Questions for Coaching: 85 All-Purpose Killer Questions

Questions for Coaching: 85 All-Purpose Killer Questions

By Theo Winter White

Therapist: Did you try using the mantra? (“Every day, in every way, I am getting better and better.”) Jessica: Yeah. Not really working for me. At all. Therapist: Then you should create your own mantra. One that works just for you. Jessica: How about… “I give up. Everything is terrifying and I’m not going to do this job.”

— Justice League vs. the Fatal Five


Greetings, beautiful earthlings of the internet, and happy 2020. Let’s get this jolly good show on the road with — what better topic? — Questions.

There’s nothing more special and important in the whole entire universe than questions.

I mean, is there? Maybe not, but also maybe not not. You know?

Sorry, double negatives can be super annoying. I prefer visual metaphors anyway, so let me think… what’s a good, inclusive metaphor here that everyone can enjoy? Hop skippy do, I know. Sword fighting!

Until I come up with something better (the unstated premise behind everything I think and write), let’s imagine a friendly joust with swords: Lunge forth with an idea, anything you can think of — the purpose of life, your best hot take on success, any passing observation about, I don’t know, ducks on a pond — and your intellectual fencing partner can parry with a question.

On guard!

By gosh, Jill, the world is such a horrible place, filled with monstrous evil and violence and hideously ugly ducklings — it’s all utterly hopeless. I’m telling you, we should purge the land and start over. Ah, indeed Jack, but isn’t there also good and beauty in the world and happy reasons not to fly into a murderous rage? Also, what do you have against ducks exactly?

Attractive analogy. Check. True to life depiction of human interaction. Check.

Okay, great, moving on.

In contrast with answers, which are by definition end-of-the-line, questions seek: they are the purest symbolic expressions of truth seeking. Spiritual kin to the mad scientist as much as the serial entrepreneur, questions open the door to possibility — and they leave the door open. If intelligence itself could choose to be a symbol, I wonder if it wouldn’t choose to be a question mark. And I don’t mean the “are you stupid or something, son?” kind of rhetorical questions you hurl at Forrest Gump (who, as it turns out, might not be so stupid after all). I mean the primordial baby gurgles of truth, ignition sparks of every reformation and revolution; the original “wait, but what about…” instinct that, in every bundle of bright-eyed hatchlings, inevitably bumps into the reigning lords of ESTABLISHED TRUTH. You know, the government-approved teacher quite at home in institutions more like prisons than schools who displays dutiful obedience to ancient edifices yet simultaneously warns us to be on guard against the evils of tyranny. (But hang on, Superintendent This Is Sparta, is intellectual tyranny not, quite possibly, similar to political tyranny?).


tyrant | noun

a person exercising power or control in a cruel, unreasonable, or arbitrary way.


To escape the shackles of our socially-conditions patterns and tyrannical overlords (which can include our own minds), the task is not so much “in seeking new landscapes” as Marcel Proust said, “but in having new eyes.” Questions are this power. They help precisely to bend one’s looking-lens the way a prism bends a beam of light. Nothing about reality is changed by the introduction of the prism, except suddenly everything has changed. The jumbled mess becomes orderly. The unclear, coherent. A structured mathematical harmony appears where there was once only strangeness and mystery. The slave becomes the sorcerer supreme.

What follows is a list of all-purpose questions that, while perhaps best suited to coaching conversations, can be applied to a wide variety of contexts, supplementing any facilitator or curious human’s mental tool kit. Mix, match, and remould as you see fit. Create potent combinations the way a battle-scarred Mortal Kombat gamer develops devastating martial arts moves by pressing the right buttons in judicious, well-chosen sequences. Test your might. Except, you know, the coaching process will probably involve less hand-to-hand combat, bloodshed, and shocking violence. Maybe not the best metaphor. Anyway, what I’m saying is, I think, if the mantra doesn’t work for you, terminate everything ugly and get a new mantra.


85 Killer Questions White

1. What’s on your mind / what would you like to discuss? 2. How will I know you’ve got your money’s worth from our time together? 3. What’s the most important thing you want to take away from our time together? 4. What does success look like? 5. What’s your goal? 6. What’s the context? 7. Why is that important to you? 8. How could we put that in the form of a goal or objective? 9. Could we make that even [simpler, clearer, easier]? 10. What’s essential? 11. What do you need from the situation? 12. What’s nice-to-have vs. must-have? 13. In what way, specifically? 14. Can you describe a week in your life? 15. What would a week-in-the-life of the best version of you look like? 16. How long has this been an issue? 17. How much [time, effort, energy, thought] have you been giving this? 18. Is this new territory or old territory for you? 19. What, if anything, have you already tried? 20. How are your habits helping / hindering you? 21. How are your systems helping / hindering you? 22. How is your environment helping / hindering you? 23. If you keep going that way, what’s likely to happen? 24. Could you give me an example? 25. Do you have a set of guiding principles or values? 26. Do you have a foundational vision or mission? 27. Thinking out loud, could you give me a rough idea? 28. How do you think that would play out? 29. If you had to pick [2, 3, 5] things, what would they be? 30. How would you prioritise those / put those in order? 31. What are the pro’s and con’s? 32. Are there individual pro's that might outweigh a heap of negatives? 33. What risks might you be overlooking? 34. Putting aside what you think you should do; what things could you do? 35. What’s getting in the way? 36. Thinking ahead, what does the downstream, long-term impact look like? 37. What do you need to communicate to others to help you progress? 38. How would you describe the situation without assigning any value judgements? 39. Are we addressing symptoms or causes? 40. What’s the real [problem, cause, root issue]? 41. If you [changed, added, removed] that, how would it affect the situation? 42. Would that result in a net positive gain or net negative loss? 43. What does your head tell you? 44. What does your heart tell you? 45. What models, blueprints, or templates are available? 46. Can you break that down for me? 47. If you broke that into [2, 3, 5] steps what would they be? 48. On a scale of 1-10, where would you rate that? 49. What are your options? 50. What’s the most practical action? 51. Who has already solved this problem? 52. What problem solving methods do you depend on? 53. What else is available? (Tools, technology, information, people, systems) 54. Who can help? 55. Have you exhausted all possibilities? 56. What if you tried / tested another approach for a short time? 57. Is that the best way of looking at it? 58. Is there another way? 59. What if you did the opposite? 60. By when? 61. What’s your deadline? 62. Do you need to decide now? 63. How is your emotional state affecting your judgement? 64. What’s working well? 65. What’s not working? 66. What do you want more of? 67. What do you want less of? 68. Best case scenario? 69. Worst case scenario? 70. What’s not negotiable? 71. What’s a deal breaker? 72. What can you cut / eliminate / remove? 73. If I came to you with that problem, what would you say? 74. From the outside looking in, how does the situation look? 75. If that wasn’t an issue, what would you do? 76. What’s the cost of doing nothing? 77. What’s the shortest distance between you and your outcome? 78. What’s the easiest action step you can take right now? 79. What if you took massive action? 80. Where will you go from here? 81. What are the next steps? 82. What does the process of accountability look like? 83. Is there a best time to take action? 84. What research or further reflection needs to happen? 85. What follow up needs to happen?

White White


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