Are Blind Spots Holding You Back?

This article was originally featured in Forbes.

If you’ve been leading a business for a long time, chances are you’ve gotten quite good at it. You’ve learned how to anticipate the moves of competitors, weather economic cycles and hire the right people. You’ve probably built a culture that reflects your values, and you even may have grown your company into a market leader.

But here’s the challenge: The better you get, the harder it becomes to see your own blind spots.

Years ago, when I sold my first business to a publicly traded company in exchange for stock in the acquiring company, I hesitated. In hindsight, I should have followed the same advice I gave to others. That’s the nature of blind spots: They’re easy to spot in others, and hard to see in the mirror.

Stephen Covey once wrote, “We see the world not as it is, but as we are.” That’s especially true in leadership. Our experience sharpens our instincts, but it can also dull our ability to perceive risk, invite feedback or recognize when it’s time to change course.

Succession Planning Starts With You

One of the biggest blind spots I see among mature leaders is around succession planning. At my firm, we’ve had countless conversations about this—with clients in regards to their own businesses, of course, but also internally about our business. Many founders think they’re being prudent by waiting until “the right time” to name a successor. But in my experience, if you wait until it feels urgent, you’ve probably waited too long.

Planning for succession isn’t just about ensuring business continuity; it’s a reflection of whether you’re building something that can outlast you. Years ago, when I formally named my successor, it lifted a weight from my shoulders and gave me the space to focus on the business instead of working in it. That kind of elevation is what gives a founder the chance to shape legacy.

Alignment Isn’t Just For Clients

A second blind spot? Misalignment. We often talk about this with the families we counsel, especially how critical it is for parents to be aligned in how they raise children or manage finances. But the same is true in business, particularly during periods of growth or acquisition.

We’ve seen firsthand that, when M&A deals fall apart, it’s rarely because the math didn’t work. It’s usually a cultural mismatch—a failure of alignment. At my company, we work hard to avoid the trap of creating “silos” that pit colleagues or offices against one another. Internal competition may feel like healthy tension, but it often masks perverse incentives that do more harm than good.

If you want to build an enduring business, invest in alignment across teams, across offices and especially across generations.

Ask Others To Question Your Thinking

It’s a peculiar irony that as leaders grow in experience, they often grow in isolation. Their input is sought far more than their output is questioned. But at some point, the danger becomes this: You stop learning.

One of the best ways to avoid that? Create intentional opportunities for what I call reverse mentoring. Solicit feedback from those several layers down. Ask your younger team members what they’re seeing. Let them surprise you with what they know.

One of the winningest basketball coaches in history, John Wooden, famously said, “It’s what you learn after you know it all that counts.” I’ve seen that principle play out time and again. The moment you feel most confident in a decision is often the best time to pause and ask for input. Cognitive diversity isn’t a buzzword, it’s a strategic advantage. If everyone around the table thinks like you, you’ve limited your field of vision.

And here’s the truth: To give power is to receive power. When you invite new voices to the table, you don’t lose control, you gain perspective.

Avoid The Trap Of The Lifestyle Business

There’s another blind spot I see far too often: the temptation to coast.

At some point, the business gets big enough. The income is steady. The pressure eases. And before you know it, the company becomes a vehicle to fund the founder’s lifestyle, rather than a living, breathing enterprise with room to grow.

I’ve seen businesses in this stage sell too soon, or worse, slowly wither away because they stopped reinvesting. It’s a form of slow-motion decline that’s easy to justify and hard to reverse. If you’re not investing in new talent, new ideas or new opportunities, your business is likely stagnating, not thriving.

Stay Curious, Stay Humble

The best insurance against blind spots is continuous learning. The leaders I admire most never stop asking questions. They read widely, listen deeply and are open to being wrong. They also know when it is time to go.

In my office, we sometimes joke that everyone on the team’s favorite radio station is WIIFM: What’s In It For Me? But great leadership requires tuning into a different frequency—one that’s focused on shared purpose, clear communication and humble curiosity.

Whether you’re running a high-growth enterprise or a legacy family business, it pays to assume you don’t have the full picture. After all, someone else might be looking at the same facts and seeing something you don’t.

So ask yourself: What am I not seeing?

And then go find someone who will tell you the truth.

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