Having Difficult Conversations Without Destroying Relationships
We've all been there: You need to address a problem with someone, but you dread the conversation. So you avoid it. And avoid it. And avoid it.
Until the issue explodes or the relationship dies a slow death.
Les Giblin spent decades teaching people a better way—how to have difficult conversations that solve problems instead of creating new ones.
Why We Avoid Difficult Conversations
The reasons are obvious:
- Fear of conflict
- Worry about hurting feelings
- Concern about making things worse
- Uncertainty about how to start
- Past experiences that went badly
But here's what Giblin understood: Avoiding difficult conversations doesn't protect relationships—it damages them. Unaddressed issues fester. Resentment builds. Trust erodes.
The Preparation Phase
Most difficult conversations go wrong before they even start. Giblin taught that preparation is everything.
1. Clarify Your Goal
What outcome do you want? Be specific. "I want them to understand how I feel" isn't a goal. "I want us to agree on a new approach to project deadlines" is.
2. Check Your Mindset
Are you approaching this conversation to solve a problem or to prove you're right? If it's the latter, you're not ready yet.
3. Choose the Right Time and Place
Private, calm, and with enough time to talk properly. Never ambush someone or have these conversations when either of you is stressed or rushed.
4. Anticipate Their Perspective
Try to understand why they might see things differently. This doesn't mean you agree—just that you've considered their viewpoint.
The Opening Matters
How you start a difficult conversation often determines how it ends.
Bad Opening:
"We need to talk about your attitude problem."
Better Opening:
"I'd like to talk with you about how we're working together. Is now a good time?"
Notice the difference? The better opening:
- Uses "I" language
- Focuses on behavior, not character
- Asks for permission
- Signals collaboration, not confrontation
The Giblin Framework
Once you're in the conversation, follow this structure:
Step 1: State the Facts
Describe specific, observable behaviors—not your interpretations.
"You've missed the last three deadlines" (fact)
vs.
"You don't care about this project" (interpretation)
Step 2: Share the Impact
Explain how this affects you, the team, or the work.
"When deadlines are missed, it creates problems for the whole team and makes us look unreliable to clients."
Step 3: Listen Fully
This is where most people fail. After stating their case, they stop listening. Don't do this.
Ask: "What's your perspective on this?"
Then genuinely listen. Don't interrupt. Don't defend. Don't plan your rebuttal.
Step 4: Collaborate on Solutions
"What do you think we should do about this?"
Involving them in the solution increases buy-in and often leads to better ideas than you'd come up with alone.
Step 5: Agree on Next Steps
Be specific about who will do what by when. Vague agreements lead to repeated problems.
The Emotional Dimension
Difficult conversations often trigger strong emotions—in both people.
Giblin's advice:
- Acknowledge emotions (yours and theirs) without letting them drive the conversation
- Take breaks if things get too heated
- Stay curious instead of defensive
- Separate the person from the problem
If someone gets emotional, don't dismiss it: "I can see this is upsetting. Should we take a few minutes?"
Common Mistakes to Avoid
The Kitchen Sink
Bringing up every grievance from the past five years. Stick to the current issue.
The Ambush
Surprising someone with a difficult conversation when they're unprepared.
The Monologue
Talking at someone instead of with them.
The Assumption
Assuming you know their motives or intentions.
The Ultimatum
Threatening consequences before exploring solutions.
When They Get Defensive
Defensiveness is normal. When it happens:
- Slow down - Your pace might be too aggressive
- Acknowledge their perspective - "I hear what you're saying"
- Reframe - "I'm not trying to attack you. I want to solve this together"
- Take responsibility - "I may not be explaining this well"
The Follow-Up
The conversation doesn't end when you stop talking.
- Check in a few days later
- Acknowledge improvements when you see them
- Adjust the plan if it's not working
- Rebuild trust through consistent actions
The Relationship Test
Giblin had a simple test for whether you handled a difficult conversation well:
Is the relationship stronger or weaker afterward?
If it's weaker, something went wrong—even if you "won" the argument.
If it's stronger, you did it right. You addressed a real issue while demonstrating respect and care.
Practice Makes Progress
Start with lower-stakes difficult conversations. Build your skills and confidence before tackling the really hard ones.
And remember Giblin's core insight: The goal isn't to avoid difficult conversations. The goal is to become someone who can have them skillfully.
That's a skill that will serve you for life.
Your Next Step
Is there a difficult conversation you've been avoiding? Use the Giblin framework to prepare for it. Then schedule it.
The temporary discomfort of a difficult conversation is always better than the permanent damage of avoidance.