The quality of our questions determines the quality of our lives and the outcomes we get. Ask stupid, limiting or self-defeating questions will always condemn us to spin our wheels emotionally and intellectually.

Some examples:

  • “Why me?” – Helps us feel and act like a victim.
  • “How can I get them to approve/like me?” – A recipe for mediocrity.
  • “How can I do this perfectly” – Will always lead to feeling of inadequacy and failure.
  • “How can I control this situation.” – Control is an illusion, better to learn to deal with the unfamiliar.

Leaders need to ask great questions and they need to have some questions that will lead to superior results over time? Having a bank of questions that you ask yourself and others semi-regularly is like the dials on a cockpit. The dashboard is easy to see and understand the state of the airplane. Every dial on the dashboard tells a story. When leaders have a dashboard, not just of hard results, they can assess the health of the organisation or team.

I deal with questions every day as a leadership coach. Here are some questions that I have found to be really helpful when coaching leaders over the years. These questions are inspired by a podcast by Andy Stanely.

Some of these questions will be more applicable to your situation. You probably wouldn’t use all these questions all the time, maybe once a month or once a quarter. But there may be one or two questions that are particularly relevant for you right now. Pick one of more questions and play with them for a month and see what the results are.

Question 1: Which gauges should we be watching? What questions are you asking?

  • We direct the values, behavior and culture of those we lead more by what we ask, than what we tell.
  • Listen to what you ask – do I really want to direct the behavior of people with that question.
  • If you want to know what someone values, listens to their questions.
  • What we ask is a mirror to what is most valuable to us as opposed to what we say is most important.
  • What are the behaviors that would be best for this organisation, then, what question(s) can I begin to ask that will start to direct their behavior in a certain (desired) direction.

Question 2: Who needs to be sitting at the table?

  • Do I have the right people sitting at the table?
  • Who needs to be here as part of the decision-making process?

Question 3: Where are we manufacturing energy?

  • Where are we pretending (to create a sense of excitement) to be more excited about something than we’re really excited about?
  • It forces us to face realities that many times we don’t want to mess with. We don’t want to changes things because it’s too hard, etc.

Question 4: Where do I make the greatest contribution to the organization?

  • In both my immediate responsibilities as well as the broad scheme of the organization am I the best fit?
  • Don’t ask the question just once. It needs to be asked at least annually, maybe even more frequently.
  • I don’t help the other people around find their best and highest usefulness when I don’t ask that about myself and about them. There maybe things I’m doing that someone else could thrive in if I would simply get out-of-the-way. Ask myself the question, “Is there a higher and best use of my talent in the organization?”
  • The flip side, “What should I stop doing?”

Question 5: Who’s not keeping up?

  • Always a hard question to ask. There is always a way to transition someone with dignity.
  • No one likes to ask this question. It’s painful. But it’s inevitable that as your organization hits 60 kph, there will be some still moving at 45 kph.
  • As painful as this question is, the truth is that other people already know the answer. They are wondering if you know. Accommodating people who are falling behind hurts the organization, dishonors those people, and will ultimately keep them from finding their areas of success.
  • Another way to find the answer to this question is by asking: “Who do I or others have to work around?”

Question 6: What have we fallen in love with that is no longer the best way to…

  • Everyone loves the way they do things or they wouldn’t do them that way.
  • Over time, the way we do things becomes emotional for us, part of our culture.
  • What have we become emotionally engaged with or attached with that is really not the best way to do it any longer?
  • Andy Groves, “Only the Paranoid Survive” asks the question –

“I looked out the window at the Ferris wheel of the Great American amusement park revolving in the distance when I turned back to Gordon [Moore, CEO of Intel], and asked ‘If we got kicked out and the board brought in a new CEO, what do you think he would do?’ Gordon answered without hesitation, “He would get us out of memories.’ [memory chips] I stared at him, numb, and then said ‘Why shouldn’t you and I walk out the door, come back, and do it ourselves?”

Question 7: What would a great leader do?

  • It takes me beyond average. It drags me out of my comfort zone.
  • What would Winston Churchill do? Martin Luther King Jr.? Gandhi? Jesus?
  • What would they do that would be the unusual thing, bold thing, the courageous thing, the vision thing? The thing that took them beyond personal gain and personal reputation.
  • Even in the small issues, pause to give yourself permission to know the answer to the question, “If I were a great leader… truly selfless, truly committed to the organization more than I am committed to myself, more than my own ego or my own reputation, my income, my bonus, (my…my…my…my…) what would a great leader do?”
  • Even if I wouldn’t do what a great leader would do, you owe it to yourself to at least give yourself the margin to discover what a great leader would do, maybe just the though of what a great leader, if I were a great leader (if I were selfless), sometimes just knowing that is enough to pull us beyond the boundaries of our own ego and self-centeredness to actually do the great thing.

Question 8 – What happened yesterday that made you feel like you were successful in what you came here to do?

  • Momentum and motivation come as we can see progress.
  • Leaders need to keep an eye on what they are paid to do, in turn avoiding mission creep.
  • The enemy of great is good. Staying focused and celebrating the wins is crucial to playing a long game.


Leave a Reply

Your email address will not be published. Required fields are marked *