As a leader, my most important meetings are my 1-on-1’s with my direct reports. It is the single best investment of my time, and yet I have seen most leaders clueless about its importance.

These 20 questions will help you turn your 1-on-1 meetings into sources of insights and connection. Insights into the desires and fears of the human being sitting beside you, and an opportunity to create a real human connection based on care, impact, and meaning.

There is nothing more powerful than asking the right question at the right time. Powerful questions like these can become your prized tools of leverage as a leader and coach. Here they go :

One Powerful Question Can Transform Your Life
One Powerful Question Can Transform Your Life
  1. Tell me something I don’t know about you?

    This question never ceases to amaze me. It is such an open-ended question that the answers you get surprises you. This question can reveal a lot that you might not be aware of, about the other person. This question works wonderfully whether you are talking to somebody who is new in your team, or to someone whom you have known for years.
  2. Where do you want to be in the next 1, 5, and 10 years?

    This question provides a window into people’s dreams. You might have to ask a few questions to uncover them, but once you get to know where somebody wants to be in the future, you can use that knowledge as leverage when you assign work to them. This can help you to allow them to do the best work of their lives.
  3. What are you excited about?
  4. What are you worried about?

    These two questions will tell you what the other person cares about. Questions like this will reveal what is important to them in their lives – whether it is their family, their health, a particular hobby, sports, or something else.

    The answer to these questions will help you better deal with future situations when they are overly excited or worried. You will be able to understand what happened that caused them to be excited or worried.
  5. If you were to donate everything you have to a cause or charity, which would it be?
  6. What one word do you want people to use to describe you? What word do you think people currently use?

    The above two questions will make people reveal their most important values. Asking them to come up with one word can be very challenging but it can reveal something very deep and meaningful in their life.
  7. What did you do recently that you are proud of?

    This question will reveal a recent act which the person is proud of. It will reveal what the person values, and will also help them connect with their own values, which often people are unaware of.
Are You Asking Powerful Questions - To Yourself and Your Team
Are You Asking Enough Powerful Questions – To Yourself and Your Team?
  1. When was the last time you told a lie? Why? What would have happened if you had told the truth?

    We all tell lies – in different areas of our lives. And there is nothing right or wrong about them. However, I feel that a totally different outcome/result could be possible if we were to tell the truth in such circumstances.

    Asking this question can reveal hidden possibilities in people’s futures which they themselves might have closed doors on. It shows people alternate options that would become available for people if they were to choose courage over comfort the next time.
  2. What do you want to do that you will be proud of in 5 years’ time?

    We can all work just for the sake of work. Or we can do work which we can remember decades down the line. Work that makes us proud, work that makes an impact, and work that makes a difference. This question will help you figure this out.
  3. How are you special? What makes you stand out?

    I believe we all are unique in our own ways. We all have our strengths and things we do well. However, our work likes to put us into boxes of pre-defined roles and responsibilities.

    As a leader, it is very important to understand what makes each person tick in your team, and what is unique about them? This will help you find work for them that are suited to their strengths, and they have the best chance of succeeding.
  4. When was the last time you stepped out of your comfort zone? What was the result?

    This is another question that touches on the idea of courage. This question can reveal what someone has been missing out on because of a lack of courage. I have seen that when asked this question, people see hidden opportunities for themselves in the future if they were to gather the courage to step out of their comfort zones.
  5. Tell me about your biggest failure in life? Biggest success? What did you learn from the experience?

    We all learn from ups and downs in life. There are moments in everyone’s life when we are forced to re-evaluate our life priorities. Moments like these, which are called ‘crucibles’ by Bill George, the author of Discover Your True North, can reveal a lot about what we value and who we are.
  6. When was the last time you laughed at work?

    If the answer to this question is “too long ago”, you know as a leader you have your task cut out. You need to do something to make the environment more fun. Always being busy at work can make life boring if you don’t have friends at work.

    Life is always more fun, and work is more productive if we have people with whom we can laugh.
  7. If you had the opportunity to get a message across to a large group of people, what would you say?

    Everyone has a message inside of them dying to get out. Everyone wants to say something which they don’t because of certain societal pressures or internal battles.

    Asking this question will help you get that message out, and if you can create a culture where people can express themselves fully without pretensions, engagement and productivity will go up by many notches.
  8. What would your day look like if money was not a concern?

    Often people feel powerless and trapped by money. I have felt that way for a long time, and I have seen that asking this question forces people to think for themselves about what their world would look like if money was not a concern. Ask this question and be amazed by the answers people give.
  9. Who do you look up to? Who are your mentors, both those you know personally and those who inspire you from afar?

    We all have people in life who inspire us and whom we look up to. These could be people we have met, like our parents or our teachers. Or these could be people whom we have known and heard from far, as someone from politics or business. Knowing who people look up to can give an insight into their values and ideals.
  10. What do you do after work? What are your hobbies?

    People have a life after work, and knowing about what keeps them busy at work can help you get a better picture of their personality. I have found that talking to people about their hobbies, and motivating them to do more of it, can increase their engagement and productivity at work.
  11. What are your highest priorities in life? Where does work fit in?

    We all have priorities in life other than work like family, health, a hobby, or volunteering. For some people, work is the number one priority, while for others it is not. Knowing where work fits in someone’s life priorities can help you communicate and coach them accordingly.
  12. As a child, what did you want to do when you grew up?
  13. What in your life is ‘on hold’? Until you lose weight, until you retire, etc. What are you waiting for?

    The above two questions try to bring to the surface deep desires which we might have given up on. We all dream a lot as children but give those dreams up when we are faced with the reality of adult life. However, it doesn’t have to be so, and tapping into those dreams can be a great source of motivation and satisfaction.

    All of us have something in life which we plan to do “one day”. These items are usually on hold and we are waiting for some ideal condition to be met. Asking this question will help you understand people better, and connect with them on a deeper level.