The senior managers of Timbuk2, a San Francisco-based manufacturer of messenger bags, gathered on a gently sloping granite ledge at an altitude of 12,000 feet, overlooking the blue-gray shimmer of one of the dozen or so Ice Lakes, slopes of stubby pine trees, and beyond onto ragged peaks. It was the middle of June, but snow still mounded on the ground. A thunderstorm had just skirted the campsite and the wind screamed constantly, cold and fierce.

These four men and two women lead a growing company of 70 employees back at sea level, where they'd typically be worrying about things like financing, brand management, e-commerce, and retail sales. But for the past four days they'd been in the backcountry, and their concerns had been somewhat more basic: Would that small blister turn into a festering sore? Would those dark clouds bring rain? Does that bear paw print in the mud mean there's an actual bear nearby?

The group was halfway through a seven-day backpacking trip organized by the National Outdoor Leadership School, or NOLS. Accompanying them were two NOLS instructors and me; I'd tagged along to see what would happen. It had been nearly 100 hours since any of us had had a shower, or used a flushing toilet, cradled a cell phone to our ear, or run our fingers across a keyboard. As the sun started to set, the temperature, which had hit the high 80s when we'd set out from the town of Lander, Wyoming, just four days before, was hovering just above freezing.

The reason we were all sitting there that night, in varying degrees of ache, chill, and fatigue, was that Timbuk2 CEO Perry Klebahn had an audacious goal: to accomplish six months of team building in six nights in the wilderness. The company was in the midst of a turnaround, and this particular group--the CFO, the directors of operations, sales, and e-commerce, and a manager of international sales--were all recent hires and had worked together for less than two months. "In six months to a year, this will be a great team, but I can't wait for that," Klebahn said to me when we first talked on the phone, about a month before we left for Wyoming. The company, he said, was completely overhauling its infrastructure and operations to keep up with growing demand. "We're not used to working together. We don't know one another's sense of humor, what stresses us out. My hope is that this trip will get us down to that level, so that we can understand one another--what we're all like and what makes us tick."

In theory, I understood what Perry was talking about. But as I shivered that night, I had to ask myself the question that had brought me to Wyoming in the first place: Does getting cold, smelly, achy, and tired with your co-workers really accelerate a team's development? After all, there are any number of team-building exercises out there, and, as I thought about them that frigid night, each struck me as a good deal easier than what the Timbuk2 team was up to. Some companies build rapport by taking cooking, dancing, or drumming classes together. Others stage role-playing team challenges, where you just pretend to rescue someone, from, say, a windswept peak, instead of actually sitting on one wondering how bad your altitude-induced headache is going to be the next morning. Others try to tap creativity--challenging teams to, say, design a package to keep an egg from breaking when it is dropped. Then there are what have become corporate team-building clichés: paintball competitions, ropes courses, trust falls, and my personal favorite--the luxury resort.

But while all those things can be fun, they don't have a track record for building bonds between people as effectively as good old-fashioned discomfort and suffering. In fact, very few things work better, says Robert Sutton, an organizational psychologist at Stanford. "Boot camp and other forms of extreme indoctrination work because of the suffering," he says. "This is what military boot camp does, fraternity hazing does, medical school does. It congeals people and convinces them that some cause is important." Cults and other various and sundry brainwashers, of course, have known this forever.

I got to know Perry Klebahn pretty well, and I can say with certainty that he is not a sadistic brainwasher or a cult leader. But it's hard not to notice that the psychological theory of…let's call it extreme team building seemed consistent with his goals for the expedition. During our phone conversation before leaving on the trip, he said, "We're trying to get everyone to work together, and we're very committed to the idea of removing status. Status gets in the way of things. This will be an interesting way to put us all off balance, and then get us down to a team that can function better together."

