Asking better questions

I have an admission to make. 

I spend most of my time facilitating workshops, and conducting ethnographic research — this means I am constantly asking questions.

My admission is that I'm not that great at asking questions — meaning, I have to work hard to find the good questions to ask whereas others ask them naturally.  

I was recently given some feedback that I could try to find better questions to ask. This had me thinking about the types of questions I currently ask, and why. 

See, I tend to do one of two things. Blunt and to the point, or silent.

When asking questions, I need to find a middle ground that sits well with my values and of course helps elicit authentic answers from the people I ask them of. This is important because I ask questions for a living.

Looking back at my younger self I wondered how many times I would answer the question that more often than not, ended interviews.

"Do you have any questions?" I’m sure, ever so wrongly, I met this with silence. Little did I know that intelligent people judge us by the questions we ask, not by the answers we give them.

One of my favourite journalists once said in an interview that she likes to ask a question and follow it with silence. Leaving the question to hang in the air, to grow in meaning and weight.

I think of how so many of us ask questions and quickly follow by asking even more and then explaining why we are asking them; instead of simply asking better questions and then shutting up. 

In my research over the last week, I’ve gathered for you here some of the best questions to ask, to:

  • demonstrate your leadership potential

  • better start a conversation

  • discover whether the person who is interviewing you is worth working for you


I hope you enjoy these.

Leadership questions

  1. What do you like about managing people?

  2. What do you think are good leadership qualities?

  3. How do you celebrate high performance?

  4. How do you handle low performers?

  5. What makes you proud at work?

  6. How would you rate your/my communication skills? Why?

  7. What are your values and how have they come to life at work?

  8. How does the team handle failure?

  9. What is your team’s best example of leadership?

  10. What do you do when your team’s back is against the wall?


Better conversation questions

  1. What lights you up?

  2. What are you learning at the moment?

  3. What was it like for you when...

  4. What’s your favourite way to waste time?

  5. Are you where you want to be?

  6. Do you have an idea for a business you’re wishing you could start?

  7. Tell me about a time when you felt fulfilled at work.

  8. Tell me about a passion project you’re working on.

  9. What makes you smile?

  10. Where will you be a year from now?


Discovery questions for job interviews

  1. How do you motivate your team?

  2. How might you help someone who I struggling, reach their potential?

  3. How do you monitor performance?

  4. What are your personal values and how do you bring them to work?

  5. How would you describe your leadership style?

  6. Tell me about a time when you’ve struggled with work/life balance - does this happen often?

  7. What are your teams principles and how do they come to life?

  8. How do you get the best out of people?

  9. What do you fear?

  10. How might you handle a situation where a client isn’t aligned with your values?