The Thinking Edge

The Thinking Edge

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The Thinking Edge
The Thinking Edge
Be the One Who Asks the Better Question

Be the One Who Asks the Better Question

How smart questions can make you the most valuable voice in the room

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Chris Thomason
May 20, 2025
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The Thinking Edge
The Thinking Edge
Be the One Who Asks the Better Question
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You’re in a meeting to kick off a new piece of work.

It’s not routine.
It’s not the daily grind.
It’s something new. A fresh challenge.
We’ll call it a project.

Projects start every day, in every department, in every industry, on every continent.
They begin with energy, ambition, perhaps even a little anxiety.
They come with a desire to prove, perform, and deliver.

But here’s something we don’t always acknowledge: the questions you ask at the beginning and end of a project can be the most powerful contributions you make.

Because in a world where AI can generate answers at scale, your value increasingly lies not in what you know – but in what you ask.

Why better questions matter

In many work environments, people are rewarded for having answers.
Fast answers.
Confident answers.

But the people who truly shape direction – the ones whose contributions ripple out long after the meeting ends – are the ones who dare to ask better questions.

Yet asking questions takes courage.

Courage to risk sounding naïve.
Courage to challenge assumptions.
Courage to pause the momentum and ask, “Are we sure this is the right path?”

But in doing so, you’re not holding things up.
You’re lifting them higher.

You’re giving the room permission to think, not just execute.
And in that space, the most remarkable work can begin.

Stand out at the start

There’s something uniquely powerful about the beginning of a project.
Because, at this moment, direction isn’t yet fixed.
Outcomes aren’t yet locked in.

Which means it’s the perfect time to shape the room’s thinking.
And to demonstrate your value.

Here are seven high-impact questions to ask at the start of a project.

Each one signals strategic depth, ambition, and clarity of thought:

“What would success look like if this project delivered 10 times the expected value?”
You’re inviting bold thinking from the outset. Not reckless, but visionary. Not unrealistic, but unconstrained.

“Will this project solve the right problem, or just the most visible one?”
You’re directing the spotlight from symptoms to root causes – a shift that can save months of misdirected effort.

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