How Experience Can Bankrupt Your Business

General Norman Schwarzkopf, the four-star U.S. Army general who commanded coalition forces during the Gulf War, is widely quoted as saying, “Your organization will never get better unless you are willing to admit that there is something wrong with it.”

Many leaders struggle with that concept because admitting something is wrong can feel a lot like admitting failure. We made the decision. We built the system. We hired the person. We developed the strategy. Naturally, we want to believe we got it right.

But organizations do not improve because their leaders ferociously defend everything they have done. They improve because someone is willing to look honestly at what is no longer working and say, “We need to fix this.”

Lamentations 3:40 says, “Let us test and examine our ways.”

Every once in a while, we need to look at the way we are operating and ask whether what we are doing still makes sense.

That’s leadership in action.

This is not about creating another checklist of things to do. It’s about being willing to question the way you operate every day.

Is the way we serve our customers still working? Are our systems making things easier or getting in the way? Is our training preparing people for where the market is going, or for the way business used to be done?

The more we defend the way we do things today, the less willing we become to examine whether those things still make sense. And the less we examine them, the less likely we are to discover a better, more efficient, or more profitable way forward.

Business is moving too fast for that kind of limited thinking.

I have been in the real estate business for more than 25 years, and I still learn something new almost every day.

Real estate has changed dramatically during that time. Technology has changed how buyers search for homes, how agents communicate, how transactions are managed, and even how consumers decide which real estate professional they want to work with. The business I entered more than two decades ago is not the same business I work in today.

It bothers me when I hear another real estate agent say, “I have been doing this for 20 years,” as though that should automatically settle any question about how much they know or how good they are.

I understand the point they are trying to make. Experience matters. I would much rather have 25 years of experience than 25 months.

But the biggest lesson experience should teach you is that there is always more to learn.

Clinical psychologist Diana Hill makes an interesting point in her book Wise Effort. The same strengths and experience that helped build our success can eventually work against us when we rely on them too heavily. In other words, the more experienced we become, the easier it is to default to solutions we already know and overlook a newer and better one right in front of us. Experience helps us recognize what worked before, but it can also make us slower to recognize when something better has come along.

Twenty-five years of doing something does not automatically mean you have 25 years of knowledge, skill, and growth. There is a difference between experience that deepens your understanding and experience that simply repeats what you already know. That is where experience can become dangerous.

Proverbs 15:31–32 says, “If you listen to constructive criticism, you will be at home among the wise. If you reject discipline, you only harm yourself; but if you listen to correction, you grow in understanding.”

Are you still willing to listen and learn?

Sometimes the person who sees the problem first is not the person in charge. It might be someone on your team who deals with an outdated system every day. It might be a customer who finally tells you why doing business with your company is harder than it should be.

A wise leader should be able to hear something that challenges the usual way of doing business without becoming defensive. Sometimes the best response is simply, “Is there something here I need to take a look at?”

There is a familiar principle that says we cannot solve a problem using the same thinking that helped create it. Whether we are talking about business, leadership, or our own habits, there is a lot of truth in that.

Sometimes the strategy that created your growth eventually becomes the strategy that holds back your growth. A process designed five years ago might have been exactly what you needed at the time. But that does not mean it still is.

A marketing strategy that once produced great results might stop working. A management structure that worked with ten employees might become a mess with fifty. Even a good system has a shelf life.

There comes a point when experience has to do more than remind us what worked before. It has to help us recognize when what worked before is no longer working.

If the leader cannot admit mistakes, everyone else eventually learns not to admit them either.

People figure this out pretty quickly. If every piece of bad news is met with blame, defensiveness, or an argument, people eventually stop bringing bad news to you. The problem will not disappear, and you will become the last person to know about it.

That is a dangerous place for a leader to be.

I want the people around me to be comfortable saying, “Hey Dennis, I don’t think this is working,” or “I think we need to look at this differently.” I might disagree. And ultimately, I might decide we are going to stay the course. But I never want someone to believe they are better off keeping quiet because I have already made up my mind.

Proverbs 9:9 says, “Instruct the wise, and they will be even wiser.”

Wise people are still learning. They have not arrived. Their experience has not made them unteachable. In fact, wisdom seems to make them even more interested in learning what they might be missing.

What are you defending right now that might need another look?

Maybe it is a system you created years ago. Maybe it is a strategy that has always worked. Maybe somebody on your team has already tried to tell you something you did not want to hear.

Experience gives us confidence, and it should. But confidence can quietly become certainty, and certainty makes it easy to stop asking questions.

So here is the harder question:

If someone you trust walked into your office tomorrow and told you there was a serious problem in your business, would you be more interested in understanding the problem or defending what you have already done?

Your answer might tell you whether your experience is still serving your business or whether your business has started serving your experience.

Take one part of your business and look at it as though you were seeing it for the first time.

Ask yourself, “What are we still doing today simply because this is the way we have always done it?”

Experience is one of the greatest assets you can bring to a business. It gives you perspective. It gives you judgment. It helps you recognize patterns you could not see when you were starting out.

But experience was never meant to become a finish line.

The best leaders I know keep learning because they know how much they still do not know. They are willing to question something that worked yesterday if there is a better way to do it tomorrow.

Maybe that is the real lesson in Schwarzkopf’s words. Experience becomes dangerous when it convinces us there is nothing left to question, and nothing left to learn. Your business gets better when you are secure enough to admit there might be something wrong with it.

Let's keep walking the Road together,

Dennis Jones
Founder and Publisher