The Awkward Conversations No One Prepares You for as a Dental Practice Owner

Why Growing a Practice Means Getting Better at the Conversations You Never Expected to Have

There are a lot of things you expect to deal with when you become a dental practice owner. You expect staffing problems, scheduling issues, difficult cases, overhead decisions, and the occasional upset patient. What nobody really prepares you for are all the bizarre human situations that come with putting dozens of employees and thousands of patients under one roof. Eventually, someone says something completely inappropriate. A patient asks you a question you never imagined answering in dental school. Two employees have history you knew nothing about. Someone complains about another employee's bathroom habits. You make a joke that sounds much funnier in your head than it does when it comes out of your mouth. As your practice grows, there are simply more people, more personalities, and more opportunities for things to get weird.

I used to think being a better leader meant getting better at preventing these situations. I don't anymore. You cannot systematize human beings to the point where nothing uncomfortable ever happens. In fact, some of the strangest situations tend to show up as the practice gets bigger because there are so many more interpersonal touchpoints. The real leadership skill is learning how to respond when they do. Some moments require a serious conversation. Some require you to protect your team. Some require you to admit that you handled something poorly. Others require absolutely nothing except the ability to laugh and move on. The difficult part is knowing which is which.

When the Conversation Is Uncomfortable, Don't Make It More Uncomfortable

One of my more memorable leadership failures happened during a team meeting with probably 30 or 35 people. We had an employee who was great in a lot of ways. Patients liked her, she had a positive attitude, and if you asked her to do something, she would get it done. She also loved to talk and could get distracted pretty easily. During the meeting, she asked me a question, and I made a joke about how she would probably just be in the back room talking all day anyway. I thought I was being funny. The room went completely silent, she started crying, and she ran out. It was one of those moments where you immediately realize that what sounded funny in your head was not funny at all once it left your mouth.

What I learned from that experience is that context matters enormously when you are the practice owner. Something you might jokingly say to someone one-on-one can feel completely different when you say it in front of the entire team. There is also a power dynamic that owners sometimes forget. You may think you are simply another person joking around, but you are also the boss. When you criticize or embarrass someone publicly, even unintentionally, it carries more weight. This applies beyond jokes. There are times when employees absolutely need feedback, and avoiding those conversations because they might be uncomfortable is not good leadership. However, accountability does not require an audience. If the purpose of the conversation is to help someone improve, having it privately usually gives you a much better chance of accomplishing that without making the person defensive or embarrassed.

At the same time, avoiding uncomfortable subjects altogether creates a different problem. During one of the stories Dr. Henry Ernst shared, he was walking a potential new office manager through his practice. They entered a break room filled with employees, the candidate recognized one of the team members, and the team member immediately said, "Yeah, you fired me at my last job." The entire room went silent. It was incredibly awkward, but in a strange way, it was probably better that it happened. The history was suddenly out in the open, and the two people were eventually able to discuss what had actually happened. Had nobody acknowledged it, that tension could have quietly followed them into their working relationship, with everyone around them sensing that something was wrong without understanding why.

That is an important distinction for practice owners. You do not want to create unnecessary discomfort, but you also do not want a culture where everyone avoids difficult subjects because they are afraid of an awkward conversation. Unspoken tension does not disappear. It usually turns into resentment, gossip, passive aggression, or people creating their own explanations for what is happening. Sometimes the healthiest thing a leader can do is get the issue into the open, create an appropriate place to talk about it, and allow the people involved to move forward.

Your Team Is Watching What You Are Willing to Tolerate

There is another category of uncomfortable conversation that practice owners cannot afford to avoid: protecting the team when someone crosses a line. Henry shared a situation involving a patient who had become increasingly rude after treatment. The patient repeatedly contacted the practice asking for medication and eventually began cursing at team members. Henry stepped in, moved the conversation away from his employees, and made it clear that the behavior was not acceptable and the patient needed to leave. He remembered that his heart rate was up because he did not know exactly how the patient would respond, but he also remembered how his team looked at him afterward. They knew their practice owner was willing to step in when someone was mistreating them.

That matters more than owners sometimes realize. We ask our teams to provide incredible service. We want them to be patient with anxious patients, empathetic when someone is frustrated, flexible when things do not go perfectly, and professional even when the person across from them is not. Those are reasonable expectations, but there has to be a boundary. Great customer service cannot mean that your employees are expected to accept abuse. Henry described another situation involving the husband of a patient who repeatedly spoke disrespectfully to his employees. His wife was a wonderful patient, so instead of treating the situation as all or nothing, Henry told her she was still welcome in the practice but her husband was no longer allowed there. For him, the line became very clear when the team's discomfort started becoming a question of whether they felt safe.

