Tag: hobbit-lessons

The most famous chapter in The Hobbit has no battle in it. Bilbo is lost in the dark, deep under a mountain, facing a creature that means to eat him. What carries him through is a conversation. The riddle game with Gollum works because Bilbo does three hard things at once under pressure: he stays calm, he listens closely, and he plays for a way out rather than for victory.

I think about that chapter whenever I have to walk into a room where the relationship was already broken.

The meeting I was told to avoid

Years ago I was sent to meet the chief executive of a major client, in his own city, on his own ground. The relationship with the provider I represented had deteriorated badly. He opened, more or less, by asking how I dared to show up at all, given how strongly he stood against working with us. There was no goodwill in the room and no leverage in my pocket.

So I didn’t argue, and I didn’t sell. I treated it as a riddle game: I came to understand. I spent the meeting asking and listening — really listening, not waiting for my turn. What came back was specific, factual, and in several places entirely justified. Naming the gaps out loud, instead of defending them, changed the temperature of the room. We stopped being two parties bracing against each other and became two people looking honestly at the same broken situation.

Here is the honest ending, because it matters. The client still decided to leave. I did not save the contract. What the conversation produced instead was clarity: on where the service had failed, on what could realistically be done, and on why, in a very political situation, the decision was what it was. Both sides walked out understanding each other, without rancour. In hostile territory, that kind of clarity is sometimes the most valuable thing you can carry back into the light.

The riddle game, played again years later

The same craft showed up again in a quieter room, on a large and difficult account. The client’s chief architect and I sat down over disaster-recovery readiness — and instead of the usual vendor theatre, we told each other the truth: this is not in good shape, on your side or on ours, and if there is ever a real DR test, we would both rather be on vacation, because it is going to fail badly. Then I did the genuinely uncomfortable part: I carried that shared admission, openly, to his colleagues — before anyone forced it out of us.

Here is what happened contractually: nothing. No penalty claim, no comeback on that gap — ever. And I watched the opposite dynamic constantly on the same account: whenever we got defensive about a weakness, that was precisely when the attacks came. Openness about a known gap converts it from ammunition into a shared problem. Defensiveness keeps it a weapon.

What this means for your transformation

High-stakes conversations in hostile territory follow rules that have nothing to do with org charts:

1. Listen more than you speak — especially when you are sure you are right. Bilbo wins the riddle game by paying attention to his opponent, not by being cleverer.
2. Acknowledge what is valid in the other side’s position before defending your own. It costs nothing and changes everything. Most deadlocked conflicts contain at least one real grievance that nobody has ever simply admitted.
3. Play for clarity, not for victory. A “won” argument that leaves both sides more confused is a loss. A hard conversation that ends in genuine understanding — even when the answer is no — is a result you can stand behind.

This is becoming relevant in a new arena. As companies negotiate AI commitments with vendors, and face regulators under real uncertainty, the riddle-game skills matter: calm, precision under pressure, and finding shared ground where there seems to be none. The technology is new. The conversation craft is very old.

Sometimes you walk into the dark, have the conversation, and still don’t get what you came for. You get the truth instead. That is worth the walk.

“What have I got in my pocket?”
— The Hobbit, Chapter 5

Part 3 of ten in There and Back Again — Transformation Lessons from an Unexpected Journey. Previous: The Tookish Side. Next: Navigating Mirkwood — on holding the path when everyone wants a shortcut.

Tolkien gives Bilbo two inheritances. From his father’s side, the Baggins: respectable, predictable, suspicious of anything that might make you late for dinner. From his mother’s side, the Took: the streak of adventurousness that polite hobbit society pretends not to notice. The whole book turns on which side wins. The moment it shifts is wonderful: “Then something Tookish woke up inside him, and he wished to go and see the great mountains.”

Every organisation has the same two sides. The Baggins side keeps the lights on, follows the process, and protects what works. The Took side asks the awkward questions. Most companies say they want more Took. Their meeting culture rewards Baggins.

The hero is usually closest to the problem

The unlikely hero is rarely the senior consultant or the C-suite sponsor. It is almost always the person closest to the problem who dared to speak up — the one who keeps raising the concern everyone else has learned to talk around. The only real question is whether your organisation makes that daring cheap or expensive.

The Took I almost didn’t see

One of the people I am proudest of from my delivery years arrived through a company acquisition, with a modest title: service-desk team lead. On the org chart he was — I will be honest about the phrase that was used — a glorified team lead. Respectable, reliable, Baggins through and through.

Except he wasn’t. In the daily work I kept seeing flashes of something more: he cared about outcomes well beyond his own box, asked questions above his pay grade, and people followed him naturally. So I gave him real management responsibility — end-user computing and user services — and then the stretch that mattered. Most of his team sat in India. He was afraid of flying.

I sent him anyway — with support, and with the honest message that you cannot lead a team you have never sat with. Something Tookish woke up. He went, fell in love with his Indian team, and made hard people-decisions there that I am not sure I would have made better. He grew into a genuine manager — not because anyone taught him management, but because he was finally somewhere his potential had no alternative but to show up. Years later, we still value each other, and his growth remains one of the results I count first from that entire engagement.

A few things I look for in every engagement:

1. Who gets interrupted in meetings? The pattern is remarkably consistent. The people with the most direct knowledge of a problem often have the least airtime.
2. Who has already done unrequested homework? People who quietly map solutions to problems nobody assigned them are telling you where the real risks are. That work is free intelligence, and most organisations throw it away.
3. Whose warnings are in the minutes? Go back twelve months in your own meeting notes. The uncomfortable truth is that most crises were predicted by somebody — usually somebody junior.

This will only matter more as AI reshapes how teams work. The person who first notices that a model’s outputs are drifting, or that a workaround has quietly become the real process, is rarely the most senior in the room. Whether that signal travels upward is a question of culture, not technology.

Gandalf’s genius in The Hobbit isn’t fighting the dragon. It is seeing what the dwarves cannot: that the small, overlooked member of the party is exactly what the quest needs. That is a leadership skill, and it can be practised.

“There is a lot more in him than you guess, and a deal more than he has any idea of himself.”
— The Hobbit, Chapter 1

Part 2 of ten in There and Back Again — Transformation Lessons from an Unexpected Journey. Previous: The Unexpected Journey. Next: Riddles in the Dark — on the highest-stakes conversation of my consulting life.

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:

1. The fear is rational. People who resist a transformation usually understand the current system better than the people proposing the change. Respect that.
2. 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.
3. 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.