I was recently speaking with MBA students about my varied career across multiple industries. One student astutely asked how changing industries so often had shaped me and why I found those experiences enjoyable. After some thought, my answer was simple: I learned the immense power of being the “dumb guy in the room.” As James Thurber wisely said, “It is better to know some of the questions than all of the answers.”

The “Dumb Guy” Advantage: A Fresh Perspective

It might seem odd to aspire to be the “dumb guy,” but when you enter a new business, industry, or even just a new project, your lack of ingrained history, assumptions, and knowledge of “how things have always been done” is a powerful asset. This “naive view” allows you to ask fundamental questions that insiders might overlook or be hesitant to voice. You have a choice: quickly learn and adopt the existing norms, or leverage your fresh perspective to challenge them by asking those “dumb” (but often profound) questions.

Warren Berger’s book, “A More Beautiful Question,” brilliantly explores this power of a questioning culture. Paul Bennett, Chief Creative Officer at IDEO, famously said he consistently positions himself as an “idiot” to disarm people and force them away from stock answers, creating space for new learning. Imagine asking a banker, “Why do we really charge these specific fees?” or a retail leader, “Why is produce always at the store entrance?”

I’ve asked many such naive questions. The initial reaction is often an odd look, followed by a stock answer. But a simple follow-up, “Could there be another way to look at it?”, frequently leads to a blank stare, and then, often, a breakthrough. In almost every business, there are “things that just are,” unquestioned for years. Being comfortable asking naive questions forces a re-examination of these underlying assumptions.

A Case Study: Naive Questions Surface Huge Opportunities

In one role, I was involved in digitizing a paper-based process for a heavily regulated industry. The company had extensive policies for document storage, retention, and destruction, written years ago to manage the costs and compliance of physical paper. The team designed an elegant (and incredibly complex) digital solution to meticulously replicate these paper-centric rules in the digital world; tracking usage, managing countdowns to destruction, ensuring secure digital deletion.

My first, naive question was: “What are the actual regulations for the storage, retention, and destruction of digital documents?” Blank stares. The team had based their entire complex design on the old paper policy.

Further naive questioning revealed:

• Regulations only mandated minimum retention for certain digital document types.
• There was no regulation preventing permanent digital storage.
• The old company policy’s destruction rules were primarily to minimize physical off-site storage costs; irrelevant for digital!

By asking that one “dumb” question, we eliminated enormous complexity. No more usage tracking for destruction, no countdowns, no complex secure deletion protocols for most documents. The cost of the digital solution was cut by an estimated 80%.

Leveraging the Power of the “Dumb Guy” in Your SMB

Whether you’ve been in your industry for three days or thirty years, you can harness this power. Every time you find yourself or your team reaching for a stock answer or relying on an unquestioned “industry standard,” stop. That’s your cue to find a naive question. As a fractional CIO, this is a core part of how I help Small and Medium-Sized Businesses (SMBs). I bring that external perspective, unburdened by “how we’ve always done IT here,” to ask:

• Why is this technology process so complex?
• Is this IT investment truly solving the core business problem, or just a symptom?
• Are our IT policies aligned with current digital realities and regulations, or based on outdated assumptions?

If you’re struggling to find the right naive questions internally:

• Seek out the newest person in your company; their fresh eyes are invaluable.
• Ask friends or family in completely different industries for their take on your challenge.
• Engage an external advisor (like a fractional CIO for your technology concerns) specifically to bring this “outsider” questioning lens.

What’s Next

Don’t accept stock answers or long-held assumptions as immutable facts. Empower your inner “dumb guy in the room” and foster your naivety. There is incredible power, and often, significant savings and innovation, in those seemingly simple questions. It’s a key to helping your SMB “Succeed Sooner.”

Is your SMB ready to challenge its own assumptions and uncover hidden opportunities by asking more “naive” questions, especially about its technology and processes? If you’re looking for a strategic partner to bring that fresh, questioning perspective to your IT challenges, let’s connect with Succeed Sooner Consulting.