Not every difficult patient needs to be dismissed. I have had conversations with patients about how they were treating my team and been surprised by how receptive they were. One patient in particular was consistently passive-aggressive with employees while always being extremely nice to me. I finally told her that several people felt she was rude to them. To my surprise, she immediately acknowledged it and explained that she knew she sometimes came across too aggressively and was working on it. The conversation did not magically change her personality, but it reinforced something important for my team: I saw what was happening, and I was willing to address it.

Your employees notice what you tolerate. If someone repeatedly disrespects them and you look the other way because you do not want to lose a patient, that communicates something about the culture. If you immediately fire every mildly annoying patient, that creates a different set of problems. Leadership is rarely that black and white. The goal is to develop enough judgment to recognize when someone is frustrated and needs empathy, when someone needs a clear boundary, and when behavior has reached a point where protecting your people matters more than preserving the relationship.

Not Every Awkward Moment Is a Leadership Problem

One of the traps of becoming more intentional about leadership is starting to believe every strange interaction needs a policy, a meeting, or a deep conversation. It doesn't. Sometimes a patient says something weird. Sometimes somebody misunderstands a social cue. Sometimes you forget the name of a former employee who worked for you for two years and then realize it while you are already talking to them. Sometimes you reach toward a patient's bib and they think you are going in for a hug. When you work with the public long enough, you accumulate stories that could never have been included in any dental practice management course.

This is where a sense of humor becomes a surprisingly important leadership skill. Dr. Steve Markowitz told a story about sitting next to someone at a dental conference and casually asking where she worked, only to have her angrily remind him that she had worked for him for two years. It was embarrassing, but there was not much to "solve." He laughed at himself and later shared the story with his team. Henry told stories about patients asking incredibly personal questions after treatment. We all had stories about older patients saying things to us that would be completely unexpected in almost any other professional setting. The common thread was not that we had discovered a perfect response to every situation. It was that after enough years of practice ownership, you stop expecting every interaction to go according to script.

That perspective becomes increasingly important as your practice grows. A six-doctor dental practice with dozens of employees is going to have more interpersonal complexity than a small office with one dentist and five team members. Add associates, department leaders, spouses, vendors, hundreds of patients every week, and eventually something unexpected is going to happen. If every strange interaction rattles you, practice ownership becomes exhausting. You need the emotional flexibility to recognize when something truly matters and when it is simply another funny story you are going to tell later.

The distinction I try to make is whether the situation is affecting trust, performance, culture, or safety. If it is, leadership probably needs to get involved. If an employee needs corrective feedback, have the conversation privately. If there is unresolved tension between two people, help bring it into the open. If a patient is making your employees feel unsafe or repeatedly treating them disrespectfully, establish a boundary. If you are the one who handled something poorly, own it and repair the relationship. If none of those things are happening and the situation is simply awkward, laugh at it and keep moving.

The Bigger Your Practice Gets, the More Human Leadership Becomes

Dentists often approach practice growth as a systems problem. We think if we can build the right systems, hire the right people, create the right accountability structure, and train everyone properly, the practice will eventually run smoothly enough that the problems disappear. Good systems absolutely reduce chaos, and they are essential if you want a team-driven practice that does not depend on constant owner involvement. What systems cannot do is remove the human element from the business.

In fact, one of the strange things about dental practice growth is that the better your systems become, the more your leadership can shift toward the situations that cannot be solved by a checklist. You should not be the person answering every scheduling question or fixing every routine operational issue. Your leaders and systems should handle those things. Your value as the owner increasingly comes from navigating the gray areas: coaching a leader through a difficult employee issue, deciding where a patient boundary should be, repairing trust after a mistake, helping two people work through conflict, or simply setting the emotional tone when something unexpected happens.

That is why I no longer think great leadership means always knowing the perfect thing to say. You will say the wrong thing sometimes. I certainly have. You will misread a situation, make a joke that does not land, or walk away from a conversation thinking, "Why did I say that?" The owners I respect most are not somehow immune to those moments. They are simply willing to deal with what happens next. They apologize when necessary, have the conversation when it matters, protect their people when a boundary has been crossed, and do not turn every weird interaction into a catastrophe.

Practice ownership gets messy because people are messy. That does not mean something is wrong with your practice. In many cases, it simply means your practice has grown enough that you are interacting with a lot more human beings every day. Build great systems. Develop strong leaders. Set clear expectations. Create healthy boundaries. Then accept that occasionally, despite all of that, something completely bizarre is going to happen.

When it does, figure out whether it needs a conversation, a boundary, an apology, or just a laugh. Then lead accordingly.