How to Challenge People in Power (Without Making Enemies)

The most dangerous word in an executive meeting is 'no.' My boss was about to say it—to the CTO of Fortune 1.

The new CTO of Walmart leaned back in his chair, scanning the square room.

His request had been clear: move an entire Walmart store fully to the cloud.

No on-prem. No hybrid. All in.

He gave us two weeks to come back with an answer.

And now, he was waiting.

Around the room, SVPs and VPs sat frozen, their words measured like chess moves.

On the conference call, static buzzed over muted lines.

This wasn’t a debate. This wasn’t just another tech project. This was a directive—from the top of Fortune 1.

And the man sitting across from him, MJ, my boss, the VP of Engineering, was the one delivering the verdict. No.

The CTO wasn’t just any executive.

I had worked with him at Microsoft a year earlier. I knew how he operated.

He didn’t just lead with authority—he dismantled weak arguments like a surgeon. Most people who told him “no” found themselves agreeing with him 10 minutes later.

MJ knew that too.

So as I watched him sit there—calm, collected, his thumb running over the edge of his wedding band—I wasn’t worried about him getting steamrolled.

I was just curious to see how he was going to win.

Because MJ wasn’t like the other execs in the room.

Others talked in corporate lingo. MJ spoke in straight shots.

Others let emotion cloud their decisions. MJ was impossible to rattle.

Others fought to be heard. MJ made people listen.

And when he disagreed, he didn’t argue.

He led.

Step 1: Don’t Start With “No”

The CTO finished making his case. Then, he looked at MJ.

MJ let the silence stretch—just a beat longer than expected.

Then, he nodded, leaned forward, and spoke.

"I see what we’re trying to do here."

No resistance. No pushback. Just alignment.

The CTO waited. The room waited.

"It makes sense," MJ continued. "We want consistency, efficiency, and a scalable model across stores."

At that moment, MJ wasn’t an obstacle. He was a partner.

The CTO nodded. “So you agree with the direction?”

MJ held his gaze. "I agree with the outcome."

Then—he moved the goalposts.

"Now let’s talk about the path."

Because executives don’t look for permission. They look for solutions.

Step 2: Expose the Tradeoffs, Not the Flaws

Bad ideas collapse under their own weight—if you let them.

MJ didn’t say, "This is unrealistic."
MJ didn’t say, "We don’t have the time."
MJ didn’t say, "That’s not how our infrastructure works."

He said:

"To move an entire store fully to the cloud, we’d need to replace every existing in-store system."

"That includes finance, inventory tracking, security, and fulfillment."

"None of them are fully cloud-native today."

The CTO leaned forward. “How long would that take?”

MJ didn’t flinch.

"If we go all in? 18 months of foundational work before we even start migration."

A few people in the room shifted uncomfortably.

MJ let that sink in. Then, he moved in with the pivot.

"Or, we take a hybrid approach. We move fulfillment and inventory first—where cloud gives us the biggest advantage. Then we expand."

The CTO tapped his pen against the table. He didn’t interrupt.

He was thinking.

Because executives don’t respond to resistance.

They respond to tradeoffs.

Show them the cost. Let them make the call.

Step 3: Bring a Better Alternative

Shooting down an idea is easy.

What makes you valuable? Offering a smarter path forward.

MJ glanced at the screen, where dozens of global leaders were watching. Then back at the CTO.

"Instead of flipping a switch and hoping it works, let’s test this on a smaller scale."

"We migrate fulfillment first. That’s where cloud gives us the biggest advantage—predictive demand, real-time inventory."

"If that works, we expand to other systems."

"That keeps the store running, minimizes risk, and gets us real results faster."

No emotion. No resistance.

Just a better path forward.

A “no” without a solution is a complaint.
A “no” with a solution is leadership.

The CTO leaned back again. Quiet. Calculating.

The room held its breath.

Then—a small nod.

"I like it. Let’s start with fulfillment."

Silence.

Then—an exhale from the far side of the table.

A pen tapped. Someone scribbled a note. A few exchanged glances, recalibrating.

MJ leaned back, unfazed.

Like he already knew how this was going to end.

He had pushed back—without ever saying "no."

The meeting moved on, but something stuck with me.

People always talk about executive presence as if it’s about commanding the room.

MJ didn’t fight for control. He let the CTO take the wheel—then rewrote the map.

That’s what top leadership looks like.

Key Takeaways

🔹 Alignment beats resistance.

Don’t start with "this won’t work."
Start with "let’s make this work the right way."

🔹 Tradeoffs beat rejection.

Don’t say "this is impossible."
Show what’s required to make it happen—and let decision-makers decide.

🔹 Better solutions beat better arguments.

Don’t just say no.
Offer a smarter way forward.

MJ didn’t win because he was the loudest voice in the room.

He won because he understood how influence works:

Make people rethink their own decisions—without forcing them.

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