Questions to get you unstuck…

A good question can be just the trick you need to remove the block and get things flowing again.

Credit — Pexel

Warren Berger writes in his book and blog “A Beautiful Question”

A beautiful question is an ambitious yet actionable question that can begin to shift the way we perceive or think about something — and that might serve as a catalyst to bring about change.

Further the World Cafe Organisation identifies a powerful question as one that:

• Is thought provoking
• Challenges assumptions
• Generates Energy
• Focuses enquiry and reflection
• Touches a deeper meaning
• Evokes related questions

Here is an eclectic collection of great questions, accumulated from numerous sources over the years. I’d love to see any good ones you have..

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Dan Sullivan Question

If we were meeting three years from today — and you were to look back over those three years to today — what has to have happened during that period, both personally and professionally, for you to feel happy about your progress?

Specifically, what dangers do you have now that need to be eliminated, what opportunities need to be captured, and what strengths need to be maximized?

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Amy Edmondson — The Fearless organisation — (Chapter 7)

To broaden understanding of a situation or expand an option set, ask,

• “what might we be missing?”,
• “what other ideas could we generate?”, or
• “who has a different perspective?”

Other questions are designed to deepen understanding. Ask,

• “what leads you to think so?” or
• “can you give me an example?”

When we’re discussing an idea,

• “What did the dissenter say?” If there isn’t one then you need to go out and find them!

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Beyond Measure — The big impact of small changes — Margaret Heffernan

Better questions = better decisions

• Who need to benefit from our decision? How?
• What else would we need to know to be more confident of this decision?
• Who are the people affected by this decision; who have the least power to influence it?
• How much of this decision must we make today?
• Why is this important? and what’s important about that?
• If we had infinite resources — time, money, people — what would we do? What would we do if we had none?
• What are the reasons this is the right decision? What are all the reasons it is the wrong decision?

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Ryan Holiday — Books

• What’s a book that changed your life?
• What book do you wish you read earlier in life?”
• “What book shaped your career as a _______ more than any other?”
• “Is there a book out there that really changed your mind?”
• “I’m dealing with ___________ right now; what authors would you recommend on that topic?”

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4 questions of a Leader — Abhijit Bhaduri

• Am I a barrier buster? What roadblocks can I remove to make them better and their jobs easier
• Am I a bouncing board? Can they come to me with their ideas?
• Am I providing air cover? Do I have their back?
• How can I run with the troops to make them more effective?

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Know your Team Manager Checklist

• Question #1: How can I create an environment for people to do their best work?
• Question #2: How can I create as much clarity and coherence about what needs to get done and why?
• Question #3: How can I personally model the behavior I want to be true across my team?
• Question #4: How can I see things for what they are, instead of what I want them to be?

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How to Solve Impossible Problems: The Phoenix Checklist | by Jennifer Clinehens | Growth Habits Lab | Medium

• Why do we need to solve this problem?
• What benefits will you get when you solve this problem?
• What do we know? What don’t we know for sure?
• Can you break out the different aspects of the problem?
• What is NOT the problem?
• Do we have enough information or not enough?
• What would happen if we drew a picture of the problem?
• Where are the boundaries of the problem?
• Has anyone else already solved a problem like ours? What method did they use? Can we copy it?
• How will you know when you are successful?

Thinking Tools/Phoenix Checklist — Wikiversity

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Don’t Just Ask — “What’s the Matter?” Ask “What Matters to you?”

Chip and Dan Heath

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Seth Godin — This is Marketing

A Simple Marketing Worksheet — people like us do things like this

• Who’s it for?
• What’s it for?
• What is the worldview of the audience you’re seeking to reach?
• What are they afraid of?
• What story will you tell? Is it true?
• What change are you seeking to make?
• How will it change their status?
• How will you reach the early adopters and neophiliacs?
• Why will they tell their friends?
• What will they tell their friends?
• Where’s the network effect that will propel this forward?
• What asset are you building?
• Are you proud of it?

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Tara Gentile — How can you do it quicker?

What would you have to do differently to reach your goal for this entire year in the next 6 weeks, without working more?

