I’ve spent much of my career asking questions that weren’t always particularly comfortable:
- Why are we doing this?
- What problem are we actually trying to solve?
- Why have we made this so complicated?
- What would happen if we did it completely differently?
For a long time, I wondered whether that tendency was a weakness.
I’ve worked in large global organisations, smaller businesses and startups. I’ve experienced restructures, redundancies and all the usual frustrations of organisational life.
At various points, it was difficult not to wonder whether I was simply the common denominator… perhaps the problem wasn’t the organisations I was working in… perhaps the problem was me.
Perhaps I was too challenging… too impatient… too willing to question things other people had accepted?
I’m starting to think I was asking the wrong question.
The question wasn’t whether I needed to stop challenging systems.
It was whether I was working in systems that genuinely wanted to be challenged.
There is another uncomfortable possibility, of course; sometimes the disruptor really is the problem…
Challenging everything without understanding why something exists isn’t innovation - It’s just noise.
I couldn’t have built the ideas I’m exploring today when I was 22 - not because I lacked ambition, I lacked context.
I didn’t understand organisations well enough, I hadn’t seen enough transformation programmes succeed and fail.
I also hadn’t watched technology solve one problem while creating three others or worked with enough different cultures, functions and personalities.
I hadn’t yet learned the difference between a constraint that should be challenged and one that exists for a very good reason.
One of the most important things I’ve learned is that being wrong isn’t particularly dangerous but being expensively wrong is.
The objective shouldn’t be to eliminate failure; it should be to reduce the cost of discovering that an assumption was wrong.
Ideate -> Prototype -> Test -> Analyse -> Iterate.
Sometimes… stop.
Failure can be enormously valuable when it is fast, cheap and produces learning.
The older I’ve become, the less interested I am in being the smartest person in the room - I’d much rather be in a room where nobody sees the problem in quite the same way.
Put a technologist beside a commercial strategist, add someone who understands people and organisational behaviour.
Bring in somebody from another country, industry or culture who doesn’t share any of their assumptions - give them a difficult problem and permission to challenge one another.
That’s where things become interesting.
At 46, I’ve realised that perhaps I haven’t suddenly become entrepreneurial - I’ve been thinking this way for most of my career.
What has changed is that I now have enough experience to understand what I’m challenging, enough failures to know I won’t always be right, and enough confidence to surround myself with people who will tell me when I’m not.
Perhaps careers aren’t always about climbing towards the role you were eventually supposed to have.
Sometimes they’re about accumulating enough experience to understand the problem you were eventually supposed to solve.
