John Caswell, Confidently Creative?
Four decades in rooms where organisations try to solve hard problems, and what most of them get wrong.
‘Confidently Creative?’ is a joint series created with Sven Brodmerkel (PhD). Together we are talking to original thinkers across different fields about creative confidence: what it is, why so few people act on it, and what makes conditions either conducive or hostile to it.
Our first guest is John Caswell.
John calls himself Head of Crayons. At Group Partners, the visual strategy consultancy he founded in 2001, that title is not whimsical. It is a signal: drawing and storifying a challenge achieves something that verbal discussion cannot.
He has been proving this for over four decades. He began his career at Acorn Computer in Cambridge, during the BBC Micro launch. He built a marketing agency that won awards for Benetton, SAP and IBM, sold it to WPP in 1996, and went on to create Structured Visual Thinking™ and Framework Science™. His conviction, running through all of it: organisations fail not because they lack ideas, but because they design conditions that prevent those ideas from ever being said aloud.
He writes All In Our Imagination on Substack.
Q1. Is creativity something you do or is creative something you are?
Both are correct. But the question raises a bugbear. The ‘something you do’ lobby is what gets us process frameworks, ideation sprints, and post-it notes arranged in herringbone patterns on glass walls. It’s characterised as a deployable skill. A toolkit. Something you switch on as you go to work. It’s the least interesting part.
Something you are is closer to the truth. Not the ‘creative person’ title that ends up on a LinkedIn profile. I mean the frequency you were born tuned to. And that society has a knack of beating out of you in favour of conformity.
My dad was a Draughtsman, an engineer, an avid fly fisherman and a water bailiff. As a small child I watched him wade chest-deep in a chalk stream with a scythe, clearing reeds, oxygenating the water. Much later I realised one of many lessons. I saw how the world actually works and that things left to stagnate die, that keeping something alive requires the willingness to get wet, to cut back, to disturb the surface.
Creativity wasn’t just a tool. It was the physics of that river and a tremendous lesson in solving any problem in life. If you allow it, creativity runs through you, whether or not you wish to label it or how you wish to label it. I guess another question is what made folk forget that, and what will it take to get them to remember.
Q2. Was there a moment when you first felt creatively confident or a moment when you realised you hadn’t been?
This is an interesting question. I was confident when I was a child with a sketchbook, colouring in, using pencils, paint, and a pair of scissors for chopping things up.
I would draw pictures of boxes. After a while, I was showing my friends how, when they asked me how come I can draw and they couldn’t, to teach them how to draw a box. I couldn’t stop shading the box to make it look real on the page. I couldn’t stop wanting to give everyone the skill and the capability to do it.
I was very lucky. I went to a school where they saw that and encouraged it. When I left that school and came into the real world, my confidence was shattered by art school. My confidence was shattered because they tried to teach me creativity as if it were maths. There was something formulaic and institutional about it that I absolutely couldn’t bear. The illusions of my definition of creativity were in bits.
I became a DJ. My confidence was restored by choosing the right music to keep the crowds dancing.
My confidence lifted again as I realised that the kinds of things I learned would help me in my first real job. I would start drawing again on the walls to help people comprehend what they were trying to say, to help them say it better.
I used that confidence to start my own business. I could use it with clients to get better answers for them and greater outcomes.
In those days, the use of the word creative was what I did. I created ads and campaigns and brands and stories. A narrow definition to be sure. I sold into a creative holding company. It wasn’t creative. It was a financial company.
My confidence was shattered again.
I realised that some clients couldn’t appreciate the value of creativity as a way to achieve genuine performance. They did everything they could to avoid the truth that I could see, but they chose not to.
That was then. I’m confident again now because I start each day with a clean sheet of paper.
Q3. How do you distinguish creative confidence from creative ability?
Creative ability is the raw material, the capacity everyone is born with. Creative confidence is the willingness to deploy it. They are not the same thing, and they are not guaranteed to travel together.
Everyone is born with creativity. The acid test is how much permission they’re given to exercise the muscle. And once that muscle is exercised and allowed to flourish, in a culture where it’s okay to make mistakes, where it’s allowed to make a mess and break things, where experimentation is genuinely welcome, creative ability can only grow.
