The CEO Headhunter's Guide to Difficult Conversations

I’ve always been a data person. I love data.

I built airtight PowerPoint decks, packed with facts. I thought if I just presented the right data, I could persuade anyone.

Then I entered the worlds of politics and business—and learned the hard way that decisions aren’t made by logic alone.

More often than not, decisions are made by emotion—and then justified with data.

And the most powerful emotional tool? Tone.

The High-Stakes Art of Tone in CEO Headhunting

Nowhere was this clearer than in executive search.

As a Fortune 500 CEO headhunter, I had a problem.

For every search, we evaluated over 100 top candidates—each one a sitting CEO or a rising star, powerful, successful, and unaccustomed to hearing “no.”

And yet, we had to reject every single one—except one.

Here’s the catch: Every candidate was also a client or potential client. Mishandle their rejection, and we weren’t just burning a bridge—we were risking millions of dollars in future business.

How do you tell someone at the top of their field that they weren’t chosen—without damaging the relationship?

The answer: Tone.

The Four-Step Formula for Giving Bad News Strategically

When rejecting a CEO, we couldn’t just say, “Sorry, you didn’t get the job.” Instead, we followed a precise four-step formula, in which the NO is folded into a bunch of YES statements.

1️⃣ YES! Start with affirmation.

2️⃣ YES! State the pillar—a value we must uphold.

3️⃣ NO. Deliver the bad news as the inevitable result of the pillar.

4️⃣ YES? End with a new proposal.

This isn’t about flattery. It’s about respect.

📞 Real Rejection Call Example

"Hi John! It’s Joy. I’m calling to let you know that the Board of ABC Company has selected Jane Doe as its next CEO.

1️⃣ You are great: The Board was deeply impressed with you, as were we. You have an outstanding track record.

2️⃣ The pillar (strong value we must uphold): The Board has made overseas expansion its top priority.

3️⃣ The inevitable result (bad news): Therefore, they had to go with Jane, based on her extensive global markets background.

4️⃣ The new proposal: But John, we’d love to stay in touch for future opportunities. That OK with you?"

Why This Works: Human Psychology

Our interactions with others are not just about information—they’re about identity.

If they walk away feeling cast aside, they’ll forever resent you. Only if they walk away feeling valued will they work with you again.

The key to this is Step 2: The pillar—a value we must uphold.

Here’s the strategy: Identify the clear contrast between the newly announced CEO and John, and point to that as the deciding factor.

This gives John an explanation to preserve his dignity he can use with himself—and with his close confidants.

Once you establish that pillar, the ‘therefore’ in Step 3 becomes inescapable:

"Therefore, we had to go with another candidate."

Then—before the sting of rejection sets in—you immediately pivot:

"Let’s find another way to work together."

This formula works because it turns loss into opportunity and rejection into relationship-building.

How to Use This in Business and Life

This structure isn’t just for rejecting CEOs—it’s for any difficult conversation.

1️⃣ Giving feedback to an employee

📞 "Hi Sarah! We really value your work. Your execution is exceptional, and you consistently deliver results.

2️⃣ The pillar: For this leadership role, we need someone who not only executes but also drives strategy and proactively shapes direction.

3️⃣ The bad news: Therefore, we aren’t able to move forward with your promotion at this time.

4️⃣ The new proposal: Let’s work together on developing this skill so you’re fully ready next time."

2️⃣ Telling a client you can’t meet their request

📞 "Hi Mark! You are one of our most valued clients, and we truly appreciate working with you.

2️⃣ The pillar: We’re committed to delivering work at the highest quality, and to pull together the necessary experts, we require a lead time of at least one week.

3️⃣ The bad news: Therefore, we can’t meet your proposed deadline.

4️⃣ The new proposal: But let’s figure out a schedule that does work—perhaps we can plan ahead for your next project?"

3️⃣ Even breaking up with someone

📞 "Hey Alex, you’re an incredible person, and I have so much respect for you.

2️⃣ The pillar: A great relationship works when both people want the same future, and I’ve come to realize we’re not on the same path.

3️⃣ The bad news: Therefore, I don’t think it’s fair to keep moving forward.

4️⃣ The new proposal: I really appreciate our time together, and I hope we can part on good terms. No matter what, I’ll always be rooting for you.

Final Thought: Your Tone Shapes Your Outcomes

Saying no is inevitable. But how you say no determines everything.

• Handled poorly, rejection burns bridges.

• Handled well, it builds trust.

The best leaders and relationship builders all understand this:

Tone can get you what you want—or destroy it.

People may forget what you say.

But they’ll never forget how you made them feel.

Decode Corporate America’s Unwritten Rules—Free 5-Day Email Course

Mastering tone is just one piece of the puzzle. Corporate America runs on unwritten rules—and if you don’t know them, you risk being overlooked, no matter how smart or hardworking you are.

Decode how decisions really get made, who gets promoted, and why.

📩 Sign up for my free 5-day email course: thejoychen.com/unwrittenrules

Each day, you’ll get one actionable insight to help you navigate the workplace with more confidence, influence, and success.

Because once you understand the game, you can play it—and win it—on your terms.