An Entrepreneur’s Secret Weapon: the Right Question

An Entrepreneur’s Secret Weapon: the Right Question

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.

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.

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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.;

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