are more open to you. And in those difficult situations, listening is more important than ever!

I have found that listening skills are too often inadequate. People want to get their point across, often before understanding an individual’s perspective. I often engage my graduate students in an experience where they are invited to listen for 2-3 minutes to a colleague talk about something of interest. I tell the listener, “You may only comment in one of two ways. You may affirm something they say, or you may ask clarifying questions about what they are saying. You may not bring the conversation back to you. In other words, if you had a similar experience, or can relate, you may not comment about how this relates to your experience.” The reason we do this is to have people practice truly listening to understand, rather than listening to respond. Obviously, conversations should be a two-way street, and I find this exercise in (and review of) empathic listening helps people practice focusing on the most important part of communication: listening for understanding.

Guiding Principle #4: Be Succinct

During difficult situations, employees must understand the message that you are conveying. Sometimes we go into meetings as an investigator, other times we are helping to coach or improve an employee and still other times we are there to deliver a message about expectations, discipline or even termination. In any case, we must go into the meeting knowing the intent of the meeting and being

clear to the employee about that intent. For example, you might say, “The purpose of this meeting is for us to review your progress over the last few weeks and determine next steps.” This might be a message for someone with whom you are working on an improvement plan. You might state, “The reason we are here today is for me to ask you some questions about some concerns that have come to my attention. This is just a fact finding meeting, and at the end, I will let you know next steps.” Finally, your message

might be, “This situation is very serious and today I want to ask you some questions, clarify some expectations and then I’ll let you know next steps.” These kinds of statements not only clarify the intent

of the meeting, but can also be calming to the employee. Nobody likes to sit with their boss and not know what is happening or why!

In any case, it is crucial to be sure that the employee know exactly what is happening in the meeting and what will happen after the meeting. I often ask people to tell me their understanding of what was going to happen next, or have them repeat my expectations so that I know they are clear. This helps me to know what the employee understands. Of course, meetings are also followed up with written documentation of some kind. This is a critical step in working with employees who are struggling, for many procedural and legal reasons, and it helps ensure the messages are clear.

Guiding Principle #5: Find Common Ground

It is always helpful if you can build on an agreement rather than argue about a disagreement. Find areas where you both agree and start there, for example, “I know we both want everyone in the department to be comfortable,” or “Everyone is looking for the most efficient and timely way to get this done.” One thing we know, when you are having a difficult conversation, if you can agree with even a piece of what someone saying, he or she is more likely to engage with you than if you immediately take an opposing position.

Guiding Principle #6: Treat People with Dignity and Respect

My goal is always to be kind and respectful, even if someone has acted with gross negligence. When coaching, disciplining or terminating an employee, it is not my place to embarrass or humiliate them. While it might be my place to inform them that they are under investigation or that they are suspended or that their last day is today, it is still best to treat people with respect. In so many situations, the person knew of their mistake or poor performance. In almost every situation, I found that if I had done an effective job in offering support, communicating clearly, asking questions and listening and documenting often, then those “final” meetings were much easier and more productive. Treating people with respect actually makes these difficult meetings easier to have, because the focus is on violation of district policy or law, not your judgement of a person. In every meeting, I pretend that others are watching, and ask myself would I be proud of the way that I interacted with the other person. I also keep this in mind, “Is this the way I would want to be treated if that were me?”

Closing Thoughts

Administration can be a very challenging career choice often because it involves being responsible for the performance of other adults. Difficult conversations were never something I enjoyed however by having some principles to guide me, I was more confident and comfortable leading the conversation, knowing what to do and delivering a tough message. The more I practiced, and I had lots of practice in 22 years of administration, the more it became second nature and the better employees felt through the process. As a result, more problems were resolved in a positive manner.

This article originally appeared in the April 2019 issue of School Business Affairs magazine and is reprinted with permission of the Association of School Business Officials International (www/asbointl.org). The text herein does not necessarily represent the views or policies of ASBO International, and use of this imprint does not imply any endorsement or recognition by ASBO International and its officers or affiliates.