Socratic Questioning: Why Entrepreneurs Question the Unquestionable and Why You Should, Too

Socratic questioning

More than fifty years ago, Peter Drucker raised our attention to the power of asking intriguing questions. “The important and difficult job is never to find the right answers, it is to find the right question,” he said. We all know when we hear a good question; it’s the one that makes us uncomfortable and curious at the same time. This forces us to reevaluate what we know to be true. And if the question is really that good, it may lead us to start “questioning the unquestionable,” as Raman Tata said once.  

The one man who dedicated his life to asking right questions was Socrates, a Greek philosopher. Socrates used questions and queries as a tool to stimulate thinking through dialogue. Along the way, he invented what we call Socratic questioning.

I learned about Socrates and Socratic questioning in my twenties as a young screenwriter, and it changed my life. Socratic questioning helped me understand how important it is to ask many good questions so that along the way, one might stumble upon the right question.

In the late 90s, I was working with a group of writers on a new television series in Turkey. Our leader was Yavuz Turgul, one of the most successful producers who had started his career as a writer. To outsiders, he was known to be demanding and challenging. For anyone eager to learn and grow, he was a great mentor. He loved asking questions, and those questions helped him and us to create.  

“What do we know about him” he would ask one writer referring to a new character one writer was developing. “What might cause his reaction to be that way?” would ask another one trying to gauge whether the proposed action made sense in the broader context. “What if this happened, instead? How might that change what you just proposed?”

You see, when writers create a new screenplay, the process is not unlike creating a new business. There are people (characters) in this new world, and their interactions or lack of them cause the story to move forward. If a writer fails to set up the characters in the right way, they would never do what the writer might like them to do. To create believable characters, one needs to get deep in understanding the inner mechanics of them and their interaction with the world and the context. These questions allowed all of us to do just that and do so collectively. They helped us to build worlds that never existed. I later learned that this approach was called Socratic questioning. And the methods we used were not too different from creating a new enterprise or a new product.

In Innovator’s DNA, Clay Christensen and co-authors describe how most innovative entrepreneurs use questions to understand the world that they want to change. Michael Dell stumbled upon his idea for founding Dell Computer from his asking why a computer cost five times as much as the sum of its parts.

“I would take computers apart…and would observe that $600 worth of parts were sold for $3,000.”

Michael Dell, Founder and CEO of Dell Technologies

In trying to answer the question, Michael Dell hit on his revolutionary business model. He is not the only one. I wrote in another article how Elon Musk asked similar questions that eventually resulted in him founding SpaceX. 

Three questions appear to be critical for innovative entrepreneurs. They use them to create new worlds. Those are “Why” “Why not” and “What If.” 

These questions helped create Netflix, Salesforce.com, SpaceX, Dell Computers, and many other companies. The power of these questions is that they help us engage in conversations, uncover truths, and make important decisions.

“Questions are like keys that unlock doors in our lives and in our work. The challenge is to find the right key to unlock the right door,”

Hal Gregersen, Executive Director of the MIT Leadership Center

Most of us are not taught how to ask good questions or use conversation as a decision tool. We are used to didactic leaders, authority, and direction. We need leaders that guide and inspire vs. teach or direct. What we need is more conversation. 

How many good conversations do you have in your meetings? As a consultant, I attend thousands of meetings, and have worked with more than 100 organizations over my career. Most of the sessions I attended were to show and tell.

The tight agendas, the style of the room, the approach of presenters is not conducive to dialogue. You usually have someone that represents a team who walks through a PowerPoint presentation in front of leadership or an audience. Most of the time, there are too many pages. And by the time the presenter is ready for questions, coincidentally, the allocated time for a meeting would be almost fully consumed. And people would rush to the next meeting.

How could this allow for any dialogue?

Reality is that meetings have become a tool for showing management that the team has a proposed action. The desired outcome for the presenters is to get support for that proposed action. Anything less than that is a lost opportunity — what a waste of leadership intellect. Innovative entrepreneurs act very differently. Senior executives of the most innovative companies don’t delegate creative work. They do it themselves.

Very rarely would a team engage their leaders or audience to collectively think through what the best course of action would be. That would be considered a weakness in many organizations. Dialogue in a meeting is a no-no! 

Is it the case in your organization? Be honest!

Socrates believed “that all of us, we know more than we know,”

Sira Abenoza, Founder of the Institute for Socratic Dialogue

She is the Founder of the Institute for Socratic Dialogue. She is also a professor at ESADE Business and Law School. “We’re going to help each other to become more aware of that knowledge…. And dialogue will be about collaborating; it’ll be about teamwork. It’ll be about helping each other to give birth to those ideas, to that knowledge that we have without knowing.”

Socratic questioning is not about overpowering an opponent. Our entire life, we are taught how to win an argument. We are taught how to fight with words, how to win an argument. This aggressiveness is considered smart in certain cultures.

Socrates had quite a different perspective on this. He thought that every one of us have a fantastic knowledge about things, yet we needed others to give birth to it.

The fact that my creative team was thinking together made a difference. Having a good dialogue made us stronger and better. It allowed us to collaborate. It also helped our collective creativity reach levels that we would likely not achieve if we were to write on our own.

Our team ended up creating Ikinci Bahar, a TV show which broke ratings records in Turkey and became the most-watched television series that year. Even after 20 years of its first airtime, in 2019 this show was selected this year as the best series ever produced in Turkey.

Later in my career as a strategist, I relied on Socratic questioning to help my teams challenge their assumptions, as well as challenge my own assumptions. In doing so, we were able to identify the first principles of the system we were working on. That helped us improve our collective ability to innovate. We achieved it with some teams and failed with others.

There were times when I was able to achieve it easier with some teams. The culture of our team members, their diversity and the organizational context mattered. Most importantly the level of curiosity and drive to change the world mattered most.

The best innovators have a deep curiosity about the world. They don’t accept the way things are. They probe and engage in conversations, ask the unquestionable. That approach leads them to new answers. 

So next time you’re in a meeting, go ahead and question the unquestionable. It will lead your team to new insights. Along the way, you might discover many new opportunities. Worst that can happen is you will end up having a meaningful dialogue. It’s well worth a shot, in my humble opinion.