A few weeks ago, I was having breakfast with another Chicago-based CEO. We were talking shop. I was seeking advice on how to handle company growth beyond 40 people. (She runs a much larger company than mine.) At the end of the meeting, she pulled out a little notebook, wrote some stuff, tore out the page, and slid it across the table.

At the top, it said Next 5 Years. Below that, there were three questions: 1. What's important? 2. What should be the same? 3. What needs to change? Simple questions, but I'd never really asked them of myself. I'm usually focused on the now. I folded up the little piece of paper and stuck it in my wallet, and for the next couple of weeks, I found myself taking it out and looking at it every few days, then folding it back up and putting it away. Then, one day, I looked at the questions, sat down at my computer, and started banging away at the keyboard. I can't share everything I wrote, but I will talk about the thought process I went through. It might be something you will want to do yourself.

1. What's important? I immediately started to think about what I would miss most if it were taken away from me. Material stuff fell way down to the bottom of the list, and people and relationships rose to the top. So I wrote up how important my team is to me, how much I care about whom I hire, and how those people create the company that I get to work at every day. If they weren't around, I wouldn't want to be around, either.

So one of the most important things over the next five years is maintaining an environment where the people who work at Basecamp can do the best work of their careers. I also want to make sure to provide better opportunities for people to learn and experience new things. That's important.

2. What should be the same? These answers focused mostly on the basics, things such as being polite, honest, and straightforward. I talked about making sure we deliver a product we're proud of and one that we use ourselves every day. I also touched on making sure that we never do things just for the money. And we certainly have to continue to delight our customers. As Basecamp moves through the years, we want to leave a wake of good feelings, quality, and fundamental decency.

3. What needs to change? This was my longest answer by far; I had to dig deeply to see our deficiencies and blind spots, but the answers ultimately flowed and flowed. I wrote about new approaches to marketing and sales, software integrations with other companies, and plenty of other tactical matters. But as I typed, I noticed a common theme emerging: The things that will have to change in the next five years are all the ones we're especially comfortable with today.

When I came to the issue that had prompted this whole exercise--how to grow healthily past a head count of 40--I pointed the spotlight at my own leadership. A healthy company can't depend on a couple of people at the top to make all the key decisions. The right calls need to be spread throughout the company. We've been getting better at this, but it's been a challenge. As we grow, part of the solution might include hiring people differently. We tend to look for like-minded folks when we hire; maybe we should reconsider that.

The bottom line is that these three simple questions forced me to see that 10 years of success has made us too comfortable with long-held positions. We could be knocked off balance, because if we think the next 10 years will get any easier, we're fooling ourselves.