How to Have the Conversations You’re Avoiding

A client reached out to me this week with a challenge many founders face: dealing with a highly valued but difficult team member. This particular individual, let’s call him Aaron, is an exceptionally talented designer with years of institutional knowledge. He’s been with the company since day one and has contributed significantly to its success.

But Aaron has a habit of reacting prematurely, jumping to conclusions without all the information, and escalating situations that lead to unnecessary drama. His behavior is draining my client’s time and energy, not to mention the emotional bandwidth of the team.

Sound familiar? Do you have someone on your team—or in your life—who’s brilliant at what they do but comes with a piece of “baggage” you can’t afford?

Here’s a step-by-step framework for addressing the conversations you may be avoiding:

1. Stop Stepping Over Problems

When something or someone isn’t working, don’t sweep it under the rug. Ignoring it might seem easier today, but unresolved issues always grow. They disrupt productivity, strain relationships, and signal to the rest of your team that subpar behavior is tolerable.

The longer you let it fester, the harder it becomes to address. Deal with it early. The best time to address this was yesterday; the next best time is now.

That said, consider timing. Just before this person walks into a big sales pitch may be a bad moment. Tomorrow, or even next week, might make more sense.

2. Make the Business Case Front and Center

Yes, my client finds Aaron’s behavior annoying and upsetting. However, that’s not the real issue. When you get ready to have the conversation, make sure you’re clear on the business case, not just your personal feelings.

Aaron’s behavior wasn’t just “annoying” or “judgmental”—it was wasting valuable time. And no one, not even Aaron, wants to waste time.

Reframe the issue around a shared priority. For example:

• “When someone reacts without complete information, everyone involved wastes time chasing the wrong problems or having to smooth it over.”
• “Your insights are valuable, so I always take them seriously. When they’re based on assumptions or insufficient information, and I have to address them and smooth over the ripples, they cause disruption that neither one of us can afford.”

When the issue connects to the business case, like wasted time or diminished team morale, it becomes easier for everyone to see the issue as their issue.

3. Acknowledge Their Value

Before diving into the issue, consider acknowledging their importance. This creates the right context for why you’re bringing this to them.

In Aaron’s case, my client could say something like: “You’ve been with us since the beginning, and your design work has been instrumental in shaping our brand. You’re an essential part of this team, so I listen carefully to everything you say, and what you say carries weight.”

By starting with appreciation, you set the tone for a constructive conversation. It shows that you value them, and that’s why you are personally bringing this to them.

4. State the Issue Clearly and Specifically

Lay out the problem as you see it, backing it up with specific examples. Be honest, but remain empathetic.

For instance: “I’ve noticed that when you react without all the information, it creates confusion and leads to unnecessary follow-ups. This not only affects the team but also takes time I can’t afford to spend. For example, yesterday when you…”

Avoid vague criticisms like “You’re too judgmental” or “You cause drama.” Instead, focus on behaviors and their impacts, ones for which you can give specific examples.

5. Make Your Problem Their Problem

Most people love to solve problems. Additionally, people are more likely to help when they feel ownership of the solution. Turn your issue into something they can help solve.

Try this approach: “I need your help. I need you to keep contributing your insights, and I can’t afford to keep having situations where you react and/or make criticisms based on incomplete information. How do we solve this?”

This collaborative tone shifts the dynamic from blame to partnership. It also encourages them to take responsibility for their actions.

6. Hold Space for Their Reaction

It’s natural for someone to react defensively when confronted. Acknowledge their feelings without losing sight of the bigger picture.

You can say: “I understand this feedback might feel uncomfortable. I want to make sure we’re on the same page because I value what you bring to the team.”

However, watch carefully to see if they’re genuinely open to addressing the issue. If they’re focused solely on defending themselves without considering your perspective, it may point to a deeper problem.

7. Focus on the Big Picture: Fulfilling Your Vision

Every team member’s ultimate responsibility is to align with and fulfill the company’s vision and the CEO’s intentions.

I’m not saying CEOs should act like omnipotent dictators. People can disagree, debate, and offer suggestions. However, at the end of the day, once a call gets made, everyone’s job is to empower that decision.

If someone consistently acts in ways that undermine the company vision or the CEO’s intention, no matter how talented they are, it’s a deal-breaker.

As a leader, make that point clear: “We all have the same goal here—to fulfill the company’s mission and grow together. If something isn’t working, it’s my job to address it, and I need everyone on the team to work toward solutions.”

If they can’t see the issue as a problem, that’s the real issue. They’re not working to fulfill your intention—they’re doing their own thing. That won’t work.

Final Thoughts: Clear Is Kind

At the end of the day, professionals appreciate clarity. They want to know where they stand and how they can improve. Avoiding tough conversations isn’t kindness—it’s a disservice to your team, your mission, and ultimately, the individual.

In the words of Brené Brown, “Clear is kind.”

When you approach these conversations with appreciation, specificity, and collaboration, you empower your team to grow. And if someone can’t align with your vision despite your best efforts, that’s a sign you need to make a hard call.

In either case, you won’t even know where you stand until you take a stand. So, take it.

You’ve got this.

P.S. If this resonated with you, share it with other founders, CEOs, leaders or entrepreneurs who you think would benefit. Let's support each other in having clear and kind conversations in the workplace!