Good Questions

Our conversations are not as productive as they could be. We often ask questions to fill out a conversation, without considering the exact value their answer will provide. We also fail to evaluate whether or not a person is qualified to inform us about that specific question — if they are not, their ability to answer will be limited. There are a few major problems with asking the wrong questions.

The first problem is that if you don’t ask the right questions, then you will not be able to tap into the full knowledge an individual holds. If someone is interested in an area you are pursuing, you should ask them specific questions that you are interested in learning more about. There is very little point in asking a random question without first considering whether or not their answer will assist you in any way. Asking the wrong questions can also make the person on the other end of the conversation uncomfortable — you may be asking them about something they do not feel qualified to answer.

Asking the wrong questions is even worse if you are engaging in a panel interview, a group meeting, or any other social occasion wherein multiple parties could benefit from the question you answer. If you ask the wrong question, your and their time will be wasted because they may not be able to provide a specific answer. In a group environment, other people may also have questions to ask, and if you ask the wrong question, then there may not be time left for other people to ask their more meaningful question.

Our conversations could be significantly more productive if we were more intentional with the questions that we asked. This does not mean that we need to prepare a professionally-formatted document with a list of questions, but rather we should spend more time considering the value a specific question will yield for us, the individual who will be answering the question, and anyone else involved in the discussion.

One way to ask better questions is to think about how you would answer the question if you had been asked it. This is a great litmus test which will allow you to understand whether your question is clear, relevant, and simple — three elements needed to engage in thoughtful discourse about that question. Thinking about the question you are going to ask also gives you a moment to question whether the question has any real value, or whether you are just asking it because you want to ask a question — this does not help anyone.

It is also great to ask more open-ended questions: “What are your thoughts on X, and why do you think that way?”, for example.. My thoughts on this topic will likely make their way into a new essay, but, in sum, asking open-ended questions gives someone more freedom to answer your question. The individual does not have to worry about whether what they are saying is on-topic, which generally leads to a more productive discussion. If the person answering the question goes on a tangent, this gives you a new opportunity to learn even more about the individual, and how they think. Asking open-ended questions also prevents people from filtering out things they may think are irrelevant, but would indeed add more value to the discussion. It is worth noting that, in some cases, asking specific questions would be better, but there are still many instances where an open-ended question would be more appropriate.

You should also not be afraid to follow-up on a question. If someone has provided you with a thoughtful answer that leaves you with another question to ask, then you should ask the question that you have. In a group conversation, it is likely that someone else will have the same thought as you. The worst thing that can happen is that the person delivers a short answer and the conversation moves on. The best thing that can happen is that you get to know the person in more depth. I think that too many people think about the specific set of questions they want to answer and stick to that schedule, and do not leave enough time to ask a follow-up question about an individual’s answer. If you are curious about something, there is no harm in asking more about it.

I have also noticed that in cases where the person being asked the question is famous or popular, the interviewer will spend time asking rudimentary questions. Indeed, these questions are important in conversation — they help people better understand the foundation of the individual’s work. However, I think that we spend too much time on these questions and do not ask enough unusual questions that the person would have a lot of great insights on. We often look for an easy question to ask, because it reduces the chance that the other person will be unable to answer. A lot of value in conversations is lost because people are not willing to ask a question that the interviewer may not have received before, but would likely be able to answer effectively.

The value of conversational flow is also not considered. This is more difficult to maintain in group discussions, but in one-on-one meetings and interviews, the questions that you ask should follow a specific flow. Perhaps you start by asking the individual about their past work, then you delve deep into the questions that you want to ask about their thoughts on a specific subject, why they think that, et cetera. Following that, you could then ask the person about what they are going to do in the future, and start to ask some final questions before concluding the discussion. Conversational flow helps ensure that everyone stays on-topic, and that the individual has enough time to effectively answer a question and discuss their thoughts, without being asked a completely different question after they have finished talking.

The interesting thing about asking good questions is that it does not take that much time, but can yield a lot of value. Individuals who spend time thinking about what they want to ask, account for serendipity, and are willing to ask follow-up questions will likely be able to cultivate a better relationship with the individual answering the question, and yield higher quality responses to the questions they have prepared.

Be intentional. Account for serendipity. Ask follow-ups. Consider the flow of the conversation.