How to ask Great Questions (and Listen Actively)

I’ve been on my first long distance travels for the last 2 years. I am in Montevideo, Uruguay this week teaching at IEEM Business School. I’ve been coming here for the last 12 years (last year was a virtual visit via zoom). Many of my classes this week finished with participants commenting on the importance of listening to others before jumping to conclusions. A big part of listening is learning to ask great questions.

There are several good frameworks to structure your questions… one good framework is this one from RAIN sales. A longer explanation of their framework and approach to questions in the context of sales training is available in this pdf: Keys to Leading Masterful Sales Conversations (pdf from the RAIN group).

The 4 levels of Questions

The 4 levels of questions are listed and described below:

  1. Facts – questions about what is basically true for us both and we can agree upon.
  2. Opinions – questions about the other person’s opinion about the facts, the trends in the facts, what is important about the facts, what does it mean, who else is affected.
  3. Impact – questions about the short, medium and long term impact if we do or do not take action. The secret to a good impact question? it has the word “impact” in it.
  4. Change – questions about what it would be worth to achieve a change, what actions we are willing to commit to, what it would be worth to us if we could achieve a better future.

Here’s a list of 50 great sales questions divided into these 4 types of question from the RAIN Group blog.

If you liked this post, you will also like How to Take Better Business Decisions: 50 Great Questions for Critical Thinking and Jim Collins: How to Build an Enduring Great Company (12 Questions for Leaders).

Postcards from Montevideo

A few more images of my adventures in Montevideo

Questions from Timoney Leadership Institute Webinar

On Tuesday 26th May I had the privilege of speaking with over 50 leaders across Ireland who are alumni of Timoney Leadership Institute. Timoney has had a great relationship with IESE Business School and many of their leadership programs are taught by IESE Business School faculty.

This is a wide ranging conversation about leadership and learning in these times of uncertainty.

Questions that I didn’t get around to answer during the webinar:

James G. : How do you communicate your vision in times of challenge without being selfish

In Vistage when we talk about the 7 critical skills of leadership, number 1 is “Create a Shared Vision“. What is important is not so much that a vision exists, but that it is the result of input from every person involved in the organisation. The leader’s role is not to create the vision. The leader’s role is to cultivate an environment and facilitate an ongoing process where every person contributes in some way to the vision.

If you as a leader know the vision, but if I enter your building and speak to the receptionist and ask “what is the vision?” and his or her answer is a blank stare… you have not been effective in creating a shared vision.

As I mentioned in my answer to Ann M’s question… a lot of this process is run by active listening. The 4 questions that I recommended that you ask over and over again are:

  1. “What’s going well?”
  2. “What’s not going well?”
  3. “What would you change?”
  4. “What else?”

It is more important that everyone believes that you care, and you understand their specific joys and difficulties, than having a beautiful well crafted poetic vision statement.

Before any work on vision, one of the activities that I do with people that work with me is ask “What are the characteristics of the best Vistage team mates?” “What are the poisonous characteristics that we must avoid in new people?” and make sure that everyone has explicitly contributed to articulate what type of people we want to spend our time around.

Dermot D. : Great talk, Conor! Any tips on how to become more courageous, in business leadership terms??

Dermot, I believe that courage is a practice. If you practice small brave actions in the little things, you prepare yourself to take brave actions in the big things. A friend of mine says that there are no big things… the big achievements arrive out of a series of small things. If you do the small things well, you don’t need to worry about the big things.

When I take a group of leaders on a retreat, we work on trust and vulnerability. If I can create an environment where you are willing to be honest with what really challenges you… then there is a high possibility that you will take valuable experiences out of the time we share together. If you choose not to be honest, there is little we can do to support you. When someone says “but I don’t know what type of vulnerability you are looking for”… my answer is “are your hands sweating as you think about sharing it?” If no, it is not honest sharing.

One of the bravest actions of leadership is to admit what you don’t know, admit what scares you, admit that sometimes you our way out of your depth. Your role is not to know the answers. Your role is to facilitate a process that leads to answers.

PS Admitting that you don’t know is not a ticket to enter the state of victim… you don’t get to not take responsibility for facilitating the search for good answers.

Philip C. : Conor, your conversation and guidance is very inspiring. I have just signed up for your YouTube channel. Can you tell me if you have any books and if so where can I obtain them.

