Have you ever wondered if you're asking yourself the right questions to become a successful leader? We've compiled key leadership questions from our Leadership Moments Podcast to help you find clarity in any situation.

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

Like to add your own insights? Please click the button below to share your leadership questions.

Diana Renner

Diana Renner

Educator, Consultant and Award-Winning Author

Leadership Questions

  1. What else could be true?

Question Context

Asking "What else could be true" opens up the possibility that we might be wrong. It challenges our cognitive biases and invites new perspectives. It helps us seek other people’s views rather than just take the position or 'my way or the highway’.

It challenges that narrow settling on the first thing that comes to mind, which again as human beings we do. Our brains take shortcuts, heuristics. There's been a lot written about heuristics. They're useful until again they're not because those shortcuts can get in the way of us making good decisions and seeing more than otherwise we would.

Self reflection

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Professor Peter Hawkins

Professor Peter Hawkins

Author, Consultant and Researcher

Leadership Questions

  1. What can I uniquely do that the world of tomorrow needs?
  2. What is it we need to achieve together that we cannot achieve apart?
  3. How are we positively contributing to the environment and the ecology around us?
  4. How do we recognize the decisions we're making today will have implications for not just the next generation but the one after that?
  5. How do we work from source rather the from effort?

Question Context

Team development is based on the erroneous belief that it is enough that we have good relationships and we trust each other for us to have an effective leadership team. The research, however, does not support that. The research tells us that the most important thing to be successful is having a very clear collective purpose and every member of the team recognizing they can only achieve it through collaboration.

We should not just coach on how the team relates to itself but on how the team relates to its investors, its customers, suppliers, its employees, it's wider community and increasingly, the ecology and that this should be more focal in team coaching.

The unrecognized stakeholder refers not only to the unrecognized human stakeholder. Often the stakeholder we are ignoring at our peril is the more than human ones - our environment, ecology and climate change among others.

Part of leading beyond the heroic leader to collective leadership is also each of us learning to work from collective and renewable energy rather than from determination and effort because otherwise we won't grow in individual and collective capacity to step up to the challenges that are now facing us. We should realize that 99% of what keeps us alive isn't done by us. It's the sun. it's the rain. It's the wind. It's the earth. We can also use that for our psychological energy and mental energy, not just for food and air and water.

Self reflection, Coaching & developing others

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Jill Livesey

Jill Livesey

Career Coach

Leadership Questions

  1. What would I do if I could?
  2. What would I do if I had to?
  3. Identify five questions that you want to ask yourself that you must answer every three or two months?

Question Context

1. What would I do if I could?
It's balancing the art of possibility with the reality of life. keeping that open mind as to future possibilities, keeping your learning going and having conversations and checking back to what matters to your values, the things you enjoy in work so that you can think about what's possible in the future.

2. What would you do if you had to?
Someone turns up at work that changes the whole place and you don't want to be there or you get fired or made redundant, at the very least you want your résumé and profiles to be up-to-date and you want to have kept connected with the industry, the sector, the people who are in your network so that you're in a position to move if you had to.

3. Identify five questions that you want to ask yourself that you must answer every three or two months?
It might be something like, “How do I feel on a Sunday night?” “What have I learned lately?” “Am I happy?” Program them in your phone and have them pop up every three months. So come up with your own questions, check in and answer those same questions every three months and then ask yourself, “What do I need to do as a result of those?”

Self reflection, Coaching & developing others

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James Kemp

James Kemp

Leadership Questions

  1. What is your passion?
  2. What do you love doing?
  3. What would you balance that for?
  4. What gives you the biggest smile on your face?"

Question Context

Getting under the skin of what an individual's ‘why’ is, not why they're in this particular job but why are they alive? What is it they're looking to achieve with their life and ultimately helping to give them some clarity around that which then helps them work out whether they're in the right job and in the right environment to do that. It's having the opportunity to explore someone’s ‘why’.

Self reflection

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Phil Cross

Phil Cross

Digital Consultant and Strategist

Leadership Questions

  1. What if it works?
  2. What's next?
  3. What if we suddenly start bringing in a hundred times more customers than we had last month?
  4. What if you achieve your goal of finishing this race? - What then?

Question Context

Asking 'What if it works?' opens up people’s thinking beyond the problems of getting there and the challenges of getting there to thinking forward and figuring out what have to be in place to manage it when it does work. The planning doesn't stop with achieving the goal. One must move further on for when this goal is actually achieved because you will need the logistics to handle the success.

Self reflection, Strategy

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Tony Mansfield

Tony Mansfield

Partner, Contentious Character

Leadership Questions

It needs to be a ‘how’ question around:

  1. How did you arrive at the conclusion which you are currently putting forward?
  2. How did you arrive at the position that you are currently putting forward?
  3. How did you arrive at that?