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John Whitmore — Coaching for Performance

• “What else?” used at the end of most answers will evoke more. Plain silence, while allowing a coach to think, often evokes more too.
• “If you knew the answer what would it be?” is not as daft as it sounds, since it enables the coachee to look beyond the blockage.
• “What would the consequences of that be for you or for others?”
• “What criteria are you using?”
• “What is the hardest/most challenging part of this for you?”
• “What advice would you give to a friend in your situation?”
• “Imagine having a dialog with the wisest person you know or can think of. What would he or she tell you to do?”
• “I don’t know where to go next with this. Where would you go?”
• “What would you gain/lose by doing/saying that?”
• “If someone said/did that to you, what would you feel/think/do?”

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Tim ferris — 17 Questions That Changed My Life

1. What if I did the opposite for 48 hours?
2. What do I spend a silly amount of money on? How might I scratch my own itch?
3. What would I do/have/be if I had $10 million? What’s my real TMI?
4. What are the worst things that could happen? Could I get back here?
5. If I could only work 2 hours per week on my business, what would I do?
6. What if I let them make decisions up to $100? $500? $1,000?
7. What’s the least crowded channel?
8. What if I couldn’t pitch my product directly?
9. What if I created my own real-world MBA?
10. Do I need to make it back the way I lost it?
11. What if I could only subtract to solve problems?
12. What might I put in place to allow me to go off the grid for 4 to 8 weeks, with no phone or email?
13. Am I hunting antelope or field mice?
14. Could it be that everything is fine and complete as is?
15. What would this look like if it were easy?
16. How can I throw money at this problem? How can I “waste” money to improve the quality of my life?
17. No hurry, no pause.

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Peter Thiel — Interview question

“What important truth do very few people agree with you on?”

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Strategic Coach — Impact Filter Questions

1. Purpose — what to you want to accomplish
2. Importance — whats the biggest difference this will make
3. Ideal outcome — what does the completed project look like
4. Success criteria — what has to be true when the project is finished
5. What is the best result if you do take action
6. What is the worst result if you don’t

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Reflection Question — Dickie Bush

1. Where am I feeling the Resistance?
2. What would I do to make today horrible?
3. Where am I making things more complex than they need to be?
4. How would the type of person I want to become handle this?
5. How could I achieve my 10-year goals in six months?
6. What would I do if it was impossible for me to fail?

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Accidental Creative — Todd Henry

• Phrasing your problem as a question immediately gets your mind working on solutions rather than on the pragmatics associated with the project.
• Future. What would a solution to this problem look like? What would it feel like? What is the ultimate state that would describe that the problem has been solved? Write a few words, then start generating ideas off of them.
• Past. What are some assumptions that are presently keeping us in gridlock around this problem? Are there any assumptions that need to be challenged or that could serve as a starting point for idea generation? Try to challenge one of these assumptions by generating ideas designed to disprove it.
• Conceptual. What are other problems and corresponding solutions that I know of that are similar to this one? Are there any learnings from case studies or other items I’ve been exposed to that could apply to this problem? Try to force a connection between something you’re familiar with and the problem you’re currently working on.
• Concrete. What are the specific and concrete attributes of the problem? Can the problem be broken down into three words? If so, do these words give me a new way of perceiving or attacking the problem? Free-associate new words off these concrete attributes and see if they spark any new ideas.
• Once you’ve written ten to twelve words per column, start choosing two words, each from a different column, and see if an idea is sparked

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Dan Sullivan (Again!) — How far can I go?

I tell them that I’m not looking for an answer; I’m just following a question. No matter what level of success I’ve achieved, no matter how much [my career] has grown, when I’ve achieved a major life goal, the question always comes into my mind: Now I wonder how far I can go?

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WRAP framework — Chip and Dan Heath

Widen your options

• Look for bright spots; Look across industry;
• look at doing this AND that rather than this OR that
• What would you do if your current option vanished?
• Simplicity — how can you make this easier
• 10x your solution. Consider 10x based on impacting
• the process outcome
• the cost or value
• the effort
• The time
• the perception — e.g. do nothing but sell it better.

