The Greatest Question of All Time

We spend a lot of time looking for better answers.

• Better strategies.
• Better tools.
• Better frameworks.

But every once in a while, you come across something more useful than a better answer.

A better question.

And in my experience, there’s one that stands above the rest - and we use this question in almost every client engagement:

“What would need to be true?”

If we’re borrowing from sports… this might just be the GOAT. 

Why this question matters

Asking good questions is one of the fastest ways to bring clarity.  If someone is considering a decision—entering a new market, changing roles, even borrowing Mom’s car—we can ask all kinds of reasonable questions:

• How much does it cost?
• Where are you going?
• What’s the plan?

These are good questions. But they’re not the GOAT.

Most discussions—whether in boardrooms or around kitchen tables—tend to follow a predictable pattern:

• People state opinions 
• Others challenge them 
• The conversation drifts 
• Decisions get made… or don’t 

It feels like progress. But it rarely is. Because opinions are hard to resolve. “What would need to be true?” changes that. It shifts the conversation from:

"Do we like this idea?”      

to

"Under what conditions does this actually work?”

From arguing… to understanding.    From positions… to possibilities. 

A simple example

A company is debating whether to enter a new market.  The room fills with familiar comments:

• “It’s a big opportunity” 
• “It’s too competitive” 
• “We’ve never done this before” 

Round and round it goes.Then someone asks: “What would need to be true for this to be a good decision?  Now the conversation sharpens:

• The market needs to be large enough to matter 
• We must be able to displace incumbents 
• Our logistics need to support it 
• The margins need to justify the effort 

Now we’re not debating opinions.  We’re identifying conditions for success.  And more importantly—we can test those conditions. 

Why it works so well

This question does three things almost instantly:

1. It forces clarity.   Vague thinking doesn’t survive long when you have to define what “true” looks like.

2. It exposes assumptions.   Every strategy rests on a handful of things we’re quietly hoping are true. This brings them into the open.

3. It creates action.   Each “must be true” becomes something you can validate, de-risk, or reject. In other words, it turns conversation into progress. 

It’s not just for business

This isn’t a consulting trick. It works just as well in everyday life.

• Thinking about a big move?  What would need to be true for this to be the right decision?
• Considering a new role? What would need to be true for this to be a step forward?
• Even something as simple as a purchase:  What would need to be true for this to be worth it?
• Child wants to borrow the car:  What would need to be true for this to be a good idea?

Clarity shows up quickly. 

It’s simple

We tend to admire complex thinking. But in practice, the most useful tools are often the simplest. This question won’t impress anyone in the moment. It won’t feel like a breakthrough. But used consistently, it quietly improves the quality of decisions—again and again. Which is probably the best definition of “great” there is. 

Final thought

If this really is the greatest question of all time…What would need to be true for us to work together this year?

Andrew