Nobody ever spotted famous creativity at birth. But we know what happens when the conditions exist. Creative confidence is the result.
Without conditions that make it safe to put something half-formed into the world (without fear of it being used against you) you can definitely have extraordinary ability and zero confidence.
The history of every organisation that has ever bored itself to death is largely the story of those people sitting quietly in meetings, knowing they’re never going to feel quite safe enough to say anything. Creativity denied.
Q4. Can you walk us through a specific moment when you had an idea and chose not to share it? What was the context? And what role did the environment play?
Japan. A long while back. A large pharmaceutical organisation, a third party who had brought me in, and a conversation that was heading steadily in the wrong direction.
I was doing what I always do, working visually, collaboratively, in a way that was genuinely unusual in that context and in that era. Highly physical. Highly different from the way that room expected a meeting to be run. I was running side by side with my partner but somewhere in the middle of it, I could see clearly what the client actually needed. A reframe. A different conversation entirely. One that would have cut through everything and landed somewhere useful.
I didn’t say it.
Because saying it would have flown directly in the face of the colleague who had brought me in. It would have been obvious to everyone present that I was repositioning the entire conversation, and in doing so, I would have undermined him in front of his own client. He could have lost the business. I chose not to do that.
Looking back, this was totally my fault. And a big error not to have done the right thing for the client at the expense of someone intent on not solving the real problem.
It was the first time I’d been in that situation and I hadn’t set the rules of the engagement clearly enough beforehand. Now I do.
Before any collaboration, I make it explicit: I may well see things differently, I may push in a direction you don’t expect, and that needs to be acceptable to everyone in the room before we start. In this case it wasn’t, in any case over the weeks that followed it became clear we wouldn’t work together again.
The environment? It played no role. The room didn’t suppress the idea. I did.
Q5. What are the signs that creative leadership is absent and what can get in its way?
Creative leadership is absent when whoever is being creative has ignored the reason why creativity was required in the first place.
The solution, the reframe, the suggested strategy - however brilliant in isolation - bears no relation to what was actually needed.
What definitely gets in the way in a corporate environment is the absence of values, principles, and contextual understanding: the things that keep creative energy pointed at the right problem rather than simply an interesting one.
Which raises the deeper point for me. In the purest sense, true creativity doesn’t require leadership at all. What it requires is experience - the hard-won internal understanding of why and how creative thinking should be deployed in a specific situation. And that could be to wander through a forest.
This is what I think of as ingenuity - the conjoining of the words creativity and innovation. Not creativity as self-expression, but creativity as the art of using what’s already lying around, bringing disparate things together until a problem disappears, or until the sum of the parts becomes something greater than its individual components.
That is craft. And craft comes from experience, not from a leadership model.
Q6. Think of someone you’ve helped become more creatively confident. What did you actually do and what did you deliberately not do?
I didn’t start out by trying to help them become more creatively confident. That wasn’t the framing and it wasn’t the goal. I think creativity is an output of curiosity, passion, determination, and the desire to understand how things work - and how the best answer is phrased or achieved. The moment you start calling it creativity, you’ve already made it harder.
I’m thinking of a senior leader I worked with over several months. Intelligent, experienced, capable, completely convinced that creativity was something other people did.
My job (in my own mind) wasn’t to fix that belief. It was to make it irrelevant.
What I actually did was ask questions. To make the familiar strange again. And then I got them to draw. Not drawing as art. Drawing as thinking made visible. The moment someone externalises an idea on a surface rather than describing it to present, something shifts. They stop performing and start exploring.
What I deliberately didn’t do was label any of it. I didn’t say this is the creative part. I didn’t frame it as a skill to develop. The more you explain creativity as a specific thing that needs to be achieved over time, the more it becomes a mountain, and most people will look for a way around rather than up it.
Which is exactly what’s happening now. People are defaulting to AI to produce answers they would never have reached themselves - skipping the curiosity, the wrestle, the determination that would have made the answer genuinely theirs.
The output just arrives. The thinking never happened. And the confidence that comes from having genuinely worked something out? Gone before it ever had a chance.
Q7. To what extent is creative thinking domain-specific?
