Say the Hard Thing

I recently began coaching a tech leader who is clearly exhausted. 

He works for a household name company and last quarter was rough. His team is burned out and running on fumes, thanks to the unfortunate combination of restructuring and overwork. 

But they missed some deadlines, and he needed to have some tough conversations. He was dreading them, and even acknowledged that he is “direct feedback averse.” 

He’s not alone. I see this in coaching all the time. 

And it’s no wonder. One report found that 70 percent of employees avoid difficult conversations with their boss, colleagues, and direct reports. Seven out of 10! 🫣

Chances are, you’re in the majority. Even if that’s the case, you can still understand how a lack of communication can be bad for business and relationships. 

Think about it this way: if a child’s bad behavior goes unaddressed, how will they learn what’s acceptable? If you never name that stealing is wrong, how would they know? The same is true at work. If someone on your team isn’t meeting clearly communicated expectations*, what would prompt them to change if you don’t hold them accountable?

I recently led a related workshop at an event for women in business hosted by the Georgetown-Scott County Chamber of Commerce. Participants shared several reasons why you might dance around what you’re really trying to say: You want to be liked. You don’t want to be the “bad guy.” You’re not sure how the other person will respond — or how to handle it if it goes sideways.

So you wait. You soften. You tell yourself you’ll get to it later, when things calm down.

But later has a cost.

What could have been a clear, contained conversation often becomes a pattern. Then, frustration builds, trust erodes, and the issue rarely resolves itself.

Here’s the deal. You don’t have to be a jerk when you have a difficult conversation, and it doesn’t have to turn into a full-blown confrontation. But you owe it to your organization, yourself and to the other person involved to channel Brené Brown when she says, “Clear is kind. Unclear is unkind.”

That’s exactly what we do in my new signature workshop, “Say the Hard Thing.” We work through the CLEAR communication framework, which blends clarity and curiosity to ensure alignment and preserve the relationship. And we practice with real-world scenarios so the next time you’re up at bat, you don’t swing and miss. (Or worse, deliver a compliment sandwich.) 

As for my client, he left our session committed to and comfortable with his next steps – having challenging conversations with intention, compassion, accountability, and timeliness.

After all, most leaders don’t regret the difficult conversations they had. They regret the ones they didn’t.

Real Talk 

At a PRSA Thoroughbred Chapter event, a man with a storied 30-year career shared he’d been laid off. As a comms leader-turned-executive coach, I’ve seen how layoffs can shake confidence and clarity. The good news? You can’t control what happened, but you can control what’s next. Last week, I wrote about 10 strategies to bounce back from a layoff and move forward with intention.

Brain Food

Recently, at the Women in Business Summit hosted by the Women’s Business Center of Kentucky, I spoke to leaders about how perfectionism often disguises itself as high standards, but keeps us overthinking, playing it safe, and feeling stuck. What does that look like in real life? You can catch a glimpse of it on WLEX-TV, then explore the bigger idea in my TEDx talk: "The Perfectionism Trap: The Hidden Cost of Doing It Right."

In the Spotlight

Leadership Workshop Facilitation

When was the last time your team prioritized the space to step back and think about how you show up? In my recent work with New Vista, we brought together about 100 colleagues to focus on the intersection of leadership and communication, reinforcing how to best represent the org with clarity, consistency, and confidence. What stood out most was their intentionality. What is your team working through? I’d love to help.

*Re: "Clearly Communicated Expectations"

If the need to say the hard thing resonates with you, pause for a moment before you do it. Were your expectations truly clear? Written down, discussed, understood, and agreed upon? If so, proceed with confidence.

But if there’s even a chance you assumed, implied, or hoped they’d “figure it out,” that’s not a failure — it’s an opportunity. An opportunity to elevate how you communicate, how you lead, and how you set others up to succeed. And, if you need a wing person, remember: I’m always in your corner. 💪