The Questioner's Guidebook: Decoding the Art of Insightful and Empathetic Questioning
The best questions are not just insightful but also deeply empathetic. We explore the importance of asking insightful and empathetic questions, as well as the mindset and techniques required.
Have you ever wondered why some people always seem to be able to ask the perfect questions at the right moment, while you sometimes feel stuck in conversation wondering how to carry a discussion on?
You would think that given how much we rely on questions on a day-to-day basis and how we’ve all been doing so since we were kids, we would all be pros at asking questions. Yet this is often not the case. In many work places, the incentives are flipped, with both leaders and staff feeling that if they need to ask questions, they end up looking like they don’t know how to do their job, and are therefore not as valuable as those who carry on in ignorant silence and faux stoicism.
This is a big problem . In our personal lives, business endeavours, or leadership roles, it's often the quality of our questions that dictate our success. This importance is further amplified in a world of constant flux and uncertainty, where the need for continuous learning and anticipation is increasingly the norm and no longer a nice-to-have.
So what does asking the “right question” entail? Clearly, a great question isn't simply a string of words ending with a question mark. Instead, I would argue that the best questions reflect an intricate dance which balances being insights-driven with demonstrating genuine empathy.
Great questioning is therefore not just about curiosity, but also about setting aside our assumptions, judgments, and preconceived notions. It’s about stepping into the shoes of our counterparts and being ready to build a real and genuine connection. That can be uncomfortable. But it’s this very discomfort, this willingness to open up and connect, that can lead us to the kind of deep understanding and empathy that makes the struggle worth it.
The ability to ask insightful and empathetic questions is a skill that many of the great leaders and communicators have in abundance. Take for instance Satya Nadella, Microsoft’s current CEO, who is renown for his empathetic and curiosity-driven leadership style. Nadella famously started his leadership tenure with an email to the entire company asking everyone to reflect upon the questions, “Why are we here?” and “What do we do next?” and since then has evolved Microsoft’s culture from one of adversarial inquisition to empathy-led questioning. Oprah Winfrey has also been another great communicator of our time. When asked about the secret to her success, she had this lesson to share, “Whether you're trying to create a great conversation or a great life, it's the questions that count. Ask the right questions, and the answers will always reveal themselves.”
Over the rest of this article, we will explore the mindset, techniques, and skills needed for asking great questions.
Asking great questions requires the right mindset
Even more so than skills and techniques, the right mindset is arguably the most critical prerequisite for asking insightful and empathetic questions. Without the right intent and frame of mind, our body language, tone, and facial expressions tend to quickly and significantly reveal us to those whom we are speaking.
I was introduced to someone in a professional context several years but still keenly remember the experience for all the wrong reasons. He commanded the room with confidence, dressed smartly, and said a lot of the right things that got many people at a meeting nodding. He even asked interesting questions. Yet his haughty body language, in particular the upward tilt of his head as he spoke down to us, as well as the condescending tone in which he asked questions, made it clear what he thought about most people in the room. I left the meeting with the clear feeling that I had absolutely no desire to work with the individual in question.
While it is fairly clear that we should probably try not to exude arrogance and condescension, or to look at someone with pity, what exactly is the right mindset to have?
#1: Adopt a Learner Mindset
The Learner / Judger Mindset model[1] is a good starting point. It explains that individuals generally adopt one of two mindsets, a Learner Mindset or a Judger Mindset.
The Learner Mindset is focused on understanding, open to new ideas, and flexible enough to shift and adapt based on new learnings. The critical underlying mental model is one of humility and curiosity, with a strong willingness to admit that “I don’t know the answer, but am very willing to learn.” A Learner also needs to be courageous enough to put him- or herself out there to ask potentially difficult questions, not necessarily with the intent to “rock the boat” but to genuinely find solutions and enrich everyone’s learning.
The Judger Mindset is focused on judgment (of self and others), is closed to new and different perspectives, and rigidly holds to a pre-established point of view. A person with such a mindset tends to believe that he or she “knows it already”. Judger Mindsets are sometimes adopted as a “coping mechanism” in response to uncertainty or stress. A Judger is therefore more likely to adopt aggressive (e.g. criticising others) or defensive (e.g. unyieldingly guarding certain assumptions or beliefs) stances.
Yet adopting a Learner Mindset is hard to do. For many of us, myself included, it can be very difficult to admit that you are wrong, especially when the issue at hand is close to your heart. For me, self-reflection has been a critical part of my journey.
