The Conversation You’re Avoiding Is Probably the One You Need to Have

Why having difficult conversations sooner, and balancing them with positive communication, is one of the most important things you can do as a business owner.

We’ve all been there. Something isn’t going quite right with an employee, a colleague, or even a business partner. You recognize the issue, know it needs to be addressed, and perhaps even rehearse the conversation in your head.

But then you hesitate.

Maybe it’s not that big of a deal. Maybe they’ll figure it out on their own. Maybe bringing it up will create tension, hurt feelings, or make an already challenging situation worse.

So you wait.

And wait.

Until that relatively small issue becomes a much bigger problem.

As a business consultant, I see this happen all the time, particularly in healthcare practices where relationships are such an important part of the business. Practice owners are often reluctant to address performance concerns because they genuinely care about their employees. They don’t want to discourage someone, create conflict, or risk losing a valuable team member.

The irony is that avoiding a difficult conversation in an effort to protect a relationship can ultimately do more damage to that relationship than having the conversation in the first place.

Why Are Difficult Conversations So Difficult?

I think part of the answer is that we’ve been burned before.

Maybe we were honest about something in the past and the other person became defensive. Maybe we tried to address a concern and it escalated into something much bigger. Or perhaps we simply don’t like the uncomfortable feeling of knowing someone is disappointed or upset with us.

Those experiences teach us to protect ourselves. We begin filtering what we say, softening our expectations, or avoiding certain topics altogether.

But here’s something worth considering: Being kind and being direct are not mutually exclusive.

In fact, I would argue that one of the kindest things we can do for someone is to give them the information they need to be successful.

If an employee is consistently falling short of expectations but nobody tells them, how can we reasonably expect improvement?

And what happens when that same employee eventually discovers that their performance has been a concern for months?

Suddenly, the conversation isn’t just about performance. It’s also about trust.

Have the Conversation Before You Feel Ready

One of the most valuable habits a business owner can develop is addressing concerns sooner than feels comfortable.

I’m not suggesting that we react emotionally to every frustration or point out every little mistake. There’s certainly value in giving ourselves time to process our thoughts and determine whether something truly needs to be addressed.

But once you’ve identified a pattern, an unmet expectation, or a behavior that is affecting the team or patient experience, waiting rarely makes the conversation easier.

In fact, the longer we wait, the more likely we are to attach additional frustration and emotion to the situation.

Consider the difference between these two approaches:

After months of frustration:

“I’ve asked you repeatedly to follow this process, and you still aren’t doing it. I don’t understand why this continues to be an issue.”

Addressing the concern early:

“I noticed we’ve had a few situations where this process wasn’t followed. Can you walk me through what’s happening? I want to understand if something is getting in the way so we can make sure we’re consistent moving forward.”

The second conversation creates an opportunity for understanding, accountability, and improvement before resentment has a chance to build.

It also communicates something important: I care enough about your success to have this conversation with you.

The Emotional Bank Account: Are You Making Enough Deposits?

There’s another important piece to having difficult conversations successfully, and it has everything to do with what happens between those conversations.

Think of every relationship as having an emotional bank account.

Each time you recognize someone’s effort, express appreciation, offer encouragement, or show genuine interest in them, you’re making a deposit.

When you criticize, correct, or have a difficult conversation, you may make a withdrawal.

That doesn’t mean the withdrawal was wrong or unnecessary. Sometimes it’s exactly what the relationship or business needs.

But if we’re constantly making withdrawals without replenishing the account, eventually there’s very little trust or goodwill left to draw from.

You’ve probably heard recommendations suggesting that it can take five, eight, or even more positive interactions to offset a single negative one. While there isn’t a universal magic number, I think the concept is incredibly valuable.

What if we challenged ourselves to offer eight genuine, positive interactions for every critical one?

Not because we’re trying to manipulate someone’s feelings or keep score, but because it reminds us just how intentional we need to be about recognizing what’s going right.

Think about your typical workday.

How often do you notice an employee doing something well and actually say something?

How often do you walk past a team member who is quietly doing exactly what you’ve asked, without acknowledging their consistency?

Now compare that to how quickly we notice when something goes wrong.

It’s human nature to focus on problems. As business owners, we’re practically trained to look for opportunities to improve!

But when our communication becomes disproportionately focused on what’s wrong, our teams can begin to feel that nothing they do is ever quite good enough.

And when that’s the environment we’ve created, even a well-intentioned conversation about improvement can feel like another attack.

Positive Feedback Should Be Specific, Not Just Frequent

Making deposits into someone’s emotional bank account doesn’t mean showering them with generic compliments.

In fact, meaningful recognition often comes from noticing the little things.

Instead of simply saying, “Great job today,” consider something more specific:

• “I noticed how patiently you explained that situation to the patient. You really helped put her at ease.”
• “Thank you for stepping in to help when we got behind. I know that wasn’t your main responsibility, and I appreciated it.”
• “I can see how much effort you’ve put into improving this process. It’s making a difference.”

These moments don’t require a formal meeting, an elaborate employee recognition program, or even much time.

They simply require us to pay attention.

And when someone consistently feels seen, valued, and appreciated, they’re more likely to interpret constructive feedback as an effort to help them grow rather than as evidence that they’re failing.

That’s the real value of those emotional deposits.

Don’t Forget to Repair When a Conversation Goes Poorly

Even with the best intentions, we won’t always get communication right.

Sometimes we choose the wrong words. Sometimes our tone doesn’t reflect our intentions. Sometimes we’re tired, stressed, or distracted and respond in a way we wish we hadn’t.

The important thing is what happens next.

I think there’s tremendous value in being willing to revisit a conversation and acknowledge when it didn’t go the way we intended.

Something as simple as:

“I’ve been thinking about our conversation earlier, and I don’t think I communicated that as well as I could have. My intention was to help us find a solution, and I want to make sure you know that I value what you bring to this team.”

That doesn’t mean retracting the expectation or pretending the concern wasn’t valid.

We can apologize for how we communicated something without apologizing for the standard we’re asking someone to meet.

That distinction is important.

Repairing a conversation isn’t a sign of weak leadership. It’s an example of the accountability and emotional maturity we hope to see in our teams.

A Challenge for Business Owners

If you’re leading a team, I’d encourage you to think about two things this week.

First, what conversation have you been avoiding?

Is there an expectation that needs clarification? A behavior that needs to change? A team member who would benefit from some honest feedback?

Ask yourself whether waiting is truly helping the situation or simply allowing you to avoid a few uncomfortable minutes.

Then consider how you could approach that conversation with curiosity, clarity, and genuine concern for the other person’s success.

Second, how healthy are the emotional bank accounts within your team?

When was the last time you told someone specifically what you appreciate about them?

Are your employees hearing more about what they’re doing right or what they need to improve?

Are you creating an environment where people feel valued enough to receive feedback without immediately becoming defensive?

These questions matter because effective leadership isn’t about choosing between being liked and holding people accountable.

It’s about creating a culture where both appreciation and accountability are part of everyday communication.

The Bottom Line

We spend so much time as business owners thinking about systems, productivity, profitability, and patient or customer experience.

But underneath all of those things are people.

People who want to feel valued. People who make mistakes. People who need guidance, encouragement, and occasionally a difficult conversation to help them become better.

The goal isn’t to eliminate uncomfortable conversations. It’s to become more comfortable having them, and to create relationships strong enough to withstand them.

Have the conversation sooner. Lead with curiosity. Be clear about expectations. And make far more deposits than withdrawals into the emotional bank accounts of the people around you.

Because sometimes the conversation you’re most hesitant to have is the very one that will make the biggest difference.