How to Have, and Not Have, Difficult Conversations

Have you ever had to have a tough conversation with someone who reports to you? What about your boss or a customer? I’d like to share examples of some of my experiences in these situations. Some of these went well, some were extremely uncomfortable, and a with a few, I was ashamed of how I handled them. Sharing my failures and successes with these experiences is a great opportunity to show you that everyone makes mistakes. Learning from those mistakes, however, is important and powerful for your leadership development.

Leadership Can Be Hard

One of the toughest things for a leader to do is have a conversation with someone knowing it will not be comfortable for either of you. This can be related to job performance issues, bad office behavior, or any number of things encountered in the workplace.

One of the toughest things for a leader to do is have a conversation with someone knowing it will not be comfortable for either of you.

Being at the top of the food chain should be easy for human beings. But when it comes to having tough conversations, many people either become savages or softies. Neither is a recipe for success, nor would they fit into Darwin’s theory of leadership evolution if he had one.

What if I told you there is a way to have these conversations without always being uncomfortable? These conversations can be successful without you coming across as mean or confusing people by sugarcoating the issue.

No Theories, Just Experience and Advice

Unlike Charles Darwin, I am not a scientist by any measure of the word. But I have been a leader for several decades, both a bad one and a decent one. I want to share some of my experiences with you, both good and bad.

The Good

One of my favorite things to do now is have conversations with people who are struggling. This could be an employee, a peer, a friend, or even a stranger. Yes, I know that sounds crazy, but I mean it. This part of my role really jazzes me the most. I enjoy helping people who are struggling in their careers work to get better.

In recent years, I had a particular challenge with an employee who my peers struggled with prior to him being assigned to me. This situation changed how I now approach conversations with struggling employees.

This person had several bad office behaviors and exhibited work fatigue as well. The list was so long that I decided the only way to handle this was to show him the list and discuss the issues one at a time. To be fair, I wrote out each issue with a problem statement and how it was impacting the team.

When we sat down to meet, I handed him the document which was basically the start of a performance improvement plan, and let him read. After he finished reading, he looked up very emotionally shook and said, “I had no idea.” I thought to myself “Really? Are you blind?” but kept quiet.

This is when it struck me that people who are struggling often don’t even know it. If they do not know it, they certainly cannot help themselves improve. So, immediately I took the empathy track and let him know he was not going to be terminated, yet. Together we talked about the issues and what was unacceptable and where he needed to be. But instead of telling him how to improve, we used the SMART goal process to help us come up with ways for him to improve. While I steered him in the direction of success, it was important that he came up with the plan. After all, this would not work without his buy in.

He did start to improve, and we continued to meet weekly for a month to make sure he understood the goals, resolve any questions either of us had, and provide him real feedback on a regular basis. In less than a year, not only did he improve, he got promoted.

The Bad

Having tough conversations with employees and peers is not easy. But can you imagine having one of those conversations with your boss? I found myself in this situation, and it was the toughest conversation I have ever had with anyone in my career.

In a past organization, one of my peers became our boss. He was a very data driven person and loved technology, not a bad thing for a manager. But, when he got promoted, his new role was supposed to be more vision, strategy, and direction. He struggled for a long time trying to break out of being in the weeds of the daily operations and became what most people labeled a micromanager.

During a one-on-one meeting with him, I decided to have that tough conversation letting him know how people felt. Having been in this position before I wanted to help him overcome the transition from mid-level manager to senior leader. While I kept it professional, everything said was real and to the point. I did not sugarcoat anything even though he was my boss. As you can imagine, this did not sit well with him at first even though he knew I never gave him trouble. For the record, I was not lobbying for his job.

The day after we met, I heard from a peer that my boss thought I was just having a bad day and unloaded on him. At our next one-on-one meeting, I decided to revisit the topic. I made sure to start the conversation calm and positive and avoided what could be perceived as a personal attack. This conversation went better than the first one because I had already laid out the problem previously and continued this one with empathy and understanding. While he got better, I understand to this day he still struggles with keeping his focus on his role and not his past position.

The Ugly

The worst conversation I have ever had with someone was with a customer when I was a help desk manager. We had a person who would come in five minutes before we closed for the day on a regular basis just to antagonize the team. His favorite thing to do was ask the service desk staff questions to which he either already knew the answer or had already asked other teams the same question waiting to get different answers from mine. Frequently, he would criticize our team for not having the same answer as a tier 2- or tier 3-level team. He would spend 30 minutes complaining and belittling them about their lack of knowledge.

One day shortly after I started managing this group, he showed up at the help desk and started to berate my team for not knowing something. As any good leader would do, I stepped in to handle the situation. This person did not like the fact I was owning the problem for my team and not cowering to his tantrum. He started making rude remarks to me about integrity and honesty. For me, this was like calling Marty McFly (Back to the Future) chicken. My temper went from 0 to 60 faster than a Bugatti Chiron.

What happened next was satisfying but also unprofessional, and I regretted it later. I will spare you the explicative language I used to tell, not ask, him to leave the office and get out of my face. When he left the help desk my staff all stood up and applauded me for my performance. Once I calmed down, I explained to them, while it felt satisfying at first, this was not the way to handle a situation with a customer or anyone else for that matter. I apologized to them and felt really embarrassed. I was a professional for crying out loud and certainly not new to this game of customer service or leadership.

I immediately went to my boss and told him what I had done. He acknowledged this guy was a regular bad customer and did understand my reaction to the situation as well as my team’s. We agreed to my plan to setup a meeting with this customer to apologize and set expectations for future interactions when he visited the service desk. As it turned out, this customer was not mad at me (after a cooling off period) and started treating me with a little more respect since then. He told me he likes people who are direct and to the point and not afraid to say what they mean.

Keep Calm and Carry On

When you are dealing with struggling employees, it is important to involve them in the solution. If you create the plan and the SMART goals alone, most likely they will not improve and possibly get worse. Make sure they are involved in the process and feel they can accomplish what they came up with. If it is their plan they helped create with expectations and goals they came up with, their chances of success will be greater.

If you have to have a tough conversation with a peer or a boss, try setting the tone right at the beginning. Keep calm and positive, and let them know up front you want to help them. There is no need to treat it like an intervention, make it a one-on-one friendly conversation.

At some point in your career, you will be confronted with an irate customer. As hard as it might be, do not go off the rails like I did. Try to keep your cool. If you cannot keep it positive, ask the person if you can schedule a time for coffee to discuss it further. Take some time to collect your thoughts, and try and see things from the other person’s perspective. Even if they are being obtuse, usually there is a reason.