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An Entrepreneur's Secret Weapon: the Right Question The 'right question' always means the bigger, badder, better, bolder one.

By AmyK Hutchens Edited by Jessica Thomas

Opinions expressed by Entrepreneur contributors are their own.


Many years ago a senior executive VP of operations faced an awkward conversation. Upon arriving at work one Monday morning, she learned that the company's VP of sales had thought it a good idea to swim naked at a client's pool party over the weekend.

Related: Disrupting Behavior: 4 Companies Boosting Business By Changing Behaviors

In front of employees, independent contractors and customers, he had dived into a pool of disrepute.

At first, the senior VP considered this an open-and-shut case. Swimming naked? Ask for the man's resignation. But it was not that easy. Before she'd even had a chance to re-heat her coffee, the company's CEO politely informed her that while swimming naked was indeed a bad idea, it wasn't the end of this person's job.

In fact, the senior VP interpreted the CEO to be saying that the offending skinny-dipper was a sacred cow. Continued the executive: "Please reprimand him before the day is over so that I can tell the client we've dealt with it."

"Are you kidding me?!" may have been an honest, but not-so-helpful question to pose at this particular juncture. And yet asking questions is a fantastic weapon for helping us get the results we want. For instance, the senior VP could have asked the CEO: "Please define "reprimand' so I may better understand what you seek for consequences. What are we expecting in terms of his changed behaviors? How much authority do I have to ensure commitment to these new expectations?

"How might we as a company respond to the client or others who inquire as to our thought process? Shall I buy him a Speedo or trunks for his next party appearance?!"

And . . . what about this difficult employee himself? Too many times, leaders -- especially entrepreneurs facing a scenario as difficult as that of the naked swimmer -- shoulder the responsibility for critical thinking. We believe that we must figure out all the answers prior to a challenging conversation.

But, instead, if we arm ourselves with thoughtful, high-level questions, we may succeed in getting others to squirm for us -- mentally squirm, that is.

In fact, that's what the senior VP did. Unsure quite how to handle the birthday-suit bather she did some heavy lifting prior to their meeting. She brainstormed a list of questions, including, but not limited to, How stupid are you? How do you expect the company to respond to your choices? How might we best rectify your actions? How much did you drink?

If roles were reversed, how would you respond? Help me understand… what was the thought process behind your action? and: What are the possible unintended consequences we need to mitigate right now?"

Though tempting, she kept all but the stupidity and drinking questions on her agenda and felt more prepared than she had before embarking on her framing of the issue. Armed and dangerous, she then met the VP of sales off-site and led with her opening question, "If roles were reversed, how would you respond?"

The swim champ replied, "Knowing I'd just seen you naked, I think I'd be responding with a smile."

Time stood still. The woman says she felt her heart skip a beat in panic as her internal thoughts raced. How stupid are you? How stupid am I?! Did I really just ask that? Did he really just say that?! I am in over my head. He just totally zinged me . . . were some of those thoughts.

Related: How should I handle the loud and distracting employee that sits next to me?

Wait! she then thought to herself. Take a deep breath. Wrong question: Score one slimy point for this guy. Questions work; questions always work -- they just need to be the right questions.

Ignoring the swimmer's snarky remark, she continued with her second question, "How do you expect the company to respond to your choices? We're not pleased. I met with our CEO this morning, and he and I agree this was quite the choice. He had to call the client this afternoon. How are you expecting us to play this one out?"

The VP of sales broke eye contact and shifted in his seat. His face reddened. Forty minutes passed, during which he did most of the talking. Then, she concluded with her final question, "What can I count on you doing differently going forward?"

Lessons learned

More than 2,000 years ago, the Greek philosopher Socrates was said to have asked, "What's the benefit of answering a question with more questions?" That question got misinterpreted over time.

People assumed that responding with questions was a means to avoid answering the original question. But "avoidance" was not the intent of the Socratic methodology. Instead, Socrates wanted us to challenge our thinking, own our ignorance and then expand our perspective so we might gain greater understanding. No pressure.

In our world today, entrepreneurs get paid to answer questions all day long. And that makes sense: We entrepreneurs are smart. We know stuff. We're in a leadership position. So, answering low-level recall questions and firing out quick responses nonstop is our habit, pattern, routine and rut.

In the 90-miles-an-hour entrepreneurial lifestyle, we need to get things done quickly, get things off our plates, move someone forward in his or her task completion -- all without any critical thinking: Let's not actually stop to do any critical thinking about how we might improve things, the thinking goes. Let's just make it better, impart our knowledge and make someone more autonomous, independent or accountable.

Yet, asking questions is the better habit. And asking bigger, badder, better, bolder questions amounts to pulling out your secret weapon.

Posing "better" questions, mind you, does not mean employing interrogation tactics. Rather, it's more about finding the one or two best questions that will raise the level of critical thinking at any given moment, expand the dialogue and ensure a high return on investment from the conversation.

How does it work? Start with a 50,000-foot-high question. Examples:

  • How do we define a healthy company culture?
  • What makes for a great decision?
  • What makes for a high-performing team?
  • How might we define great leadership?
  • How might we define an ideal client relationship?
  • How might we judge great performance and productivity?

Instead of answering each question yourself, generate 11 to 17 more questions that will help you answer one of the above questions. Typically, you can generate three to four questions rather quickly before your brain uses up all its local neural-synaptic connections and you hit a lull.

To get to the bigger, badder, better, bolder questions, you must push past this initial barrier. Suppose you selected:

How might we define an ideal client relationship? Typically, the first few questions you might generate are:

  • Who was/is a great client?
  • What do we mean by "ideal"?
  • Why does this matter?
  • Do they pay on time?

Your brain then hits a lull: What else? What else? What else? When you get stuck -- push through! Challenge yourself to expand your perspective. You then might generate the following additional questions.

  • What contributes to a great relationship?
  • When are great client relationships most valuable?
  • Which of our client relationships need the most work? ?
  • Why did one of our better client relationships go bad?
  • Why else does a client relationship sometimes go bad?
  • How can we improve client relationships to make them great?
  • Who is responsible for a great client relationship?
  • What will the costs be of a mediocre client relationship?
  • Where/when do the best client relationships begin?
  • Which client relationships started off poor, but became great?
  • What characteristics or sub-categories might help us define an ideal client?
  • How might we set up every relationship so that it will be great?

From this robust list you, can then select the three-to-five best questions for a meeting's agenda, or you can answer them yourself. Either way, you'll generate insights that will improve how you play going forward.

Importantly, asking questions just for the sake of asking questions is not helpful. The goal of generating better questions is to raise the level of critical thinking and be able to change behaviors. Changed behaviors lead to changed results.

How might a sales team benefit from answering the above questions about defining an ideal client relationship? With more sales. Why? The questions above spark critical thinking that will yield greater clarity and allow for more focused behaviors.

Related: When the CEO Goes Bad, the Whole Company Needs a Fresh Look

Asking questions is not a big secret, then. But asking the bigger, badder, better, bolder questions is an ideal secret weapon for success.

AmyK Hutchens

Award-winning Speaker. Author. Coach. Master Communicator.

AmyK Hutchens is an international, award-winning speaker and author of the Amazon bestseller, GET IT: Five Steps to the Sex, Salary and Success You Want. AmyK shares with entrepreneurs, go-getters and influencers how to be Master Communicators.

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