NOLS, for its part, would object to the idea that it is trying to make people suffer needlessly. It sends its students out into the field with plenty of food, fuel canisters for cooking, and the appropriate gear to cope with weather extremes in relative comfort, says Dave Glenn, director of NOLS Professional Training, the division of the organization that deals with corporate groups, when I met with him in his Lander office the day before we set out for the Popo Agie Wilderness, deep in Wyoming's Wind River Peak Range. But the courses are designed to be physically demanding--hard enough to make you drop your public persona and act like who you really are. Indeed, the reason outdoors courses are more effective than, say, team challenges involving keeping eggs from breaking is that this isn't make-believe. "You really have to do it out there," said Glenn, gesturing out his window toward the mountains. "If you decide not to set up your tent, and it rains, or if you get lost--the consequences are real." For 11 students out of 85,000 taught by NOLS since 1965, the consequences have been fatal. (Most of those incidents, it should be noted, occurred during the organization's early years.)

When people camp together, Glenn continued, the concept of privacy entirely disappears: From the time you first open your eyes in your tent to the moment you fall asleep to the sound of your colleagues' snores, you are together. What's more, you're isolated from your friends and family and all of your normal support systems. You have no choice but to interact with the people around you. You also have no choice but to exhibit all of your less than pleasant qualities--early morning crankiness, passing anxieties, and full-on temper-tantrum meltdowns--in front of everyone. As I got up to leave Glenn's office, he shook my hand and gave me a big broad smile. "You can't escape."

Orientation Day: Lander, Wyoming, elevation 5,357 feet

The Timbuk2 team arrived in Lander the night before we were to head out onto the trail. Clad in clean jeans, dark T-shirts, and nametags, they were dining on a greasy takeout dinner in Styrofoam containers. Laughing and joking, with just a thin undercurrent of tension beneath the surface, they seemed less like a group of co-workers than a group of friends, getting together to do something a little crazy.

They assembled on burgundy easy chairs and couches in the high-ceilinged reading room library at the Noble Hotel, where we'd stay that night. Missy White, our team's leader, sat at the front of the room, near a blank flip chart, and started the introductions. She's been with NOLS since 1987, has a master's degree in organizational psychology, and runs her own consulting firm. Kat Smithhammer, with NOLS since 1996, was our other instructor.

Missy explained that she and Kat had extensive training in first aid, and that they would be carrying a satellite phone programmed with a number to a line monitored 24-7. If something were to go seriously awry, there were options--you could walk out, a horse would be sent in to pack you out, or a helicopter would come to the rescue. The Timbuk2 crew listened intently but didn't seem particularly fazed by the physical challenges ahead. After all, this was an athletic bunch, including a couple of surfers, a triathlete, a rock climber, and a former Eagle Scout with extensive backcountry experience. More potentially treacherous, it seemed likely, would be the interpersonal terrain they'd encounter.

Back in San Francisco, for example, Perry and his director of operations, Nancy Spector, work closely together--but tend to approach problems in very different ways. As a result, they get on each other's nerves. "I need to find a way to get more functional with my boss," Nancy had told me. But at the same time, she worried that the stress of being in the wild would cause a major blowup. "This trip has the potential to break wide open all the little fissures in the team." There were similar tensions between Andy Howe, the company's director of sales, and Patti Roll, the director of e-commerce and marketing. The two had been close friends before they started working together, but recently their friendship and their working relationship had become strained. The youngest member of the team was Chris Hansel, 31, manager of retail and international sales; he had been with Timbuk2 for only a couple of months. Finally, Tony Meneghetti, the CFO, had been on the job just six weeks. He saw the NOLS course as an analogy for what the team would face in the months ahead at the office. "At some point, one of us is going to be faced with something beyond our limits, just as we will in the business," he said. "One of us is going to have to say, 'I can't do this alone, I need the help and support of the team."

"What did you all think when Perry said, let's do this?" Missy asked the group.

"I thought, it's never going to happen," said Patti. "And then, two weeks ago, I thought, this just cannot happen. The entire executive staff gone for a week? At a time of deadlines? And then it was, wow, we're really going to do this. And by last Friday, I was in a borderline temper tantrum over it: I don't want to go!"

