The Benefits Of Open-Ended Questions In Business

Dan Sullivan
4 min readJul 28, 2022

I always advise people to ask open-ended questions to which they don’t already know the answer. The benefits of open-ended questions in business are endless, as possible answers are many and can provide massive, often unexpected breakthroughs.

As a child, I can’t remember teachers ever asking open-ended questions they didn’t already know the answer to. It was about memorization and getting the one “correct” answer.

This is still the case in many areas of life and business.

For example, in sales presentations, they say to never ask a question unless the prospect will agree with you.

Facilitating breakthroughs with open-ended questions.

Open-ended questions result in unique answers derived from deeper thinking and discovery. In the entrepreneurial world, breakthroughs often happen because of great open-ended questioning. In the scientific world, discoveries are made precisely because people are asking questions nobody knows the answer to. It’s not about having the right answer; it’s about asking great questions that open up the possibility for new, unpredictable, and surprising responses.

In Strategic Coach, we talk about The Entrepreneurial Time System of Free Days, Focus Days, and Buffer Days. In our workshops, instead of reviewing what they are by definition or in theory, I like to ask questions like:

“What are three great things you’ve experienced because of Free Days?”

“What are three great things you’ve experienced because of Focus Days and Buffer Days?”

I have no idea what people’s answers to these open-ended questions will be because they are specific to each person’s experience. However, I know that their answers will reinforce the concept I teach. Their answers prove that the concept works. This is a clear benefit of open-ended questions in business — people can see that what you provide makes a difference in their lives.

Our tools maximize the benefits of open-ended questions in business, raise morale, and drive momentum forward. The tools also renew the entrepreneur’s confidence in new possibilities as they’re guided to think differently about what’s already — or could be — in motion.

At Strategic Coach, we don’t know ahead of time what you’ll fill in when you complete our tools, and we don’t want to. Creative entrepreneurs don’t conform anyway, so there’d be no way to predict their responses!

The path to success with open-ended questions.

Asking open-ended questions requires courage because you’re entering an unpredictable and interactive realm. You must be truly open to learning from the answers, even if they’re unexpected and surprising. Remember, when asking open-ended questions you don’t know the answer to, both sides learn something new. To me, this is true learning, and it’s what happens inside Strategic Coach.

With the open-ended approach, any unpredictable answer can be the right one, and there are many paths to success. The unpredictability of people’s answers is enriching because it immediately opens the door to new thought processes. With closed-ended questions, there’s no room for that; every answer that isn’t right is considered wrong.

Open-ended questions require a willingness to be conversational rather than just one-directional. They create a two-sided learning dynamic that leads to new insights that you could never get otherwise.

Putting open-ended questions into practice in business.

To reap the benefits of open-ended questions in business, it’s important to consider the origin of the knowledge needed to be successful in the 21st century. Is it the knowledge outside the person, or the knowledge created from within?

I’ve placed all my bets on the latter.

The knowledge already out in the world is available to anybody who wants to find it. Today, children can (and do!) go on YouTube to learn more on any subject than they will learn in school. With the internet and technology today, we have no problem finding outside knowledge, in business or otherwise.

What’s most valuable today, especially in business, is extracting unique, individual knowledge and experiences. This knowledge leads to the many benefits of open-ended questions, including new learning, innovation, discoveries, and breakthroughs.

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I hope this article triggered some new ideas, projects, initiatives, and thinking for you and your business.

Thanks for reading,


If you’d like to learn more about the power of open-ended questions, download your free copy of my eBook, Deep D.O.S. Innovation, where I share how to discover what matters most to your clients and prospects by asking the right questions.

Make sure to check out more of my latest articles because little things keep becoming bigger and better when you think about them in new and different ways.

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Dan Sullivan

World’s foremost expert on entrepreneurship in action. Co-founder and President of The Strategic Coach Inc. Find out more: