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The Power of Asking the Right Questions and How to Do it Right

More than a decade ago, someone told me that when you are given a promotion, it means that you did a good job solving the problems in your previous role and you now qualify to solve bigger problems. Think about that for a moment. Leadership and entrepreneurship rotate around solving problems or facilitating the resolution of problems.

In order to find and solve problems as a leader or business owner, you have to learn how to ask the right questions at the right time. This also applies in your personal life if you would like to make progress in any undertaking. We discuss some approaches that can help you develop the skill of asking the right questions at the right time.

Adopt the Perspective of an Outsider

It is ironical that the more you become an expert in a given field, the less able you are to solve the problems within that field. This may sound unbelievable, but the thinking that brought about a set of problems cannot help to solve those problems.

One way to ask the right question at the right time is to look at things the way an outsider would. This perspective is what brings to life ‘thinking outside the box’ because you aren’t constrained by the norms, traditions and rigidities that have crept into the industry over time.

When you look at things or situations as an outsider, you are able to get insights and sparks of creativity that generate new solutions to longstanding problems.

For example, think about ride-hailing firms like Uber, Lyft and hundreds of others that have sprouted to offer this service. Someone must have thought, “Why do I have to stand on the street waiting for a cab that I can hail to take me home? Why do I have to call a taxi company and ask them to send a taxi to my location and I wait for a long time before that taxi arrives?” such questions from an outsider-point-of-view could have contributed to the birth of these apps that put available rideshare vehicles in contact with a customer within their location.

In a similar way, try to look at a challenge you are facing from the perspective of an outsider and come up with questions that can lead you to finding novel solutions which you can even build a business around or accelerate your progress towards the goals that you have set.

Always Be Curious

Learning to ask the right question at the right time calls for cultivating your curiosity and sense of wonder. Think about young kids for example. They ask question after question to the point that some adults get tired out and silence the child. Kids learn a lot, and that comes from their boundless curiosity and ability to ask questions without second-guessing themselves.

You too can reawaken this ability to always be curious. By asking lots of questions, you will sharpen your ability to ask the right question at the precise moment when such a question is needed.

Some professions have the benefit of training their practitioners how to ask the right questions. For example, the success of any doctor or lawyer largely depends on their ability to ask the right questions and act upon the information they collect.

Learn from those professions and always be curious. Question the status quo, challenge commonly held beliefs, and reexamine any assumptions you may have about a given situation. In so doing, you will widen the scope of possible solutions and you can then choose the most suitable approach to resolve a challenge.

Break Big Problems into Manageable Bits

In order to ask the right question at the right time, you need to segment a big problem into smaller problems so that you can focus on each tiny bit in its own right. For example, if your relationship with your significant other is going south and you would like to turn things around, take a systems approach and identify the ‘mini-systems’ which constitute the ‘big system’ called your relationship.

For example, one mini-system could be how you communicate with each other. Another mini-system could be how each of you views money and how those views are affecting the relationship. Another could be your sex life (does one partner have a higher need for sex than the other, etc.)

All these mini-systems work together and affect each other in ways that define your overall relationship. By breaking down the relationship into those constituent smaller components, you can shine the torch on each aspect and ask questions that result in fixing any deficiency that caused the quality of the relationship to gradually deteriorate.

This approach of breaking down a problem into smaller bits can be applied to every aspect of your life, and the questions you pose can then help you come up with the right answers that move you forward.

3 Major Questions

If you would like your questions to have a greater impact at a given moment, always sieve them through a screener containing the following three questions;

Why this? If, for example, you plan on starting a business, ask yourself why you think that business idea is the right one. Is it solving a problem that no one else has attempted to solve? Is it solving an existing problem in a unique way? If you cannot convincingly answer the ‘why this’ question, it might be time to go back to the drawing board.

Why now? Ask yourself whether now is the right time to pose the question that you would like to pose. The question may be the right one, but if it is asked at the wrong time then it is moot. Let me give an outrageous example to illustrate this. Imagine there is someone you have had romantic interest in but they were already in another relationship. When you learn that they have lost their spouse, do you immediately rush in and state your interest in becoming romantically involved with them? The timing would be wrong and would guarantee that your chances of ever winning the heart of that person are forever doomed! So, for greater effectiveness of your questions, ensure that they pass the ‘why now’ test before you pose those questions.

Why me? Is there a unique reason why customers should think of your business or solution when they have a problem? What sets you apart from all others in the field? Why should you even think customers will give your product or service a second glance? As you aim to ask the right question at the right time, screen those different questions coming to your mind through the ‘why me’ sieve and select those that pass this test.

Learning to ask the right question at the right time doesn’t come overnight. It takes plenty of practice, and the skill is refined the more you go at it. Let us not focus on just having the right answer, which is an exhibition of knowledge. Instead, let us focus on asking the right question, which is a manifestation of intelligence. Knowledge can become obsolete, but intelligence is eternal.