Tag: hobbit-lessons

Bilbo’s own title for his memoirs was “There and Back Again.” Not “How I Helped Kill a Dragon.” The destination gets second billing; the return gets equal weight with the adventure. Tolkien knew that coming home changed is its own chapter — and often the hardest one.

When Bilbo returns to the Shire, he finds his belongings being auctioned off and his reputation altered for good. He is no longer quite respectable. He has seen mountains, talked with a dragon, and can never fully explain any of it to neighbours who measure life in mealtimes. He is also — and this is the point — richer in every way that matters, and becomes a source of stories, perspective, and quiet wisdom for the people around him.

Coming back changed

I have felt a smaller version of that more than once. You go through a hard transformation — a client’s, or your own — and you come back carrying lessons that don’t always translate to people who stayed home. The temptation is to dial yourself back down to fit in again. The better path, I have found, is to stay changed but learn to tell the story in plain language: fewer frameworks, more “here is what went wrong and what it cost.” Hard-won wisdom is only worth something if you can hand it over in a currency the other person accepts. The challenge was never just going there. It is coming back again.

What forty years add up to

This series has been my own attempt at handing it over — ten scenes, ten true stories. Underneath them, when I look back across forty years, sit a small number of threads that turn out to have been the journey all along.

Systems should adapt to humans, not humans to the system. I have believed this since a school system in one country could not bend for our children and a school system in another could — it is why I live in Finland, and it is the test I now apply to every operating model and every AI rollout I meet.

Say the true thing plainly, before you are forced to. Every trust I have ever built — the smoking-corner platform strategy, union negotiations in two cultures, admitting a shared disaster-recovery gap out loud — rested on that one move.

Build the muscle before the fire. Every rescue in this series that looked like composure in the moment was, in truth, rehearsed years earlier.

Being right and being chosen are not the same thing. That lesson cost me twice, and I would not trade it away: it is what taught me that holding your own line matters more than winning the room.

And the most personal homecoming: when a health scare pulled me up short, I finally turned the same discipline on myself. I built what I call a faithfulness coach — a personal operating system with daily reflection, honest reviews, and an audit trail — that coaches me toward what I actually intend to do, rather than what the treadmill demands. Forty years of building systems for organisations, brought home to one human. Bilbo would have understood: the journey only counts once its wisdom lives in your own house.

Why this company is called BilboConsult

This post closes the series, so let me finally answer the question that started it.

I named my company after a hobbit because Bilbo is the most honest picture of the work I know. He is not the strongest member of the company, or the most senior. He is the one who goes into the tunnel alone — fighting the real battle in his own head before he ever sees the dragon. He asks naive questions, finds rough ways through, stays calm in the dark, values the right treasure over the big pile, and comes home changed but still himself — still fond of tea at four, still keeping the door open to unexpected company.

Forty years in IT transformation — across large global organisations, and now my own small consultancy in Helsinki — have convinced me that this is what the work really is. Not slaying dragons for clients. Walking with them: there, and back again, until the wisdom of the journey lives in their house rather than in my invoice.

Thank you for reading this far — through Mirkwood, the barrels, the riddles, and the mountain. The whole journey is linked below. And if you are standing at your own front door with a quest you didn’t ask for: I know the feeling. It is worth going.

“And he lived happily ever after to the end of his days.”
— The Hobbit, Chapter 19

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This was part 10 of ten in There and Back Again — Transformation Lessons from an Unexpected Journey, built on the advent calendar I posted on LinkedIn last December. All ten parts: https://bilboconsult.com/tag/hobbit-lessons/.

Here is a structural fact about The Hobbit that most readers forget: the company reaches the Lonely Mountain — the destination, the goal of the whole quest — with nearly a third of the book still to go. The dragon, the treasure, the thing they came for: achieved. And then come the hardest chapters. Lake-town burns. Armies march. Old alliances fracture over the spoils. Thorin, victorious, nearly destroys everything through what victory does to him.

