29. Why You Dread Difficult Conversations as a Leader (And How to Handle Them With Confidence)

Ever find yourself lying awake rehearsing a conversation you really don't want to have? 

Maybe it's a performance issue, a behavior problem, or that feedback you know you need to give, but keep putting off.

When you own a practice or step into a leadership role, these conversations are no longer optional. They come with the job, whether you feel ready for them or not.

The good news is this:

If difficult conversations feel hard, it is not because you are “bad” at leadership. Often, several challenges are happening at once.

Here are the three most common reasons difficult conversations feel so challenging for physician practice owners, and what to do about each one.

Hurdle #1: You are not fully confident about the topic itself

One of the biggest reasons conversations feel difficult is uncertainty. Not emotional uncertainty, but intellectual uncertainty.

Many physician leaders have an underlying fear they can’t quite name:

What if I am not seeing this clearly?
What if I do not fully understand the issue?
What if I say the wrong thing?

This is especially common when physicians move into leadership or administrative roles. You may be clinically excellent, respected by patients and staff, and still feel unsteady when the issue involves performance metrics, behavior standards, finances, or HR policies.

When the topic itself feels fuzzy, your brain tries to protect you by avoiding the conversation altogether.

What helps:

• Get very specific about what is actually happening. Facts before interpretations.
  
  
• Ask yourself where the uncertainty is coming from. Is it legal, operational, financial, or relational?
  
  
• Bring in expertise when needed. HR, legal counsel, accounting, or coaching support can help you pressure-test your thinking.
  
  

When you feel grounded in your assessment of the issue, the emotional charge of the conversation usually drops significantly.

Hurdle #2: Your role has shifted, but your instincts have not caught up yet

The transition from physician colleague to practice owner or CEO is one of the most underestimated challenges in medicine. 

For years, you may have built strong relationships through shared experiences, humor, venting, and camaraderie. Those instincts served you well and helped you succeed. But once you step into the role of decision-maker, the power dynamics shift, even if no one ever names it out loud.

This is where many physician leaders experience real internal conflict. You still want to be liked, trusted, fair and compassionate. You want to stay connected to the people you work with. At the same time, you are now responsible for the health of the entire organization, not just individual relationships. That tension can feel exhausting and disorienting.

Empathy has likely been one of your greatest strengths throughout your career. It helped you read the room, build rapport, and care deeply for patients and colleagues alike. But at the CEO level, unfiltered empathy can start to work against you. 

When you are overly focused on how others might feel, it becomes much harder to deliver clear feedback, set firm boundaries, or make decisions that may cause short-term discomfort in service of long-term stability.

Many physician leaders notice this shows up in familiar ways:

• Hesitating to give direct feedback
  
• Softening messages until the point gets lost
  
• Avoiding difficult conversations to spare someone else’s feelings, while carrying all the stress internally

Over time, this dynamic can make leadership feel isolating, especially when there are fewer safe places to process what you are holding.

What helps:

• Recognize that stepping into the CEO role requires a different kind of empathy—one that considers the whole organization, not just the person in front of you.
• Accept that some distance is necessary, and it does not mean you have stopped caring. It means you are caring differently.
• Find outlets outside the organization to process what you are holding. A coach, a peer group, or a mentor who understands leadership can make a significant difference.
• Practice wearing your "CEO hat" intentionally. Before difficult conversations, remind yourself of the role you are in and what the organization needs from you in that moment.

The loneliness of leadership is real. Many of my clients describe feeling relieved just to have a space where they can finally say what they have been carrying all week. You do not have to hold it all alone.

Hurdle #3: You do not have a clear framework for the conversation

This one surprises many physician leaders. You can have nuanced, compassionate, highly technical conversations with patients all day long. But when it comes to a workplace conversation about performance or behavior, it suddenly feels impossible to know where to start.

Without a structure, conversations tend to wander. You might over-explain, get pulled off track, or leave without having addressed the actual issue. The other person walks away confused, and you walk away frustrated.

What helps:

• Get clear on the goal before you begin. What is the purpose of this meeting? What does success look like?
• Anchor the conversation in organizational values. If the issue involves behavior that compromised patient safety or violated a core standard, say so. Framing the conversation around shared values takes some of the subjectivity out of it and gives both of you something concrete to refer back to.
• Keep your talking points simple. You do not need a script, but you do need a “North Star”, aka a clear sense of where the conversation is heading and why it matters.

For example, you might open with: "We are here to talk about an incident that happened on [date]. One of the consequences was [X]. A core value of our organization is [Y], and this conversation is about making sure we support you and ensure this does not happen again."

When you have a framework, you spend less energy figuring out what to say in the moment and more energy actually listening.

Your feelings are information, not obstacles

If you have a difficult conversation on the horizon and you notice anxiety, dread, or overwhelm building up, that is worth paying attention to.

Often, when I ask clients to name the feeling and then explain it in one sentence, something useful emerges. They might say, "I feel anxious because I am afraid I will do it wrong." That is not just a feeling, it’s a clue.

Once you name the underlying fear, you can address it directly. Maybe you need more information, a chance to practice the conversation out loud, or maybe you just need someone to remind you that you are more prepared than you think.

Feelings are messengers. They are not there to stop you. They are there to tell you where to shine the light.

Difficult conversations do not get easier by avoiding them. But they do get easier when you understand what is actually making them hard.

Most of the time, it is not one thing. It is a combination of uncertainty about the topic, discomfort with your evolving role, a lack of structure, and emotions that have not been fully processed.

When you untangle those pieces and address them one by one, the conversation starts to feel less like a threat and more like something you can actually handle.

Listen to the full episode to hear more about navigating difficult conversations as a physician leader. And if you're a physician leader navigating this transition and could use some support, reach out to me at [email protected].