Many readers of this blog tell me their favorite posts are the ones that feel very real, very practical, and that “hit home.”

I think this one will do exactly that.

Before getting into a very interesting story, let me start with a few questions that leaders ask me all the time:

• “I need my team to make better business decisions—what can I do?”
• “I manage a team with very different personalities—how do I get everyone working together effectively?”
• “How do you rebuild a strong culture after a difficult situation on a team?”

These are not theoretical leadership questions. They are real-world challenges that leaders face every day. And interestingly, they all came together during a recent conversation I had with a sales leader while conducting subject matter expert interviews for a new business acumen simulation we are building.

There was an old saying in Sales: The moment you win a new customer is the moment you start losing that customer.

The job of the account team was simple, deliver great products and services, deepen trust, and retain the relationship for 5–10 years… at least until your champion got promoted.

That world is gone.

In today’s volatile business environment, turnover is constant. Restructuring. Layoffs. M&A. PE ownership. “Strategic realignment.”

In many industries, 70–90% of your direct customer contacts may change within 2–3 years.

As part of a Commercial Leadership program I’m building for a pharmaceutical client, a sales manager told me:

“You spend years building trust, winning the business, growing the account. Then one day, you find out your customer was escorted out of the building. And now every competitor is flooding the zone, discounting, and trying to reset the narrative with their ‘latest and greatest’ product.”

That’s not bad luck. That’s the new normal.

So the question isn’t if your direct customer will leave.

The question is:

Are you proactively preparing for it?

Here are five ways to do exactly that.

Some of my best blogs come directly from interviews with subject-matter experts while we are designing business acumen simulations.

Recently, I interviewed a senior line manager at a high-tech company. He shared a story that was equally hilarious and horrifying.

They were launching a major AI-enabled services initiative to support their core hardware platform. Big opportunity. Big revenue potential. Big margin expansion if executed well.

The marketing team was already a little chaotic. Eight people. Project managers. Event planners. Administrators. Everyone busy. No one is quite sure who owned what.

And then…

Corporate procurement stepped in.

“We were told we had to route every vendor, every venue contract, every service agreement through corporate procurement,” he said. “It turned managed chaos into mismanaged chaos.”

Procurement didn’t understand the product. They didn’t understand the launch strategy. They didn’t understand the revenue objectives. They didn’t understand the margin profile of the new services.

But they absolutely understood how to slow things down.

The tipping point?

Today’s blog takes me back to one of my favorite sources of insight: real executives wrestling with very real leadership dilemmas, the kind that eventually become powerful leadership simulations.

This person was crushing his numbers. He was innovative, decisive, and charismatic.

He forged loyal followership. He moved fast. He broke things. He got results.

He was, in the executive’s words, a “bull in a China shop who went to President’s Club every year for great performance.”

And here was the problem:

“In every role he’s had, he’s essentially planned for and executed a coup. But he never sees himself as leading the coup. He always feels like he’s just adjacent to it. Like the organization is dysfunctional and he’s simply stepping in to fix it.”

That phrase stuck with me.

Coup-adjacent leadership.

Not openly rebellious. Not formally insubordinate. But constantly destabilizing the system in the name of results.

The executive’s question to me was simple and profound:

“How do we develop leaders who can recognize this pattern, and neutralize it, without killing innovation?”

That’s a serious leadership challenge.

Here are five lessons in business acumen and leadership created from understanding the dynamics of the “coup-adjacent” environment.

Picture a world without the internet. And no voicemail. And no email.

Business hours were 8:30 a.m. to 5:30 p.m., excluding the commute, which could easily stretch to an hour each way, and everyone was expected to be in the office five days a week.

Companies functioned through receptionists who took messages on pink message slips. If you were in sales or on the road, you called in a few times a day to retrieve them. Gentlemen wore suits and ties. Women wore professional attire. That was the norm.

This was the late 1980s into the early 1990s.

Then, around 1992, Dockers launched a campaign encouraging professionals to dress “down” on Fridays. Levi Strauss & Co. followed by mailing a brochure titled A Guide to Casual Businesswear to 25,000 HR managers across corporate America.

And the debate was on. Some leaders argued it was unprofessional and would start a slippery slope. Others believed it would create a more relaxed, collegial workplace.

At the time, it felt like a big cultural moment. But here’s the thing:

It was never really about the pants.