The Power of Questions

July 26, 2021

In late 1989, just after starting at Stanford Law School, I briefly explored a project to use Lotus Agenda for document management at law firms. The opportunity arose from my work at a Los Angeles law firm as a paralegal the previous year, after graduation from university. Although Lotus Agenda only survived a few years, it was beloved by its devotees as extremely flexible “personal information manager” software. A law firm partner was so impressed with what I had done with this software on a big case that he recommended me to a San Francisco consultant (whose name I have long since forgotten) to cooperate on turning my work into a product.

The project did not last long, and its failure was mostly my fault. After an initial meeting with the consultant, I did not hear from him for many weeks, during which I tried to call him a few times. Fearing the worst, and without a legal agreement, I decided to write him a letter (this was before widespread email), explaining that I had trusted him with my ideas, and was unhappy that he had taken them and used them without me. He responded quickly that he had been about to get back in touch with me, but had found my letter offensive. He paid me modestly for the time I had spent with him, and said he wanted nothing more to do with me.

With the benefit of hindsight (and I should have known better even in my early twenties), writing an aggressive letter without knowing what the consultant was up to was a bad idea. But what else should I have done, given that the risk of theft of my ideas felt real? The answer is simple – I should have asked questions. Like “when will I hear from you?” and “are you planning to use my ideas?”

The Power of Questions

Questions are an extremely powerful tool. We tend to think about them primarily as a device to elicit information – like answers to a test or directions to the nearest bank. But they can do much more.

In personal interactions, like mine with the consultant, properly-asked questions give space and respect to the person questioned to explain their views or behavior. While statements (or accusations) are generally presented for consumption by the recipient, questions draw valuable information from their recipient. Health warning: this is not true of all questions, for example aggressive questions that are rhetorical (“Why do I have to listen to this nonsense?”) or accusatory (“Why do you make so many mistakes?”).

Questions can also facilitate discussion and exploration, because they challenge us to consider new angles rather than adopting or reacting to a fixed point of view. For examples of how to do this well, I like this blog about how to ask good questions and this site of curated questions on a variety of topics. As explained further below, this is a key use of questions at LearnerShape, to allow us to understand what customers need rather than assuming we already know.

The more general point is that questions have different meanings in different circumstances. I have written at length about the related point that information can have different roles in different circumstances. If we miss such distinctions, we miss fundamental aspects of the nature and power of human discourse.

Developing a Question Reflex

From a practical point of view in business, the key insight is that the power of questions is a valuable tool. It can facilitate better outcomes with little or no cost. They say that there is no such thing as a free lunch, but there are exceptions. Questions can be a free lunch.

I have worked to develop a reflex to ask myself, when confronted with a challenging communication, whether there is an opportunity to improve the communication by asking a question – rather than offering an opinion, or a criticism, or whatever. Frequently the answer is yes, and when I deploy questions I am regularly surprised at how much they can improve communication. I urge you to give it a try, and – if you like it – to work on developing your own question reflex.

Questions and LearnerShape

At LearnerShape, there are a couple of ways that the power of questions helps our business. First, as CEO I use the question reflex to improve communications with our team, customers and partners, and I encourage the rest of our team to do the same.

More importantly, asking questions is fundamental to what we do. Our AI-based learning infrastructure is intended as an alternative to the usual approach of giving customers a platform that tells them what they need. Instead, we ask our customers about their requirements and use our learning infrastructure to deliver targeted learning applications that meet their specific needs. Our e-book explains in more detail how we do this.

For one of our key customers, we have developed an interface that identifies individual learning needs by asking a series of questions. And we worked out that approach with the customer through a discussion involving numerous questions about their needs. Two levels of questions aimed at effective learning!

In sum, education, business and life are inherently complex and uncertain, and it usually improves outcomes to ask about the real requirements of a situation rather than assuming the solution. This is the power of questions. I urge you to embrace it – you won’t regret it!

Maury Shenk, Co-Founder & CEO, LearnerShape