The Power of Consistent Questions

Why asking the same questions helps you learn more

I recently discovered a simple trick for asking more effective questions.

It turns out I was too focused on the content of my questions, which is not as important as I thought. My recent transition to a new job taught me the power of asking the same questions, over and over.

In this article, I’ll give three examples of how asking consistent questions has been valuable to me. I’ll also give examples of the questions I’ve found most helpful in each case.

Understanding a New Company

My recent job transition took me from a mid-level manager to a senior leader. This meant I needed to hit the ground running and make a good impression. As a leader, I had to digest the situation I’d inherited before forming a strategy for the coming year.

Armed with my copy of The First 90 Days, I devised a plan for evaluating my team, our product and the company. I would recommend this book to anyone moving job, whether to a senior position or not. It helps you hit the ground running by focussing on what matters and discarding the rest.

The book’s most useful advice was to ask the same set of questions to everyone I meet. This approach helped me discover common opinions as well as areas of disagreement or confusion. The alternative would have been to play it by ear, asking whatever questions occurred in the moment. While that’s great fun and appropriate for most discussions, it’s not a rapid way to learn.

In my opening discussions, I saved the final ten minutes for rapid-fire questions. Here’s the list I used with everyone I met:

  • What are the biggest challenges we’re facing right now?
  • Why are we facing those challenges?
  • What are the best opportunities for growth we haven’t exploited?
  • What’s needed to exploit those opportunities?
  • If you were me, what would you focus on?

The questions were broad enough to allow a range of answers. How someone chooses to answer is as illuminating as the answers they give. For instance, consider the “biggest challenge” question. Some people focus on their immediate day-to-day jobs, while others think strategically. It’s an early hint about different personality types.

Although I found the rapid-fire questions awkward to introduce, their value was immense. Clear themes emerged, with some questions triggering similar answers. While other questions highlighted a lack of group consensus. The answers helped me identify quick wins, as well as strategic issues to address over time.

This was my “a-ha” moment about asking consistent questions.

Upon reflection, I realised I had already employed this technique in other areas of my life and hadn’t acknowledged it. Let’s move to the next example — interviewing new hires.

Hiring Great People

Interviews are another area where asking consistent questions leads to great results.

Objective interviews are the fairest and most effective way to examine a candidate. By asking each candidate the same set of questions, you give everyone a fair chance to demonstrate their skills.

Consistent questions are also the only way to compare candidates. If you ask two candidates different questions and they both answer well, how do you decide who to hire? By asking the same questions to both candidates, you can find the strongest candidate.

On many occasions I’ve asked a candidate a question and their answer impressed me. Yet, I asked another candidate the same question and discovered what a great answer looks like. Consistency turns subjective questions into an objective interview.

Along the way, I’ve collected a few questions that help differentiate candidates. Here are some favourites:

  • What do you enjoy doing, professionally? This question gives the candidate space to tell you why you should hire them. Great candidates recognise this and approach the question from that perspective. Weaker candidates miss that point and drone on about how much they enjoy reviewing code or stapling.
  • Nobody enjoys every part of their job. What don’t you enjoy doing, professionally? This question helps identify the areas of work that don’t excite the candidate. People seem to answer this honestly, which helps you assess their fit for the role. It also gives you a glimpse of their personality.
  • What worries you about your fit for this role? This is a direct question that most candidates answer honestly. They do half your job for you, by saying things like “I’m a bit worried whether I’ve got enough finance skills” or similar. If they say nothing at all, it can be a sign they are not open and honest, or that the role is not enough of a stretch for them.


Self-improvement is built on the foundations of self-reflection. You cannot improve what you don’t understand.

If you ask yourself the same questions, consistently over time, you can learn a lot. Much like finding consensus in a new organisation, your answers will reveal trends and changes.

If you form your questions around the topics you want to improve, you can use your answers as a barometer of your progress. If the answers are not improving, you know your methods are not working.

Self-reflection is a continuous process. Yet, it also benefits from structure and repetition. Set aside time every month to answer questions that assess your current state. Here are some questions I find helpful:

  • What would this look like if it was easy? This is a question I stole from Tim Ferriss and you can apply it to many areas of your life. By imagining an ideal life, you can assess the gap between reality and perfection. Often, you will discover the ideal outcome is completely achievable.
  • Does my schedule reflect my true priorities? If you consider family to be your highest priority, does your schedule reflect that? You can ask the same questions about health and exercise. Take control of your schedule and make it match your priorities.
  • What am I distracting myself from? This is a question I ask myself more often than once a month. Whenever I find myself reaching for unhealthy food or social media, I look for the unpleasant emotion I’m escaping from.

I’m sure there are many more areas in life that would benefit from consistent questions. I’ve only just begun exploring this topic, but I’ve already found it to be a powerful tool. I hope you find it helpful as well.

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