Tolkien understood something that transformation programmes routinely get wrong. Reaching the mountain is not the end of the story. It is where the real story starts.

The battle after the party

I have watched this pattern play out more times than I can count. The technical migration succeeds. There is a go-live celebration with speeches, and the programme team begins to roll off. Mission, officially, accomplished.

Then, within a few months, the battle of five armies arrives. The retained organisation keeps working around the new processes instead of through them, because the old ways are comfortable and nobody is watching anymore. Managers who quietly opposed the model all along, sensing the sponsors have moved on, stop being quiet. New suppliers, measured on contracts written before reality arrived, fall into conflict over every gap between them. None of it appears on a risk register, because the programme that owned the risk register was disbanded at the party.

The unglamorous months after the celebration are where the business case is actually won or lost: renegotiating a supplier boundary, coaching managers who have never worked in the new model, making process adoption somebody’s real job with real consequences. It is far less exciting than the build. It is also where the value lives.

The decade after the decision

In the first post of this series I told the story of a contested platform strategy — moving a large financial-services group off an expensive proprietary Unix platform and onto Intel and Linux, around 2001. I told it there as a story about resistance. Here is the part I left out: winning the decision was the summit, and the summit turned out to be the beginning.

The strategy was agreed in 2001. The actual mountain came afterwards: a hard push to eliminate the old platform within eighteen months, then years of consolidation and virtualisation, wave after unglamorous wave of migrations, long after the strategic applause had faded. Nobody celebrates a migration in year three the way they celebrate a strategy paper in month one. But the value never lived in the decision. It lived in the decade of holding it.

And it held for ten years — through reorganisations, through new architects with new preferences, through my own moves into other roles. Not by luck: the sustaining had been designed in from the start. The decision had been derived together with the people who would have to run it, so no successor ever had an appetite for reversing it. Contested strategies that are imposed get reversed at the first change of the guard. This one outlasted several.

Somewhere in my archive is a photo from those years: my young daughter sitting on a decommissioned server box as we rolled it out of the data centre. That is what year three of a winning strategy actually looks like — a child on a box, a corridor, another migration weekend. Unglamorous, and the whole point.

The treasure is not the decision you win. It is what still stands a decade later — and that is decided in the years after the party, not at it.

What this means for your transformation

Plan past the mountain. The standard transformation budget spends almost everything getting to go-live and almost nothing on the eighteen months after — which is precisely backwards, because that is where the value is decided.

A few rules I now treat as non-negotiable:

1. Fund the period after go-live as a phase, not a contingency. Adoption, stabilisation, and supplier tuning are work packages with owners — not things that happen on their own.
2. Keep sponsors visibly engaged after the party. Resistance waits for the sponsors’ eyes to move. The cheapest counter-measure is for them not to move.
3. Measure adoption, not just deployment. “The system is live” and “people work the new way” are different claims, usually about a year apart.

The summit is not the destination. Sustainable change is. Bilbo’s quest didn’t end when Smaug died. Neither does yours.

“So comes snow after fire, and even dragons have their ending!”
— The Hobbit, Chapter 18

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Part 9 of ten in There and Back Again — Transformation Lessons from an Unexpected Journey. Previous: The Arkenstone. Next, the finale: There and Back Again — on bringing the journey’s wisdom home.

Under the Lonely Mountain lies a hoard beyond counting — gold, gems, mithril. And in the middle of it, one stone unlike the rest: the Arkenstone, the Heart of the Mountain. Thorin would trade any amount of gold for it. The tragedy of the book’s final act is that he briefly forgets the difference between the treasure and the Treasure, and nearly loses everything over the pile.

Organisations make Thorin’s mistake constantly. Usually it happens in the middle of a cost programme.

The cut that could have broken the team

I once led a delivery organisation of around two thousand people with a hard mandate: improve the margin, which meant taking ten per cent out of the cost base. There is no gentle version of that. It meant roles. It meant union negotiations. It meant a long run of conversations nobody wants to have.

