Once a year or so, everyone at our company gets together for a week to hang out, work together, and socialize. Because 37signals consists of 28 people located in nearly 20 cities around the world, these get-togethers are rare—and important.

Before our most recent get-together, in the summer, I wanted to focus on improving our products. I felt we were getting a little complacent. Sales were rising, and customers seemed happy, but it seemed as if it had been a long time since any of our products had gotten materially better. We weren't adding as many killer features as we used to.

A couple of days before the crew arrived in Chicago, I found myself watching a celebrity roast on Comedy Central. The guest of honor was Joan Rivers. One at a time, comics like Carl Reiner, Gilbert Gottfried, and Tom Arnold took the stage and just ripped poor Joan to shreds. "When Joan was born, the doctors took a look at her and said, 'Holy shit. We're going to make a fortune on this one,'" quipped the show's host, Kathy Griffin. "And then they got on the Mayflower and set sail for America." The camera cut to Rivers, who was laughing just as raucously as her tormentors and the live audience.

That's when it hit me: What 37signals needed was a roast.

We wouldn't be ripping on any individuals. Instead, we would roast one of our products. I figured the best victim would be Basecamp, our project management and collaboration software. Basecamp has long been 37signals's most popular product—and as a result, it was also the most sacred. Of course, because every employee works on Basecamp in one way or another, we'd also be roasting ourselves. It wouldn't be as racy, or nearly as funny, as the filleting of Joan Rivers, but discussion would be no-holds-barred.

The crew gathered in the small theater at our headquarters. I announced the Basecamp roast. I saw some smiles, though I wasn't sure if they reflected anticipation or anxiety. To break the ice and set the tone, I went first.

I put an image from Basecamp's "people" page up on the screen and began discussing the process by which users invite others to join a particular project. It's pretty simple and seldom leads to complaints from customers. But there are some rough spots if users don't complete the process in exactly the right way. I tried to join a project and made some intentional mistakes. The ensuing error messages sparked some laughter in the crowd. I doubt an outsider would find it funny, but to those of us who really know Basecamp, seeing those messages was like an inside joke—at our own expense.

It turned out that a lot of us had been unhappy with the invitation process for a while, but no one had ever made an issue of it. The roast made it an issue. More people chimed in with their own gripes. We embarrassed ourselves. And it felt really great.

Once we had dispatched with the invitation process, we moved on to more features of Basecamp. Ryan, a senior product designer, attacked a form that was particularly confusing; Ann, from our support team, savaged a sentence that made no sense. Yes, Basecamp is a huge success, but it was full of flaws. The roast helped get this out into the open.

How was this different than the usual product meeting? For one thing, everyone was there. Designers, programmers, customer service folks—everyone had an opportunity to rip on something without worrying about hurt feelings. People understood the spirit of the roast and felt free to take a jab.

The next day, we started fixing some of the stuff that was brought up in the roast. And over the next few weeks, we began working on solving some deeper problems that emerged through the laughs. The roast even spawned some new ideas that will be making their way to our customers in 2012.

The roast hit all the right notes: It brought us together, generated some laughs, broke the ice on the first day of a long week together, highlighted a bunch of issues, and motivated us to dig in. I have a feeling 37signals has a new company tradition.

Jason Fried is co-founder of 37signals, a Chicago-based software firm, and co-author of the book Rework.