Into the Wild

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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."

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