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leadership questions

Leadership Questions

Have you ever wondered if you’re asking yourself the right questions to get the best out of yourself and the people around you? We’ve compiled key leadership questions from our Leadership Moments Podcast to help in any situation.

Please feel free to read through - or use our filter below to find questions relating to a particular aspect of leadership.
Michael Gysi

Michael Gysi

LEADERSHIP QUESTIONS

No favourite question

answer context

Michael does not have a favorite question because according to him the connection he seeks to establish involves a conversation that has to be unique to the circumstance in which he finds himself with the indiviual he seeks to connect with. He offers the example of a scenario where he is sitting at an airport next to somebody who is reading a paper. He says that you can start a conversation by saying, “That’s an interesting article.” And you can go on from there and find out who they are, where they work, where they're going, if they're going on a holiday, if they're going on business. Each question is unique and tailored according to the circumstances of the setting.

Building Connection and Understanding

Oscar Trimboli

Oscar Trimboli

Leadership Coach, Mentor & Author

LEADERSHIP QUESTIONS

  1. If we were to come back in 12 months’ time what is the question you didn’t ask me that we should have explored today?

answer context

The question Oscar always asks is how do you explore the unsaid? He likes getting people to think about what is going on further than just today.

Coaching and Developing Others
Strategy

Giselle Collins

Giselle Collins

Professional Director

LEADERSHIP QUESTIONS

  1. How clear is your vision and strategy, whether it be for yourself, the team or the business?
  2. Does everyone understand and are they on board?
  3. What culture are you creating by the examples you set?
  4. What it is that you most enjoy about being a leader or being where you are?

answer context

A leader must have an agenda, a strategy, a vision and understand that everyone has his own lens that he applies and that if a leader doesn't understand that lens, the perspective of the person he is trying to influence, he is less likely to get them on board.

A leader has to be attuned to that cultural pre-setting that each person has that come from where they've been, how they look at things and in that way he can work through the different views around the table for the right outcome.

Leaders have to have fun and fun is a word that's not a corporate word. You can have a light-hearted chat or have a bit of laughter sometimes, be relaxed enough to be yourself because quite often you feel you have to be, look and behave like some sort of mythical perfect creature.

Coaching and Developing Others
Strategy

Murray Wright

Murray Wright

Principal, Murray Wright & Associates

LEADERSHIP QUESTIONS

  1. Why am I here?
  2. What am I trying to achieve?

answer context

These two questions presented by Pia Lee in Episode 19 are thought-provoking and although it may take some time to answer, they are a fundamentally important and powerful leadership practice because you're putting the answer back into the person that you are talking to and you're getting them to think and search for the answer. Telling them things is the short cut. Asking a good quality question like that is much more empowering and much more useful to them.

Self Reflection

Phil Preston

Phil Preston

Collaborative Advantage

LEADERSHIP QUESTIONS

  1. How do you think so and so would see that from their perspective?

answer context

In talking to different stakeholders who come from different sectors, it is more effective not to challenge them on things they say and believe but instead to ask this question. It is better just to ask them to think and it gets better results.

Building Connection and Understanding

Murray Paterson

Murray Paterson

LEADERSHIP QUESTIONS

My favourite two questions - perhaps with the same intention:

  1. Why is it so? (Professor Julius Sumner Miller - his signature question to explore many scientific principles, famous on TV from the 1960s to the 1980s)
  2. I'm really curious about that. Tell me more.

answer context

Building Connection and Understanding
Self Reflection

Nicole McAuliffe

Nicole McAuliffe

Director, Create Wellbeing Group

LEADERSHIP QUESTIONS

  1. What are the things that give you purpose and meaning?
  2. Why now have you come to talk to me about this? What might be the issue?
  3. Why today? Why do you want to start making some changes around your health and wellbeing?

answer context

Question number one gives you an insight as to what drives that person? What their values are?

The second and third questions give you an insight on how committed they are today to make those changes and what is the history behind getting them to where they are today that they are seeking help and support.

Building Connection and Understanding
Self Reflection

Liane McGrath

Liane McGrath

Director & Founder, ThinkTime

LEADERSHIP QUESTIONS

  • Why is this important and who is it important to?

answer context

This is an important question to ask because we have a tendency for our thinking to be insular and to think about things from only our perspective. We need to expand context so that we reach more enlightened conclusions.

Building Connection and Understanding
Self Reflection

Sharon Cauldwell

Sharon Cauldwell

Director of Sales, NEXT Hotels

LEADERSHIP QUESTIONS

  • What's the difference I have made today?

answer context

A great question for people who want to make a difference, do a good job and take accountability.

Building Connection and Understanding
Self Reflection

Jason Beck & Hans Melo

Jason Beck & Hans Melo

The Potential Project

LEADERSHIP QUESTIONS

 

  • HANS MELO
  • Why are you doing this?
  • JASON BECK
  • What are your fears?
  • What does your best day at work feel like?

