How to Be Ready for That Difficult Conversation
MONTHLY NEWSLETTER | April 2025
Last month, we explored why difficult conversations matter and how to recognize when you need to have one. Thank you for the thoughtful responses many of you shared about conversations you've been avoiding and the insights you gained from reflecting on them.
As promised, this month we'll focus on effective preparation for difficult conversations. As one of my clients recently noted, "I realized that 80% of my difficult conversation success comes from what I do before I even open my mouth."
Let's dive into the essential steps for preparing yourself to engage in these important conversations with confidence and purpose.
WHY PREPARATION MATTERS
Preparation isn't about scripting every word or anticipating every possible response. Rather, it's about:
Creating clarity: Understanding what you really want to achieve
Building emotional readiness: Managing your own reactions and triggers
Developing flexibility: Being prepared to adapt as the conversation unfolds
Increasing confidence: Knowing you've thought through your approach
Good preparation transforms a potentially reactive exchange into a thoughtful dialogue.
STEP 1: CLARIFY YOUR INTENTION
Before approaching any difficult conversation, ask yourself:
What outcome would truly serve all parties involved? Look beyond immediate relief to long-term relationship benefits.
Is your goal to be right or to be effective? These are often mutually exclusive in difficult conversations.
What's the minimum you need from this conversation? Having a clear "must have" helps focus your approach.
What's your higher purpose for this conversation? Connect to your values and vision as a leader.
One client prepared for a difficult performance conversation by shifting her intention from "making sure he knows he's underperforming" to "helping him align his strengths with our team needs." This completely changed her approach and resulted in a productive conversation rather than a defensive one.
STEP 2: EXAMINE YOUR CONTRIBUTION
Every situation has multiple perspectives. Before the conversation:
Reflect on how you might have contributed to the situation. Even if it's minimal, acknowledging your part reduces defensiveness.
Question your assumptions. What facts do you actually have vs. interpretations you've made?
Consider the other person's constraints and pressures. What might be influencing their behavior that you don't see?
Identify any "stories" you're telling yourself. Are you making meaning that may not be accurate?
A director I worked with realized she had been interpreting a colleague's brief emails as rudeness, when in reality, he was managing a family health crisis and trying to maintain minimal communication during a difficult time. This realization completely shifted her approach from confrontation to support.
STEP 3: MANAGE YOUR EMOTIONAL STATE
Your emotional state will significantly impact the conversation. Before engaging:
Identify your emotional triggers. What specific words, tones, or behaviors might cause you to react strongly?
Develop specific strategies for managing reactions. This might include taking a breath, having a grounding phrase, or simply naming your emotion internally.
Practice emotional distancing. Separate the person from the issue and your identity from your position.
Consider timing. Choose a time when you're emotionally balanced and not rushed.
One executive I coach uses a specific preparation ritual before difficult conversations: 10 minutes of focused breathing, followed by writing down three things she appreciates about the other person, and finally, visualizing a successful outcome.
STEP 4: PLAN YOUR APPROACH
While remaining flexible, it helps to have a structured approach:
Opening statement: How will you begin in a way that sets a constructive tone?
Key points: What are the 2-3 most important points you need to convey?
Questions: What genuine questions will help you understand their perspective?
Potential reactions: How might they respond, and how will you handle each possibility?
Desired agreements: What specific outcomes or next steps are you hoping for?
A CEO I work with prepares for difficult conversations by writing down her opening statement verbatim, then practicing it until it feels natural. She finds that if she can start strong, the rest of the conversation flows more easily.
STEP 5: CREATE THE RIGHT ENVIRONMENT
The physical and temporal context matters more than many leaders realize:
Choose a neutral location when possible
Ensure privacy and freedom from interruptions
Consider seating arrangements that promote collaboration rather than confrontation
Allow sufficient time without creating pressure from looming deadlines
Minimize distractions including phones, computers, and notifications
One leader transformed her difficult conversations by moving them from her office to a casual seating area with comfortable chairs and no desk between them. This simple change significantly improved the quality of these exchanges.
SUCCESS STORY: THE POWER OF PREPARATION
One of my clients needed to have a difficult conversation with her CEO about realistic timelines for a major product launch. Previous attempts had led to tension and misalignment.
Before her next conversation, Sarah:
Clarified that her intention was to ensure company success, not defend her department
Examined how her communication style (technical and detailed) might be contributing to the disconnect
Prepared specific, concise examples that would resonate with the CEO's business focus
Chose a time when both would be fresh (morning rather than end-of-day)
Selected a neutral meeting room rather than either of their offices
The result? "For the first time, we had a real dialogue instead of a debate," Sarah reported. "We established a realistic timeline that everyone could commit to, and I felt heard rather than dismissed."
THIS MONTH'S REFLECTION QUESTIONS
Think of a difficult conversation you need to have. What is your true intention for this conversation?
How might you have contributed to the current situation, even in a small way?
What emotional triggers should you prepare to manage during this conversation?
What environment would best support the kind of exchange you hope to have?
Remember, the quality of your preparation often determines the quality of your conversation. By taking time to clarify your intention, examine your contribution, manage your emotions, plan your approach, and create the right environment, you set the stage for meaningful dialogue rather than difficult debate.
As always, I'm here to support your journey toward purposeful leadership.
Kindly,
COMING NEXT MONTH
In our May newsletter, we'll explore "Holding the Conversation with Proper Wrap-up," focusing on communication techniques during the conversation and how to ensure clear outcomes and follow-through.
"The conversation is not about the relationship; the conversation is the relationship."
—Susan Scott