Reality test

• How can you find proof now your current decision is a terrible one?
• Zoom out and look at the base rate;
• how can you test the solution by ooching
• Are you absolutely sure it is true?
• Turnaround the statement to self, other, opposite.

Attain distance

• What would your successor do?
• 6 months from now why would I regret this decision?
• What needs to be true for this to be the best possible choice?
• 10/10/10 decision making

Prepare to be wrong

• Its a year from now and it have failed utterly — Why?
• What trip wires do you need to set to tell you to review or reconsider your option

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Dane Maxwell — Thefoundation.com Idea Extraction

• What are the big projects you are working on right now? What seems to be taking up the most mental energy for you in the last couple days or weeks?
• What are the first few things you do each morning? OR…
• What are the first few things you’ve done TODAY.
• What are the things that you love to do? When are you in flow?
• What keeps you from being in flow.

You can do by repeating 2 simple phrases 1. “That’s interesting” 2. “Tell me more”

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Lean Customer Development — Cindy Alvarez

BASIC CUSTOMER DEVELOPMENT QUESTIONS

• Tell me about how you do _________ today….
• Do you use any [tools/products/apps/tricks] to help you get ________ done?
• If you could wave a magic wand and be able to do anything that you can’t do today, what would it be? Don’t worry about whether it’s possible, just anything.
• Last time you did ___________, what were you doing right before you got started? Once you finished, what did you do afterward?
• Is there anything else about _________ that I should have asked?”
• “Can you tell me more about how that process goes?
• Who is involved in making that decision?
• Last time you did ______, how long did it take?
• Where did you most recently go to buy ______?”

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Something Really New — Denis Hauptly

• Step 1: What tasks is the product really used for?
• Step 2: When I know what task a product is really used for, are there any steps that I can remove from that task?
• Step 3: What tasks are the very next tasks that the customer will want to perform after using my product?

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The Mom Test —Rob Fitzpatrick

• Talk about their life instead of your idea
  Ask about specifics in the past instead of generics or opinions about the future
  Talk less and listen more
• “Tell me more about that.”
• “That seems to really bug you — I bet there’s a story here.”
• “What makes it so awful?”
• “Why haven’t you been able to fix this already?”
• “You seem pretty excited about that — it’s a big deal?”
• “Why so happy?”
• “Go on.”

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Positive Deviance

GOOD QUESTIONS — PD MRSA initiative:

• What do you know about MRSA?
• What do you do to prevent patients under your care from getting MRSA?
• What are the barriers that keep you from doing it 100 percent of the time?
• Do you know of anyone who has figured out strategies to overcome these challenges? If so, how?
• Do you have any ideas about new strategies?
• What would it take to implement them in this unit?
• Who is willing to take the next steps

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Bright Spot Questions

• Ask the exception question — when does the problem you are fighting not happen?
• Ask the miracle question — You wake up in the morning and your problems are solved. What’s the first small sign that things have changed?
• Make sure the bright spot is about you — Bright spots are specific to you and your team. Where are YOU succeeding now, or where have YOU succeeded before? By pinpointing those moments, you can avoid triggering the “not invented here” reaction.
• What is working today and how can you do more of it?
• Not “Why are staph infections so high in the hospital?” but “Why are staph infections lower on the third floor?”
• Not “Why are sales down in Regions 6 and 9?” but “Why are sales up in Region 4?”
• Not “Why do so few graduates of our leadership academy get promoted?” but “Why did these seven graduates get promoted?”

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Difference: The one-page method for reimagining your business and reinventing your marketing — Bernadette Jiwa

Work through defining the following to clarify your position

• Principles
• Purpose — Why do we exist
• People — Who is this for? What do they care about?
• Personal — How can we change how people feel? How can we help then live better lives?
• Perception — What do they believe? What do we want them to believe about us?
• Product — What do people really want or need? How do we create value for our customers?