Nancy listened intently. She had her own concerns. After all, this group had never even had dinner together. Wasn't this a case of too much too soon? "At first, my gut was saying, this is going to be fantastic, a once-in-a-lifetime opportunity," she told the group. "But then I said to myself, if I don't have a great experience, it's going to be a fork in the road with this group and this job. If I can't have fun with these people doing this, I'll have to rethink what I'm doing at the company."

Perry didn't say anything, but he said later that his mind was racing. Up until this point, he'd been thinking of this almost as a kind of theoretical exercise, a way of testing out his ideas on collaboration and team building. It seemed obvious once Nancy said it, but he hadn't seriously considered the consequences if the trip, for which he'd spent $22,000, went badly. And who knew? It might. The executive team that he'd just finished carefully constructing could fall apart. "If two people quit as a result of this trip," he thought, looking around the room, "I'm screwed."

But it was too late for regrets. Missy and Kat discussed the plan for the next day. The first hike would be an easy one, just a mile and a half, to see how everyone was feeling in their boots and with their packs. Then we'd really get going and eventually cover a loop of about 30 miles before being picked up again seven days later. "Look," Missy said, before she sent us off for the night, "I don't know what's going to happen out there. This is like how life is at the office. You can know the terrain, the category of things that could happen--it could rain, we could see a bear, and there are a few grizzlies out there. But we don't really know exactly what's going to happen. The only question will be, how do we respond to it?"

Day One: Setting out from NOLS headquarters

The first hike, which began in midafternoon, actually turned out to be as easy as advertised. We entered the Winds at an area called the Sinks, at about 7,300 feet, and followed the Middle Fork Trail for about a mile and a half, through a postcardlike setting of pine trees, frothy mountain streams, yellow wildflowers, and bleached white boulders, until we reached a place called the Granite Buttress, an expanse of rock, interspersed with grass, looking out onto a tree-lined ridge. We ate dinner and learned how to set up our tents. Kat and Missy demonstrated the fine art of digging a latrine in the woods and then we went to sleep as the sun was going down.

Day Two: Granite Buttress, in the Fossil Hill area of the Shoshone National Forest, east of the Freak Mountains, 7,800 feet

Waking up in the wilderness that morning, our first task was to get comfortable, and that meant getting personal. It was weird to open your eyes in the morning and be immediately confronted by people you're not related to. "Now I know you even wake up perky," Nancy said to Chris, over a breakfast of oatmeal, fruit cobbler, and strong coffee. "I only got up to pee once in the night," announced Patti when she arrived at breakfast. "You peed on Tony," joked Chris. "Oh, was that that warm feeling?" Tony said.

After breakfast, it was time to start NOLS' formal leadership curriculum, with an exercise designed to tease out leadership styles. With birds chirping and butterflies swooping overhead, Missy placed two green ropes on the ground in the shape of a cross, and based on the answers to a series of questions had the group sort itself until each person ended up in one of four quadrants that corresponded to four types: analyst architect, relationship master, driver, spontaneous motivator. Perry, it turned out, was a relationship master--which seemed to surprise many of his co-workers.

This wasn't much different than what consultants do in conference rooms all across the country--except in terms of what came next. The group was to think about this exercise and its implications while we got actual exercise--hiking to our next camp. "Here's a thought for the day, to think about when we're hiking," said Missy. "Where do you slide? In what kind of a situation do you move from one style to another?" "And another thing to think about," added Kat. "How do you define progress? How do you define success?"

Soon, it was time to get going. We hoisted our 45-pound packs onto our backs and split into two groups to hike, stopping every hour or so to refuel. We hiked four miles deeper into the forest, hanging along the Popo Agie River, past the picturesque Popo Agie waterfall, and eventually reached a wooded spot called Sheep Bridge. Upon arriving in camp, we pitched tents and cooked dinner. Not long after the sun went down, we strapped on our miner-style headlamps to find our way back to our tents and our sleeping bags, and everyone quickly fell asleep.

