The outdoor CIO: Lessons from the wilderness

Like any father with a busy day job, Dale Mills wanted to make sure that, amid various IT-related projects, he carved out some quality time with his two children this summer.

Whereas some families might be booking some R&R at the cottage or catching up on blockbuster movies like Inception, however, Mills had a different idea: Take his 20-year-old daughter and 14-year-old son on a four-day hike through the Tombstone Mountains, which stand approximately 2,193 meters high in Yukon territory.

For some of us, that would be a pretty ambitious vacation. For Mills, it’s . . . well, a walk in the park.

The vice-president of technology at Chartwell Seniors REIT in Kitchener, Ont., Mills has probably spent more time in the great outdoors than he’ll ever spend in a data centre. This includes 13 trips north of 60 degrees latitude, from skiing on the North Pole, climbing the highest mountain (Mt. Aconcagua, 23,000 ft.) in the Western hemisphere to canoeing 1,600 km from the Great Slave Lake to the Arctic Ocean. He’s managed to pack this in over a 30-year career occupying various IT and business management roles, providing leadership in governance, IT, human resources, financial operations, e-business and senior management in the public and private sector.

Mills says his love of travel began shortly after finishing university, when he decided to follow the original Gold Rush route of the pioneers in 1898. That trek involved a 140 km journey from Scagway, Alaska to Whitehorse, canoeing 600 km down the Yukon River panning for gold. Later, at a conference, he was motivated by a speaker who had been on a team to scale Mount Everest. Mills decided he had to climb it, too.

There’s no unusual reason behind Mills’ adventure travel. When he talks about his journeys, he sounds a lot like the people who spend their summers in Muskoka or Algonquin Park.

“I think it’s sort of the love of nature and the simplicity of life when you’re out in the wilderness,” he says. “My preference is wilderness where very few people go. Where you can be days, weeks, from seeing another soul. That can be a real pleasure.”

Not that Mills is a misanthrope, or that he goes entirely on his own. In fact, the main difference between him and other nature-lovers is his consistent strategy of choosing fellow-travellers he can learn from — including Laurie Skreslet, who scaled more than twenty-nine thousand feet to become the first Canadian on Mount Everest in 1982 — and thinking deeply about how those experiences can translate into on-the-job performance.

When he’s not working at Chartwell or running his own consultancy (, Mills also offers leadership workshops based on some of his adventures. We asked him to give a few examples of what going into the wild has taught him about being an IT executive.

Lesson 1:
Treat IT as a
death-defying act

A lot can happen when you leave the office behind and head into an unfamiliar climate or territory. Mills sees such expeditions as honing his project management skill set. “Just think about the overall planning required, and putting in contingencies around people, equipment and materials,” he says. Much like virtualizing your IT infrastructure or moving a set of applications from on-premise to cloud computing, every trip has a start and end date, as well as milestones you have to meet along the way. When most people think about their worst-case scenario, however, they don’t come up with anything close to what can happen in the wild. “At the North Pole, it can be minus 30 degrees outside,” Mills says. “If you’re prepared, it’s quite nice, but if you’re not prepared, it’s deadly.” Maybe it’s worth taking a second look at that white paper or trying that online assessment tool after all.

Lesson 2:
Risk around
the clock

If you’re climbing a mountain, one of the risks you take might be going over a crevasse, in which case you need to make sure you’re roped in. “Then other things come up, like a bad snowstorm,” Mills says. “Just like a project, things don’t always occur exactly on schedule.” So why do we only act if the risks happen when we deploy a new application or migrate from one set of hardware to another? Adventure travelers don’t deliberately court trouble, but when it hits them they deal with it and keep moving. Do the same and you’ll make achieve your business goals, rather than putting off projects because you want to avoid the unknown.

Lesson 3:
Ask yourself: Are they ready to scale this mountain?

Mills has travelled and explored with some of the best, but that doesn’t mean they were at their best every minute. “People might be totally fit one day and other days have trouble with a load that they’re carrying. It’s up to the group to redistribute the load,” he said. The same is true of resource allocation in an IT project. We tend to treat certain employees as though they are always prepared to behave as though they were at their peak performance. Be realistic, and perhaps consider adding some variety to the duties. In the wild, Mills has dealt with first aid and safety to kitchen duties, to setting up the camp or tearing it down. “That teamwork and communication – it’s just as critical as it is in a project.”

Lesson 4:
Take baby steps

While crossing some icy territory in Greenland, Mills’ team took a dog with them. At the ice cap, there were a number of crevasses. To ensure they had safe spots to cross, they would send the dog out first. “The dog might fall through the thin ice, but he was on a leash, so he was able to warn us,” he said. This is a key crisis management technique: before you dive deep into a business transformation initiative, venture out gingerly with a project that’s a bit smaller in scope. If cracks begin to show, you’ll know you need to look elsewhere for success.

Lesson 5: Establish the
“all for one” mentality

In the wilderness, teams can be literally roped together. That can be one sure-fire way to prevent horrible injuries. “If someone yells ‘Down!’ you get down as fast as you can and dig your ice axe into the ground,” he says. “The same kind of thing happens if you’re climbing up a steep cliff and someone causes a rock to dislodge.” We lose this sense of connectedness in the enterprise: people tend to see big IT initiatives as only something of concern to the CIO and his team. What kind of outcomes can you describe to illustrate that all departments are hanging on to the same rope?

Lesson 6:
Don’t wait to
reach the summit

Most of the expeditions Mills has taken required leaders who were very good at marshalling everyone’s energies around a common goal, and motivating them to move out of their comfort zones. In the enterprise, people really, really like their comfort zones. “There’s a lot of coaching and developing that goes on, and it’s about assessing progress and recognizing people, celebrating accomplishments,” Mills says. That doesn’t mean you have to celebrate at the end of a trip, however. Do it part-way, which may give the stragglers the impetus they need to carry on. “Fun has to be the most important part of it. People have to enjoy themselves and the people around them,” he says.

There’s no reason to kiss the fun good-bye when you get back to work, either. After all, as Mills points out, you’ll inevitably end up spending the bulk of your time pursuing business goals. The trick is harnessing the sense of urgency and purpose that exists in adventure travel and transferring it to the enterprise. That includes the pressures that come with fulfilling work activities.

“Stresses aren’t necessarily bad. They can heighten awareness,” Mills says. “Obviously there are negative stresses which you want to avoid, but even when you’re travelling up a mountain, you’re trying to meet a deadline. On the positive side, once you meet that deadline, it’s over. But if the deadline wasn’t there, you would have had to spend more time reaching that point, so it motivates you to do your best.”

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