5 Questions That Will Transform Your Decision-Making Process

Harvard Business Review spent 3 years researching decision-making.

3 years.

That’s longer than most startups survive.

They dug deep. They analyzed. They uncovered patterns.

And what they found?

It’s a game-changer.

They discovered 5 types of questions that separate great decision-makers from everyone else.

Yet most people aren’t asking these questions.

They’re fumbling in the dark, making decisions based on gut feeling or incomplete information.

But not you. Not after reading this.

You’re about to learn what HBR took 3 years to uncover.

Ready to level up your decision-making?

Let’s dive in.

1. Investigative: “What’s Known?”

This is where you play detective.

You dig. You probe. You ask “Why?” over and over again until you hit bedrock.

I once worked with a company that skipped this step. They launched a product without truly understanding their market.

It bombed. Hard.

Don’t be that company. Always start here.

2. Speculative: “What If?”

This is where the magic happens.

It’s where you break free from conventional thinking.

Remember when Emirates Team New Zealand won the America’s Cup? They didn’t just ask, “What if we use leg power?”

They went further: “What else could a pedal system allow?”

That’s the power of speculative thinking.

3. Productive: “Now What?”

This is where dreams meet reality.

It’s about resources. Capabilities. Timelines.

I’ve seen too many entrepreneurs crash and burn because they ignored this question.

They had great ideas but no plan to execute.

Don’t fall into that trap.

4. Interpretive: “So What?”

This is where you make sense of it all.

It’s not enough to gather information. You need to understand what it means.

I once consulted for a tech company that had all the data in the world.

But they couldn’t interpret it.

They missed a massive market shift and lost millions.

Always ask: “So what does this mean for us?”

5. Subjective: “What’s Unsaid?”

This is the secret weapon.

It’s about emotions. Hidden agendas. The stuff nobody talks about but everyone feels.

I’ve seen million-dollar deals fall apart because nobody addressed the elephant in the room.

Don’t let that be you.

Here’s the truth:

Most people only use one or two of these questions.

But the real magic happens when you use all five.

It’s like unlocking a superpower.

You’ll see opportunities others miss.

You’ll avoid pitfalls that trap your competitors.

You’ll make decisions with clarity and confidence.

Want to upgrade your decision-making so you think smarter about your business?

Every week I send a thought exercise to founders and CEOs so they can take intentional time to think *about* their business.

(Instead of always living in the weeds of the day-to-day operations).

The thought exercises are copy-and-paste prompts that turn Claude.ai into your personal business strategist, thought partner, and soundboard.

There are 3 free prompts here if you want to check them out.