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:
- 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.
- 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.
- 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.
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