A Digital Sherpa Can Steady Your Step — and Spare You a Great Deal of Pain
Twenty-five years ago I joined a ten-person trek up Mount Kilimanjaro. Four of us made it to the summit. I was one of them, though I am not sure I would list physical grace under pressure as among my natural gifts. There is no way any of us would have made it without the expert guidance, infectious energy, quiet encouragement and endless patience of our sherpas.
Since then I have worked on many complex, technology-enabled business transformations — in corporate roles, in consulting engagements and as an advisor to boards and senior leadership teams. I have learned that transformation is about so much more than having the right equipment, appropriate resources and adequate funding. The greatest successes I have seen benefited from someone who had been up this particular mountain before and could guide the team through the inevitable ups and downs of the journey. That role has a name: the Digital Sherpa.
Today's business leaders are compelled to embark on the digital transformation journey whether they choose to or not. Heightened expectations among users and customers, combined with enormous opportunities for operational excellence, mean digital capability is now essential across every sector — from universities and health departments to banks, super funds and energy utilities.
But as most executives who have grappled with it can attest, digital transformation is fraught with difficulty. Cost overruns, scope creep, security vulnerabilities and reputational damage are common companions, and unaddressed they frequently combine into outright failure. Around 70% of digital transformation programmes fail to achieve their objectives — a figure that has barely shifted in a decade of effort, investment and intent.
What a Digital Sherpa actually does
A sherpa is not a porter. They do not carry your load. They have been up this specific mountain before, in different conditions, with different groups. They know where the altitude sickness tends to hit, which routes close in bad weather and when to push and when to rest.
Applied to transformation, a Digital Sherpa helps organise and accelerate your programme, anticipating risks based on experience across similar journeys. They empower leaders and staff, helping define the skills required at each stage and building the capability to use them. They help build the external partnerships — with technology vendors, delivery partners and specialist advisors — that no organisation navigates well alone. And at the critical junctures where you must decide whether to persevere, pivot, postpone or abandon an initiative, they bring the dispassionate, enterprise-wide view that internal teams, close to the work, find genuinely difficult to maintain.
One thing a Digital Sherpa cannot do: the climbing for you. You cannot contract out the journey and sit at base camp waiting for results. The leaders I have seen fail most consistently at transformation are the ones who delegated the climb and waited for the summit to be delivered. It does not work that way.
There is no single route to the top
Kilimanjaro has seven routes to the summit. Our group took the Marangu Route — known, with good reason, as the Coca-Cola Route — which suited the mixed skill levels of our eclectic group of business executives and school leavers. The point is that route selection matters. The right choice depends on where you are starting from, not just where you want to go.
Digital transformation is similar. Organisations typically take one of four approaches: large-scale enterprise-wide transformation; building a dedicated digital challenger brand alongside the incumbent; investing in a customer-facing digital platform while legacy systems remain; or deploying targeted point solutions for rapid returns. Each has its logic. Each has its failure modes. The right route depends on competitive position, regulatory environment, staff capability, customer relationship strength and available funding — not on what a technology vendor has proposed.
The terrain has changed
I wrote the first version of this piece in 2020. Since then, the mountain has gotten taller.
The transformation journey I described then was digital. The journey leaders are now being asked to make is AI — and the gradient is steeper, the weather is less predictable and the route changes faster than anything I observed in the previous two decades of digital transformation work. The failure rate of AI initiatives currently exceeds the already-poor failure rate of digital transformation programmes. The governance requirements are more demanding. And the temptation to sit at base camp — to treat AI as an IT department problem, to wait for the technology team to return with results — is even more acute, because generative AI appears, from a sufficient distance, to be something you can simply procure.
It is not. The argument for an experienced guide has not weakened since 2020. It has become considerably more urgent.
The summit is worth reaching. The view from the top is everything the brochure promises. But no serious mountaineer, from Hillary in 1953 onwards, has made it there by underestimating the climb.
