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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.
Fiona Pearman

Fiona Pearman

Co-Author Core Confidence, Founder at Pearman & Partners

LEADERSHIP QUESTIONS

If you could change one thing right now to create the outcome you were looking for, what would that be?

answer context

There's something about the one thing, just narrowing that right down to a focal point that gets people able to say something. It does seem to really yield some thoughts, they're right there but they're just out of reach, out of consciousness and it also allows people to focus.

Self Reflection
Strategy

Audrey McGibbon

Audrey McGibbon

Psychologist, Business Leader, Wellbeing Expert and Co-Creator of the Global Leadership Wellbeing Survey

LEADERSHIP QUESTIONS

If nothing changes, how will your life be in 12 months from now?

answer context

I ask people to think about how they're leading their life now? How they show up at work now? How they look after themselves now? How they look after their families now? How they manage their time now? And get a clear picture of how they're going about their daily habits and routines and then I say, “If nothing changes, how will your life be in 12 months from now?

Self Reflection

David Anderson

David Anderson

Group CEO and Co-founder of the Big Red Group

LEADERSHIP QUESTIONS

  1. How do you feel about that?

answer context

In the context of my team, I often would take them back to personal connection. So I think in the event where I want to create change it's about, How do they feel about that?

Building Connection and Understanding
Coaching and Developing Others

Diana Renner

Diana Renner

Educator, Consultant and Award-Winning Author

LEADERSHIP QUESTIONS

  1. What else could be true?

answer 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

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?

answer 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.

Coaching and Developing Others
Self Reflection

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?

answer 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?”

Coaching and Developing Others
Self Reflection

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?

answer 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

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?

answer 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

Tony Mansfield

Tony Mansfield

Partner, Contentious Character

LEADERSHIP QUESTIONS

It needs to be a ‘how’ question around:

How did you arrive at the conclusion which you are currently putting forward?
How did you arrive at the position that you are currently putting forward?
How did you arrive at that?

answer 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.

Building Connection and Understanding
Self Reflection

Warren Hogan

Warren Hogan

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

LEADERSHIP QUESTIONS

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

answer 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.

Building Connection and Understanding
Self Reflection

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

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