Asking the Right Questions

I once worked for a CTO who had a very different leadership style than any other manager I had ever worked for in the past. He pulled from several different management techniques, but was ultimately rooted in the Socratic Method. Yes, he asked questions. Better still, he encouraged questions from those around him.

If you’re not familiar with the Socratic Method, it’s actually rather straight forward. This is the practice of teaching by asking open-ended questions with the intent on the students answering through examining their knowledge and beliefs. It is done to get students to think on the fly and not have to always rely on straight fact memorization. This discussion among students (and the instructor or leader) also adds the benefit of everyone involved buying in to the proposed answer, or at least knowing their their dissent was recognized and discussed and not just dismissed.

This CTO would quietly sit in meetings and listen. When the meeting was about over he would pose one, maybe two questions, and then watch and listen as we debated further. Occasionally he would have a predetermined outcome he wanted us to all reach, but more often than not he was just as interested in our discussion and path as we were.

More than once I would find myself in a one on one discussion with him and the only thing he’d say was a variant of “you make a valid point, but what is the real question you are trying to solve?” He challenged me to think deeper; to try and find the underlying question to the problem I was trying to solve. Some days it drove me crazy, but then I’d have that epiphany when I hit upon the “right question,” and it all became clearer to me.

I have always been inquisitive. It’s just my nature to ask questions. However, watching him in action was enlightening. I could wax poetic about how he had elevated it to an art form.

Those who didn’t like his methodology felt he was ineffectual because he didn’t always have a clearly defined agenda. They couldn’t have been more wrong. He knew what he wanted to achieve from the very beginning, but he asked us questions which in the end made all of us feel as though we had the ideas. In turn, that gave us a deeper ownership in the project as individual contributors as opposed to just receiving marching orders and being told what to do.

Since working under this person I’ve tried hard to “step my game up” with Socratic Management. I’ve tried to not just manage those around me, but lead them by asking questions and getting them to buy in to the ideas I have on their own. I’ve had some strange looks from some people, and have even had a few tell me that they’d rather just have me tell them what to do instead of asking all those questions. That’s fine, and I am happy to adjust for them. Others though really took to the questions, and I’ve watched them grow and become leaders in their own rights.

I still hear that CTO as a little voice in my head, telling me “You still haven’t asked the right question.” It drives me every day.