Every week, I try to make time (just 30-45 minutes or so) to consider the key events of the week and more importantly my resultant thoughts, emotions and responses. I have also found it useful to subconsciously vocalise reflective questions during the course of the day, not only when thinking through a problem but even in the course of conversations with others (e.g. “Am I being honest with myself?”, “How else could I interpret what he / she is saying”). For much of the day, our subconscious mind often works on autopilot, assembling responses (both questions and answers) based on our beliefs, past experiences and emotional state at the point in time. When I actively sub-vocalize a question however, I find that the conscious and more deliberative part of my mind is more likely to take charge of my thought processes, taking me closer to adopting a Learner Mindset.
Asking great questions requires good technique
While we are all born with the penchant for asking “why”, insightful and empathetic questioning goes beyond natural curiosity and requires good techniques.
#2: Understand our objectives
The primary objective of asking questions is to gather information, ideas and concepts. When we ask questions however, most of us also have a number of secondary objectives, usually related to managing impressions and relationships.
Asking questions helps to build trust and respect between parties. Questioning is also a key part of negotiations and conflict management, and also plays a key role in many business functions such as managing people, building teams, and facilitating organisational change.
To quote Benjamin Franklin, “By failing to prepare, you are preparing to fail.” Whatever the case may be, it is important to fully understand our objectives to better prepare for the discussion and the questions (and potential follow-up questions) we want to ask. For instance, if we are entering into negotiations, it is useful to consider questions that could serve to subtly tease out the other party’s underlying positions, such as “no-go zones” or potential areas of compromise. If on the other hand, we are looking to provide comfort to a friend who has been through a traumatic experience, we should probably aim to listen more than speak, and when we do ask questions, we should consider questions that are not overly probing unless we are sure that they are ready to reveal the details.
#3: Frame our questions
Context is key. A great question in one situation may be highly inappropriate in other settings. This is why good questioning requires one to frame the conversation appropriately by setting up the right structure.
The first step involves laying out the context before the questioning even starts. For instance, if you are asking a colleague to provide feedback about one of your subordinates, you might want to start off by clarifying why you are asking for such feedback, what it will be used for and ensuring your colleague that their comments will be kept strictly confidential. Failure to do so could mean that he or she may not feel comfortable providing the feedback or be certain about which areas of feedback to focus on. Likewise, if we are trying to ascertain what went wrong in a particular situation, it might be helpful to say in advance that we are not looking to assign blame but are instead trying to ensure that similar problems do not arise again in the future.
It is important to consider the sequencing of questions. In general, and in particular when we are trying to establish or build new relationships, it is more effective to go in with “ice breaker” questions (e.g. “How was your weekend?”, “Did I catch you at the right time?”) and gradually build up the conversation towards more difficult or serious questions. Indeed, many of us might find it abrupt and rude if the person we are speaking to jumps straight into business and only bothered to asked “How was your day?” at the end of a conversation. However, the opposite is occasionally true. As a result of their studies, two Harvard Business School professors found that especially in tense situations, “people are more willing to reveal sensitive information” when they are straight away asked more intrusiveness questions (e.g. “Have you ever thought about taking revenge on someone?”). Follow-up questions are then likely to feel less invasive[2]. However, this technique is difficult to get right and therefore best used sparingly due to the risk of being perceived as offensive.
A conversation should be a two-way dialogue. Have you ever been in a situation when you felt the questions kept coming one after the other? It probably felt unpleasant and very much like an interrogation. I made this mistake early on in my career as a consultant. I prepared long lists of questions for my interviews with clients and kept up a constant barrage until they were answered. This got the immediate job done but probably left a sour taste in the mouths of many clients. It is far more effective in the longer-term, especially from a relationship-building perspective, to give all parties a chance to ask their own questions. Furthermore, in order to get someone to share information, especially when it is personal in nature, it helps if we start by also sharing information of a similar nature with them. This is not merely a case of quid-pro-quo, but reflects the fact that people are much more likely to open up when you have shown that you are willing to trust them with your own “vulnerability”.
#4: Consider our language
In the hands of great speakers such as Winston Churchill and Martin Luther King, language has the power to transform reality. This same understanding should apply not only to events on the world stage, but also to our everyday lives, and everyday questioning. When questioning, the language we use should always be considered within the bounds of our objectives, the person we are speaking to, and the context we find ourselves in.
Most importantly, and even when we are overcome with strong emotions, it is absolutely essential to avoid questions which are not asked in the genuine spirit of learning, such as rhetorical questions (e.g. “How did you manage to fail so spectacularly?”), sarcastic questions (e.g. “You are quite the genius, aren’t you?”), leading questions (e.g. “Don’t you think that he is the cause of all our problems?”) or disempowering questions (e.g. “Why is your work not on my desk?”), which are almost certain to generate resentment, fear and distrust between the parties involved.