Creative thinking is not domain specific at all.
Q8. What’s the relationship between creative thinking and being wrong in public? Can you have one without a tolerance for the other? If so, what can you do to become more tolerant/resilient?
The question assumes resilience is the desired outcome. I’m not sure it is. I think it goes deeper than that, to motivation and intent.
If your motivation is always to be seen as right, then being wrong in public is a catastrophe. It undermines everything.
You’ll stay quiet, you’ll wait until the idea is airtight before you let it anywhere near anyone. At which point it’s too polished to be dangerous and too safe to be interesting.
But if your motivation is a genuine desire to find the best answer, to make something work that currently doesn’t, then being publicly wrong is just information. Expensive or uncomfortable sometimes. But useful. It tells you something. It moves you forward.
This is why I don’t think you can build tolerance for being wrong in public by working on resilience directly. You build it by getting clearer on why you’re in the middle of the challenge. If you’re there to protect a position, no amount of resilience training will save you. If you’re there because you care about the outcome more than the appearance of it, being wrong stops being the threat and starts being part of the process.
As a DJ you play the wrong record and the floor tells you immediately. There’s no ambiguity and no appeal. You adjust and try again. The DJ who can’t tolerate that feedback loop doesn’t last long, not because they lack resilience, but because they made a mistake, didn’t read the energy or were playing for themselves rather than the room.
Q9. What role does AI play in your creative endeavours? How does it affect your creative process and agency?
I use AI(s) rather like an increasing number of people. That is by using my imagination throughout if I can. I have an idea, write as much of it down as I can, live with it, reflect on it, sit with it, improve it, get it as far as I can. If i’m comfortable with it, then that’s good. No AI.
But summarising and research is well done by AI. Business documents and proposals, pretty much the core of it is done by hand and my own imagination, but I use AI to do aspects of it that are a time suck.
AI helps me riff with myself. I imagine I’m a more sophisticated user by now, having been on AI since it first became widely available. I’ve trained it extensively with my own nuances and my own versions and definitions of my skills, my own likes and dislikes, so that it knows me better than any other co-partner.
As a creative person from both an agency and consulting perspective now preoccupied with solving complex problems, I need a partner to help me avoid driving over a cliff or getting too close to see the bigger picture.
AI is a critical friend that’s prepared to tell me something is rubbish or I’ve disappeared down a rabbit hole. I use AI, like a lot of other people, to summarise, research, and identify dimensions that I just may have missed.
It’s rather like having a conversation with someone I’ve come to trust and respect over time. It affects my creative process in very positive ways, and a lot of the time I just ignore the response because it’s my judgement that makes the difference. I will never use it if it starts replacing the areas where my imagination is being bypassed.
There’s a seagull sitting on a fence.
No AI was used writing any of this.
Q10. What do you know now about building creative capability that you wish you’d understood years ago?
This is a personal journey so it will be unique to each individual. Someone bought me juggling balls as a present. Leather things. Fine items they were. Great to hold but the juggling bit was frustrating as hell.
There was a small diagram that gave me the instructions. They were more frustrating as they were extremely simple. And like all instructions you felt they were aimed at other people.
After several hours of immense unenjoyment, I sat and read them one more time. I finally noticed a small line running up the side of the diagram, the typeface was tiny, that said something like: if you can’t do it, don’t worry, go to sleep, and in the morning you will be able to juggle.
Well, blow me down.
The mind is an incredible thing. You could argue it doesn’t need us. I wish I had learned far earlier that if you have patience, then your mind is there for you. You can go and do something else. It won’t be forgotten. Do as much as you can to spark that creativity in real time but then stop. Forget it. Go for that walk. Listen to music or a podcast. Sleep.
As long as you are pushing that imagination all over the place it will spring back when you are least expecting it and you will be juggling.
Those juggling balls taught me as much about building creative capability than any workshop, framework, or methodology I’ve either attended or delivered since.
Creative capability isn’t something you install. It’s something you exercise or, at worst, have to unblock.
I wish I’d understood earlier the value of the pause. The deliberate act of sitting with something unresolved, of letting the not-knowing do its work before the answer is ready to appear. I was in too much of a hurry for too long.
