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The 10 Ways Executing a Digital Strategy is Like a Hike in the Mountains

Updated: Jun 9, 2022

I’ve always loved walking as a form of exercise. It feels like meditation that helps me relax and clarify my thoughts. While on a hike in the Nelson Lakes district, I got to thinking about the similarity between a multi-day hike and executing a digital strategy. I came up with these ten items that seemed to resonate with my team, and wanted to share them with you.

1. Preparation affects the outcome

When you go into the wilderness, you can only be sure of what you bring, and you must bring things that you may not need. I find a checklist is a crucial tool to ensure that I don’t forget anything. On this occasion, a particular essential was on my checklist, but I didn’t actually check it off and didn’t notice until I was well on my way. A management tool is only as good as its user – it doesn’t work unless you use it properly.

2. Every little thing has weight

There’s nothing like hoisting 15kg of pack onto your back to concentrate your mind on the essentials. In business as in hiking, there are lots of things that we might like, but a smaller number of things that we really need. Carrying too many things will ultimately slow us down, but that doesn't mean we should leave out the emergency items that we only need when things go wrong. Prioritising is essential and quite hard to do.

3. Don’t start what you can’t finish

Once you’re up in the mountains, there’s no point in stopping halfway to complain that the goal is too hard. If you get halfway there, it is probably just as hard to retreat as to go forward. We can always do more than we think we can, and if it seems hard or even impossible, the best answer is often to just keep going.

4. Keep an eye on the weather

Keeping going doesn’t mean pushing ahead mindlessly in a particular direction regardless of changing circumstances. Many hikers have been swept away in swollen rivers that they had assumed would be safe to cross. Similarly, many digital strategies have failed because the underlying assumptions proved to be false, or the situation changed dramatically and no one noticed.

Stay agile and change plans when the occasion demands, making sure that everyone knows what the new plan is and why the change.

5. There’s always someone faster than you

I made an early start one morning and an hour later I stood on the top of a ridge looking back at the hut I had just left. A lone hiker was leaving the hut and my thought was that we would be well ahead of him at the car park. Not only was I wrong, but he also overtook us faster than I would have believed possible. It turned out that he was a former special forces soldier. No matter how good we are, we should never overestimate our advantage or underestimate the competition.

6. You can do more than you think

Most hikers have had the experience of pushing themselves a bit further than they imagined they would be capable of and being pleasantly surprised at how well they coped with the challenge. If we have the determination to achieve our goals, we will be amazed at what we can achieve.

7. Know when to take a break

Constant effort without pause for sustenance and regeneration will cause burnout and under-performance. It’s also very rewarding to pause and look back at how far you’ve come.

8. Ignore the big picture

When you’re at the bottom of a very steep hill, looking up at what you have ahead of you can be very daunting. Experienced hikers learn to look down at their feet and focus on keeping moving. This also has the effect of tricking the mind into thinking that the slope is less steep.

Implementing a digital strategy will always have moments equivalent to a steep hill. When this happens, focusing on completing the next step instead of worrying about the end state can help to push through these challenges.

9. The last mile is the hardest

The first sight of your destination is always heartening, but that feeling is usually followed by the understanding that just because you can see something doesn't mean you’re close. At the end of a long day, a single kilometre can be surprisingly challenging. It’s easy to get frustrated when you’re tired. Stay focused and determined until completely finished - don’t celebrate prematurely.

10. The journey is what counts

When we do get to the end, a good celebration to mark the occasion is a must. Hikers have been known to accept the extra weight of a hip flask or even a bottle of wine to ensure a good arrival at the hut. Just as a hiker knows that the morning brings a new trek, every business continues to face new challenges.

Every strategy is a journey, and the best strategies are hard work, great fun and make us better and stronger.

We can’t promise to make you physically fitter, but we can promise to make your digital journey fun as well as challenging and ultimately make your business more resilient.

Ray Delany is the Founder of CIO Studio and has been doing this for a while. Why not ask for a no-obligation discussion to help plan your change?


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