The easy way — the spreadsheet way — would have treated every part of the organisation as interchangeable gold, to be shaved evenly and quickly. I was fairly sure that would hit the number and quietly destroy the thing underneath it: the trust and motivation of the people who would remain. That was the Arkenstone. Lose it and you make the saving while wrecking the capability that makes the organisation worth anything at all.

So we did it the harder way. I took the team into the real picture — the actual financials, the actual constraints, the actual options — rather than managing the message. I worked directly with the union representatives, who had good ideas of their own. We were honest about what was happening and why. The reductions still went ahead. They were real, and they were painful. But there was no industrial action, the team stayed aligned, and we met the targets.

Anyone can put a cost reduction into a spreadsheet and take people out. Doing it without shattering the trust of the people who stay — that is the Arkenstone, and no saving buys it back once it is gone.

What this means for your transformation

Before any major change, the question that matters most is rarely asked out loud: which of our assets is the Arkenstone — the one thing that, if lost, cannot be bought back? A few tests help:

1. What could you not rebuild? Most capabilities can be re-hired or re-tooled. Trust, culture, and the knowledge in people’s heads cannot — not on any useful timescale.
2. What does the change tempt you to treat as interchangeable? Treating everything “fairly” and evenly is exactly how the Arkenstone ends up in the general pile. Fairness and value are not the same test.
3. What survives the spreadsheet but not the human cost? A target can be hit on paper while the thing that made the numbers possible walks out the door.

The AI version of this question is arriving in every boardroom now: which judgments must stay human? Automating the routine is gold-pile work — do it. But automating away the capability, the trust, or the judgement your organisation actually runs on is selling the Arkenstone by accident, and no efficiency gain buys it back.

“If more of us valued food and cheer and song above hoarded gold, it would be a merrier world.”
— The Hobbit, Chapter 18

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Part 8 of ten in There and Back Again — Transformation Lessons from an Unexpected Journey. Previous: The Burglar’s Role. Next: The Lonely Mountain — on why reaching the goal is where the hardest part begins.

There is a detail in The Hobbit that is easy to read past. Thorin’s company doesn’t recruit Bilbo despite him not being a dwarf. They recruit him because he isn’t one. Gandalf’s logic is explicit: the quest needs someone the dragon won’t recognise — someone who doesn’t smell like a dwarf, doesn’t think like one, and can therefore go where dwarves cannot.

That is the most honest job description of consulting I know. Clients don’t need a fourteenth dwarf. They already have thirteen excellent dwarves. They need a burglar.

The naive question

My most useful contribution in the first weeks of an engagement is often embarrassingly simple: I ask naive questions. “Why do you need three approval layers for this?” “What value does this weekly meeting actually create?” The answers are revealing because the insiders can no longer see them — the approval layer that solved a quality problem years ago and was never removed; the standing meeting whose original programme ended long before the calendar invite did.

None of this requires brilliance. It requires not belonging. The insiders can’t ask these questions. Partly the answers have become invisible to them, like furniture you have stopped noticing. Partly asking would be politically awkward. The burglar has no furniture and no politics. That is the whole job.

The burglar between two kingdoms

The burglar’s position — inside the company, but not of it — is one I have held literally. At a global technology company, the central architecture team sat in the headquarters country and the biggest operations site sat in another, and the two were at war. The site felt looked down on, with some justification; the centre could be startlingly condescending about it. Years of mutual contempt had hardened into the furniture.

I belonged to neither camp. I was not from the headquarters country, and I was not a local at the site either. I was simply the architect assigned to operations — structurally in the middle, smelling like neither a dwarf nor an elf. That turned out to be the entire value. I spent time with the site team and they felt genuinely understood, perhaps for the first time in years. The architecture side, meanwhile, treated me as one of their own with something worth hearing. Both sides trusted me before I had any mandate over either.