When questioning, we also have a choice between open-ended questions (e.g. “What do you think about the latest developments?”) or close-ended ones (e.g. “Do you prefer Option 1 or Option 2?”). Open-ended questions are useful when we are:
Starting a conversation and are looking to get people to open up
Trying to solve problems or challenge existing ways of working (e.g. “What other approaches could we try?”)
Facilitating exploratory or creative discussion (e.g. “What would you do in such a scenario?)
Getting people to reflect about their choices and actions (e.g. “What prompted you to act the way you did?”)
Close-ended questions are usually accompanied by a statement and are meant to establish “yes” or “no” responses. They tend to be more appropriate when we are:
Providing an easy question for people to answer prior to starting a conversation (e.g. “Is this a good time to chat?”)
Attempting to establish the accuracy of certain facts (e.g. “Has the team managed to complete the task?”)
Clarifying parts of a discussion that have taken place (e.g. “What you are saying is that our current approach is not working. Is that correct?”)
An often-overlooked component of using the right language is the ability to step into our audience’s shoes. In our rush to ascertain certain truths or uncover new information, it is easy to forget that our questions can sometimes be seen in a very different lens by others. Where possible, we should always strive to consider if the language we use could lead to unintended interpretations.
Yet truly feeling and experiencing what another person is going through can be difficult, if not impossible in some cases. For instance, I intellectually understand that war veterans can suffer horrendous post-traumatic stress disorder (PTSD) but because I have never been in a war zone or come even close to experience such an ordeal, I might find it hard to step into his or her shoes. Nonetheless it can be helpful if we acknowledge this gulf in experiences, by saying for instance, “I can’t even begin to understand what you went through”. If we remain unsure as to how our questions might be interpreted then we also have the option to be frank and say so (e.g. “I am not really sure how to ask this question but am going to try to do so anyway”, “I apologise in advance if this question ends up offending as that is not my intention”).
One final consideration is the use of positive as opposed to negative language when asking questions. In general, I prefer to use positive language (e.g. “Are we going to be ready for this next phase of the project?”) most of the time. It is the default way in which questions are asked and is generally easier to understand. Using negative language can also result in leading questions (e.g. “We are not going to be ready for this next phase of the project, are we?”), which as mentioned earlier should be avoided.
#5: Listen actively and respond thoughtfully
Too many of us, myself included, “do not listen with the intent to understand, [only] with the intent to reply”[3]. Impatiently asking a follow-up question that has nothing at all to do with the other party’s reply is usually a dead giveaway. Yet listening actively and with the intent to understand is the whole point of asking a question!
The Learner Mindset is particularly important for active listening. I sometimes find myself critiquing, in my mind, the arguments or responses of the people I am speaking to even whilst they are speaking. Instead I should be trying my best to “suspend preconceptions, associations and judgments”[4] so as to allow me to fully understand what is being said.
As we listen, it is just as critical that we listen to what is not being said. Especially in situations where there is tension or strong emotions, reading between the lines is a critical skill. Communication goes beyond the spoken word – as discussed above, body language, tone and facial expressions are often very revealing. This is particular important when communicating with someone from a high context culture, such as in Japan, China, Saudi Arabia and Pakistan, which rely heavily on implicit communication and non-verbal cues. In Japan for instance, it is considered disrespectful to directly say “no” and an evasive response is most likely to be associated with negative intent.
Once we have listened, we should also carefully consider our follow-up questions and responses. These are important not only for information-gathering purposes but also because they signal that we have been listening attentively and that we value the other person’s perspective. This builds trust and mutual respect and is beneficial for relationships.
An appropriate response also requires that we take the time to fully consider the implications of what the other party has shared with us. Equally, we should be sure to give our counterparts the time to reflect. I used to have the bad habit of jumping in with another question when I felt a growing silence because I felt uncomfortable. Yet the best questions are the type that invite silence and reflection. Rather than being afraid of silences, they should be seen as a positive sign that the person we are speaking to is actively considering their response. If it seems like the person that we are talking to needs further time to think, then we should let them know that it is fine to do so or to come back to us at a later point in time.
Conclusion
My journey to asking great questions is ongoing and will likely continue for as long as I live. I would love to hear from you about your experiences (please feel free to share in the comments) about being asked and asking the right questions, and the steps that you are taking to improve your ability to become a more insightful and empathetic questioner.
[1] Adams, M.G., Schiller, M., & Cooperrider. (2004), D.L. Constructive Discourse and Human Organization Advances in Appreciative Inquiry, Volume 1, 105–124
[2] Brooks, A.W. & John, L. K. (2018). The surprising power of questions. Harvard Business Review, May-June 2018, 60-67
[3] Covey, S. R. (1989). The 7 habits of highly effective people: Powerful lessons in personal change
[4] Marquardt, M. (2005). Leading with questions: How leaders find the right solutions by knowing what to ask