How to Ask Questions..... #143

Business 737

The Skill Every Business Owner Needs to Master

Countless entrepreneurs and founders pour time, money, and energy into the wrong business strategy—not because they lacked ambition, but because they didn’t ask the right questions.

It might sound strange, but asking better questions has helped my clients land corporate deals, unlock hidden revenue, and scale their expertise-based businesses faster than ever.

In fact, if you’re a solopreneur or small business owner who sells knowledge, services, or strategic thinking—learning how to ask powerful questions is one of the most underrated tools for accelerating business growth.

In a world where AI can generate answers in seconds, it’s the person who can ask the right question who stands out. Great questioning isn’t just a communication skill—it’s a business strategy.

1. Questions Are More Valuable Than Answers

There’s a reason top performers in Silicon Valley now say:“Questions are the new answers.”

Why? Because answers are cheap. A quick Google search, a swipe on ChatGPT, a scroll through LinkedIn—there they are.

But great questions? Those are rare. And they’re what drive breakthroughs.

Whether you’re a founder looking to reposition your offer or a solopreneur trying to land your first corporate client, the right question can help you:

• Understand what your customer really wants (not just what they say they want)

  
  

• Break out of stale thinking and reimagine your niche

  
  

• Discover high-leverage growth opportunities hidden in plain sight

  
  

When I work with clients through Business 737, we don’t begin with tactics—we begin with questions. Because strategy starts by clarifying what matters.

And for anyone looking for real small business advice, this is your first principle:Answers change. But the right questions are timeless.

2. The Decline of Curiosity—And How It Costs You Clients.

As a business consultant, I’ve coached dozens of entrepreneurs who were brilliant at what they do but were conditioned to chase the “right” answers instead of digging for the right problems.

They’d say things like:

• “What’s the best way to market this?”

  
  

• “How do I close more sales?”

  
  

But these aren’t the real questions. The real questions sound like:

• “Why aren’t the right people noticing this offer?”

  
  

• “What problem does this solve so well that someone would pay a premium?”

This shift—from rushing to the solution to slowing down and asking the right diagnostic questions—is the turning point that changes businesses.

Curiosity is a business asset. Reclaim it.

3. Naive Questions Open Doors (Even Corporate Ones)

Some of the best strategies I’ve used with clients came from what others might call “dumb” or naive questions.

A solopreneur I worked with had been stuck for over a year trying to get in front of corporate buyers. She’d refined her offer, optimized her website, and spent hours networking—but nothing landed.

So we asked a question that seemed absurd at first:

“What if the companies already want what you offer, but you’re not showing up in the right place?”

That question changed everything. Instead of pitching from scratch, she started positioning herself inside existing supplier networks, using a proven strategy—and landed her first corporate retainer 45 days later.

The brilliance wasn’t in the answer. It was in the question.

That’s the power of structured curiosity.

4. Asking Better Questions = Better Client Acquisition

If you want to grow a business—especially a knowledge-based business—you need a content strategy, a sales process, and a clear offer. But none of those will matter if you’re not asking:

• “Who is already searching for what I offer?”

  
  

• “What problem does this solve so well that someone’s budget is already allocated for it?”

  
  

• “What words do my ideal clients use when they talk about this issue?”

  
  

These are questions I guide every client through in Business 737, whether they’re a seasoned founder or an emerging entrepreneur still finding product-market fit.

The result? They stop creating content that goes unnoticed. They stop pitching irrelevant services. And they start designing a business strategy that speaks to real problems.

5. The Second Question Is the Real One

Be cautious of binary questions.

“Should I launch this new offer?”“Is LinkedIn the best place to find clients?”“Should I raise my prices?”

These sound strategic, but they’re often traps. They limit your thinking to yes/no, this/that. Instead, go deeper:

• “What signals will tell me this offer is worth launching?”

  
  

• “How can I validate demand before building anything?”

  
  

• “What price makes this a no-brainer for my ideal client and highly profitable for me?”

  
  

Great small business advice always includes this:Don’t stop at the first question. Follow the second.

6. Replace “Tell” with “Ask” in Client Conversations

Want to build trust faster in sales? Ask better questions. Here’s what that looks like:

Instead of:

“Here’s how I can help.”

Ask:

“What’s been your experience trying to solve this so far?”“What have you tried that didn’t work?”“If I could wave a wand and fix one thing in your business, what would it be?”

These are the types of questions I build into sales frameworks for founders and solopreneurs in my consultancy. The result? Prospects feel understood—and that’s what drives conversions.

In fact, most of my clients close more deals not by changing their offer, but by changing their questions.

Ask to Win

If there’s one piece of small business advice I wish more solopreneurs and founders heard, it’s this:

Asking better questions is a business strategy.

It’s not fluffy. It’s not soft. It’s how you find clarity, grow faster, sell more, and stop wasting time on things that don’t move the needle.

If you're tired of guesswork, confusion, or slow progress—and you're ready to take control with step-by-step clarity—let’s talk.