The conversation you've been avoiding may be the one that strengthens trust, improves performance, and moves your team forward. Difficult conversations are part of leadership—but avoiding them only creates confusion and erodes trust. Learn practical ways to approach challenging conversations with clarity, curiosity, and confidence.
As leaders, there are conversations we look forward to—celebrating success, recognizing achievements, and welcoming new team members.
Then there are the conversations many leaders delay...
Providing constructive feedback. Addressing conflict. Clarifying expectations. Discussing poor performance.
These difficult conversations can feel uncomfortable, and it's tempting to hope the issue will resolve itself.
The reality?
Avoiding a difficult conversation rarely makes the situation better. In fact, waiting often allows frustration, assumptions, and misunderstandings to grow—making the conversation even harder when it finally happens.
Leadership isn't about avoiding discomfort.
It's about creating clarity.
Share with a friend!
Why Leaders Avoid the Difficult Conversation
Most leaders don't avoid conversations because they don't care.
They avoid them because they do.
We worry about saying the wrong thing.
We don't want to damage a relationship.
We imagine the worst possible outcome before the conversation has even begun.
But when we delay meaningful conversations, we often create exactly what we're trying to avoid:
- More uncertainty
- More confusion
- More frustration
- Less trust
Leadership communication isn't about saying everything perfectly.
It's about saying what needs to be said with honesty, empathy, and respect.
When we delay because we don't want to upset someone, we're usually making things worse.
The conversation you're avoiding is often the one that creates the greatest opportunity for growth.
Clarity Is an Act of Kindness
One of my favorite leadership reminders is from Brene Brown:
"Clear is kind. Unclear is unkind."
People deserve to know where they stand.
Whether you're discussing expectations, employee performance, or a challenge within the team, clarity gives people the opportunity to improve, ask questions, and move forward.
When leaders avoid these conversations, employees are often left wondering:
- Am I meeting expectations?
- Have I done something wrong?
- Why hasn't anyone told me?
Clear communication builds trust.
Silence creates uncertainty.
If you've read Teri's article on The Right Way Isn't Always My Way, you'll recognize another important leadership principle: approaching conversations with curiosity instead of assuming our perspective is the only one.
"Clear is kind. Unclear is unkind."
Prepare Before You Speak
The best difficult conversations don't happen by accident.
They happen because leaders prepare.
Before you begin, ask yourself:
- What is the purpose of this conversation?
- What outcome am I hoping to achieve?
- How can I help the other person feel heard?
When your goal is curiosity instead of judgment, or clarity instead of criticism, the conversation changes.
Instead of trying to "win," you're working together to solve a problem.
A Simple Framework for Difficult Conversations
When preparing for a difficult conversation, remember CARE:
This simple framework helps difficult conversations become productive communication.
Listen More Than You Talk
One of the most valuable leadership communication skills is active listening.
Many difficult conversations become more productive when people genuinely feel heard.
Instead of assuming you already know someone's intentions, ask questions.
Instead of preparing your next response, listen carefully to theirs.
Understanding someone's perspective doesn't mean you have to agree with it.
It simply allows you to respond more thoughtfully.
If you'd like to strengthen this skill even further, you may also enjoy The Value Behind Perspective-Taking, where we explore why understanding another person's viewpoint leads to better communication and stronger relationships.
Share with a friend!
Stop Making Assumptions
Before difficult conversations even begin, many leaders create stories in their own minds. It's easy to predict how someone will react before the conversation even begins.
"They'll get defensive."
"They won't understand."
"They'll be upset."
Often, these assumptions prevent the conversation from happening at all.
The only way to know how someone feels is to ask.
Curiosity builds trust.
Assumptions build walls.
While researching Lead With Moxie, I had the privilege of interviewing more than 100 accomplished leaders.
Although their industries, titles, and businesses were different, one pattern kept emerging. The conversations they dreaded most were rarely about strategy. They were the conversations that required courage.
Giving honest feedback.
Addressing conflict.
Setting boundaries.
Clarifying expectations.
And almost every leader admitted that putting those conversations off never made them easier—it only made them bigger.
Courage Creates Better Leadership
Every meaningful conversation is an opportunity.
- An opportunity to build trust.
- An opportunity to strengthen communication.
- An opportunity to help someone grow. (And growing yourself intentionally.)
The conversation you've been avoiding may be the very conversation that creates the greatest positive change for your team.
Don't wait for the "perfect" moment.
Leadership isn't about avoiding difficult conversations.
It's about having them with courage, empathy, and clarity.
Watch this video "Say What Needs to Be Said."
Share with a friend!
Reflection
As you think about your own leadership, consider:
- Is there a difficult conversation you've been putting off?
- What's stopping you from having it?
- What assumptions might you be making?
- How could approaching the conversation with curiosity change the outcome?
- What small step could you take today?
Great leaders don't avoid difficult conversations.
They prepare for them. They approach them with empathy.
And they recognize that clarity is one of the greatest gifts they can give the people they lead.
In the spirit of moxie,
Ready to Move Forward on the Leadership Priorities You've Been Avoiding?
Sometimes the most important breakthrough isn't learning something new—it's finally taking action on what you already know needs to happen.
If you've been putting off an important leadership conversation or another strategic priority, a Breakthrough Day provides the dedicated time, structure, and guidance to help you move forward with confidence.
Learn more about Breakthrough Day , The Leadership Legacy Mastermind, or schedule a Breakthrough Call to discuss your leadership impact.
The Bottom Line: The conversation you've been avoiding may be the one your team needs most.
Great leaders don't wait for the perfect moment—they prepare thoughtfully, communicate with empathy, listen with curiosity, and create clarity. Difficult conversations aren't obstacles to leadership; they're opportunities to build trust, strengthen relationships, and help others succeed.