Point Lookout: a free weekly publication of Chaco Canyon Consulting
Volume 19, Issue 46;   November 13, 2019: Thirty Useful Questions

Thirty Useful Questions

by

Whether solving technical problems, creating plans, or puzzling through political tangles, asking the right questions can be the key to finding useful approaches. An example: What questions would I like to know the answers to?
Clouds at sea

Clouds at sea. Most of us cannot imagine any way of computing the shape and content of a cloud. Meteorologists use computers to do so, but even then, what they're actually doing is simulating the cloud formation.

Most of us have toolkits that contain whatever is needed for addressing problems that have inherently well-defined structure. For example, we can all calculate how long a project will take given the list of tasks, their dependencies, and the effort and time required for each task. It might be laborious, but it's doable. And if we give that same set of data to two different people, the results would be in close agreement.

But some problems don't have inherently clear structure. Some cannot be expressed mathematically. For example, to determine why Lisa and Louis can't get along, mathematics is of no use. Even when we can imagine calculating an answer to a problem, we must be certain that we've expressed the problem completely, without duplication. For example, to determine the capital needs of a startup company, we need to have a complete list of its equipment needs. In that case, it's easy to generate a list, but not so easy to determine that the list is complete.

For unstructured For unstructured problems, it's useful
to have a list of questions to ask that
might serve as guides for ensuring
that we understand the problem
problems, it's useful to have a list of questions to ask that might serve as guides for ensuring that we understand the problem. For that purpose, I offer the list below, in no particular order.

  • What questions would I like to know the answers to?
  • If I had the answer to question X, what do I think the answer would be?
  • If I had the answer to question X, what questions would I ask next?
  • I don't know the answer to question X, but what do I know about the answer to question X?
  • I don't know the answer to question X, but what do I know about the answer to question X that I've forgotten I know?
  • What's the significance of the answer to question X? What does it matter?
  • If I had the answer to question X how could it change what I'm doing now? How would it change what I plan to do next?
  • The answer to question X was Y last week. Is the answer still Y this week?
  • What did I believe to be true in the past that turned out not to be true?
  • Among those of my past beliefs that turned out to be mistaken, is there any discernable pattern?
  • Which cognitive biases have affected my judgment in the past?
  • Which cognitive biases might at this moment be affecting my judgment?
  • Among the cognitive biases that affected my judgment in the past, is there any discernible pattern?
  • What questions would have been useful to ask in the past if only I had asked them?
  • How do we know that we've included all the risks (all the expenses, all the revenue, all the …) that we needed to include?
  • What am I assuming that I'm unaware I'm assuming?
  • Why am I asking question X?
  • How do I know what I know about X?
  • Why do I not know the answer to question X? What missing pieces would let me find that answer?
  • What am I not asking questions about?
  • I know that solution S is a solution to Problem P, but how do I know that there isn't a better solution?
  • Have I confirmed that this problem is my problem to solve?
  • How do I know that this problem is my problem to solve?
  • How do I know that solving this problem is necessary?
  • How much is the solution to this problem worth?
  • How much will solving this problem cost?
  • If X worked so well in situation S, why is X not working in situation S'?
  • If X and Y both worked well in situation S, why is X working in S' while Y isn't working at all in S'?
  • If X always produces Y in situation S, and Y always produces Z in situation S, why doesn't X produce Z in situation S?
  • If Person A works well with Person B, and Person C works well with Person B, why can't Person A work well with Person C?

One final question: if you were to add four questions to this list, what would they be? Go to top Top  Next issue: Paid-Time-Off Risks  Next Issue

52 Tips for Leaders of Project-Oriented OrganizationsAre your projects always (or almost always) late and over budget? Are your project teams plagued by turnover, burnout, and high defect rates? Turn your culture around. Read 52 Tips for Leaders of Project-Oriented Organizations, filled with tips and techniques for organizational leaders. Order Now!

Your comments are welcome

Would you like to see your comments posted here? rbrenrDUDwWaUxOAJtKFRner@ChaclWPJpPZohNvtYLEJoCanyon.comSend me your comments by email, or by Web form.

About Point Lookout

Thank you for reading this article. I hope you enjoyed it and found it useful, and that you'll consider recommending it to a friend.

Point Lookout is a free weekly email newsletter. Browse the archive of past issues. Subscribe for free.

Support Point Lookout by joining the Friends of Point Lookout, as an individual or as an organization.

Do you face a complex interpersonal situation? Send it in, anonymously if you like, and I'll give you my two cents.

