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

Guest Post by Conor Neill

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…


  1. …benefits from this?
  2. …is this harmful to?
  3. …makes decisions about this?
  4. …is most directly affected?
  5. …have you also heard discuss this?
  6. …would be the best person to consult?
  7. …else has overcome a similar challenge?
  8. …will be the key people in this?
  9. …deserves recognition for this?


  1. …is the impact on you?
  2. …is the impact on those close to you?
  3. …are the strengths/weaknesses?
  4. …is another perspective?
  5. …is another alternative?
  6. …would be a counter-argument?
  7. …is the best/worst case scenario?
  8. …is the most/least important?
  9. …can we do to make a positive change?
  10. …is getting in the way of taking action?


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


  1. …is this acceptable/unacceptable?
  2. …would this benefit you?
  3. …would this cause a problem?
  4. …is the best time to take action?
  5. …will we know we’ve succeeded?
  6. …has this played a part in your past?
  7. …can we expect this to change?
  8. …should we ask for help with this?


  1. …is this a problem/challenge?
  2. …is it relevant to your goals?
  3. …is this the best/worst scenario?
  4. …are people influenced by this?
  5. …should people know about this?
  6. …has it been this way for so long?
  7. …is there a need for this today?


  1. …is this similar to _____?
  2. …does this disrupt things?
  3. …do we know the truth about this?
  4. …does this benefit you/us/others?
  5. …does this harm you/us/others?
  6. …do we see this playing out in the future?
  7. …can we help you?

Note Conor – 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 

Conor Neill


Conor Neill is a sought-after keynote speaker on resilient leadership. He is President of Vistage Spain, part of the worlds leading CEO organisation.  As an entrepreneur, he has founded 4 companies, selling 16 private jets and building the 3rd largest fleet of private jets in Spain. He teaches leadership at IESE Business School, and is a visiting professor at University College Dublin.  Conor can help you sell a private jet, or how to get the resources to build anything else that you truly believe in.


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