Day Three: Sheep Bridge, just east of the national wilderness area boundary, 8,600 feet

By the next day, it had begun to feel like we'd settled into a kind of routine: up with the sun, pop some vitamin I (that would be ibuprofen) for the stiffness, aches, and pains, cook breakfast over the two stoves we carried in. Then Missy or Kat would lead a class on leadership, with the group sitting on whatever rock outcropping was handy. The team would talk about the content of the class, relating it back to issues they were dealing with at work--often discussing specific people at the office and how they might approach personnel changes. Then we'd pack up, split into two groups, and hike again.

This was one of our longer days, a six-mile trek in which we gained about 1,500 feet of elevation, a lot of it in a few very steep stretches. The path took us through deeply wooded areas, where we spotted a baby moose in the distance, and some open marshy areas, where we were plagued by mosquitoes. It took us to streams that we had to balance on rocks or logs to cross. Just before we arrived at our camp, Missy spotted a black bear track in the mud.

Day Four: En route to high camp, just below 12,000 feet

We planned to follow the long hike with a shorter one today and find a camp that we'd stay at for two nights, ideally one close enough to the Wind River Peak so that those who wanted to could take a day trip to the summit without their heavy packs. As we put our packs on, the chatter was about family. Patti said her grandfather had taught her and her sister a lot of silly songs. She started singing one with great gusto: "Oh, Alice, where art thou going? Upstairs to take a bath. Hey, Alice, shaped like a toothpick and a head like a tack!" She finished to applause and cheers and the day was off on a fun note.

As usual, we'd hike in two groups, today to be led by Nancy and Andy. Whichever group got to a predetermined spot on the map first would drop packs and search for a truly excellent campsite. When the other group arrived, they would also drop packs and scout, and then we'd compare notes. I hiked with Nancy's group, which included Perry, Chris, and Missy. Since she didn't have a lot of experience reading topographical maps, Nancy delegated that task to Missy and Chris, and asked them to take the lead. And since she'd already observed that I was a good deal slower than the rest of the group on the trail, she decided to hike with me, to keep me going and help me out.

We were now high enough into the mountains for it to be cold; snow was still on the ground. We caught up with the other group and all of us managed, somehow, to cross a rapidly flowing rocky river. It was just slightly upstream from a waterfall. "If you fall in the water, get your feet downstream and get your head above water," Chris advised me. Once on the other side, we dropped packs and had snacks. Perry took off his boots to see how his feet were doing. The answer: not well. He'd bought the first pair of boots he tried on the weekend before, which had turned out to be a huge mistake. They were just a bit too big on him, and as his feet slid around inside, they were transformed into a bleeding, blistering mess. While everyone ate and rested, he tended to the padding and bandages on his feet. He didn't eat anything. This also turned out to be a mistake.

About an hour later, after we'd lost the trail, crossed a snowfield, and found the trail again, we stopped for a water break in the middle of an alpine meadow. "Can we do a little debrief now?" asked Perry. "If Nancy is the leader, why are Missy and Chris making all of our navigational decisions?" He was thinking that this was exactly what Nancy did at the office: Instead of making decisions up front, she's in the back, building up the information and seeing what the right move is.

Nancy was caught off-guard by the question. "I was making a conscious leadership choice," she said. "I took the role that I thought would be less fun." She shot me a quick apologetic look. The way she saw it, her job as a leader was to get us to the destination safely and to ensure the comfort of the people on the team.

"But which role would be the one you'd be least comfortable with?" Perry asked.

"Leading and reading the map," she said.

"So do that."

Nancy was upset. She felt criticized and frustrated. Just like at the office, she and Perry were butting heads. In his view, she thought, the whole point of the trip was to push people outside their comfort zones. "But in that moment, I was thinking of the group's comfort," she told me later. But she didn't argue. She moved to the front and we set off again.

Not long after that, as ominously gray clouds began to rush in, we spotted four backpacks on the side of the trail. It was at least half a mile before our prearranged rendezvous, so, in some confusion, we stopped to wait and find out what was going on with the rest of the team. Perry was exhausted, too tired to take off his pack. He just leaned up against a rock.

