How To Lead A Tough
Conversation With Leadership

Ever had a solution that could really help your team—but leadership wasn’t on board?

You knew it would fix a core issue. But they didn’t see the problem. Or worse, they thought your idea was too bureaucratic, too soon, or too risky.

That’s exactly where Julia found herself.

She wanted to bring a performance management system to her startup. Employees were asking for it. She had tools ready. But her co-founders weren’t convinced it was necessary. They saw it as red tape.

So we walked through a 5-step approach to open that conversation with clarity, empathy, and credibility.

Unfortunately…

Most professionals rush these moments.

They start with their solution instead of their strategy. And the conversation falls flat.

Here’s why that happens:

• They assume their audience already agrees with the core problem
• They jump to the “ask” before building alignment
• They pitch tools before earning trust
• They don’t tailor their message to the listener’s mindset
• They skip the emotional buy-in

But there’s a better way.

Here’s how, step by step:

Step 1: Map the current state

Start with the basics:

• Who’s your audience?
• What’s the setting (presentation, 1:1, group)?
• What’s their attitude toward this topic… and toward you?

For Julia:

• Audience = 2 co-founders + 3 leads
• Setting = small group meeting
• Attitude = skeptical about performance management; see it as bureaucratic

We wrote this down before she said a single word.

Step 2: Define your future state

Next, decide what “success” looks like for this conversation.

We used a simple formula:

Julia’s version:

Notice she didn’t say “I want them to approve this tool.”

That might come later. But first, we need to win hearts and minds.

Step 3: Choose your credibility levers

How do you show this isn’t just your personal opinion?

We listed a few credibility moves:

• Reference performance gaps tied to revenue per employee (a shared metric they care about)
• Bring data from similarly-sized companies
• Share feedback from other team leads
• Point to Julia’s prior experience scaling startups

Step 4: Use relatability to lower resistance

Here’s where Julia made a shift.

Instead of defending her proposal, she decided to invite a conversation:

This one move turns a pitch into a dialogue.

Step 5: Align around a shared outcome

This is your anchor metric.

In Julia’s case, it was revenue per employee. We reframed her message not as "let’s launch performance reviews,” but as “let’s grow smarter.”

That’s a vision everyone can get behind.

If you’re preparing for a high-stakes conversation like this…

Take 5 minutes and map out:

• Audience
• Setting
• Attitude
• What you want them to Know / Feel / Do
• How you’ll be Credible and Relatable

You’ll walk in with more clarity—and leave with more alignment.

Quick favor before you go:

I'd love to learn more about what your needs are and how I can best help you.

👉 Mind taking 20 seconds to answer 5 short questions? Click HERE to take the survey.

– Preston

Preston Chin

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