Shake the Magic 8 Ball: Why the Best Leaders Ask Better Questions

“Will this project succeed?” Shake shake shake. “Outlook good.”

“Should we pivot our strategy?” Shake shake shake. “Reply hazy, try again.”

The Magic 8 Ball was never about right answers. It was about loosening up, getting curious, and sitting (playfully!) with the unknown.

Why did we love it, even as kids? Because shaking the ball gave us a moment of movement, of possibility. It let us get unstuck and move closer to a decision, sparking just enough curiosity to wonder, “What else could happen here?”

When Vicki T. , author of Ask This Book a Question, joined me on The Brainy Business podcast, she explained why she opened the book with the idea of a Magic 8-Ball. The goal isn’t to lock in certainty or jump to the closest answer (our outlook on that path is “not so good”). It’s to help people explore, rethink, and expand before they narrow in (increasing the likelihood that they narrow in on the right thing). 

Great leaders do this regularly, but here’s the challenge:

Even when we want to lead this way, day-to-day business pressures make it hard. We fall into predictable traps not because we’re careless, but because we’re human.

Understanding where leaders get stuck is the first step toward shaking things loose. Here are 3 key problems and ways to avoid making the mistakes in your own work.

Problem 1: Rushing to Solve the Wrong Problem

Humans crave closure. In fast-paced work, this can spiral out of control fast. Teams grab the nearest problem and start fixing. But often, that “nearest” problem isn’t the most important one. (“Visible” “Close” and “Easy” don’t equal “Important.”)

Vicki’s approach: Start broad. Bring in questions from engineers, product leads, researchers, designers. She called this the “Swiss cheese method” that helps fill in blind spots, and recommends asking what’s really going on before jumping into solutions.

The science: Behavioral research shows we have a strong need for cognitive closure. This drive to end uncertainty fast makes many people jump to solving the wrong problem. Resisting that impulse, even briefly, improves decision quality.

Problem 2: Ignoring Ripple Effects

We often measure success in the immediate moment: the metric, the milestone, the launch. But complex systems ripple outward, and what looks like success today can cause friction tomorrow.

Vicki’s approach: Go beyond first-order outcomes. Ask about focus, attention, and emotional experience. Wonder what this choice might feel like for the human on the other side today, tomorrow, and two years from now.

The science: This aligns with second order thinking, which is used by behavioral scientists to surface unintended consequences. It’s how we avoid narrow framing and consider the ripples in advance so we can design for long-term impact.

Problem 3: Narrowing Too Soon

The pressure to prioritize can push teams to collapse possibilities too quickly. This results in completely missing surprising ideas or novel connections that could have given you an edge against the competition.

Vicki’s approach: Only narrow after you’ve gone wide. Explore fully, then get practical. Instead of rushing to the finish line, take the time to toggle between expansive and constrictive thinking.

The science: This connects to the focusing illusion, the behavioral principle that says what we focus on feels exaggerated in importance. When we zoom in too fast, we overemphasize what’s in front of us and lose sight of other factors that matter just as much (or more). Leaders need to deliberately balance broad exploration with focused execution to avoid tunnel vision.

🧠 Brainy Bite of the Week

Humans will always be wired to jump to answers…even if they’re low-quality, incomplete, or downright nonsense (looking at you, Magic 8 Ball). That instinct can steer even the best leaders off course.

In today’s AI-driven world, the ability to ask good questions isn’t just a nice-to-have, it’s essential. AI can provide endless data and suggestions, but they can’t care whether your question is meaningful, human-centered, or aligned with your values. What counts, it turns out, is learning how to ask better questions (to machines and humans alike). 

In other words: It is way too easy (and expensive) to find the right answer to the wrong question. 

While the Magic 8 Ball wasn’t about truth, it can provide one useful opportunity by giving us the space to wonder. As you take a moment to pause and wonder today, here are a few quick questions you can try in the spirit of today’s article. Before your next decision, pause and ask:

• Have we gone wide enough?
• What ripple effects are we overlooking?
• Are we narrowing focus too early — risking tunnel vision?

Questions are so important to the growth of your business. That’s why I love teaching teams how to Questionstorm. My process gives teams the framework to methodically slow down to find the right questions before hunting for answers. Curious about bringing this important skill to your team? Send an email to melina@thebrainybusiness.com to learn more.

And now, I’m curious…

💬 What’s YOUR go-to question for getting unstuck? Drop it in the comments so we can build a question toolkit together!

Want to learn more about Vicki’s insights? Check out our full conversation on The Brainy Business podcast (episode 519). We go deep into curiosity, design, and the human side of better decision-making both personally and professionally.

Thanks for reading. Until next time, BE thoughtful.

Melina Palmer