Learning to Ask Better Questions

I have a life-long love affair with questions. Our relationship gets rocky at times, mostly when I get obsessed with finding the right answers, but I always find my way back.

The type of questions that I asked has changed over the years.

Throughout my childhood and adolescence, there was an incessant stream of “why” questions. I couldn’t always find satisfactory answers, but what I did come up with shaped my life trajectory. Questions about the role of women versus men were subjected to much contemplation. I could not reconcile why any woman would want to be totally reliant on someone (usually a husband) to provide for her. What would happen to her, or her children, if her husband leaves? I didn’t like any of the scenarios that I came up with—so one of my earliest life decisions was to not put myself in that position to begin with. It led me to value my education, which I saw as my golden ticket to being independent. My inquiry into “How do I know where I would choose to live if I have only lived in one country all my life?” resulted in me moving to Australia after completing high school in Singapore.

In my early twenties, influenced by education systems that value answers rather than inquiry, I wanted to find the “right” answers that would provide the quickest route to achieving my goals. Most semi-decent students, by the time they got to college, would have acquired tips/tricks/shortcuts to getting good academic results—such as scrutinising past papers to work out what questions would most likely be asked in an exam, to work through multiple choice questions efficiently so that you have more time for the essay questions, and so on. In other words, most good students learn to game the system. It is therefore not surprising that some of these questionable “life skills” spilled over into adulthood.

Things became more interesting after I started working and was first introduced to sales and negotiation techniques, and how to ask “good” questions. In those days, we were taught leading and closed questions to direct and control the sales process. I had long since outgrown that toolkit, but boy I have to say, those questions came in handy when negotiating with my children when they were toddlers. Instead of saying “Should we turn off the TV now?” (which could elicit a no response), I would rephrase my question as “Would you like Mummy to turn off the TV or would you like to? (either way, the TV got turned off).

Like gaming the system, leading and manipulative questions only work up to a point. When my toddlers got older, they saw through the ruse and those questions stopped working for them too.

As we approach our fourth decade together my love affair with questions has matured and deepened like a strong marriage. My repertoire of questions has increased and now includes reframing, probing, exploratory, hypothetical, and many more. Rather than be caught up by questions that keep me looping around in circles, I’ve learnt to ask better questions, to illuminate and help me figure things out.

Asking better questions has helped me to be more reflective and to think with more depth. I’ve learnt that it is okay not to have all the answers, to value the questioning process itself—as a tool that yields richness. I’ve also learnt to be more patient—instead of rushing to find answers, I now invest more time upfront to understand a problem better.

Learning to ask better questions has also helped me to become a better manager. I found that one of the most effective use of my time is not in providing answers, but to teach my team how to ask better questions. (“The Art of Asking Questions“, a Harvard Business Review article by Ron Ashkenas, provides further insight and examples on how to increase managerial effectiveness through asking questions.)

Below are three of my favourite questions that I use semi-regularly. I have found them to be simple but powerful questions, and can be asked at individual, group or organisational levels.

How Can I Best Add Value?

This question can be applied across a wide range of situations : how can I add value to my team? my company? my client? my spouse? my children? my best friend? the project? this meeting?…well, you get the gist.

Asking this question helps me think about the bigger picture and to hone in on what is most important.

I have found that my answer to this question, in its most broadest sense, has changed over the years as my skills and expertise evolved and recommend this as a good question to ask periodically.

What Do I Need to Let Go Off?

Sometimes what is keeping us stuck is less about not knowing where we want to go, but the baggage that we carry – stuff that we have accumulated in the past that no longer serves us, but we are still hanging onto, intentionally or unintentionally. Stuff like behaviours, past learning, habits, beliefs, mindsets, fears, assumptions, and relationships.

This is a question that I always ask each time I undergo a career transition or promotion. Paradoxically, often it is the very skills and behaviours that we are good at and have enabled our success that we most need to let go off, if we want to be successful beyond that point. Another way to think of this is “what are the things that I need to do less off from my previous role, in order to be successful in my current role?”.

What Next?

This question is about making choices.

Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom. – Victor Frankl

Taking action is especially difficult when it involves stepping into the unknown and we cannot see what lies ahead. Most of us are conditioned to stay in our comfort zone; But if we want to grow, we need to learn to choose and take action intentionally.

A metaphor that I find useful is to imagine driving at night in very thick fog with almost no visibility. It is certainly very unsettling and scary to drive in those conditions.  Attempting to see further by turning on your high beam lights will only make the situation worse as it would cause an instant “wall” of bright fog to be reflected in front of the car. You cannot just stop, because you might get hit by the car behind you. So you have to move forward, slowly and cautiously. The way to get through the fog is to in fact use your normal low beam lights and just focus on what what lies ahead, one white line at a time. Even if you can only see only one metre ahead, as long as your car moves forward and your lights stay on, the next small stretch of road will reveal itself.

Like the metaphor, I’ve learnt to accept that when I’m driving through a foggy patch, there is little point in worrying about not knowing what lies ahead; What I can do is focus on taking one step at a time, and trust that the path beyond that that will unfold itself.

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