Last December I posted an advent calendar on LinkedIn: twenty-four short reflections, each pairing a leadership principle with a moment from The Hobbit. Several people asked the obvious question: why does an IT transformation consultant keep quoting Tolkien? The short answer is in my company’s name. The longer answer is this series — ten posts, each pairing a scene from Bilbo Baggins’s journey with what forty years in IT transformation taught me.
We start where the book starts: with someone who very much does not want an adventure.
A hobbit-hole means comfort
Bilbo Baggins is not looking for change. He has a comfortable home, a full pantry, and a reputation for being sensible. When Gandalf appears at his door talking about an adventure, Bilbo’s answer is immediate: “We are plain quiet folk and have no use for adventures. Nasty disturbing uncomfortable things!”
I have sat across the table from many Bilbos. They are usually competent, respected people who have built something that works. And they can see — even if they won’t say it aloud — that it won’t keep working much longer. The pattern is so consistent it’s almost reassuring. The person most against the journey is usually the one who understands the present best, and so the one the journey needs most.
The platform nobody wanted to leave
Around 2001, at a large financial-services group, I led the strategy to move our server estate off an expensive proprietary Unix platform and onto Intel and Linux. Today that sounds obvious. At the time it was heresy. We had millions sunk into the incumbent platform, a community of experts whose careers were built on it, and no shortage of people telling me the idea was irresponsible.
Here is the thing: the resisters were not wrong to resist. They understood the current platform better than anyone — its strengths, its quirks, exactly what would break. They were the Bilbos, and the journey could not succeed without them.
So we did not dictate the strategy. We built it with them — much of it worked out peer to peer, and a surprising amount of it literally in the smoking corner. We collected the data and the opinions, and we derived the decision together, so that people owned it rather than having it done to them. If I had walked in and announced the target without that listening time, the strategy would not have survived my first reorganisation.
Instead it became the group’s global standard for a decade. And it delivered the surprise the sceptics ended up appreciating most: the open-source community support proved more responsive than the expensive vendor support we left behind. The adventure the Bilbos dreaded turned out to have a better pantry than the hobbit-hole.
What this means for your transformation
Resistance to change is usually treated as a problem to manage. I see it differently: resistance is information. It tells you who has the most invested in the way things are — and those are exactly the people whose knowledge the journey depends on.
Three things I have learned from the Bilbos:
- The fear is rational. People who resist a transformation usually understand the current system better than the people proposing the change. Respect that.
- Don’t sell the journey as painless. Bilbo missed his pocket-handkerchiefs the whole way. Name the losses honestly, and people will trust you about the gains.
- Keep pointing at the treasure. Not the cost savings on a slide — the concrete, specific future that makes the discomfort worth it.
The same pattern is repeating now with AI adoption. Boards want the treasure and don’t mind the danger; the people who run today’s operations are the ones who see it up close. Both are right. The work is getting them onto the same journey.
Bilbo went. That is the whole point of the story — the most reluctant person at the table turned out to be the one the quest needed most.
“There is more in you of good than you know, child of the kindly West. Some courage and some wisdom, blended in measure.”
— The Hobbit, Chapter 18
This is part 1 of ten in There and Back Again — Transformation Lessons from an Unexpected Journey. The series grew out of the advent calendar I posted on LinkedIn last December. Next: The Tookish Side — on the unlikely heroes already inside your organisation.
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