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Hooked — Nir Eyal

Ask yourself these five fundamental questions for building effective hooks:

1. What do users really want? What pain is your product relieving? (Internal Trigger)
2. What brings users to your service? (External Trigger)
3. What is the simplest action users take in anticipation of reward, and how can you simplify your product to make this action easier? (Action)
4. Are users fulfilled by the reward, yet left wanting more? (Variable Reward)
5. What “bit of work” do users invest in your product? Does it load the next trigger and store value to improve the product with use? (Investment)

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Phoenix Checklist

The Problem

1. Why is it necessary to solve the problem?
2. What benefits will you receive by solving the problem?
3. What is the unknown?
4. What is it you don’t yet understand?
5. What is the information you have?
6. What isn’t the problem?

….

The Plan

1. Can you solve the whole problem? Part of the problem?
2. What would you like the resolution to be?
3. How much of the unknown can you determine?
4. Can you derive something useful from the information you have?
5. Have you used all the information?
6. Have you taken into account all essential notions in the problem?
7. Can you separate the steps in the problem-solving process? Can you determine the correctness of each step?

…..

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Todd Henry — Questions to Ask when you are stuck

1. Is an assumption in the way?
2. What is the worst-case scenario?
3. Could I do the opposite?
4. How can I thrill the end user?
5. What am I afraid of?
6. Do I understand why?
7. Where else has something similar been done?
8. What is expected and why?
9. Who has something to lose?
10. Who is the enemy and how do we foil them?
11. Who could solve this problem with ease, and how?
12. How would my favourite super hero do it?
13. How would my favourite movie character do it?
14. Could I change the medium?
15. Could I ask the question differently?
16. How would a 3rd grader approach this problem?
17. What question do I need to answer first?
18. Is there a resource I’m lacking?
19. How would I describe the problem in three words?
20. Are there sub-problems to the main problem?
21. What’s the world like once the problem’s solved?
22. Who can I call for help?
23. Can I create a metaphor for the problem?
24. How would I start over?
25. What’s primary block and why?

One-Pager Questions — John Cutler

Use these questions while workshopping and writing.

