A privilege I enjoy in my role at the Fredericksburg Chamber of Commerce is that I get to talk with a lot of business owners.

Some conversations happen at our offices. Others happen at Chamber events, over lunch, walking down Main Street or when I make a visit to a business. Lately, many of those conversations get around to the same subject: business is changing and seemingly more challenging.

Customers are changing. Visitors are changing. Employees are changing. Technology is certainly changing. And something that worked extremely well a few years ago may not work quite as well today. Then layer on top of all of that a challenging economy.

Those conversations have made me re-examine a McKinsey & Company article centered on what they call an “inside-outside” approach to leadership. The concept is pretty simple: effective leaders need to understand their organizations like insiders while occasionally looking at them like outsiders.

And, it is easier said than done. It requires making a conscious choice to think like an outsider. 

Most businesses in Gillespie County are small or micro businesses. The owner may be CEO, marketing director, salesperson, HR department and occasionally the person taking out the trash at the end of the day.

Our nonprofits aren't much different. Executive directors manage employees, volunteers, donors, programs, fundraising and boards — sometimes, all before lunch.

When you are that close to an organization, you know an enormous amount about it. But sometimes you can also be too close to see it clearly. I've certainly experienced that at the Chamber. When you work inside an organization every day, you understand why things are done a certain way. You know the history. You know what was tried before. And pretty soon, something can make perfect sense to us simply because we understand it.

Our customers don't have that advantage. Neither do our visitors, new employees, Chamber members, donors or volunteers.

So here's an exercise worth trying.

Walk out your front door. Then turn around and walk back in pretending you've never been there before.

What do you see?

If you own a restaurant, winery, retail store or lodging property, would a first-time visitor immediately understand the experience you're trying to create? If you run a professional-service business, is it obvious why someone should choose you? If you lead a nonprofit, can someone quickly understand your mission and how their donation makes a difference?

Here's the tougher question: What are you doing simply because you've always done it that way?

I am a big believer in tradition. Fredericksburg wouldn't be Fredericksburg without it. However, tradition and habit are two very different things.

Tradition preserves something valuable. Habit sometimes preserves something just because nobody has questioned it lately. That's where the “outside” part of leadership becomes important.

Ask a new employee what doesn't make sense. Ask a longtime customer what they notice has changed or needs to change. Talk to someone who hasn't visited your business recently. Ask a new board member what they noticed during their first few meetings.

Then listen.

The goal isn't to abandon everything that made us successful. Quite the opposite. Our experience, relationships and institutional knowledge are tremendous advantages.

Gillespie County is changing, and so is the marketplace around us.

The challenge for leaders is to keep everything valuable about being an insider while maintaining enough curiosity to also see our organizations through someone else's eyes.

Sometimes good leadership starts with something remarkably simple.

Walk out the front door. Turn around. And take another look.