Q11. Do you have a ‘creative hero’? If so, what makes this person special?
I probably don’t.
My list of people I think are special is enormous. Countless heroes among them. I’ve always thought creative people are special and have looked to them for inspiration in every field. In every sector, in every industry, you can name people who didn’t give up until they had broken the problem into pieces and solved incredible puzzles.
Heroic acts everywhere - from Jobs to Einstein, Gilmour to Hemingway.
But my Dad was the most powerful proxy for all of it. He gave me the conditions to dream. He made it safe for me to have an imagination. He drew aero engines on big drawing boards and would point to a plane in the sky and explain that’s why.
I can list great guitarists, lyricists, producers, bands that have accompanied me my entire life. Artists, poets, writers. Architects, scientists, physicists, philosophers. They’ve all made me dream. Dream that everything is possible.
I feel the opposite about politicians and those who own the story. They don’t care about our imaginations or our creativity - and are perfectly happy to serve us the opposite, because creativity is deeply dangerous for them.
Which is why the comics, the satirists, and the thousand scriptwriters somewhere deep in a tsunami of new theatre and film give me such hope.
They will soon be a new addition to my menagerie of heroes.
Q12. If you could recommend a book or another relevant source on creativity, which one would it be?
My instinct is to resist recommending a book about creativity.
But I will.
You will have heard this before, so this is a little predictable. A lot of them are part of the problem; they package the thing into a process, a toolkit, a set of steps.
They make it into something you achieve rather than something you release. If you’ve read this far, you’ll know that’s precisely what I’ve spent these answers arguing against.
So instead, try Ways of Seeing by John Berger. Probably the only book I’ve properly read twice.
Written in 1972, originally to accompany a BBC television series, it is not, on the surface, about creativity at all. It’s about how we look at things. What we see and don’t see. What our assumptions, our conditioning, and our cultural context do to the act of perception before we’ve even begun to think.
Which is everything.
Because you cannot think creatively about something you haven’t learned to look at properly first. The logical structures, the drawings, the walls, the markers - everything I’ve spent my career doing - starts here.
Not with the idea but with the quality of attention brought to what’s actually in front of you. Berger’s book is short, deliberately visual, occasionally uncomfortable, and completely free of methodology. It will not teach you how to be creative. It will make you suspicious of everything you thought you could already see.
Which, in my experience, is exactly where the interesting thinking begins.
Optional extra question. What question do you wish we’d asked you and why?
Q. With all this creativity and human imagination, why isn’t there more attention given to it throughout our education?
Because the system wasn’t designed for it.
Education, as we inherited it, was built to produce reliable outputs. Compliance. Measurable achievement. People who could answer the question correctly, rather than question whether it was the right question in the first place.
It is done by design, therefore.
I was lucky. I had a school that saw something in me and made it safe to follow it. But for every school that creates the conditions for a child’s imagination to flourish, there are a hundred that quietly, efficiently, professionally do the opposite.
This is not out of malice, but because the measures they’re held to reward the expected answer, not the interesting one.
A deeper problem is that creativity is genuinely hard to measure. And in a world built on bloody KPIs and metrics, what can’t be measured tends to disappear from the agenda. So (cliche warning) we teach what we can test. We test what we’ve taught.
The curriculum becomes a loop outside which sits the imagination, waiting.
There’s a political dimension here too, which rarely gets said out loud. Creative, questioning, imaginatively alive citizens are considerably harder to manage than those trained to accept what they’re given.
Some may call it a conspiracy. But it’s, at the very least, an inconvenient alignment of incentives.
The profound irony here is that we are at the exact moment in history when this failure has its sharpest consequences. AI can produce the right answer faster than any human. The one thing it cannot do is ask the better question. That capacity, our creativity and imagination, is the one we’ve systematically under-invested in for a century, is the most valuable thing a human being can offer.
And we’re still not teaching it.
Our guest next week is Hala Al-Ajil. A decade at Google and YouTube, now working independently on AI workflows in the MENA region. She has a line on creative confidence that will stop you: "Ability without confidence is a private hobby. Confidence without ability is a career, unfortunately." More next week!
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