Take the Road Less Stupid-Business Strategy

I'm Abhi!

Host of ENTREYE podcast and Co-founder of Mish Media, a franchisor growth agency

Back in university, my philosophy class familiarized me with the Socratic method. It was interesting, but its practicality in the world of business only became apparent to me when I read “The Road Less Stupid” by Keith Cunningham. 💭

Why should businesses care about Socratic Questioning?

Socratic questioning/dialoguing/probing/debating, and every other imaginable spin on the term, was introduced by none other than Socrates himself, who used interrogative strategies to spark critical thinking.

The main idea is that by asking questions that don’t have a simple yes or no answer, we can clear up confusing ideas, question assumptions that have no evidence, and look at different ways of thinking.

Your dialogue with other parties could sound like this:

  • What do you mean by that?
  • Why do you think that’s true?
  • Are there any strong counterarguments to this?
  • Can you help me understand how you came to that conclusion?

At a glance, these questions might look easy but when you’re enjoying some success in your business, it’s easy to lose discipline and start accepting faulty concepts and weak ideas. That’s why it’s important to make this method at the top of your priority list.

How to use the Socratic method to get better results

Before you start using the Socratic method, you need to adopt an attitude of continuous learning and growth and be willing to set your ego aside. You will have to question others, and they will question you too. This might feel uncomfortable, but it’s needed for these kinds of questions to work well.

If this sounds good, here are some ways you can start using Socratic questioning in your work.

✅ Winning Over Stakeholders

If you’ve been diligent in your project, you can use Socratic questioning with stakeholders who resist your ideas without thinking them through.

Some questions you could consider in tricky situations:

  • What’s your view on the problem we’re solving?
  • Can you foresee any downsides to this project?
  • What are the keys to this project’s success?
  • What improvements could persuade you to support this project?

These questions will mostly depend on the project & situation, but the aim is to make the stakeholders share their thoughts, helping you understand their viewpoint and maybe make them reconsider theirs.

✅ Talking to Your Customers

Avoid asking leading questions or taking everything your customers say at face value during interviews. The Socratic method is really useful here. Here are some questions you could consider asking:

  • Why did you start using our company? Please explain.
  • What were you hoping to get from our product or service? Why?
  • Did you achieve it? Why?
  • What new features or services would you like to see from us? Why?

This way of asking questions can help them examine their own assumptions, which in turn helps you examine yours.

✅ Getting to Know Your Team’s Ideas Better

We are all human and can sometimes make assumptions. The Socratic method can be very useful in a team setting. For example, if a team member’s ideas aren’t hitting the mark, it might not be a lack of innovation, but a lack of the necessary resources to refine their ideas.

In such cases, you could ask something like: “Can you help me understand your thought process behind this idea?”

This method is also excellent for encouraging creative thinking toward large goals-helping identify team members’ strengths, areas for more creative thinking, and any barriers to innovative solutions.

So, what’s next?

Isn’t that a great open-ended question to end with?

The Socratic method is all about asking questions. The aim isn’t to get exact answers: it’s about viewing issues from different angles, questioning our assumptions, and getting a clear understanding.

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