The Impromptu Speakers Newsletter

You're Handling Difficult Conversations The Wrong Way

​Read On My Website / Read time: 3 minutes

A student in The Impromptu Speakers Academy recently shared a common challenge:

This is a scenario many of us face. Having the right answer isn't enough. You need to get buy-in from people who might instinctively resist your message.

Here's a strategy to turning a confrontational conversation into a collaborative one. Let's dive in.

The Traditional Approach (And Why It Fails)

Most people make a critical mistake when trying to influence others. They lead with their conclusion.

"We need to delay this promotion because..."

While this feels efficient, it immediately puts the other person on the defensive. They stop processing your points and start preparing their counterarguments.

Here's why this happens: People need to relate to a problem before they're open to your solution.

Let me show you what I mean with a real example from my coaching call...

A Better Approach: Empathy-First

In the ISA, we reworked my student's approach into three key steps. Here's how:

1. Lead With a Story That Makes Them Feel the Risk

Instead of starting with, "We should delay this promotion," we worked on opening with a story.

"A few months ago, we had a similar situation in Department X. They promoted someone right before a major reorganization. They wasted 6 months and $250K because they promoted someone in a role that was no longer needed. I want to help us avoid a similar situation."

Notice what this does:

• Shows you care about their success
• Makes the risk feel real through a concrete example
• Positions you as a partner rather than an opponent
• Gives them context they can relate to personally

2. State Your Intent as a Collaboration

Most people go into these conversations with their minds already made up. But here's a powerful shift we discovered in our coaching session.

Instead of making it about the promotion decision, reframe it as a discussion about the department's future.

Here's how we reworked my student's approach:

Why this works:

• Demonstrates genuine openness to their perspective
• Aligns everyone around a bigger shared goal (department success)
• Turns a potential confrontation into a discovery conversation

The key insight here is subtle but powerful. Lead with genuine curiosity about them so that you can both come to a conclusion together.

You're not trying to force your view or "win" the conversation. You're exploring what makes the most sense given the broader context.

3. Master the Art of Active Listening

When they speak, your goal is to seek understanding. It's not to insert your agenda.

Active listening is the act of paraphrasing what someone else has said. This helps them feel heard, which makes them more willing to listen to you.

Before Speaking:

• Take 3 deliberate seconds to pause
• Process what they've said
• Consider the emotion behind their words

While Responding:

• Summarize their main points: "So what I'm hearing is..."
• Validate their perspective: "I can understand why you'd feel that way..."
• Ask open-ended questions about their concerns

This Week's Action Step

Before your next high-stakes conversation:

1. Write down a relevant story that illustrates your concern. You can use the What - So What - Now What framework to guide you.
2. Craft your intent statement using collaborative language
3. Prepare 2-3 open-ended questions to understand their perspective

Remember: People resist conclusions they haven't participated in creating. But they support what they help build.

Do you want to speak clearly when you're put on the spot, using frameworks like these? It's crucial to show you're confident and credible during important conversations at work. The Impromptu Speakers Academy is my 3-week live bootcamp to give you tons of practice and feedback speaking in high-stakes, impromptu situations. We're wrapping up our 30-person Cohort 1 next week, and Cohort 2 begins on February 17th. As a newsletter subscriber, you can save $100 at checkout if you enroll today. The promotion will expire in a few days. Limited space is available.

Talk soon,

Preston

​