Andy and Kat came down a steep slope. It turned out that their group had misread the map. Tony and Patti had set off up the steep slope behind us to investigate a potential campsite. Nancy and Andy, the two group leaders, had a decision to make: wait to hear from them about this site or send some of us farther up the trail to start looking for alternatives. They decided to wait for Tony and Patti to report back. As we waited, Perry repeatedly asked Nancy and Andy: What is up with all this waiting? What are we waiting for? He let it be known that his feet were not up for any more climbing that day. Tony and Patti returned with news of a great location. But because getting there required a steep climb, Nancy and Andy decided to move farther down the trail to find a site that could be reached more easily.

Eventually, we assembled on that freezing cold granite ledge to debrief. Perry started the conversation. "On the trail, I saw all this checking in," he said. "My take is that there was a lot of time waiting to check in. I don't know…I felt like we were just waiting not to hurt anyone's feelings."

"But we were looking for a camp for two days, and that's an important decision," said Andy. "The due diligence slowed our decision down."

"But from where I was at," said Perry, "I wanted a minimum number of steps to the end."

"The objective changed," Tony replied. "It went from finding a primo campsite earlier in the day to finding somewhere with less 'up,' quickly."

"Let's take this back to Timbuk2," said Perry. "Are we a fast-moving organization where we're all on the same page or not? A lot of talk and a lot of check-in sounds like bureaucracy to me."

"Typically at Timbuk2, you're pushing us to move faster," Andy said. "And your objective is the one that wins. But I think this is interesting to think about: On whose agenda is it important to move fast? Should Perry feel a little pain and we all find a perfect campsite? What do you think?"

Perry suddenly grew testy. "No, I needed a comfortable campsite now, because I am sick of hiking," he said. "I'm over it! In my mind, I was thinking, 'This sucks.' And someone should say to me, 'How are you feeling?' or I'm going to be really mad."

Put this scene in a conference room, and it's easy to imagine the assembled squirming in their seats or studying their hands. But here, the group listened with sympathy. Everyone knew where he was coming from. Perry's outburst was particularly eye-opening for Nancy. "I thought he was just impatient about continuing," she told me later. "I had no idea that he was in that much pain. Had I known, I would have said, 'Hey, we have a group member in pain here, and we need to find the fastest and least painful way to camp." She also had a new perspective on Perry. "I saw him as more human. Every day, he's so good at what he does. He's so smart, accomplished, competent, and moving really quickly. But there he was, with his hurt feet. My impression of him softened."

It wasn't until a bit later, when Perry had finally warmed up and gotten some food in his stomach, that he first realized that in his pain-induced, low-blood-sugar-fueled fugue, he might not have been completely reasonable during that discussion--or, in fact, earlier in the day with Nancy.

Day Five: Second day at high camp

Andy, Chris, and Kat woke up before sunrise and summited Wind River Peak. The rest of us went on a walk to one of the nearby Ice Lakes with the idea of doing a little fishing. Everyone reconvened back at camp by midday.

Patti told me later that she'd been having a nice time up to that point--but she was troubled. She'd yet to tackle her difficult relationship with Andy. "Ultimately, there was this big festering thing to deal with," she said. "And I'm either all in, or I'm not going to get as much out of this trip as I was expecting to."

That afternoon, the group gathered again on yet another rock face for the last of the leadership classes. This one was about values. The talk turned to how the company would handle failure, and how the team could balance moving quickly against making mistakes--or, as they called it, progress over perfection. "We've got to have a culture where it's okay to try something," Perry said. He referred to the workbook, the catalog that Timbuk2 dealers use to order products. As one of her first projects, Patti had completely redesigned it. "Okay, some thought the print was too small, and our reaction was, 'Oh, shit," said Perry. "But we should reframe that: It's not perfect but it's progress, and we'll take care of it next time."

"I disagree with Perry," Andy said. "It generates $600,000 worth of business. We shouldn't just mess around with it. We should focus on getting it right."

Patti was taken aback. "Anytime you change something you're going to get a lot of feedback," she said. "My question is whether the workbook is viewed as a success or a failure."

"I don't see it as a failure," Andy replied. "I just asked you to get user feedback." They began arguing about whether she had obtained enough feedback on the mockup of the new workbook from the dealers who use it. She thought she had; he disagreed.

