A leader I had been coaching for months walked into a high-stakes review to present his plan – $100M to $125M. The kind of number that gets attention at the top.

We had done everything right.

Prepared for hours, aligned the goals, and mapped out the strategies.

We examined every slide, every assumption, and every growth lever together.

When the CEO presented the plan internally, his leaders asked one question

“Where is your partner strategy?”

The room went silent.

Because there was no partner ecosystem, no indirect channel, and not a single person assigned to build it.

A growth engine that could have driven 30–40% of his number wasn’t there.

I was sitting right there when it happened.

And the part that stayed with me long after that meeting ended?

I had been in that coaching conversation with him, week after week.

I had missed it too.

This experience forced me to confront something uncomfortable about coaching.

We get drawn into the aspiration. Where does the leader want to go? What do they want to achieve? What does success look like?

But the real work is not in what they are going after.

It is in what they are choosing to ignore.

Because avoidance rarely looks like avoidance. It looks like a full agenda, a confident plan, and a room full of people who all forgot to ask the same question.

Here are the three things I now look for in every coaching conversation:

1. What are they unconsciously deprioritising because it is hard?

Every leader has a blind spot that is shaped by discomfort. The channel they’ve never built. The conversation they keep postponing. The capability gap they are hoping won’t matter. It always matters.

2. What are they brushing over because it exposes a weakness?

Sometimes the silence in a strategy session is the most important data in the room. When a leader moves quickly past a topic, that is rarely because it is resolved. It is because it is raw.

3. What possibilities are sitting right there, being avoided?

Partner ecosystems. New geographies. Pricing models. Talent structures. The opportunities that never make it to the strategy deck are often the ones with the highest upside.

Aspiration is easy to see. Every leader walks in with it.

Avoidance is not. It hides in plain sight dressed up as prioritisation, pragmatism, or simply running out of time.

And I have learned this the hard way.

The most important part of any coaching conversation is not what gets left out.

So here is the question I now ask — and the one I leave you with today.

What is the one thing you keep skipping over in your strategy?

You already know what it is.

The moment you read that question, something came to mind.

That is the conversation worth having.

Always looking forward to helping you win more.

*** 

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