Image by midjourney prompt by the author.

What I’ve learned about the art of asking good questions

About half of my work is helping people access answers they already have. This sounds silly, but what I’ve found is that:

1. Most teams already have the answers they need, they’re just not asking the right questions to access or use them
2. There is usually more than enough value in starting with what we already know

In other words: we already have most of the answers we need, we only have to find the right questions to get them and use them.

e.g. instead of asking “how do we sell more products to parents” we can ask: “in what situations are parents using the product and what need are they solving from using it?”. In most cases when I’ve asked this question people will give me high quality answers, reflections and assumptions. Information that helps the team find, understand and prioritize the real opportunities and make better decisions (“selling more products” is not an opportunity .. it’s a result).

What I’ve learned about the art of asking good questions:

1. Most of what we do isn’t magic, it’s asking the right questions at the right time.
2. Making the questions simple enough (goodbye complicated frameworks) helps people intuitively and immediately understand how to get to a good answer.
3. Making the questions interesting enough sparks people’s curiosity and positive engagement.
4. Making the incentive big enough helps people see the value of answering questions in a good way and motivated to give high quality answers (less top-of-mind or opinions and more experience and expertise).
5. Asking questions people already have the answer to means not giving them more work or getting them stuck, but helping them move forward.

Sometimes the question takes the form of a simple question, a discussion or a reflection. And sometimes the question takes the shape of an exercise, experience, model or mindset.

Asking the right question isn’t always easy. The question takes work. Sometimes you have to ask a stupid question and sometimes you have to chase a rabbit down a rabbit hole.

But as long as I’ve followed the five bullets above, it doesn’t matter. People are engaged, they understand what to do and why, we externalize their expertise and insights and we get to paint a canvas that includes a much better picture of the opportunity to solve.

And if sometimes there truly is no answer, there are always assumptions. And assumptions are great windows into more learning, where we with clarity and precision can articulate what we want to know next.

I’m not saying this is all the work for all situations, but so much of the work can be solved better with something as simple as the right questions and the approach should always be that one or some of us already have the answer we are looking for, if only we ask the right question…