The Art of Asking ‘So What?’

Years ago, my Dad gave me a strategy. Over his long career as a salesman for Xerox and then an entrepreneur, and through too many pitches, negotiations, and handshakes to count, it had served him well enough.

He told me: “When someone starts talking to you, imagine the words ‘so what’ in a question on their forehead.”

In other words, forget the niceties.

Why am I speaking to this person?

What do the words I’m hearing actually mean?’

My Dad followed that up with another step.

“As you listen to them, and based on what you learned, answer that question for the other person.”

Along with clearing out the bullsh**, that second step of the strategy is the kicker. Asking, and then answering the other guy’s ‘so what’ shifts my focus to one thing—understanding the person in front of me.

I’m not talking Jedi mind tricks. I’m also not saying my ability to read words, facial expressions, and body language like a poker player supersedes anyone else’s… that’s human interaction 101 as far as I’m concerned.

What my Dad meant, and what I’m getting at is this: knowing myself, and being aware of the way other people are motivated are as close to my job description as it gets. It means focusing on empathy as a superpower.

In fact, think I’ll raise.

Understanding other people’s hopes, thought processes, and motivations, (their collective ‘so what’) so I can help them do what they want to do is the essence of being an entrepreneur.

Memes of the day

What It’s Really Like

By asking ‘so what’ I’m drilling for bedrock.

What are they really hoping for?

Can I work with that hope to help them do what they want to do?

While I’ll never get a perfect ten for understanding someone else, I listen as well as I can. Knowing that someone’s probably asking the same questions about me, I say exactly what I mean. If I say I’ll do it, then I go and do it. I remember that understanding people and what motivates them means deepening my grasp on human nature—and the hero’s journey that tries and strengthens said nature like a Boston marathon.

Over time, and as an added bonus, asking so what has given me a snapshot of the kind of entrepreneur (or person, or plumber) I want to work with. People think entrepreneurs are crazy and full of energy… but the best ones are consistent.

They are driven and motivated.

They show up every day and plod away.

They hang in there when other people quit.

They have, or they develop, intentionality.

They take something Bill Gates once said to heart: “People underestimate what they can do in ten years, but they overestimate what they can do in one.”

If they see the long game, then they manage expectations and hold outcomes at arm’s length. When something swell happens, they’re not pissed that it didn’t happen fast enough. Rather, they’re pleasantly surprised …and so am I.

Always in the Journey 

I know, I know.

Having laid out my dream entrepreneur like the perfect date, I’m probably due for disappointment. That is, if I want to do business with flesh and blood people. For the record, I do… and grand inquisitor that I am, I remember that so what cuts both ways.

But if you’re up for the journey, then so am I.

My team at Dare Capital brings the trust and transparency that entrepreneurs really need right to the table. We ask questions and we learn from the answers—no gimmicks, no bait and switch.

If that sounds good to you, and if you’re on the lookout for working capital, then give us a call. We might just be the guide you’re looking for.

So what?

So that.

Until next time,


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