Most leaders avoid tough conversations, not because they’re weak, but because they were never trained to have them. Here’s how to handle them with clarity, courage, and AI as your secret prep partner.
“Clear is kind. Unclear is unkind.” ~ Brené Brown
Difficult conversations are part of leadership. Yet, research shows that 67% of managers admit they avoid them with their employees. And 70% of employees say they avoid tough talks with their managers, peers, and direct reports.
We tell ourselves it’s “not the right time,” but really, we’re hoping the problem automagically disappears. But, it never does. It festers. It spreads. It becomes culture.
Why Leaders Avoid the Tough Talks
Here’s why most difficult conversations never happen:
- We don’t want to hurt someone’s feelings
- Our survival brain (fight or flight) overrides our logical one.
- We’ve never been trained to handle them well.
- We’ve been burned before and fear a repeat.
- We hope issues will just work themselves out over time.
In other words: we choose being liked over being clear or being productive.
The High Cost of Avoidance
Avoiding tough conversations has a price tag - and it’s not small.
According to research from VitalSmarts and Bravely, here’s what happens when the issue isn’t dealt with:
- 78% complain to others
- 66% do the extra work
- 53% simply ignore toxic behavior
All told, US employees waste 3 hours per week avoiding conflict, costing companies $359 billion in lost productivity each year.
Why spend 3 hours per week to avoid a 10-minute conversation?
The Hit to Your Leadership Credibility
Everyone sees the problem and silently wonders if you are going to deal with it or not.
When you don’t, here’s what happens:
- Respect erodes. Your team questions whether you’re willing to hold people accountable.
- Trust declines. Top performers lose faith that you’ll protect the culture they’re working hard to uphold.
- Morale drops. People stop bringing you problems, because they assume you won’t address them.
- Toxicity grows. Small issues become big problems, and silence becomes the norm.
Here’s something to consider:
“The culture of any organization is shaped by the worst behavior the leader is willing to tolerate.” ~ Steve Gruenert & Todd Whitaker
What Great Leaders Do Instead
As Disney executive Lee Cockerell said:
“A leader’s job is to do what has to be done, when it has to be done, in the way it should be done — whether you like it or not and whether they like it or not.”
The best leaders face hard decisions head on, with preparation, compassion, and clarity.
Here’s how you can do the same.
A Practical Playbook for Difficult Conversations
Here are some ways to do that:
When preparing for a tough conversation
- Confirm the issue. Don’t let emotion drive your judgment.
- Don’t procrastinate. The best time is almost always now.
- Meet privately. Be calm, clear, and collected.
- Assume good intent. Expect a positive outcome.
- Approach with curiosity, not condemnation.
- Practice your opening lines.
Try this phrasing:
“I love how enthusiastic you are about this project, but I hate that you’re often late to meetings. It sends the wrong message to others. What would help so you can be on time?”
It’s direct, empathetic, and solutions-focused.
How AI Can Help You Prepare
I’ve been using AI heavily for the past three years and teach workshops on how AI tools help leaders. Preparing for difficult conversations and rehearsing in advance is a great use.
AI can be your private rehearsal partner - one with no judgment or politics. When you use AI to plan your conversation, it helps you:
- Clarify your message
- Anticipate reactions
- Practice tone and phrasing
Think about it like flight simulation for leadership - you get to crash and learn before the real flight!
Two AI Prompts to Try Before Your Next Conversation
Prompt #1 – Plan Your Approach
“Please act as a communications coach to help me prepare for a difficult conversation with a team member who continues to talk over others in meetings. This is the first time I’ve brought it up. They can be outspoken. I want to be empathetic but firm. Please give me talking points for three different outcomes: receptive, shuts down, defensive.”
Prompt #2 – Role-Play the Reaction
“Using the same scenario, please role play a version where the team member becomes defensive. Write three possible openings I can use to start the conversation.”
Run these prompts through your AI tool before the conversation.
You’ll walk in calmer, clearer, and more confident.
Try This Right Now
Think of one conversation you’ve been avoiding.
Use the two AI prompts above to help you:
- Prepare your approach
- Refine your tone
- Practice what you’ll say
Then have the conversation. You’ll build more trust in 10 minutes of honesty than in six months of avoidance.
Want a Deeper Dive on How to Use AI for Difficult Conversations?
I’m leading a free one-hour Zoom call at 12:00noon CT on November 19th. Go to here to register. We’ll go deeper into AI prompts for difficult conversations. Participants will have opportunities to practice their prompting skills and role-play a challenging conversation.
Lead with Confidence
No one looks forward to a difficult conversation but with the right frameworks, guidance, and AI prompts, you can lead difficult conversations respectfully and professionally where the other person feels heard, not attacked.
That’s not an impossible dream. That’s leadership done right. I can help you get there.
You can order Practical Leadership today wherever books are sold. And if it resonates with you, please share it with a colleague who could use a little clarity, confidence, and courage in their leadership.
Because everyone deserves to work for a great leader.
Warm regards,
Janet Ply, PhD
Author, Practical Leadership
www.janetply.com
Schedule a free problem-solving call with me at janetply.me.
Connect with me on LinkedIn