3 Conversations Leaders Avoid (But Shouldn’t)

Let’s be honest, there are plenty of conversations that most of us would rather not have. They’re uncomfortable, often awkward, and sometimes emotional. So instead of diving in, we dance around them, hoping the issue will resolve itself or just go away. But it never does. All we’re doing by avoiding these conversations is creating confusion, putting performance at risk, and increasing the frustration across the rest of the team.

I’ve learned that our ability as leaders to have difficult yet productive conversations is foundational to creating sustainable growth. To simplify this even more, I’ve boiled down what we need to provide for our teams (and business) to thrive: clarity, consistency, and accountability. Let’s dive into three tough conversations leaders often avoid and some tips for how to have them.

Prefer listening? Watch this week’s Solo Session where I expand on the topic.

1. “You’re Not Meeting Expectations”

This one gets skipped a lot. Sometimes we assume we’ve already been clear. Sometimes we think the person should just know. And other times we don’t want to feel like we’re being “too hard” on someone. But skipping this conversation leads to a team that not only doesn’t clearly understand what’s expected but if it even matters to anyone.

When underperformance goes unaddressed, high performers start to feel resentful because they’re often picking up the slack. What’s worse is that we tend to be harder on our top performers because our expectations often become unreasonable while at the same time letting standards slip for the underperformers all because we’re avoiding this difficult conversation.

Here’s a few tips on creating clarity during this conversation:

• Focus on specific behaviors or missed outcomes.
• Define what success looks like in plain language and be specific.
• Offer support, but be clear about what needs to change and by when.
• Confirm understand by asking if you can clarify anything for them.

2. This Role May No Longer Be the Right Fit

This one is heavy because it feels personal. Sometimes the person has outgrown the role. Sometimes the role has outgrown them. We tend to dodge it because we feel loyal, hope they’ll “figure it out” on their own, or don’t want to deal with the emotions that come with having the conversation. But when a role and a person are no longer aligned, hanging on too long, drains energy, impacts results, and limits opportunities for everyone involved.

Here’s a few tips on creating clarity during this conversation:

• Focus on the needs of the role, not the worth of the person.
• Be clear about the gaps and why they matter now.
• Acknowledge their contributions and impact on the team.
• Depending on the situation, you may be able to offer an alternative role.

3. Here’s What’s Changing and Why

Change is hard. What makes it even harder for your team is feeling blindsided by it. Many leaders (including me in the early years) delay sharing news until everything is “final,” thinking it’s better to avoid the questions that we can’t answer yet. But the reality is that silence breeds uncertainty, and uncertainty often breeds resistance. While we’re waiting for that “perfect moment,” people are busy filling in the gaps with their own stories… which are rarely optimistic or supported by fact.

I’ve learned that it’s important to share what you know, and when you know it, even if you don’t have all of the answers. Being transparent about the process builds trust, reduces anxiety around uncertainty, and get’s everyone feeling involved in the change vs change happening to them.

Here’s a few tips on creating clarity during this conversation:

• Talk about the “Why” early and often.
• Share what you know but more importantly what you don’t.
• If possible, get more people involved.
• Keep communication flowing… no update is still an update.

Final Thoughts

The conversations that we avoid are usually the ones that matter most. They’re the difference between a team that’s guessing and a team that’s rowing in the same direction. As leaders, our job is to provide clarity, consistency, and accountability. So if you’ve been holding off on saying something, ask yourself:

• Have I been clear about what I expect?
• Am I being consistent in how I communicate and measure those expectations?
• Do I follow through when things fall short?

Remember, these conversations don’t have to be perfect but they do have to happen. Your team, and your business, will be better for it.

That’s it for today.

See you all again next week!

Dave