From Stuck to Strategic: The Leadership Shift Not Talked About

If we had a dollar for every time someone asked, "What's the deliverable here?" in a meeting where no one even knows what the problem is, we'd be sipping margaritas on a beach made of gold-plated Excel sheets.

And yet still executives everywhere are falling into the same trap:

Asking questions that don't move anything forward.

Questions that confuse more than they clarify.

Questions that serve egos instead of outcomes.

Questions that are well, sad little buzzwords strung together and dressed up like strategy.

Exhibit A: The Offender's Hall of Fame

You may recognize some of these classics:

• "What's the low-hanging fruit we can operationalize?" (Translation: I didn't do the pre-read.)

• "Have we pressure-tested the bandwidth of this pivot?" (Translation: I just learned three new business terms, and I'm gonna use them all right now.)

• "Can someone circle back on that so we don't drop the ball?" (Translation: I'm assigning this to no one and everyone at the same time.)

These are not questions. These are performance art.

But Here's the Good News:

The skill of asking great questions is a teachable one. Sharpenable. Coachable.

(And once you have it, you'll never lead the same way again.)

So What Is a Great Question?

Let's break it down. A powerful, executive-worthy question is:

🧭 Aligned

A great question connects directly to the real problem, not just the noise surrounding it.

❌ "How can we get this done faster?"

✅ "What are we optimizing for—speed or sustainability?"

🧠 Thought-Provoking

It stops people mid-sentence and makes them think, not just answer.

❌ "Who dropped the ball?"

✅ "What system allowed the ball to be dropped?"

🧹 Simple & Clear

It's not trying to win a Scrabble game. It cuts straight to the heart.

❌ "How might we best leverage our cross-functional synergies to ensure ecosystem integration?"

✅ "What's working, and what's not?"

🕵️‍♂️ Bias-Busting

It challenges assumptions and digs under the surface.

❌ "What do our customers want?"

✅ "What assumptions are we making about what our customers value?"

Why Executives Struggle With This

Because you're used to being the one with answers.

Because "good question" is rarely listed in performance reviews.

Because you've been rewarded for speed, decisiveness, and looking like you know what you're doing—even when no one knows what we're doing.

But what if we told you the real power move isn't having the answer? It's asking the question that reveals a blind spot, unlocks the team's thinking, or de-escalates a turf war in 30 seconds flat.

That's leadership.

Here's Where We Come In

At JASC Associates, we teach executives how to:

• Ditch the jargon and find clarity

• Ask aligned, strategic questions that reveal the real issues

• Shift from "command and control" to "guide and provoke."

• Use questioning as a cultural tool (not just a conversation tactic)

And we didn't learn this from a textbook.

Our team sharpened these skills through decades of consulting with leaders and teams across industries—and a background in litigation where we participated in over a thousand depositions. (Yes, thousand.)

When you've spent that many hours drilling into facts under pressure, you learn fast what makes a question clear, effective, and impossible to dodge.

We've helped uncover the truth in legal disputes, cut through the noise in boardrooms, and coached high-level leaders to stop performing and start probing. This isn't theory—it's muscle memory built through lived experience.

What You'll Get

In our workshop or private coaching, you'll walk away with the following:

✔ Real practice with your real business problems

✔ Tools to challenge assumptions without starting a fistfight

✔ Feedback from coaches who've seen the inside of both corporate boardrooms and courtrooms

And yes, there will be laughs. We want to ensure you leave us brighter and lighter.

Final Thought

If your meetings feel like endless loops of déjà vu, and you're starting to suspect that no one understands what the heck we're solving for—

👉 You don't need another dashboard.

👉 You need better questions.

👉 And you need to know how (and when) to ask them.

So here's a question to start with:

What would change if your team started asking the right questions instead of giving the same tired answers?

Let's find out together.

Book a workshop. Or grab a coaching session.

We help you unlock the inner strategy that transforms your vision into velocity and your potential into excellence.