Related articles

More articles on Problem Solving and Creativity:

A rowboatFiguring Out What to Do First
Whether we belong to a small project team or to an executive team, we have limited resources and seemingly unlimited problems to deal with. How do we decide which problems are important? How do we decide where to focus our attention first?
White water raftingWe Are All People
When a team works to solve a problem, it is the people of that team who do the work. Remembering that we're all people — and all different people — is an important key to success.
A Lockheed L-1011 Tristar aircraft like the one flown by Eastern Airlines flight 401Problem Not-Solving
Group problem solving is a common purpose of meetings. Although much group problem solving is constructive, some patterns are useless or worse. Here are some of the more popular ways to engage in problem not-solving.
Stainless steel cutleryNew Ideas: Experimentation
In collaborative problem solving, teams sometimes perform experiments to help choose a solution. These experiments sometimes lead to trouble. What are the troubles and how can we avoid them?
A collaboration session in a modern workplaceRationalizing Creativity at Work: I
Much of the work of modern organizations requires creative thinking. But financial and schedule pressures can cause us to adopt processes that unexpectedly and paradoxically suppress creativity, thereby increasing costs and stretching schedules. What are the properties of effective approaches?

See also Problem Solving and Creativity and Critical Thinking at Work for more related articles.

Forthcoming issues of Point Lookout

An onion, sliced and dicedComing December 11: The Rhyme-as-Reason Effect
When we speak or write, the phrases we use have both form and meaning. Although we usually think of form and meaning as distinct, we tend to assess as more meaningful and valid those phrases that are more beautifully formed. The rhyme-as-reason effect causes us to confuse the validity of a phrase with its aesthetics. Available here and by RSS on December 11.
Winston Churchill in the Canadian Parliament, December 30, 1941And on December 18: The Trap of Beautiful Language
As we assess the validity of others' statements, we risk making a characteristically human error — we confuse the beauty of their language with the reliability of its meaning. We're easily thrown off by alliteration, anaphora, epistrophe, and chiasmus. Available here and by RSS on December 18.

Coaching services

I offer email and telephone coaching at both corporate and individual rates. Contact Rick for details at rbrenrDUDwWaUxOAJtKFRner@ChaclWPJpPZohNvtYLEJoCanyon.com or (650) 787-6475, or toll-free in the continental US at (866) 378-5470.

Get the ebook!

Past issues of Point Lookout are available in six ebooks:

Reprinting this article

Are you a writer, editor or publisher on deadline? Are you looking for an article that will get people talking and get compliments flying your way? You can have 500 words in your inbox in one hour. License any article from this Web site. More info

Public seminars

The Power Affect: How We Express Our Personal Power

Many The
Power Affect: How We Express Personal Powerpeople who possess real organizational power have a characteristic demeanor. It's the way they project their presence. I call this the power affect. Some people — call them power pretenders — adopt the power affect well before they attain significant organizational power. Unfortunately for their colleagues, and for their organizations, power pretenders can attain organizational power out of proportion to their merit or abilities. Understanding the power affect is therefore important for anyone who aims to attain power, or anyone who works with power pretenders. Read more about this program.

Follow Rick

Send email or subscribe to one of my newsletters Follow me at LinkedIn Follow me at Twitter, or share a tweet Subscribe to RSS feeds Subscribe to RSS feeds
The message of Point Lookout is unique. Help get the message out. Please donate to help keep Point Lookout available for free to everyone.
Technical Debt for Policymakers BlogMy blog, Technical Debt for Policymakers, offers resources, insights, and conversations of interest to policymakers who are concerned with managing technical debt within their organizations. Get the millstone of technical debt off the neck of your organization!
Go For It: Sometimes It's Easier If You RunBad boss, long commute, troubling ethical questions, hateful colleague? Learn what we can do when we love the work but not the job.
303 Tips for Virtual and Global TeamsLearn how to make your virtual global team sing.
101 Tips for Managing ChangeAre you managing a change effort that faces rampant cynicism, passive non-cooperation, or maybe even outright revolt?
101 Tips for Effective MeetingsLearn how to make meetings more productive — and more rare.
Exchange your "personal trade secrets" — the tips, tricks and techniques that make you an ace — with other aces, anonymously. Visit the Library of Personal Trade Secrets.
If your teams don't yet consistently achieve state-of-the-art teamwork, check out this catalog. Help is just a few clicks/taps away!
Ebooks, booklets and tip books on project management, conflict, writing email, effective meetings and more.