Question Context

This encourages people to think about their process and their rationale and whether or not they are bringing their personality into the process and for better or for worse.

This also then gives you some understanding of the position being proposed and how they got there and may in fact alter your next step as a result of that.

It becomes a two-way interaction where both people are continuing to open up and expose the relevant information that will bring greater understanding and hopefully a better position out of the discussion.

Self reflection, Building connection and understanding

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Warren Hogan

Warren Hogan

Economist, Commentator and Executive in Residence at the University of Technology Sydney Business School

Leadership Question

  1. Getting back to the issue of difficult conversations, it is always important to ask people how they feel about something

Question Context

It is one thing, particularly in a business or organizational setting, to ask about the technical issue at hand but when it comes to issues of people, issues of leadership, you cannot try and escape from an emotional setting even if it's only to bring yourself back to some neutral emotion.

Self reflection, Building connection and understanding

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Michael Gysi

Michael Gysi

Leadership Question

  1. No favorite question

Question 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

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Oscar Trimboli

Oscar Trimboli

Leadership Coach, Mentor & Author

Leadership Question

  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?

Question 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.

Strategy and Coaching & Self Reflection

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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?

Question 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.

Strategy and Coaching & Developing Others

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Murray Wright

Murray Wright

Principal, Murray Wright & Associates

Leadership Questions

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

Question 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

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Phil Preston

Phil Preston

Collaborative Advantage

Leadership Question

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

Question 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

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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.

Question Categories

Building connection and understanding, Self reflection

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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?

Question 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

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Liane McGrath

Liane McGrath

Director & Founder, ThinkTime

Leadership Question

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

Question 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

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Sharon Cauldwell

Sharon Cauldwell

Director of Sales, NEXT Hotels

Leadership Question

  • What's the difference I have made today?

Question 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

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Hans Melo and Jason Beck

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?

Question 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

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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?

Question 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

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Mhairi Holway

Mhairi Holway

VP Human Resources Pandora Australia & NZ

Leadership Questions

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

Question 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

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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?

Question 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

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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?

Question 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.

Self reflection, Coaching and developing others

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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?

Question 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

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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?

Question 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.

Self reflection, Coaching and developing others, Strategy

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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?

Question 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.

Self reflection, Building connection and understanding

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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?

Question 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 & developing others, Strategy

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Lee Williams

Lee Williams

Director, Infinity Leadership

Leadership Questions

Looking backwards, reflecting on people, events, times in your life and answering these questions:

  1. How has that shaped the way I view the world today and my place in it?
  2. How am I showing up?
  3. What are the natural gifts that I have that are emerging from this?
  4. What are the examples in there negative or positive that I can improve on or enhance to achieve the kind of impact that I’d like to have?

Question Context

The first step is to look backwards, to reflect on people, events, times in your life and map that out and then to zoom out and look at that life history. A combination of strengths and impact is a good way to think about purpose as you move forward.

Building connection and understanding

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Dominic Wells

Dominic Wells

Director, Clearpoint Communications

Leadership Questions

  1. How do I feel? if you're being introspective
  2. How do you feel? if you're engaging with somebody else

Question Context

Holistic leadership is about the doing and the being of leadership. Doing leadership on a day to day basis, we have KPIs, quotas and budgets that we have to hit and therefore we do a lot to achieve that. That’s valuable from a outward perspective, but the risk is we do that at the cost of not focusing on or engaging with the being of leadership. The being of leadership is that emotional connection whether it's introspective around your own emotions or whether that’s the emotional connection between two people or the group. It's really important to create that balance.

Building connection and understanding

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John Raymond

John Raymond

Principal, Institute of Executive Coaching & Leadership

Leadership Questions

  1. How are you?
  2. How is my leadership style impacting you?
  3. What else could I be doing differently?
  4. As a leader, how often do I check in with everyone who are key to my success in terms of the way that I work is landing on them?

Question Context

You can never know the impact you're having on another person fully unless you have a conversation about it with them. That requires having trust there in order to have the conversation. Regularly check in and ask the questions. It's understanding that even with the best intention the impact can be quite the opposite. You'll only know that if they tell you.

Building connection and understanding

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Kevin Nuttall

Kevin Nuttall

Director, Waterfield Consulting & Strategy Facilitator.

Leadership Questions

  1. How is the world changing around us?
  2. How are our customer’s expectations going to change?
  3. How do we continue to meet those new expectations?"

Question Context

The leader’s role is to continually ask that question about how changes impact us and how we can continue to deliver value to our customers in the changes that we are all experiencing. It is that future focus. We contend that if you do a proper analysis of the future and adjust your business model to accommodate these changes your organization has the best chances of staying in business.

Strategy

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