When the reorganisation came, that bridge was the explicit reason I was asked to take over the global computing operations. And the endorsement I still value most came from the site’s most critical architect — the hardest sceptic in the building, won over argument by argument — who later wrote that my departure left “a Martin-shaped hole.” A sceptic’s endorsement is the only kind that cannot be bought.

Nobody ever wrote “burglar” on my contract. But it was the burglar’s position — trusted precisely because I belonged to neither side — that did the work.

What this means for your transformation

The outsider’s view is the insider’s blind spot. Well-run organisations build the burglar role in on purpose, rather than waiting for a crisis:

1. Protect the naive question. When a newcomer asks “why do we do this?”, the answer “that’s how we’ve always done it” should be treated as a finding, not an explanation.
2. Rotate fresh eyes through old processes. The burglar doesn’t have to be external. Anyone far enough from a process can see its furniture — if they are given permission to say so out loud.
3. Don’t ask insiders to audit themselves. Not because they are dishonest, but because expertise and blindness are the same adaptation. Knowing a system deeply means no longer seeing it.

This is exactly why boards are reaching for outside advisors on AI adoption. The internal teams know the technology better than any advisor will. What they cannot supply is distance — the burglar’s view of which approval layers, which habits, and which comfortable assumptions won’t survive contact with the dragon.

“I come from under the hill, and under the hills and over the hills my paths led. And through the air, I am he that walks unseen.”
— The Hobbit, Chapter 12

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Part 7 of ten in There and Back Again — Transformation Lessons from an Unexpected Journey. Previous: Sting Glows Blue. Next: The Arkenstone — on knowing which treasure is irreplaceable.

Bilbo’s sword Sting has one magical property: it glows blue when orcs are near. Not when they attack — when they approach. The whole value is in the gap between the glow and the danger. Bilbo gets his warning while there is still time to act.

Most transformation programmes have dashboards full of indicators that report problems after they arrive. Red status reports are not early warnings. They are obituaries. By the time a milestone officially slips, the causes are weeks old.

Rehearsing the worst day before it comes

Early in the 2000s I was responsible for IT security and continuity at a large financial-services group — before anyone used the word CISO. We survived a real worm attack, and the organisation learned plenty from it. But the work I still think about is what we did before anything happened: we rehearsed. Full crisis simulations, up to a scenario in which a plane crashes on headquarters. Managers convened offsite, stood up a provisional office, and worked the real questions under time pressure — who is dead, who may talk to the press, who must not. A colleague played the press and needled everyone relentlessly. It was uncomfortable by design.

Years later, in a different organisation entirely — a large IT services provider — I built a SWAT function for rescuing troubled projects. People ask which crisis triggered it. The honest answer: none. I built it because I had learned that the muscle has to exist before the fire.

And the pattern proved itself a third time, years later again and in yet another setting. When a real intrusion forced the full shutdown and rebuild of a client’s data centre — as political and high-stakes as incidents get — the response was calm and coordinated, decisive and focused, run by a team whose trust had been built long before the alarm sounded. Three different companies, across three decades of my career, and the same principle every time: every crisis I have seen managed well was won in advance. Sting is no use if you only go looking for a sword once the orcs arrive.

Sting metrics

Readiness is one half. The other half is knowing when to reach for it. Over the years I have come to watch a set of signals I think of as Sting metrics. They come not from the project plan, but from how the team is actually behaving:

• A sudden drop in team velocity, before anyone has reported a blocker.
• Rising email volume between two stakeholder groups. People CC-ing for self-protection is one of the most reliable conflict signals there is.
• Status reports arriving later, or growing vaguer.
• Meetings that used to produce decisions starting to produce follow-up meetings instead.

None of these appear on a conventional RAG dashboard. All of them are measurable. And, like Sting, they glow blue while there is still time to act — usually weeks before the problem shows up in red. The hard part is never collecting them. It is taking them seriously while the official dashboard is still comfortably green.

