Asking the Right Questions

Asking the right questions is an important skill to:

  • generate ideas
  • discover direction
  • reframe thoughts
  • learn about others
  • clarify communication
  • manage well

I’ve gathered together some thought provoking resources here that answer the question: “What are the right questions to ask?”


Goal setting and time management questions:
Generating Goals

What do you want more of?
What change do you want to make?
Imagine you are old and list your most important accomplishments
If you only had 6 months to live, what would you do?
What would your ideal life be like?
What would you do if money was not a concern?

Evaluating Goals

Why would this be a good goal?
Will this goal help me or others to learn? To grow?
If you could only complete one goal, which one would it be?
What resources will be needed?
Which goal will give the highest return for resources invested?
What obstacles will need to be overcome?
How difficult will it be to reach?
How much time will it take to reach?
How much do you want to achieve the goal?
Do I have the enthusiasm and the courage needed? Am I willing to make the commitment of resources required?
Are the benefits achieved worth the costs?
What is the measurable outcome?

Next Actions

What is the next physical, visible activity needed?
What needs to happen before the next step?
What can be done today?
What activities am I not doing now, that might help me reach goals if I did them?
What is the most effective use of my time right now?

Paper Management

Is this only for my information, and now I know it?
Is this quality information? Objective? Reliable? Timely? Useful? Clear?
Does this information exist elsewhere? If needed in the future, could it be replaced?
Under what circumstances would I want this information?
What words would first enter my mind when looking for it?
Where would you most likely look first?


Do I want to do this?
Do I need this?
Can I afford it?
Is this worn out, broken, or damaged?
Is this a gift that I just don’t like?
Does this fit?
Do I love the way it looks or works?
Have I used it in the past year?
Does it have strong sentimental value?
Can it be easily replaced?
Will it be used in the future?


Is this the best place to keep this?
How often do you use this?
Where do you use this?
How much space does it need?
Is this the best way to keep this?
What bothers you the most? Why?


What is the best place to do this?
What supplies and tools do I need to do this?
What organizers could be helpful?
What steps should be done in what order?
When is the best time to do this?


I seek to create order from the chaos of complex information. Join me at the Daily PlanIt to gain insights, inspiration, and information to increase skills for a better life. I unlock the power of teaching reading with phonics in the pursuit of literacy at In my spare time I explore books and movies, often choosing titles available on both screen and page.

Posted in goals, personal development, productivity
2 comments on “Asking the Right Questions
  1. Grigor says:

    at a risk to sound more conservative than I am, I think there is one more question to ask “Is there something I wan’t to keep?”. We tend to seek for a change, and this is good, but we usualy don’t have to change every last piece. To recognize what is it that already provides a good value is of equal importance as to know what has to be changed.

  2. dailyplanit says:

    Great point! It is tricky, isn’t it? how many times do we get rid of something and later regret it…it does happen sometimes. Maybe another question we should ask is “Do I love it?”

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