Ask Better Questions

I’m fascinated by the way that different people can look at the same problem and ask wildly different questions to solve it.

This fascination is one of the reasons I became a podcaster. I wanted to ask entrepreneurs about how they arrived at their ideas and spotted their opportunities. Every conversation reveals a new set of questions, a new way of approaching the challenge.

By paying attention to the questions that people ask—especially the ones I would have never thought of…

I’ve noticed that the “easy” questions are rarely the ones that unlock opportunity.

“Easy” questions are the ones that take a complex situation and reduce it to something that can be solved with a set of easy-to-follow instructions. They assume a simple, linear solution to a challenge that’s multi-layered and multi-variable.

We end up asking easy questions because they give us a sense of control and certainty. But to even ask an easy question, we have to ignore the depth of the challenge.

I see this all the time with business questions.

Someone wants to make more money so they ask, “What new offer should I create?” instead of examining what they’re already selling and what might be preventing them from selling more of it.

Or, maybe there’s a question about price: “What should I charge for this?” But there aren’t questions about what types of customers pay differing amounts for the same service, what the true range of pricing is in the market, how value is being communicated, or why someone is really buying.

Let’s look closer at a really common situation and the kind of question that most often accompanies it.

I want to reach more people with my content. An easy question to ask is, “How do I get more followers on Instagram?” which is a question that can be answered by a simple Google search and an article titled 5 Ways To Get More Followers On Instagram—although “answered” is a strong word since that kind of content rarely includes remarkable insight. I might talk to some peers and ask them how they’ve gotten more followers.

But there are other ways to approach this problem.

I might start with breaking down what I think the problem is so that I can better understand what my own needs are:

  • What do I really mean by “reach?” Do I just want more people to see my brand or am I looking to get people thinking differently by engaging with my ideas?
  • What do I really mean by “more people?” Will I be satisfied with getting in front of more people or am I looking to connect with a certain group of people who value what I share?
  • What do I really mean by “my content?” Do I really want more people to see my Instagram posts or am I actually looking to find creative ways to share my ideas with new people?

I’d also take a look at the root causes of this challenge and why those causes exist in the first place. “The 5 Whys” is a helpful exercise for this.

I might continue to explore this problem by asking why I think it’s a problem in the first place and why solving it matters. I might also probe why more of the people who are already engaged with my content haven’t bought yet.

I might look at how others are reaching larger, highly-engaged audiences and analyze how they approach turning their ideas into content and how they share that content when it’s ready.

I might even give myself a few constraints to force new ways of exploring the problem: a solution that involves less work instead of more, a solution that requires me to ask for help, a solution that doesn’t try to exert control over the outcome. I like to think of these as “What if…? What would that look like?” questions.

I’m going to seek out questions that go well beyond the easy, surface questions:

  • Systems questions: examining how challenges are interconnected and dependent on multiple variables
  • Courageous questions: considering possibilities that have been avoided out of fear or discomfort
  • Transformative questions: pondering how a challenge could point to the opportunity for major change or growth
  • Purpose questions: reflecting on why a challenge exists and why solving it matters

In order to approach a problem in this way, I need to give myself time.

Urgency leads to easy questions and band-aid solutions that rarely produce sustainable results.

Look, I don’t want to make it sound like I think easy questions are bad questions. It’s just that they’re not the only question—nor should they be the first question we ask. Going deeper, not taking a situation at face value, helps us ask the important questions that eventually lead to the right easy questions.

Learning to ask questions that get to the root of the challenge and seek to understand situations in a more systemic way doesn’t happen overnight. It’s a skill you develop through practice, curiosity, and collaboration.

But once you start to get the hang of it, you’ll notice you feel less like you’re on a hamster wheel and more like you’re making meaningful progress on what you’re building.

Cover of What Works book by Tara McMullin

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