What this means for your transformation — and your AI adoption

The principle is simple: instrument behaviour, not just deliverables. Deliverables lag. Behaviour leads.

This matters double for AI right now. Boards adopting AI are building governance dashboards full of lagging indicators: incidents, audit findings, compliance attestations. All necessary, all obituaries. The governance that actually protects you watches the leading signals: which teams have quietly started using unapproved tools, where staff are overriding model outputs (or worse, never questioning them), which decisions have drifted from human to machine without anyone deciding they should. That is Sting work, and it is governance craft, not technology.

The best leaders I have worked with share one trait: they sense danger before it strikes, and they act on the glow rather than waiting for proof. Proof always arrives. It just arrives too late to be useful.

“Never laugh at live dragons.”
— The Hobbit, Chapter 12

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Part 6 of ten in There and Back Again — Transformation Lessons from an Unexpected Journey. Previous: Barrel Riding. Next: The Burglar’s Role — on why the outsider sees what insiders cannot.

Bilbo’s escape from the Elvenking’s halls is not elegant. He packs the dwarves into empty wine barrels and floats them down a cold underground river — bruised, half-drowned, thoroughly undignified. It is also the only plan that works. The guarded gate is impossible. The wild river is merely unpleasant.

I have a soft spot for this chapter, because the most instructive delivery lesson of my career looked, from the outside, exactly like a barrel ride.

The lab that outperformed my whole organisation

At a global technology company, I ran a formal 24/7 production organisation — hundreds of people, proper service management, SLAs, escalation chains, the whole guarded-gate apparatus. Next to it sat a lab of five or six people. Whiteboards, broad skills, their own tooling, direct lines into the business. Officially an experiment shop. Unofficially, a wine barrel.

I got curious and dug into the numbers. The lab’s workload was roughly equal to my entire formal production. Many of its “experimental” systems were in fact business-critical production — running with no formal SLAs at all, just expectations that were consistently kept. And it was doing all of this far more efficiently than the formal organisation.

I started calling it an official form of shadow IT, and I meant it as admiration. What made it work was exactly what the formal apparatus had been designed to replace: direct customer connection, and pragmatic, skilled people who owned the outcome end to end. The elves guarded the gate; the barrels floated the goods downriver anyway — undignified, unapproved, and effective.

The uncomfortable conclusion was not “abolish the SLAs”. At scale you need the gate. The conclusion was that when the informal channel consistently outperforms the formal one, that is not a compliance problem — it is information about where value is actually created. Most organisations suppress that information. Very few measure it.

What this means for your transformation

Unconventional is not the same as reckless. The difference is discipline:

1. Judge routes by outcomes, not by respectability. The lab looked unserious — whiteboards, no SLAs, no steering committee — and it outperformed the formal machine. If you only trust methods that look like governance, you will systematically overpay for elegance.
2. Keep the roughness honest. The lab worked because expectations were kept, not because rules were absent. Controlled roughness stays controlled only while the trade — closeness and speed in exchange for formality — is named out loud and its promises are met.
3. Measure the informal channel instead of suppressing it. Somewhere in your organisation the barrels are already floating past the guarded gate. The only real choice is whether you learn from that or punish it.

The same tension is everywhere in AI adoption now: the exhaustive evaluation that finishes after the opportunity has passed, against the faster, rougher, transparent approach that fits the real clock. Rigour matters. But rigour that arrives too late is just a slower way to lose.

Tolkien’s joke in the chapter is that the dwarves complain bitterly about the indignity, having just been saved by it. Steering committees do the same. That is fine. They don’t have to enjoy the barrels. They have to get to Lake-town.

“There is nothing like looking, if you want to find something. You certainly usually find something, if you look, but it is not always quite the something you were after.”
— The Hobbit, Chapter 4

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Part 5 of ten in There and Back Again — Transformation Lessons from an Unexpected Journey. Previous: Navigating Mirkwood. Next: Sting Glows Blue — on the early-warning signals most programmes ignore.

