Why Lead With Questions

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Scenario: "Dude, we have to keep finding answers. We're geniuses, and we know everything. Yay. High-five!" Most entrepreneurs who start companies think this way:

  1. Start a business.
  2. Search for answers.
  3. Then, they brace themselves for success.

But, that's why 90-some-odd percent of businesses fail. Kick-booty entrepreneurs instead lead their shizzle this way:

  1. Start a business.
  2. Ask questions.
  3. Seek answers to those questions.

Why? Asking questions drives you to understand the opportunities, the booby-traps, and the best resources for your business's goals; that drives you to understand the smartest route to your destination.

What Not to Do: Follow Johnny Boy's Route

CEO Johnny Boy -- thinking he's the king of the mutha-!@^^%^ jungle -- tells his "people":

  1. "Yo Marketer! Send 1000 flyers to Jomomma City."
  2. "Yo Manager! Tell employees to increase widgets count."
  3. "Yo Finance Gal! Cut costs on benefits. We need profits!"
  4. "To Everybody Here: Dream! Dream! Dream! High-Five!"

What happens to his company's potential? Potential = Drainage. Instead of capitalizing on his people's expertise, he tries to be a jack-of-all-trades -- killing his company's potential to kick-ass in every facet of his organization.

Why Asking Questions Rocks

Your current business situation is akin to being lost in a foreign country. That is:

  • You don't understand precisely what to do next.
  • You're ignorant of the the threats to your adventure.
  • You have super-duper-knowledgeable people around you if you just ask.

So, when you're in a foreign country, what would the smart brain inside of you tell you to do?

Ask questions to those familiar with the area (e.g. the best road to get there, sections to avoid, what to expect, maps you need, etc.) That is, if your business destination is to build the next-great-sexy software company, you'd:

  • Question those who've already built successful software companies.
  • Ask analysts what's the brutal realities of the industry.
  • Ask experienced managers the best way to build software from scratch to sell.

And if you already have a business...

In the same vein for instance, if you already run a software company, your knowledge sucks compared to those already near the situation at hand. So:

  • You'd ask your managers what's holding up productivity.
  • You'd ask your marketers the best customer segments.
  • You'd ask your customers the best way to improve your service.

Result: You build a company revolving around freakish strengths to pull you through any freakish barriers to your destination. Win.

How to Ask Those Questions

Three steps:

  1. Know your company's ultimate destination.
  2. Understand what expertise you need to get there (e.g. the geography prodigy, the driving guru, the terrain wizard, etc.).
  3. Apply their expertise by asking them unbiased questions to get to that destination.


The best leaders ask the most questions; they never have all of the answers. That's according to a study by Stanford Business School researchers on leadership, as well as another study by GW Professor Michael Marquardt. Questions > Answers (x 984180958209819289421)

Ask questions, playa.


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Posted on March 21

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