Business Failing? You Might Be Asking The Wrong Questions

Going around asking for “feedback” won’t get you anything useful. Here’s how to dig deeper and find real answers.

I did fine in Catholic school, up until 6th grade. I don’t know why Sister Freda hated me, but I think she was trying to teach me a lesson. And I did learn a lesson — just not the one she had in mind.

The turning point happened like this. During a reading comprehension exercise about becoming a veterinarian, Sister Freda asked me, “Name one challenge people have in becoming a vet.” I gave an answer. It was wrong. She told the entire class that this is what happens when students don’t pay attention. If I had done the work, she explained, I would have seen the section in the reading that held the correct answer. It was intended as a humiliating lesson.

At lunch, I showed Sister Freda the reading passage in my book. She apparently wanted me to regurgitate the challenges that students face when becoming vets. But I pointed out a later paragraph that contained my answer — that many vets struggle to run their own practices as business people.

“Ah, ok,” she said, and that was it. She saw that my answer wasn’t wrong — if anything, her question had been too vague.

At that moment, I realized that teachers are like everyone else — they make mistakes. And if I was going to be a great student, I couldn’t be so passive about my education.

Starting in 7th grade, I asked a ridiculous number of questions. My hand lived above my head. I forced myself to think of hypothetical or advanced questions beyond the realm of the text or the day’s lesson. People groaned when I was called on.

I remember a fellow student turning around when tests were handed back. He noticed that I had gotten the higher score. “How did you get a 100% when you’re always so confused and have to ask so many questions?”

Despite ridicule from my peers, I kept at it. My grades soared, and at the end of 8th grade I graduated second in my class. If only I had asked more questions, sooner.

Don’t Forget The Real Question

Someone emailed me recently with the subject: “A question about start-ups.” But the email didn’t contain a question mark or anything remotely looking like a question.

Often I get advice seeking emails ending with, “Do you have any feedback?”
 But that’s not a question; it’s a cop-out.

Similarly, I’ve attended meetings where entrepreneurs make presentations to experts expected to share helpful guidance. But often the presentation is, “Here’s my product, what do you think?”

Same problem. That’s not a real question. And so a conversation with these experts is unfocused and frustrates the entrepreneur because her real problems go untouched.

I’ve made the same mistake myself, but I’ve been lucky to learn a different way. The most valuable feedback session I ever had with a mentor came before I released Draft, a software product I made to help people write better. I was prepared. Instead of asking for feedback, I asked how this mentor and successful entrepreneur would design a specific feature in Draft or how would he communicate the business model I had planned? I got much more than feedback; I got answers.

How To Ask Better Questions

There are plenty of people who’d love to help you with your business; you just have to ask, but they don’t have time to waste helping you figure out what your actual problems are. Get the most out of a potential mentor by approaching them with specific questions you’ve already identified and they’ve probably answered for themselves. How would you:

  • Increase the conversion rate?
  • Set up pricing?
  • Design this feature so that it’s clear and easy to use?

And force yourself to go deeper with your questions.

Toyota’s engineering processes are famously effective. One reason is that employees are taught to ask why five times when trying to solve a problem.

  • Why is the battery dead?
  • Why is the alternator broken?
  • Why didn’t the customer get alerted to this before?

This process helps engineers identify and fix the root problem instead of just treating symptoms. The same practice can be applied to your startup venture.

Act like a Toyota engineer and ask why at least five times.

  • Why is my business not making enough money?
  • Why am I not measuring my conversion and attrition rates?
  • Why is attrition so high?
  • Why haven’t I surveyed anyone who has canceled?
  • Why haven’t I added feature X which most canceling users are asking for?

And most importantly… Don’t worry about looking silly with the number of questions you have; just ask more of them.

P.S. It would be awesome to meet you on Twitter, or check out how we can help you start or improve your own business with Highrise.