Before the company enters Mirkwood, Gandalf gives one instruction and then — infuriatingly — leaves: “Don’t leave the path.” Inside the forest there is no light and no sense of progress, and the path seems pointless. Off to the side, there are glimpses of fires and feasting. Every instinct says the shortcut is right there. The dwarves take it, and it nearly kills them all.

Every transformation programme I have worked on has a Mirkwood phase. It usually arrives a few months in. The kickoff energy is gone, the end state is not yet visible, and the disciplined path — the governance, the sequencing, the boring weekly rhythm — starts to feel like bureaucracy. That is exactly when someone senior proposes a shortcut.

Why the shortcut is so tempting — and so dangerous

The pressure is always understandable. The board wants visible results, and in the Mirkwood phase the value of the disciplined approach is largely invisible. Holding the line is uncomfortable for everyone, the consultant included. There are weeks when you ask yourself whether you are defending good method or just your own plan. But I have watched enough rushed transformations collapse into firefighting to trust the pattern. The teams that leave the path to chase the fires are the ones who end up lost among the spiders. Slower-looking in month three is very often sustainably faster by month twelve.

The forest of a hundred service levels

The deepest Mirkwood of my career was a large account in genuine crisis. Roughly fifteen priority-one fires a year. Customer managers escalating past everyone to our chief executive. A contract with more than a hundred service levels — as complex and difficult as contracts get — and penalties running past a million euros a year. Everyone in that forest was chasing the fires off to the side of the path: the heroic quick fix, the special task force of the week, the next escalation call.

We stopped chasing and went back to the path. Rebuild the delivery team properly. Spend unglamorous time with the client. Work through the backlog of open penalty negotiations one by one. Hold the boring weekly rhythm. Nothing about it felt fast, and for months it barely felt like progress at all. But the fires became rarer, the penalties fell to a fraction of what they had been, the relationship steadied, and the account came out of crisis mode for good. The team that walked out of that forest was stronger than the one that walked in — and stayed together long after.

And one honest counterpoint, because this series does not do fairy-tale endings. At a different account — one that was never in crisis; the service was good and got measurably better while I was there — we still lost the renewal. Not for anything in the current delivery, but for a badly handled transition years before my time, which the business had never forgotten. The path does not guarantee the treasure. Trust keeps its own calendar, and it is longer than yours.

Same discipline either way. Mirkwood never promises you the mountain — it only promises that leaving the path costs more. And the discipline decides what you walk out with even when the ending is not yours to choose: in the one case a turnaround, in the other a loss that closed as a clean commercial decision instead of a collapse.

What this means for your transformation

The Mirkwood phase is not a sign that something is wrong. It is a predictable stage of any long change, and knowing that changes how you lead through it.

1. Name it in advance. At kickoff I now tell clients plainly: around month three or four, this will feel pointless, and someone will propose a shortcut. When it arrives on schedule, the team recognises it instead of panicking.
2. Distinguish the path from the furniture. Holding the line doesn’t mean refusing all change. The discipline worth defending is the sequencing and the decision structure. Almost everything else can flex.
3. Make progress visible in the dark. The deepest Mirkwood despair comes from invisible progress. Find the small, concrete markers — decisions made, risks retired — and report them relentlessly.

The enchanted river in Mirkwood makes those who drink from it forget their journey. Corporate Mirkwood does the same: teams forget why the transformation started. Part of the consultant’s job is simply to remember out loud.

“Go back? No good at all! Go sideways? Impossible! Go forward? Only thing to do! On we go!”
— The Hobbit, Chapter 5

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Part 4 of ten in There and Back Again — Transformation Lessons from an Unexpected Journey. Previous: Riddles in the Dark. Next: Barrel Riding — on the unconventional route nobody approves of until it works.

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

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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

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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

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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.