Interrogate the Brief: The Prompt That Thinks Like a Strategist

Let’s face it: not all briefs are created equal. Some are clear. Most are chaotic. Many are built by committee, approved in a rush, or loaded with unchecked assumptions disguised as “insights.”

And yet, the brief is where it all begins. If it’s off, everything that follows—strategy, creative, production—drifts with it.

That’s why we built Brief Interrogation.

✅ It’s not another prompt that formats the brief for you.
✅ It’s not a summary.
✅ It’s not a passive checklist.

It’s a GPT that challenges the brief back.

What It Does (In Plain English)

Brief Interrogation is designed to think like a senior strategist. Its job is to review a creative brief and ask the questions no one else is asking:

  • What are we assuming without evidence?

  • Is the audience as focused as we think?

  • Why this timing? Why this approach? Why now?

  • What are we not saying that we should be?

It doesn’t just highlight gaps—it cites the exact lines that triggered each question, making the critique actionable.

Why It Matters

Too many agencies treat the brief as sacred.
They nod. They accept. They start working.

But great strategy doesn’t start with agreement—it starts with tension.
That’s what this tool is built to create: strategic tension.

Because when you interrogate the brief, you uncover:

  • Blind spots in targeting

  • Flimsy rationales for campaign timing

  • Contradictions between objectives and KPIs

  • Stakeholder bias posing as truth

  • The insight that should have been the brief

Who It’s For

  • Strategists looking for a smarter way to pressure test briefs

  • Creatives who want to know what’s not being said

  • Account teams who need stronger rationale in client reviews

  • Agencies trying to push back without sounding political

How to Use It

Upload or paste a creative brief—client-provided or internal.
Brief Interrogation will read it like a strategist would, and return:

  • Strategic questions linked to specific lines in the brief

  • Assumption flags you can’t afford to overlook

  • Clear ways to strengthen or redirect the brief before it’s too late

This isn’t about playing devil’s advocate for fun.
It’s about saving creative teams from solving the wrong problem beautifully.

The Goal

Brief Interrogation exists for one reason:
To improve outcomes by improving the thinking that happens before the work.

Not just better decks.
Smarter direction. Sharper insight. Clearer creative runway.

Try the tool.

Push the brief.

And if your gut says something’s off—but you can’t quite explain it yet—this GPT probably can.

Jorge Machado

Seasoned marketing innovation director adept at surpassing company goals and improving workflows. Proven track record of raising sales, increasing market share, boosting brand awareness, and using data to chart the way forward. Committed to excellence, and training teams to achieve their best possible outcomes and beyond.

https://www.linkedin.com/in/jorgemachadocolon/
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