The $100M Question Your Strategy Team Forgot to Ask


Dear Decision Maker,

Most executives make complex decisions based on incomplete information.

Then wonder why they're surprised by outcomes.

After almost two decades advising leaders on high-stakes choices, I've noticed something consistent.

The best decision-makers don't wait for perfect information. They use a framework to navigate uncertainty.

I call it the Decision Advantage Matrix.

It's simple. Four quadrants. Two questions.

What do we know with certainty? What do we need to know to act?

Last month, a client faced a $100M market entry decision in Southeast Asia. Their due diligence showed green lights everywhere.

But they felt uneasy.

We mapped their decision through the matrix.

Known certainties: Market size was real. Regulatory approval was secured. Financial projections were solid.

Critical unknowns:

  1. Who really controlled the distribution networks?
  2. What informal power structures would they need to navigate?
  3. Which local players would see them as threat vs. opportunity?

Their due diligence team had answered every question on their checklist.

But they'd asked the wrong questions.

The Decision Advantage Matrix forces you to distinguish between:

  • Data you have vs. intelligence you need.
  • Assumptions you're making vs. realities you've verified.
  • Risks you can quantify vs. uncertainties you must navigate.
  • Questions you've answered vs. questions you haven't asked.

Here's how it works:

Map what you actually know from verified sources. Identify the intelligence gaps that matter most. Determine which unknowns are acceptable risks. Kill decisions when critical gaps can't be filled.

My client delayed their market entry by 60 days.

Used that time to answer the questions that actually mattered.

Discovered that two of their proposed local partners were locked in a blood feud that would have destroyed the venture within months.

A $100M disaster avoided because they stopped to map what they didn't know.

Most frameworks tell you how to analyze information you have.

The Decision Advantage Matrix shows you what information you're missing.

The costliest business failures don't come from bad analysis. They come from analyzing the wrong things.

What critical decision is your leadership team facing right now? Have you mapped what you don't know or just validated what you assume?


In complex markets, the competitive advantage doesn't go to those with the most data. It goes to those who know which questions they haven't asked yet.

Want to pressure-test your next major decision through the intelligence lens? Let's identify the gaps before they become disasters.

Ahmed Hassan
CEO Grey Dynamics
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