One of my big life goals that I have not yet completed is “write a book”. I write lots of blog posts, I write many articles and teaching notes for IESE Business School… but have never had the sustained discipline and clarity needed to do the 6-9 month work to complete a book.

I did write a book about my experiences of parenting… Keep Wonder Alive but it is more a manifesto than a full book.

Sean O’K.: Great talk Conor, really inspirational and helpful ideas for all of us. It sounds to me like you firmly believe that each of us can create our own life story? Would you agree?

100%.

If you don’t do the work to plan the life you want for yourself, you will contribute to someone else’s life plan. In the case of our children and our good friends, this is a wonderful opportunity. If you are just handing over your energy, your imagination, your intelligence, your activity to other people’s projects… it is no wonder that you feel that life is somewhat empty.

Burn out doesn’t come from too much activity. It comes from too much activity on stuff that is not important to your life plan.

Louis D.: Hi Conor, thanks for all your wisdom. Can I ask if faith plays a roll in your life and success? Is this a topic people are reluctant to discuss and why is that? Love all your YouTube stuff, thanks.

I have faith.

I love working with people to find their own path to self-belief. I do believe that this process is a dialogue and a mutual exploration… not a static blog post or video.

What I think about online sharing of these ideas: The concern that I have about words that capture a spiritual experience is that they can be read out of context. I am more than happy to share my experiences in private courses…. where we have had a chance to connect and build mutual trust.

Words are dangerous… If I say “honesty” we each have an interpretation of what it means… and each of us has a slightly different definition. The more abstract the word, the more our interpretations are likely to vary. Words like “airplane” and “bird” are safe on a blog post. Words like “faith” and “spiritual” and “peace of mind” are more prone to widely varying interpretation.

James G.: Is 52 yrs of age too old to be successful

As a premier league footballer, yes.

As a chess grandmaster, possibly.

As a rock star, probably.

As a leader who positively encourages others to become the best version of themselves? No. Plenty of time.

Karl D. : How important is it to learn from past decisions and experiences and do you factor those lessons in when making a decision today. Great and insightful tal Conor…well done.

Vitally important.

I love Dan Sullivan, founder of Strategic Coach. He often distinguishes between his brain and his mind. His brain is the same brain he had as a child… but his mind… is all the brains that he has access to today. His brain is limited. His mind is infinite. Our mind can take decisions not just on our own experiences, but on all of humanity’s combined experience. This type of decision making… an openness to not having to be the smartest, but to be the one willing to listen to the smartest is the greatest type of leadership.

Michael B. : Conor in our early entrepreneurial experience, would you agree that the unbridled drive and zest you need to get the plane off the ground means you tend to put projects first and people second – would you not expect this from a younger, raw, driven business person?

There is a Buddhist idea that every 7 years there is a specific phase of human development. Zero to 7 is “realise I exist”, 7 to 14 is “realise others exist” (and their dreams and fears and plans are as important to them as mine are to me), 14 to 21 is “kill your parents” (which is a metaphor!… it is a realisation that nobody is better than you, nobody is worse than you… inside you are all the positive aspects and negative aspects of humanity…) and the list goes on… you can only move to the next phase by fully living the previous phase. I can’t take a 7 year old and force them to achieve the compassion that a fully developed 70 year old can take towards the world.

I sometimes listen to my daughter talk about a difficult situation between friends, or in school… and I wish I could take what I know now and just shove it into her mind… but that is not how it works. She will live her own life and find her own way of coming to terms with life’s joys and struggles. I will always encourage her to take a positive, resourceful, creative stance towards the world… but beyond that, her answers are her answers.

I can wish that my younger self was less arrogant, less greedy…. but I wouldn’t be who I am today if I had not been that earlier arrogant and greedy self.

Mark McC. : Thanks Conor I was going to ask you what is the best way to explain resilience to a leader in these times www.createthegreatinyou.com

I took an idea from a webinar 3 weeks ago for EO with Sadhguru. He said that

Right now you are home with family. Nothing is missing.  Your memory can haunt you and your imagination can scare you. It is you who generates suffering. 

Where is your intelligence working?  For you?  Or to scare you?  Or to haunt you?

