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The Art of Asking: How the Right Question Can Change Everything

One of the smartest people I ever knew used to ask the same question of almost everyone they ever met.  


It didn’t matter if it was a retired policeman, a diplomat , a waste truck driver, or his nan. I literally heard him ask them all.



“What do you know now, that you wish you learned earlier?”


Sometimes the responses were humorous. Sometimes profound - and at times disarmingly simple. It was respectful, authentic curiosity that took years of learning, thinking, mistakes, mentors and experiences and got it distilled into a few sentences of pure wisdom.  They’d pack it away and then ask the same of the next person they’d meet.


“For better or for worse - don’t expect to come home the same way you left”, said a returned serviceman, in answer to his question. 


“Ask for help. It is never worse than the alternative ” said another.


In a world where we are hyper focused on asking Google, Siri, and now ChatGPT, for answers, we forget the importance of asking the right questions. 


A colleague leans into your office door. We can play pin the tail on the donkey in a guessing game of “How’s the Adelaide office doing/is the family well?/ What’s End of Month looking like?” Or we can pause, and ask “What’s on your mind?”


A team member spills 10 minutes of background on a rabbit warren of concerns about a contract, which is both more than we have time for and yet not enough to possibly offer advice.  We can dust away the debris and get to the heart of the matter with “What do you think the real challenge is here?” 


Taking the time to ask the right question is a hallmark of good leadership, strong relationships, and even our own personal growth.  Here are 10 of our favourites:


  1. Given  we only have 10 minutes, how can I best help?

  2. If someone was observing this objectively what would their advice be?

  3. What do you need to do to not have any regrets about how you’d dealt with this?

  4. What’s a small step, and what’s getting in the way of you acting on that?

  5. What would I say if I was going to challenge you on your part in this?

  6. What is the most important question here?

  7. Of all the parts here we could focus on, what’s going to move us forward?

  8. What would we do if we were going to make this worse? 

  9. What are your top 3 drivers here?  (Eg Keeping the contract at all costs, preserving a long term relationship with the client, maximising revenue).

  10. What opportunity is this giving us that we might be missing?


Next time you are in a meeting or listening to your partner talk about a difficulty, instead of getting lost in the content or disengaging with disinterest, imagine a thermal imaging tool and ask yourself what the hot spot of the best question looks like.  You’’ be surprised how fast it opens up more answers than you imagined.

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