Checking into the Congress Plaza Hotel in Chicago, I had a vague sense that perhaps this wasn’t quite the splendid hotel that the website had made it out to be. Was it the musty smell? The handwritten signs taped up in the hallways giving wrong directions to my room? The peeling paint and worn carpets? Or maybe it was the dead goat in the closet. OK, I’m just kidding about the goat. I was staying at this shabby old relic at the start of a weeks-long 34-city tour that I had put together to show the latest version of our software product, FogBugz, to programmers around the world.

You’re probably wondering where the idea of a grand tour came from in the first place. One thing a software company is supposed to have, after all, is a team of salespeople who fly around the country visiting customers and selling software so that the tech guys don’t have to. Unfortunately, my company doesn’t have any salespeople, so if customers want to find out how our stuff works, they’re pretty much going to have to come to our website and try it.

Not everyone finds us, of course. And it was starting to drive me crazy that FogBugz, an application that helps software developers identify and keep track of software bugs, had all kinds of great new features that nobody knew about. Then I remembered that back in the early 1990s, when I was starting my career at Microsoft (NASDAQ:MSFT), I knew a guy who was hired to spend an entire year touring the country, giving live demos of Windows, Word, and Excel. Why couldn’t Fog Creek do that? We’d go to Seattle, London, Dublin, Silicon Valley—anyplace where we could get our product in front of developers. We’d gather 100 or 200 people in a room and put FogBugz through its paces on the big screen. That’s how my odyssey began. Along the way I’ve learned a series of small lessons and one big one.

When I came up with the idea for a demo tour, the first thing I did was post a survey on our website to figure out the cities where we were likely to draw at least 100 attendees. Much number crunching later, we had identified 34 cities that filled the bill. Next, I worked up a budget, which came to about $160,000—just under $50 per expected attendee (you can check out my budget on the following page). If two or three people in each city purchased FogBugz following the demo, we’d break even. That sounded like a good bet to me. Liz, my office manager, started calling hotels to book meeting rooms. I wanted to bring my customers to a shiny, modern business hotel, where they would feel as if they were on vacation, with the giant indoor palm trees and fountains in the lobby and individual cloth hand towels in the bathrooms. And the customers would think happy thoughts.

But when you bring them to the Congress Plaza Hotel, where the carpet is stained and there are fluorescent lights everywhere and the bathroom wouldn’t be out of place in a public high school, some of that general depressing aura of shabbiness will rub off on the product you’re presenting. I want people to associate Fog Creek with fountains and palm trees, not stained acoustic ceiling tiles.

Speaking of ceilings, their height is another problem you encounter when it comes to booking hotel meeting rooms. I want to make sure everyone in the room can see my presentation, and that means I need a room with a high ceiling. But when you ask hotels how high their ceilings are, they often make promises to you that are, well, what’s the technical term for it? Oh, yes: lying. When you get there, you realize that the people in the back row can’t see much more than the bald spots of the people in front of them.

Now we’re trying to rent lecture halls at universities, libraries, and museums. A lot of these institutions have brand-new, state-of-the-art facilities set in a beautiful campus environment, with stadium seating. In London, for example, we rented a room in the spectacular new business center at the British Library. As our grand tour got under way, I also came to realize that it was going to be much cheaper to buy projectors, microphones, and extension cords than to rent this equipment. So I got all of that stuff, as well as two large, professionally made vertical banners bearing the FogBugz logo. The banners really go a long way to making Fog Creek—which is still a scrappy upstart in my mind—look legit. To make sure people could take notes, we printed pads with our company’s logo, a cute little kiwi, and ordered matching pens. We also created a 12-page brochure that people could take back to the office to show to their bosses. So, what happens at a FogBugz demo? At 9 a.m., people start showing up. We’ve got coffee and bagels. There’s happy music playing. We give people nametags and spend the first half-hour introducing ourselves and getting to know everyone. Developers love the opportunity to network.

I start my presentation promptly at 9:30. I try to move through the slide show really fast so nobody gets bored. After a half-hour demo, I do 45 minutes of Q&A. By this point, I can tell who in the audience is sold on FogBugz and just working out the buying details in his or her mind. Often, it’s not just a few people but a lot of them.

Next, I show a brief movie—featuring more mood-setting music—that gives credit to everyone at Fog Creek who worked on FogBugz. The developers like that. At the end of the movie, they inevitably applaud. It’s the polite thing to do, after all. And then a bunch of people mob me and the other Fog Creek employees to ask more questions, after which we pack up and head to the airport.

I’m writing this on the plane from San Francisco to Los Angeles. We’re about half done with our North American destinations. Europe, New Zealand, Australia, and South Africa are coming up next. I can already tell the tour—though it’s a big investment—is paying off. We are tracking direct sales to people who came to the demos, and they are solid. We will do better than break even.

More important, I believe that, beneath the surface, these live demos also have a very powerful effect in terms of brand building and indirect sales, and here’s why: The demo makes Fog Creek Software real to people. Our product, previously intangible, suddenly comes to life.

When a developer in Toronto or London or Copenhagen or Austin comes to our presentation, he sits in a room with 200 other developers. When they applaud at the end, we’ve gone a long way toward allaying the fear of buying a new product, which every potential customer has. People who buy software—especially software that, like ours, is downloaded on the Web—often view the decision to buy as a leap of faith, one that they’re taking alone. Will their boss or their team blame them if the software doesn’t work or is hard to use?

A demo tour may seem expensive, and it is certainly exhausting. But once developers have met, in the flesh, lots of other people who are buying FogBugz, they have seen social proof of our product’s value. If the cool kids are buying our software, then they can buy it, too. Ultimately, the demo tour allows us to meet thousands of potential customers, to develop a personal connection between them and our company, and to offer them a real, human reason to buy our software rather than the competitors’. At about $50 a pop, I think it’s the best investment in sales I could possibly make.