Sadhguru

Memory and Imagination – this is what we are suffering. My cancelled plans for the future… never existed except in my head. My cancelled plans for my business… never existed except in my head. My memory of how much we sold last year… is in the past.

I find it so hard to let go of what I had expected to be doing. I find a lot of motivating for me comes from working towards a future that I have imagined that is “better” than this current moment.

I think we are born resilient, but we learn to be victims. I love the book “Who moved my Cheese” by Spencer Johnson. It goes direct to this difficulty of human to let go of what I had expected.

Joseph Campbell said “we must let go of the life we have planned so as to live the life that is waiting for us”. I struggle with this. My thinking is so often focussed to avoiding change and not accepting new situations that are not what I had hoped for.

Thank you for these great questions.

Thanks again for your participation and I look forward to hearing from you.

How to Take Better Business Decisions: 50 Great Questions for Critical Thinking

A leader should be interested in developing 2 competencies in the people within their organisation:

  1. Good Decision Making (to take good choices about how to use the resources of the organisation to achieve strategic plans)
  2. Influencing Skills (because if they cannot influence their peers, people will have to involve you every time…)

If your team doesn’t have #1 they are taking poor decisions.  If your team doesn’t have #2 they cannot execute without your support (you will be sucked in to every initiative).

In order to take Good Decisions, you need to ask great questions.  

Most people ask few questions and rapidly jump to a solution.  Great decision makers ask many questions and get many perspectives before they commit to a decision.  Here’s a set of great questions…

This set of questions was inspired by the Global Digital Citizen Foundation and by Vistage Issue Processing where we help leaders develop the ability to ask great questions to help leaders think more deeply and see new perspectives, clarify objectives and take disciplined effective action.

The Ultimate Guide to Great Questions for Critical Thinking

Divided into who, what, where, when, why, how…

Who

  • …benefits from this?
  • …is this harmful to?
  • …makes decisions about this?
  • …is most directly affected?
  • …have you also heard discuss this?
  • …would be the best person to consult?
  • …else has overcome a similar challenge?
  • …will be the key people in this?
  • …deserves recognition for this?

What

  • …is the impact on you?
  • …is the impact on those close to you?
  • …are the strengths/weaknesses?
  • …is another perspective?
  • …is another alternative?
  • …would be a counter-argument?
  • …is the best/worst case scenario?
  • …is the most/least important?
  • …can we do to make a positive change?
  • …is getting in the way of taking action?

Where

  • …else would we see this problem showing up in your life?
  • …else have you overcome this type of challenge?
  • …are there similar situations?
  • …is there the most need for this?
  • …would this be the greatest problem?
  • …can we get more information?
  • …do we go for help with this?
  • …will this idea take us?
  • …are the areas for improvement?

When

  • …is this acceptable/unacceptable?
  • …would this benefit you?
  • …would this cause a problem?
  • …is the best time to take action?
  • …will we know we’ve succeeded?
  • …has this played a part in your past?
  • …can we expect this to change?
  • …should we ask for help with this?

Why

  • …is this a problem/challenge?
  • …is it relevant to your goals?
  • …is this the best/worst scenario?
  • …are people influenced by this?
  • …should people know about this?
  • …has it been this way for so long?
  • …is there a need for this today?

How

  • …is this similar to _____?
  • …does this disrupt things?
  • …do we know the truth about this?
  • …does this benefit you/us/others?
  • …does this harm you/us/others?
  • …do we see this playing out in the future?
  • …can we help you?
[Edit: this poem was shared by my Dad upon receiving this post]

I Keep Six Honest Serving Men
Rudyard Kipling
I KEEP six honest serving-men
 (They taught me all I knew);
Their names are What and Why and When 
 And How and Where and Who.
I send them over land and sea,
 I send them east and west;
But after they have worked for me,
 I give them all a rest.

I let them rest from nine till five,
 For I am busy then,
As well as breakfast, lunch, and tea,
 For they are hungry men.
But different folk have different views; 
I know a person small—
She keeps ten million serving-men,
Who get no rest at all!

She sends’em abroad on her own affairs,
 From the second she opens her eyes—
One million Hows, two million Wheres,
And seven million Whys!

The Elephant’s Child 

More Great Questions for Vistage Groups

Great Questions for Teaching & the Learning Process

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