Someone dropped out of a networking event last week. A ten-minute slot appeared from nowhere. Most people would want more warning. I quite like the lack of it. So, I willingly stepped in.
A bit of context, for those who don’t know me.
I am a Strategic Architect. I have spent over twenty years working with organisations across sectors, asking the question most leadership teams are quietly avoiding. I wrote a book about it. I spent a decade building one of the UK’s most active OKR practices, working with blue chip companies all over the world. I know what it looks like when strategy and execution decouple. It is rarely a systems problem.
What I was pitching that evening was a programme I had been developing with the help of Ben Lamorte, one of the world’s leading OKR coaches and the creator of the Identity Blueprint. The programme was designed to give growth-stage CEOs and MDs a protected space to step out of the whirlwind, away from the constant pressure to perform, respond and decide, and do the deeper thinking leadership rarely makes room for. Not a coaching programme in the conventional sense. A room where the real questions get asked. I was excitedly calling it The Forge.
The side room I found myself in had about ten people in it. Growth-stage CEOs, a couple of C-suite leaders, a VC I had known for years. I had ten minutes to talk about what I was building and five minutes for questions. I pitched what was then called The Forge, and I asked for feedback.
Two people were vociferous. They did not like the name.
I am glad they told me.
Their objection was not vague. They were fine with The Forge right up until I said it was about moulding leaders for change. That is where the metaphor collapsed. When you forge something, you produce an object. Fixed. Set. Done. That is the opposite of what any serious leader is looking for. The others in the room agreed. Not politely. With the kind of frankness that only happens when you have explicitly invited it from people who know their own minds.
I drove home and started thinking.
For a while, I played with the word Catalyst. A few people had used it to describe one of my strengths, and conceptually it seemed to fit. So, I gave it a couple of hours.
Then I ran it past my accountant, who I happened to see later that afternoon. He said what I already knew but had not quite admitted to myself:
"It is everywhere. It does not mean anything. Move on."
Another gift. Less velvet glove, more cold bucket of water.
So, I kept going.
I got out a piece of paper and started looking back across my consultancy and coaching career. Not at the labels. Not at the clever programme names. At the work itself.
What had worked?
Where had I created the most value?
What was I really trying to provide when clients brought me in?
And the more I looked, the clearer it became. The value was never in giving people another framework to admire. It was in creating the conditions for them to think properly, challenge honestly, and make better decisions about what really mattered.
The breakthrough came when I thought back to the first time I encountered Ben’s OKR work.
One of the first things that landed was not a framework or a template. It was a question. Before any organisation commits to implementing OKRs, Ben would push them: why are you doing this, and why now? Not as a preamble. As a test. If you could not answer those two questions with conviction, you were not ready. The process had not yet earned the right to begin.
That question has carried me through more OKR conversations than I can count. It is the difference between a leadership team that is serious about change and one that is performing seriousness. You know within minutes which room you are in.
I had been carrying the power of that question for years. It had just been living inside someone else’s methodology.
“The answers to how are everywhere. The courage to ask why is rare.”
That sentence arrived and nothing else was needed. The Why Room was the name. Not because it sounded good. Because it was honest. And because it had been true long before I named it.
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I told Ben what had happened in our coaching session the following day. He had just completed my Assert Report. Three legs of the stool, all at one hundred per cent. Clarity confirmed. I was ready to assert my true self into the world.
Except I was not. Not quite.
The report was right about who I am. It was wrong about what I was calling the work. The positioning was off, and no amount of internal clarity was going to correct that until I tested it against a room of people who had no reason to be kind.
This created a more interesting question than the one I had started with.
Ben has built a framework around assertion: stop prototyping, start asserting. For people in mid-career, I think that is right. You know enough. The problem is not the absence of self-knowledge. It is the failure to commit to it. Prototyping at fifty-five is procrastination dressed as prudence.
But here is the part that the session surfaced, and it has stayed with me.
Assertion is not one direction. You assert yourself outward. The world responds. At that point, you have a second test. Are you assertive enough with yourself to hear the response, accept it quickly, and adjust?
In most organisations, bad ideas live longer than they should. Not because people lack intelligence. Because certainty has become identity. The highest-paid opinion in the room. The quiet agreement to protect something that has already failed.
That is not a leadership problem. It is an assertiveness problem. The courage to put yourself into the world is visible. The courage to listen when the world pushes back is harder and rarer.
I thought I had clarity when I walked into that room. My stool stood. All three legs. And I was still wrong about one thing that mattered. The willingness to hear that, and to move in a week rather than a quarter, is what I am calling the second half of assertiveness.
The Why Room is about a day old at the point of this post. It is already truer than what it replaced.
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Ben Lamorte’s post on asserting versus prototyping is worth your time. We are writing about the same territory from different angles, and I suspect we will keep doing that. His work is at benlamorte.com.