Who's Asking Better?

A few years ago, I was at an office event. The location was ideal for networking- a bowling place with a bar in the corner. The vibes at the venue were perfect- 2000s songs playing in the background, people having a fun time with drinks, pizza, pretzels, and many other snacks and cuisines. Everyone took their turns to bowling and, once they were through, they returned to where they were having a conversation before with others. Some wore professional attires after coming directly from the office; others who worked from home were cladded differently. The latter applied to me.

Introductions filled the room. Many were catching up after a while and were pleased to see each other in person. All this was coupled with the trash talk to display competitiveness- It was decided, it didn’t matter who was in a team, everyone must be trash-talked!

I introduced myself to others and met many new individuals and got to know them a little bit. The songs were quite loud in the backdrop, but that didn’t deter anyone from holding long conversations. Some shy individuals sat in the corner and kept to themselves but didn’t mind when someone approached to talk with them. The pins were getting knocked out one by one from every alley. Some cheered their success for knocking out every pin, while some laughed from the embarrassment when the ball completely missed hitting any pins. But the encouragement and rooting for one another was also going on with great vigor.

Conversations about work, weekend plans, holidays, and future career goals were going around. Some who had recently joined the firm, were trying to impress senior managers after meeting them for the first time, and sought career tips. It was one of the fun ways of engaging in a sports activity, drinks, food, and networking with others. The networking gave deeper insights into the company’s culture as well as the leaders who shared their vision with others that provided meaning and purposes for the everyday tasks that everyone was doing. Inspiring words percolated around as the nature of everyone's work became more apparent and how it impacted the firm and the associated clients.

As the event further unfolded, I met a senior whom I had never met before. The conversation was friendly and introductory. The senior and I were getting to know each other and discussed how each of us contributed in very different ways to the same firm. Eventually, the conversation transitioned to career and personal goals. I received some great insights and by the time our conversation ended, a small crowd had already accumulated around us.

Soon others chimed in and started narrating their anecdotes about the topic we were discussing and, eventually, the conversation steered towards other topics. While I gained invaluable insights from this senior, I came to a realization. Asking the right questions at the right time in the right way is crucial to building and maintaining relationships.

This is the super skill I wish I can keep getting better. I’m calling this a super-skill than any other skill because this singular skill helped me deeply in my professional and personal life. It helped me to develop a better and deeper relationship not only with others but also with myself. One can ask questions to understand oneself better and challenge beliefs and assumptions about many ideas, thoughts, and perspectives. I think it can develop a healthier relationship with the self just as much as with others . with this skill

Asking questions, not only challenges assumptions but also provides clarity and purpose to think through actions before executing them. While asking questions is important, I think it’s more important to ask the Right Questions, at the Right Time, in the Right Way to get the most out of anyone or any literature if one is perusing for that matter.

How does one know whether a question is right? What’s the framework, philosophy, context, and rationale behind deeming whether a question is right? I take an example of a child or a kid. Since kids are curious about everything, they keep asking questions. Adults answer some of the questions but often get stumped or annoyed by the excessive questions. But how often are kids taught to ask better questions? As adults, we want to quickly answer their questions and get on with our busy lives to avoid their tantrums before they sink us into their deluge of questions.

I was reading a book the other day about mental models. The book provided instances and explanations of various ways of thinking. If mental models gave insights into thinking about “how to think better”, why can’t there be a – Asking Model? In other words, why can’t we have models that can help us to ask better questions? This doesn’t apply to just kids but everyone. There appears to be a set of expectations that every individual will just get better at asking questions. But, unfortunately, it’s not so.

From my experience, asking questions is one of the most important ways to learn. Accepting any information without first challenging it, counter-questioning it, and putting it into different perspectives, can be detrimental to growth because it can often lead to a status quo which is nothing but innovation and creativity’s arch-nemesis.

As our understanding deepens as we grow, adults evolve to ask better questions (Not everyone though!). Exposure to different knowledge, people, and other sources of information answers some of our burning questions. Every question answered further pushes us into the rabbit hole of more questions to understand a topic better than before.

However, having mere inquisitiveness is not enough to discern the complexities of the world. While passively observing how events unfold can give a good idea of how the world moves, and while it’s one of the ways to absorb knowledge with a rationale that participation might taint or sully the process, nevertheless, asking questions and challenging how things move can perhaps lead to a better understanding in some scenarios.

It's understandable that in our fast-complex world we might ask someone the right questions at the wrong time. I’m assuming as one gets older with more wisdom and experience, one learns to pick the right timing to ask the right questions. While right timings may be learned over time, nevertheless, there’s probably another important element that is linked to asking the right questions - Asking questions the Right Way. This facet can either make or break a conversation.

Tone, Timbre, expressions, grammar, appropriate pauses, body language, other gestures, etc., are some of the important attributes that go behind asking a question in the right way from my personal experience. I’m sure we’ve all experienced when a question, knowingly or unknowingly, is asked with incorrect intonation. The recipient might not usually respond properly and at times can also create an awkward situation or infuriate a person. Asking a question the right way can be a challenging task especially when we’re not in the right frame of mind. It happened to me once when I was in a different mindset fixated on an issue I was working on, and I popped a random question to my friend in a not-so-regular tone that bordered on the personal level. Fortunately, being a friend, my friend didn’t take the question too seriously. But I realized if I had asked the same question to a different person in a different setting, I surely would’ve gotten myself into big trouble.

The age-old saying: “Ask, and it shall be given!”, has been framed quite cleverly. While the saying might encourage us to be more proactive when it comes to asking, nevertheless, it can also act as a double-edged sword, for if you didn’t ask right, it can still give you, but not something you were expecting. That’s why it’s vital to be specific and mindful of intonation along with intention when asking the question at the right time.

So, how am I getting better at asking better questions? Well, firstly, I’ve thought over times when I didn’t ask questions or didn’t ask the right questions at the right time in the right way and the kind of results I got. On the flip side, there were a few instances where I asked some good questions at the perfect time, and in one of the most appropriate ways I knew and got some positive results. I think of both these times because they both serve as a good framework to remind me how to frame questions properly. When on the one side, I’m aware of how asking questions incorrectly can produce results, on the other side, I’m also mindful of asking the right questions and how that can turn out to be. Of course, it’s not a skill where I could just learn the nuts and bolts of it, and I could start building better questions because the variables and volatility involved in asking questions are just too big to get it right all the time. I know I’m not going to get it right every time, but if I don’t ever ask, I know I’m most likely never going to improve.

This is just a small step towards a big journey and from my standpoint, doesn’t have a destination, but only gets better in the journey. I’d love to know what you are doing to ask people better questions at the right time and in the right way.

Peace!