The #1 Cause of Slow Business Death

Here's a real conversation I had recently with the owner of a $6 million IT business:

Business Owner: “I wanted to get my salesperson some coaching. I think it would really help him level up his skills. But when I talked to him about it, he didn’t think coaching would help.”

Me: “He didn’t think coaching would help? Like he knows everything there is to know about sales, he's executing flawlessly every single time?”

Business Owner: “No, not necessarily. I just don’t think he believes coaching is helpful.”

Me: “Fair enough. So results aren’t where you want them to be. You offered support, and the salesperson said no.”

Business Owner: “Yeah, that’s pretty much it.”

Me: “What are you going to do instead?”

Business Owner: “I’ll let him figure it out on his own. And if he doesn’t turn things around, I’ll let him go.”

Me: “Is replacing him a quick process? Won’t that set you back in sales compared to troubleshooting with him and improving his results?”

Business Owner: “Yeah, for sure. We’d have to recruit, train, and ramp up someone new.”

Me: “So not to be harsh, but there's a problem in your business. You believe there’s a solution to it, but the source of the problem doesn't like your solution, doesn’t have an alternative, and his proposed path could significantly set your business back. And that's the direction you're going?”

Business Owner: “Yeah, I guess when you put it that way…”

How Leaders Add Value

Now, let’s briefly set aside the issue of a salesperson feeling above coaching. As someone who's spent over 20 years in sales, even as a teacher, I'm always still a student. But that's a topic for another newsletter.

The real point of this conversation was the decision-making process. Here was a business owner knowingly putting the feelings of his salesperson ahead of his business interests.

Frankly, I see similar decision-making frequently in other businesses:

• Employees compensated far beyond their role's value because the owner fears tough conversations.

• Perpetual underperformers sticking around because everyone likes them.

• Processes left unchanged to avoid eliminating a role or offending the person who created them.

• Contracts and vendor relationships persisting because someone’s afraid of confronting uncomfortable truths.

Why does this happen?

Ben Horowitz, co-founder of venture capital firm Andreessen Horowitz, framed it well when he said:

You add value the moment you make decisions other people disagree with.

And these disagreements can be with people inside or even outside the business, especially those whose opinions you genuinely care about. Because if you simply do what everyone else thinks you should do—or let everyone continue doing what they'd naturally do—there's no reason for you to be there.

Management Debt Monsters

Making decisions that prioritize people’s feelings ahead of business interests—or worse, avoiding those decisions entirely—results in what Horowitz calls “management debt.”

Management debt is the slow accumulation of small dysfunctions within a business, compounding into an unmanageable monster. You see it in companies that:

• Can’t execute new ideas and initiatives.

• Level off in growth despite significant investment of time and money.

• Lose good talent due to negative cultural exposure.

Much like financial debt, the more management debt you take on, the harder it becomes to dig yourself out.

Most people associate hard work with long hours, but the real hard work lies in making these emotionally difficult decisions and navigating uncomfortable situations as a leader.

You Can’t Please Everyone

Let me leave you with a story from Los Cabos, where I live.

Traffic has become notoriously bad here—a frustration for many people and businesses. The city devised a plan to fix the main bottleneck causing the problem.

Good news, right?

Well, initially, people were thrilled about the plan.

But once construction started and lanes had to close, traffic temporarily worsened. Now, everyone’s complaining about the inconvenience.

Which is a crucial lesson for leaders everywhere: If you’re in charge, people are going to complain no matter what. So why not take the path that may have people thanking you later?

And here’s my challenge for you: Look closely at your business and identify any uncomfortable decisions or conversations you’ve been avoiding. Embrace the discomfort as a sign that true leadership is needed, and be that leader.

Your business—and your future self—will thank you later.

Adios,

Ray

P.S. - Ben Horowitz is also the author of Hard Things About Hard Things, which is hands down is the most impactful leadership book I’ve ever read. 6+ years ago I wrote a book review that Horowitz shared on Twitter. You can check it out here.