21 Questions for Extraordinary Goal Setting

Business people participating in goal setting activity at whiteboard
Business people participating in goal setting activity at whiteboard

January 6, 2022

Goal setting can be a very positive activity. Goals can act as the stepping stones that lead you to achievement, a dream, or success. Goals can also be a source of motivation, especially during times of uncertainty. They keep you moving forward instead of getting stuck.

There’s a catch, though – goals can become obstacles and can backfire on you if they aren’t well thought out, are unachievable, or don’t connect to what you really want.

It would be great if you had the mental focus and motivation to stay on top of your goals; completing them as if you were checking items off your grocery list. Since most of us have multiple distractions and competing priorities that lead us astray at times, it helps when we take the necessary time upfront to create goals that are meaningful enough to hold our attention and help us stay motivated.

Instead of blindly making a list of things you want to accomplish this year, dedicate some time to ask yourself a series of questions. Doing so will help you establish goals that you truly want to achieve, and keep you motivated and engaged along the way. Here are the characteristics of great goals and 21 questions that will help you set extraordinary goals.

Great & SMART Goals

Before we dive into exploring the questions that will help you set your goals, let’s define what makes a goal a great goal. Great goals are:

  • Outcome focused. Once your WHY is understood, and it’s a good and enthusiastic WHY, you are 90% there!
  • In line with your values. The more a goal aligns with your inner or core values, the EASIER it will be to achieve. You can certainly achieve goals that don’t align with your values, but it’s usually harder and less satisfying.
  • Stated in the positive. The words you use to state your goal should reflect what you are aspiring to achieve in a positive way. For example, “I want healthy fingernails” rather than “I want to stop biting my nails”. See the difference?
  • Great goals are also SMART:
    Specific – so you know exactly what you are trying to achieve.
    Measurable – so you know when you have achieved it.
    Action-oriented – so you can DO something about it
    Realistic – so it IS achievable
    Time-bound – so you have a time frame or deadline.

21 Questions to Ask Yourself When Goal Setting

Now that you’ve had a refresher on what makes a great goal, here are 21 questions that will help you create goals that are even more believable and achievable! I’ve grouped the questions into five categories to help you zero in on the aspect of your goal-setting that might need the most help.

Questions to Help You FOCUS on Outcome:

1. What is it that you REALLY want here? Take some time to dig deep if you need to.

2. What is the SPECIFIC OUTCOME that you are looking for?

3. What is the PAIN for you if you DON’T achieve your goal? Is there a negative consequence?

Questions to Help You ALIGN Goals with Your Values

4. Is this goal in line with your LIFE VISION or overall life plan? If you aren’t sure, what is your gut feeling about it?

5. Is this goal in line with your values? Ask yourself what’s REALLY important to you in life and will this goal help you achieve more of it?

6. Is this goal something you truly want, or is it something you think you SHOULD have or SHOULD be doing? If it’s a SHOULD, it may be someone else’s dream. You may want to revaluate this goal to see if you can make it 100% yours.

7. When you think about your goal does it give you a SENSE of deep contentment or ‘rightness’, happiness, and or excitement? These are good signs that it is a healthy goal.

8. If you could have the goal RIGHT NOW, would you take it? If not, what are the issues that get in the way?

9. How does this goal FIT into your life/lifestyle? Consider the amount of time and effort involved, commitments you will need to make, and who else in your life will be impacted.

Questions to Help You Identify OBSTACLES

10. Can you start and maintain this goal/outcome? You might also ask yourself “Do I have complete CONTROL over my ability to achieve this goal

11. How will completing this goal AFFECT other aspects of your life? What else might you need to deal with as a result of achieving this goal?

12. What’s good about the CURRENT SITUATION? In other words, what’s the secondary gain for staying right where you are?

13. WHAT might you have to give up or stop doing to achieve this goal? Essentially, what is the price of making this change, and are you willing to pay it?

14. If there was SOMETHING important around achieving this goal that you haven’t mentioned yet, what would that be? This could be something that might help you achieve the goal or something that could get in the way.

15. WHO will you have to be to achieve this goal?

Questions to Help You Evaluate the SIZE of Your Goal

16. Is the goal the right size? If it feels too big, break it down into smaller goals. Too small? Trying to fit it into a larger goal.

17. What would be the MINIMUM or super easy level of achievement for this goal?

18. What would be your TARGET level of achievement for this goal?

19. What would be your EXTRAORDINARY level of achievement for this goal?

Questions to Help You Take ACTION Toward Your Goal

20. What RESOURCES do you already have to help you achieve your goal? This could include things, people, contacts, personal qualities, skills, info, finance, etc. Creating this list of all the resources you already have will help you feel motivated to keep going.

21. What RESOURCES do you NEED to help you achieve your goal? Creating this list will tell you what you need to succeed.


Goals that are meaningful – that align with your values, positive and outcome-focused – can help you achieve self-mastery, confidence and keep you moving forward in life. When you take the time to ask some or all the questions discussed in this article you are setting yourself up for success. If you find yourself veering off course or getting distracted from your goal, which is completely normal, remind yourself of your WHY and the consequences you will meet if you stop trying. And remember, goals are there to inspire you, not to discourage you.


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