Andy Capaloff
June 18, 2020

The Best Possible Answer To An Imperfect Question Is Still Wrong!

In Search Of The Best Possible Question

No beating around the bush here. I don’t care who you are, or how good you are at asking incisive questions, you simply cannot ask the best possible questions. At least not without help.

Why, you ask?

Easy answer!

We are all limited by our own life experiences. Sure, we might typically ask better questions than anyone around us. But does that make those questions perfect?

Want proof?

Do You Have One or More Brainstorming Buddies?

You may also want to read: Don’t Just Question Answers. Question Questions

You know those conversations when you butt heads – in the best possible way – with someone who you really respect? You run an idea by them. They zing one back at you. Then you’re off to the races. It’s exciting! Your back and forth goes to places you could never have thought of alone. Tell me you don’t get a buzz from that!

Finding the perfect question may not sound as sexy as brainstorming ideas. Not close. But look at the following two questions:

  1. How best can we use our website data to improve our company performance?
  2. Based on our metrics, what are our areas of concern, and where are the bright spots?

Is one better than the other? I think so. Is either as good as it could possibly be? Not even close!

What is the answer to life, the universe and everything?


Douglas Adams

How Can You Improve Your Questions?

Ask a marketer, a data person, a salesperson, a computer geek, and an angel investor to improve the above questions. Bring in people from the supply chain and from related businesses.

They’ll all frame the question from their own experience and needs.

Ask people from 3 or 4 generations.

Their questions may come from untethered excitement or cautionary tales of past failures.

Then ask someone who knows NOTHING about your business. And prepare to be zinged! Because this person is the consumer. They care about the effect what you’re doing might have on them. Does it make sense to them? Would they buy it? What do they think the question should be?


What is the question? That is the answer!

– Unknown

Set Up a Question Circle (Round Table)

Bring an eclectic group of people together – something akin to the spread of people above. The person in the consumer role, who knows nothing about what you’re doing, can moderate.

Ask a question.

Allow only questions – NO ANSWERS!

I promise you, if the group is right and directed correctly, you’ll leave the meeting with a better question than you came in with. Just as long as your ego allows you to uncouple from the thoughts that you came in with.

You may also want to read: Why You Need to Question the Answers

Remember The Reason For This Exercise

The best answer to the wrong question will send you hurtling towards glorious (or inglorious) failure if you follow it. No matter how brilliant you are, you need to run the question by others, before you even think of determining the answers.

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Andy Capaloff

Andy Capaloff is the COO of Curatti. Prior to moving into the world of Content Marketing, Social Media Management and the day-to-day running of a Digital Marketing company, Andy spent over 3 decades in various aspects of IT. It is here that he honed his writing and technical skills, and his ability to ask uncommon questions.