Many of the things we do at Basecamp would be considered unusual at most companies: paying for employees' hobbies, allowing our team to work from anywhere, even footing the bill for fresh fruits and veggies in our staff members' homes.

A common question I get from people at other companies is: "How would you recommend I encourage my boss to do some of the things you guys do?"

Such questions typically come from people low on the organizational chart who feel like they don't have much power. But at a time when the competition to attract and retain talent is fierce, I suspect there are many business owners who are asking themselves similar questions. Some of them, particularly those who started up when the rules of the workplace weren't as malleable, might desire to change their company culture but have no idea where to begin.

My suggestion is to not make an abrupt, formal change from the top down but, rather, to allow change to happen from the bottom up. Give your employees a shot at showing the company a new way, and provide the room for them to chalk up a few small victories. Once they've proved that their idea can work on a limited basis, they can begin to scale it up. Small steps lead to bigger steps. Encourage them to build their confidence and yours, too. If an employee can demonstrate results produced in a way that the company didn't think possible, then a new way forward can begin to take shape.

Take, for example, working from home. At Basecamp, everyone can do this. It's built into our culture. In fact, of the 50 employees at Basecamp, about 35 of them work in cities other than Chicago, where we have our headquarters. Most are in different states; some are in different countries.

But for a company not used to letting people work remotely, the idea could be terrifying. You might fear losing control over your people, fear that spontaneous collaboration will no longer happen, fear that your company's collective culture will suffer a blow.

Those are fears grounded in the hypo­thetical. So make changes in the least risky way possible: The next time an employee asks to start working from home, go against your instinct and give her a small shot. How about allowing her a single afternoon each month to stay at home? Maybe the first Thursday afternoon of the month. Let her leave at lunch and work the rest of the day remotely. Let her show you that the sky won't fall, that she can get her work done without physical supervision or proximity to her co-workers. Better yet, let her show you that she gets even more done at home than she does at the office.

Once she has proved it, let her aim higher. Maybe a full day a month, or one day every two weeks. When she proves that works, give her a continuing shot at expanding her request, to a day every week, or a week every month. You'll discover that the more victories she has, the more comfortable you become with the change. Then you begin to think: Maybe we should do more of this! And you let a few more people try it. Then a few more. Next time, you might even allow an employee to go even further outside your comfort zone. And that's how you get your culture to change--in the most mildly radical way possible.