A Story About Leadership, Reading Lists and the Question Beneath the Question
Why “what are the best books for leaders?” is the wrong question is something Nadia discovered only after asking it.
Every season the lists arrive.
The ten books every leader must read.
The essential reading for every new manager.
Somebody’s definitive ranking.
For more than twenty years I’ve used stories as working tools:
A novel to help someone understand a colleague they can’t read.
A character’s dilemma to untangle their own .
And I’ve helped people tell their own unique stories: stories that speak their truth.
It’s the foundation everything at School of WorkLife is built on: the conviction that stories and literature are our most powerful mechanism for teaching, learning, and communicating our thinking and ideas.
So you might expect me to have a best books list of my own.
I don’t, I never had, and I never will. Not because the books on those lists are bad — many are excellent — but because the question they answer is the wrong question.
Rankings assume readers are interchangeable.
They’re not.
Different books are right for different people, and different books are right for the same person at different times in their WorkLife.
The book that leaves you unmoved this year may be the one that reaches you in five years.
The best way I know to show you what I mean is through a story. Nadia is a character I created — her situation will be familiar to anyone who has ever tried to read their way into becoming a better leader.
Nadia
Nadia had been a team lead at an engineering consultancy for eight months — long enough for the shine to wear off, long enough to notice that the parts of the job that came hardest weren’t technical.
A difficult conversation she kept postponing.
A team member going quiet in meetings.
The creeping sense that she was managing tasks and missing people.
So she did what she always did with a problem: she researched it.
She started with the real question — how do I become a better leader? — and read what came back.
Listen actively.
Lead with integrity.
Never stop learning.
She kept searching.
And the results came with questions of their own — headlines asking what makes a good leader, what the best leaders do differently, what are the best books for leaders.
That last one felt like somewhere to start.
She built her list from the lists, ordered the top three, and set herself a schedule.
Nadia was nothing if not disciplined.
She read the first book in a week, highlighter in hand.
She read the second in ten days.
And the third over a fortnight of commutes.
Good books — she could see why people recommended them.
Her copies filled with underlinings, her notebook with frameworks.
And on Monday morning, in the meeting where her team member went quiet again, none of it came with her.
She sat across from that silence with three books’ worth of leadership thinking somewhere in her head — and nothing in her hands.
The books had answered a hundred questions.
Just not hers.
Not this person, this silence, this unease she couldn’t yet name.
Anna
She said as much to her mentor, Anna, over coffee — half-joking, mostly not. “I’m three books into becoming a better leader, and I don’t think it’s working.”
Anna didn’t recommend a fourth book.
She asked a question instead.
“What are you carrying right now that you haven’t said out loud?”
Nadia started to answer the way she’d framed it for weeks — that she needed to become a better leader. Stopped. And heard herself say: “I think someone on my team is disappearing in front of me, and I don’t know how to reach her without making it worse.”
“Then that’s what you’re reading for,” Anna said. “You don’t need the best book. You need the book that meets that.”
The Books That Met
Something reordered itself.
Because the books that had genuinely changed Nadia’s working life — she could name them.
A Man Called Ove, given to her by a friend the month she was made redundant, when what she was carrying was the fear that the setback said something final about her. A novel about a man whose work is taken from him, who believes his usefulness has ended — and is proved wrong by degrees. It met that fear and quietly dismantled it.
Stoner, found by accident the year she’d talked herself out of a role she wanted, showing her — through a man who accepts a smaller life at every turning point where he might have asked for more — what a lifetime of not asking quietly costs.
Each had arrived when she was carrying a question it happened to meet.
The wisdom had been in the books all along. But it had needed the right timing, and the meeting.
The lists had failed her because a ranking can’t know what you’re carrying. It doesn’t ask.
So this time, Nadia went looking differently.
Not for the best book — for a story about someone disappearing in plain sight, about the human experience underneath withdrawn behaviour.
She asked a colleague who read widely — not “what should I read?” but “I’m trying to understand someone who’s retreating — is there a story about that?”
The colleague didn’t hesitate: Eleanor Oliphant Is Completely Fine. Not a leadership book — there isn’t a management framework in it. A novel about a woman whose “completely fine” conceals how much she is struggling, and what patient, unforced attention makes possible.
It met her.
The Change
What changed in Monday’s meeting afterwards wasn’t a framework.
When the silence came, Nadia didn’t fill it, and she didn’t push a question across the table in front of everyone.
She let the meeting end, and then — the small thing three hundred pages had taught her — she didn’t let the moment end with it.
“I’m walking down for a coffee. Come with me?” No agenda, no “is everything okay,” no meeting-room. Just somewhere easier to talk than a table full of colleagues.
It wasn’t a breakthrough. It was ten minutes, most of it about nothing.
But it was the first time in weeks her colleague had talked to her without being asked a question — and it was somewhere to build from.
Eleanor Oliphant hadn’t given Nadia a technique.
It had shown her how much a person’s composure can conceal, and that what reaches someone isn’t scrutiny — it’s unforced company, offered without a reason attached.
The Lesson
What are the best books for leaders? assumes the answer lives in the books.
It doesn’t. It lives in the meeting between a book and what a particular reader is carrying at a particular time.
Different books are right for different people.
Different books are right for the same person at different times.
Any book — this is the quiet truth the rankings can’t accommodate — any book can be the answer when it meets the right question.
No one can hand you the list.
But you can learn to ask what the list never asks.
Nadia’s path shows the way, and it’s yours to walk:
The Steps
Name what you’re carrying. Before choosing your next book, write down — plainly, for no one but yourself — what you’re navigating in your WorkLife right now that you haven’t yet said out loud. Not the general answer; the thing underneath it. Nadia’s had been “I need to be a better leader.” Her real one was a person disappearing in front of her.
Revisit your past meetings. Recall the books that stayed with you longer than expected, and ask what you were carrying when each one found you. Nadia’s were a grumpy widower’s second life and a quiet man’s unclaimed one — nothing a list would pair, everything her moments required. Understanding how your past meetings worked teaches you to recognise the next one.
Choose by question, not by ranking. Take what you named and seek the story that walks toward it — fiction or non-fiction, on a list or nowhere near one. Ask the readers around you Nadia’s way: not “what’s good?” but “I’m trying to understand this — is there a story about it?” Then notice how differently you read a book you chose this way.
The Method
This is the work at School of WorkLife — in every story lesson, programme, and live class: pairing the story with the question it’s meant to meet. The best book for the situation, at the time it can reach you. It’s built on a conviction more than twenty years of practice has deepened: that stories and literature are our most powerful mechanism for developing the wisdom to navigate working life.
Work With Me: Commissioned learning resources, speaking engagements, and organisational partnerships.
Support This Work: Your support makes a difference and helps me to continue creating resources that are accessible to everyone. Thank you. Carmel
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