1. Would you bet $20,000 of your own money on the success of this effort? Why? Why not? On what terms? How would we know whether you had won/lost the bet? What might we learn early on that would encourage you to increase your bet to $40,000? Or decrease your bet to $5,000, or $0?
2. Fill in the blanks. With this effort — in the next 6 months — there is a 95% chance we’ll generate [some outcome], a 50% chance we’ll generate [more of that outcome], and a 10% chance we’ll generate [even more of that outcome].
3. How have we tried to solve this problem in the past? What happened? Do you mind sharing some data?
4. What status quo are we hoping to disrupt? What is actually wrong with the status quo?
5. Imagine you had to judge an internal competition to pick the best intervention to solve this problem. You’re responsible for writing judging criteria for your fellow judges. How would you rank submissions?
6. What efforts have you taken to defeat confirmation bias, the availability heuristic, information bias, the IKEA effect, and other cognitive biases? How might a less-biased person view this bet?
7. Describe the “good news” you hope to elicit as a result of this effort. How might you describe it in a company-wide presentation in a non-success-theater, non-fluffy way? Write the dream customer feedback tweet. How might the good news change in the short, mid, and long term as we realize the benefits?
8. Every idea has a “backstory”. What’s the backstory here? How might you describe this effort to a new team member without the “back story”?
9. Explain how this connects to the broader company strategy. Why is this a critical part/piece of the puzzle? Together with other initiatives, are we telling a cohesive story?
10. Why now? Why is this the most important problem to solve right now? How might the financial outcome be different if we did this in six months, one year, or never? Explain how it “beats” a handful of other things you are considering.
11. You’re about to occupy some % of the careers of a couple fellow human beings. Why should they come along for this adventure?
12. Do you imagine a team sticking around to push the actual benefits here? Or do you expect a hand-off? Or a hybrid? What early indicators might indicate that we’ve placed a good bet and would signal that it is safe to move on to other things?
13. Let’s say we don’t do this. What will actually happen to the business in the short, mid, and long term? To our customers/users/partners/team?
14. Does this effort rely on other efforts to be successful? Describe how the efforts are related. If they are truly dependent, can/should we pursue them concurrently, or combine them somehow?
15. Challenge yourself to cut the scope here by 75%. Would that deliver some value? Should we pursue that first, even if it expands the overall scope a bit?
16. How much money are we losing each week (new opportunities or cost savings) by not solving this problem? How does that compare to the money we are losing each week by not solving other problems?
17. In the spirit of challenging the sunk-cost fallacy, what might happen part-way through this effort that would persuade you to stop work?
18. Describe the various forces and shifts that must come together to make this successful? What do we control? What don’t we control? What can we influence?
19. Play your own Devil’s Advocate for a moment. Give me three good reasons why this isn’t a good idea. Now give me three good reasons why solving another problem is a better idea.
20. Who will this impact? Say I wanted to identify the customers/users this will impact, what query would I run? How might I quantify the impact over time?
21. Can we design some safe-to-fail experiments to help us solve this problem? Overall, how can we expand our “portfolio” of bets here, and get faster feedback?
22. Can you give a brief summary of the data and insights underpinning this bet? How did this data, and these insights inform your beliefs?
23. What are the known unknowns here?
24. Where are you making leaps of faith in terms of user behavior? What is your plan to close the learning gap? When will you get this into the hands of real humans, with real data, trying to do their real job?
25. Do you have a plan for regular usability testing? How often? How early? Have you set aside time to act on what you learn during these tests?
26. How will you instrument your solution to measure outcomes and learn?
27. What’s your plan to work “end-to-end” across the problem and the solution, such that we don’t arrive, finally, at a solution and discover the parts don’t fit together as expected?
28. What is the behavior you hope to change? What will customers/users do more of, less of, start doing, and stop doing as a result of this work? How will that behavior change benefit the customer/user and the company?
29. What information would make solving this problem easier? Are we missing insights that might improve our “batting average” here? How might we obtain that information?
30. What problem might we solve, such that this problem would be a non-factor? Why aren’t we trying to solve that problem?
31. How will we measure the impact and success of this effort in the short, mid, and long term?
32. What is your plan to regularly reduce “benefits risk” (the risk this effort will not achieve the desired benefits) as the effort progresses?
33. How might you describe the various other risks in this effort? How will you incrementally reduce those risk levels?
34. What must we “get right” to succeed at this effort? Where can we be less-than-awesome, and still succeed? What should we ignore? What can be “suck at”?
35. Who do we need involved to make this a success? Any special skills? Any special insights?
36. What assumptions must hold true for this initiative to remain the most important thing we can work on?
37. Is this the lowest hanging fruit? If I asked your team to spend the next week fixing “small things with a big impact” would this top the list? Would it have a greater cumulative value? Say you only had two weeks to solve the problem (or chip away at the problem)…what would you try?
38. Can you commit to a “pivot/proceed” decision point? When will we stop iterating on this? Please draw a line in the sand.
39. It is a six months from now and this effort has failed. Describe three plausible reasons why it failed. Tell a good story.
40. What is the leap of faith here? What must I believe without supporting data?

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Leadership Stand up Questions — Matt Phillips

• What process, meeting or organizational policy can I make more psychologically safe today?
• Where are silos occurring? Where are handoffs between teams and processes happening?
• What failure do I need to learn from and share to set an example for others?
• Where has it been a while since I just actually saw where work was being done and value created?
• What decisions am I planning to make that others could make?
• Whose coaching invitation might I seek today?
• What meetings am I planning to attend that I may not truly be needed at, and how can I create more space in my day to be available to others?

Noel Tichy writes in The Leadership Engine, “The ultimate test for a leader is not whether he or she makes smart decisions and takes decisive action, but whether he or she teaches others to be leaders and builds an organization that can sustain its success even when he or she is not around.”

And some more…

• Retromat — series of retrospective questions in nifty web setup by Corinna Baldauf
• Think Clearly Cards — Questions and Strategy
• 29 powerful questions to ask your team in the new year — Pagely
• 40 questions to ask yourself each year — Steven Ango
• 37 Questions to ask yourself to get you unstuck
• 36 questions to bring you closer together — Aurthur Aron
• The 4 Questions of a Retrospective and Why They Work — InfoQ
• Some Thoughtful Retrospective Questions — Chris Gange
• Questions UX Designers should be asking — Garret Kroll
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