 

answer context

Hans Melo usually asks this question and admits that it is deep and that he wants to provokes thought.

For his first question Jason Melo has taken an idea from Tim Ferriss that instead of taking a tally of one's goals one should take a tally of one's fears. For his second question he believes that if you start at an experiential level, as a leader you can draw so many golden nuggets about your followers. Find out what are this person’s strengths. What makes him come alive?

Self Reflection

Michelle Feros

Michelle Feros

National Director, People, Quality & Communications at Autism Spectrum (or Aspect)

LEADERSHIP QUESTIONS

  1. What would happen if you do?
  2. What would happen if you don’t?
  3. What wouldn't happen if you do?
  4. What wouldn't happen if you don’t?

answer context

Questions are great because they open up space. They get you information. If someone is grappling with, 'What do I do?' 'Should I do this?' 'Should I not do this?'

These four questions will help you cover all the options.

Building Connection and Understanding
Self Reflection

Mhairi Holway

Mhairi Holway

VP Human Resources Pandora Australia & NZ

LEADERSHIP QUESTIONS

  1. What do you think about this?
  2. How do you feel?

answer context

Always expect the unexpected and never assume how somebody else feels about a situation. Ask the questions and be better informed.

Building Connection and Understanding

Troy Cuthbertson

Troy Cuthbertson

GM QT Melbourne

LEADERSHIP QUESTIONS

  1. I got the right outcome, but was that the best outcome for the customer?
  2. Could I have done it better?
  3. Could have I done it differently?

answer context

Make decisions and calculate the decisions depending on potential outcomes of both the positives and negatives of the decision and then reflect on that and go, I got the right outcome, but was that the best outcome for the customer? Possibly you’ll find agreement, but again the next time, you could handle it differently.

Self Reflection

Olga Gelauff

Olga Gelauff

Manager Local Government Woerden

LEADERSHIP QUESTIONS

  1. What can I improve and what can I do better?
  2. What kind of talent has an employee of my team and how can I help to develop that talent?

answer context

Leaders especially must ask themselves about self improvement and their impact of that on the organization.

Have a strong belief that everybody in the team has talent and you have to make time to discover that talent especially when they don't see it themselves.

Coaching and Developing Others
Self Reflection

Gillian Coutts

Gillian Coutts

CEO Potential Project

LEADERSHIP QUESTIONS

  1. How is your reaction to that working out for you right now?
  2. How do you keep seeking a perspective to find that answer?

answer context

When things do not go according to plan, overreacting is just a waste of energy that takes you away from creative thinking and the capacity to connect and engage in what actually needs to be done next.

Taking perspectives from different people may give you clarity because there may be many better answers when you use and trust the people around you.

Coaching and Developing Others

Rob Metcalfe

Rob Metcalfe

Director Succeedo Global

LEADERSHIP QUESTIONS

  1. Where are you going and why?
  2. Where are you now?
  3. What are you going to do next?

answer context

If you understand the reason 'why', you can always find your own way to 'how', but if you don’t understand 'why', the 'how' you come up with may be irrelevant to what the overall intention is.

Using the three questions associated with the leadership mindset to clear the thinking, will enable better decisions.

Coaching and Developing Others
Self Reflection
Strategy

Sarah Cornally

Sarah Cornally

Organisation Transformation

LEADERSHIP QUESTIONS

  1. As a leader are you willing to be guilty? Are you willing to do something that many people in society will not understand and you will be judged and judged harshly for what you are about to do?
  2. What is the story behind the story?

answer context

Leadership requires you to have the courage to do what you know is right even though it scares the pants off you because you're doing it for the greater good and you've done all your due diligence to make sure that as best as you can work out, this is the right way to go as you know.

Avoid huge judgements against people. When you get under and you get close to people and you seek to understand their perspective and their point of view and you genuinely walk in their shoes, you realize from their perspective what they're doing makes complete sense.

Building Connection and Understanding
Self Reflection

Pia Lee

Pia Lee

CEO LIW

LEADERSHIP QUESTIONS

  1. Do you understand? - For Clarity
  2. What type of high performing culture do you have inside your team or organization to enable you to deliver on the vision of the organization? - For climate
  3. What do you want to have in terms of behaviours and attitude for people that are in your team and how do you nurture and develop that? - For Competence
  4. Why am I here?
  5. What am I trying to achieve?

answer context

The 3Cs - Clarity, Climate and Competence - the three conditions that leaders need to create for themselves and for others for their team or organization to be successful.

The quality of your questions creates the quality of outcomes. Quite often we feel we have to tell people the answers. The question, 'What are you actually trying to achieve and why?' is the most powerful leadership practice because you're putting the answer back into the person that you are talking to and you're getting them to think and search for the answer. Telling them things is the short cut. Asking a good quality question like that is much more empowering and much more useful to them.

Coaching and Developing Others
Strategy

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