The curious case of asking questions

I recently mentored a group of up and coming leaders at Spikes Asia. The people I worked with were amazing, and I walked away inspired by the next generation of leaders.

I’ve had some amazing conversations recently – as well as some super boring, one-sided, uninspiring sessions. But these conversations got me thinking: the one question everyone had in common was, “What should I do to get ahead and progress?”

The answer to this, in my opinion, is curiosity.  Whoever asks questions leads and, most importantly, learns.  But it’s not always easy to ask questions — many people shy away for fear of embarrassing themselves, either by asking the ‘wrong’ questions or showing they don’t understand something simple.

Here are five examples of how to ask great questions in important situations:


1. When you first meet someone 


Whether you’re at a conference, an event, a meeting or even a social gathering where some better conversation would be welcome, try asking people:

  • “What do you do?”
  • “What did you learn today?” Or, “Why are you here?”
  • “How is your business faring? What drives you to get up in the morning?”
  • “What are your plans?”
  • “What have you seen recently that’s really cool and inspiring?”


2. When you don’t understand something 


Many of us work across countries and cultures, in both physical and virtual spaces – so I appreciate that it’s not always possible to ask this type of question immediately. But if you’re lost in translation, odds are there will be other people in the room (or on that call or webex) that don’t understand either. Find the right moment to ask for an explanation and keep following up if you need further clarification. Some questions to ask when you don’t understand something are:

  • “Why is this the chosen approach?”
  • “Why are we doing this?”
  • “Which other options were considered?”
  • “Has this been done before, and if so, what were the learnings?”
  • “Can you explain the details?”
  • “Does anyone have experience doing this?”
  • “Is there anything to watch out for?”
  • “Can I do anything to help?”

3. When you stop listening 


I can put my hand up here – guilty of turning off when I think “been here, done that”. But in truth every day is a school day – and you will learn something if you listen. It may be something that you’ve heard before but haven’t understood – or you could get a new perspective if the world has moved on (& it does with technology).

  • “What’s new?”
  • “What’s next?”
  • “What’s changed in the past quarter/year?” (Depending on when you did this the last time)
  • “What’s surprised people?”

4. When you fail 


Everybody makes mistakes. I know I do (often multiple times, and in places that I didn’t even think about). And if I don’t question these mistakes or try to grow from them, I’ll do the same thing again tomorrow. Reflection is important for us to learn and grow. It’s also a good sign for a growth mindset — without it, you’ll keep doing the same thing over and over again. Here are some examples of questions to ask when you fail:

  • “Why did that happen?”
  • “What did I learn?”
  • “What would I do differently next time?”
  • “What do I do next?”

5. When you explore the world  


 I recently flew back from Australia to Singapore and had the good fortune of a delayed flight — and then an incredibly interesting conversation with the strangers around me as we sat in the lounge waiting. If you’re looking to broaden your mindset by exploring the world, it’s important to ask people for their viewpoints along the way. Moreover, it’s important to watch, listen, learn and take everything in. Here are some examples of questions to ask when exploring the world:

  • Ask to hear people’s stories
  • Ask for people’s opinions
  • Ask for viewpoints – good, bad & ugly


If you’re looking to discover, grow and help others, the only difference between living in the world and understanding it is asking the right questions.  If you have any questions I could help answer, don’t hesitate to get in touch with me directly.


Cat Williams-Treloar founded Humanisation, a Human-Centered Marketing Consultancy. Humanisation was born to help startups make a human impact in a digital world as they Go-To-Market across APAC.


Read more about Humanisation & our why here, or get in contact with

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