Let’s face it—entrepreneurs are idea machines. We’re visionaries, builders, and problem-solvers. But here’s the catch: the same laser-focus that drives innovation can also blind us to obvious flaws, risks, or overlooked opportunities. And that’s exactly why every business—yes, every business—needs a Jester.
Historically, jesters were more than court entertainers. They were the only ones allowed to speak truth to power, to poke holes in the royal logic without losing their heads. They saw what others ignored or were afraid to say. In today’s world, a “business jester” plays a similar role: they challenge the status quo, question assumptions, and help leaders see what’s hiding in plain sight.
Here’s the science behind it. Our brains filter information constantly. It’s how we stay focused. But this process—called selective attention—also causes us to miss what’s right in front of us. Remember the Invisible Gorilla experiment above? People were so focused on counting basketball passes that they completely missed a gorilla walking through the scene. In business, this happens when leaders become so obsessed with a product launch, a KPI, or a revenue target that they miss glaring issues like declining morale, shifting market trends, or customer complaints.
That’s where the Jester comes in.
A business jester might be a contrarian team member, a trusted mentor, a mastermind group, or even an AI tool trained to challenge your logic. Their job is to step outside the echo chamber and ask uncomfortable questions like:
What if we’re solving the wrong problem?
Who is this really for?
What are we assuming that might not be true?
Having a Jester doesn’t mean inviting constant negativity. It means encouraging a space where critical thinking is valued and blind spots are illuminated.
ChatGPT Prompt:
You are to act as my Jester. Your role is to challenge my assumptions, pressure-test my thinking, and help surface blind spots that may be hiding in plain sight. Your role is not to shoot down my ideas but to sharpen them by asking me the questions others avoid.
Think about the stars in the sky. They don’t disappear during the day—you just can’t see them because the sun is too bright. In your business, your “sun” might be your most exciting project, your leading product, or your current strategy. But while you’re basking in its glow, you could be missing the smaller, vital signals that only a jester would dare to point out.
Want to improve your odds of success? Appoint a Jester. Make it someone who isn’t afraid to say, “You might be missing the obvious.” Better yet, create a culture where everyone feels safe to play that role from time to time.
Still unsure? Start small. Invite someone from outside your team to review your latest idea. Or train your AI assistant to flag assumptions. You’ll be amazed at what a fresh perspective can reveal.
Because sometimes, the truth is hiding in plain sight—and only a Jester can help you see it.
Who plays the role of the Jester in your business—and what truths might they be trying to show you?