As they went back and forth, the rest of the group sat quietly, listening and occasionally looking off into the distance, at the mountains or at the sky. Besides Perry, most hadn't realized that Andy and Patti were so tense around each other--there wasn't time for this type of issue-airing during weekly executive team meetings. "It was a little awkward," Chris told me later. "A bit like watching your friend's parents fight."

"What I hear you saying is that yours is the better perspective, and mine is the lesser one," Andy said.

"It's just different," Patti said. "And that dealer workbook, it feels right to me."

"I hear you saying that, but what I need is usability. I have to have that, or I'm dealing with complaints."

"The workbook is much more usable than before. And you're saying it was a failure."

"I don't think it was a failure," Andy said. "I think the process was a failure because we had conflict over this. What I admire about you is that you take something and you make it your own. But I feel I gave you my input of what's important, and you take it, and then you go do your own thing."

Perry interjected. "Andy, what I hear you saying is that you don't feel respected."

Andy nodded. "The No. 1 thing I feel is disrespected when we have these conflicts."

Patti stopped. She nodded and said, "Okay." And she thought: Oh my God, he's right.

At this point, Perry stepped in. "You know, yesterday I was in a big downward spiral," he said. "My feet hurt and I didn't eat when we stopped and I was so pissed about all the waiting to make camp. It wasn't until last night that I understood that my perspective was really limited."

Then he added, wryly, "And I guess what I do in those situations is, I take it out on Nancy."

Everyone laughed. And Nancy took it as Perry meant it--as an apology.

One Month Later: Timbuk2 headquarters, Mission district, San Francisco, sea level

We all hiked out together after that, and after one more night in our tents, we got back on the bus. Everyone survived. Injuries were minimal. Perry got a tick bite, but it didn't turn into Rocky Mountain spotted fever and his feet healed. I mildly sprained both of my ankles, but I could walk out.

Timbuk2 also survived in the absence of its leaders. And when they all returned, it was obvious to Kristel Craven, the company's director of logistics, that it hadn't been a vacation. "I could see from the looks on their faces, it had been a lot of hard work," she said. "But it also seemed to me that everyone seems a little bit more comfortable together, like there's more trust than there was before, and that's never a bad thing."

Indeed, each member of the team that went to Wyoming describes their relationship as tighter, closer, warmer.

Andy and Patti turned a corner in their friendship and their professional relationship. Same with Nancy and Perry. And Tony and Chris, the two newbies, are now much more integrated into the team. "I feel like I've known them for several years," Tony said.

There's no question in Perry's mind that the trip was worthwhile. "It created a familiarity that wasn't there before," he said. "Maybe you grab lunch with the people you work with, but it's different when you drink out of the same water bottle and someone teaches you the proper way to make pancakes over a camp stove. I feel now like I'm working with friends." As for his own personal experience, his feelings are a bit more mixed. "I had been interested in this as a theoretical question: Could you break people down and build a team? But it's different when you're actually doing it, being hungry and super tired, and having the bloody feet." He couldn't help thinking about his meltdown on the trail. "That was great CEO behavior right there," he said, with a rueful laugh.

But as embarrassing as it was, the experience gave him a key insight into the way he approaches leadership. "I'm not used to being in situations of uncertainty where I have little experience or authority," he said. That day on the trail, he was in the unusual position of being uncomfortable, vulnerable, and not in charge. "I came out of it thinking what it must be like to be just an employee at Timbuk2, to not be a manager and to be in a situation of uncertainty and without authority." It remains to be seen exactly how his new rank-and-file employee empathy will affect his management style, but he's been giving it some thought.

There are two big tests of any team-building exercise: whether its benefits are long-lasting, and whether the company would invest in doing it again. On the first measure, it's probably too soon to say. As for the second, the signs are encouraging. Perry says that Timbuk2 will probably do the whole thing all over again next year, sending a different group of employees. He's not so sure he'll join them, though. He's not eager to haul a backpack 30 miles in the Wyoming backcountry anytime soon.

Alison Stein Wellner ( is an Inc. contributing editor.