40+ Powerful Mastermind Group Questions & Ideas

The mastermind group facilitator doesn’t have to be the smartest in the room. Your role is to create the space, hold the space, and lead the space. On way to do that is by presenting the group with the right questions at the right time in the conversation. The reason I say “right questions” is because the right answer to the wrong question doesn’t move anyone forward. The right questions lead to insights which lead to answers. So I created this list of mastermind group questions for you to help you facilitate rich conversations and deeper introspection about the way members are designing their business and life.

Everyone in your group is seeking something—likely your pre-stated mastermind group vision. If they already had that vision, they probably wouldn’t be in the group. There is something blocking them from having what they desire and it is usually mental. Rather than trying to prove to them that a new way of being, doing, and having is possible, you can have them prove it to themselves by opening up a new possibility with a question.

One question that my mastermind group, The Focused Group, keeps coming back to is “Is there someone else somewhere in the world, in my industry, or even in my company with greater or equal responsibility who is having greater success (i.e. pay, profits, promotion, productivity) without the stress I am having and the sacrifices I am making?” The answer for every is always “Yes” even if they can’t name the person. This is a question I created in advance given my role a creator, holder, and leader of the space. I thought about my members, what they desired, and what what was blocking them and out came this question that I knew would open them up to the possibility of another way.

Below are some other mastermind group questions that I have used with my group that may work for you. Even if they don’t, they may inspired new mastermind group questions for you.

Personal Mastermind Group Questions

  • How do you define success? What are the 3 ways you can measure it?
  • How to you measure happiness? What are the top 3 metrics?
  • What do you want?
  • What is the chip on your shoulder?
  • What is your relationship to failure?
  • Who and what are you grateful for?
  • Who have you helped succeed? If I asked them, they would say, “I agree.”
  • What would you name this chapter of your life?
  • What is the last intentional choice you made? How did it make you feel?
  • What question do you want to guide you day and life?
  • What do you need to say “No” to?
  • What are your gifts, talents, and strengths?
  • What would you want your best friend to say about you in your eulogy?
  • If you had to live the same day over and over again, what would you want it to look like?

Professional Mastermind Group Questions

  • What is your end game?
  • What skill or subject mastery are you selling to your company right now?
  • Are you a workaholic or high performer? What’s the difference in your eyes?
  • If you had to give me a tour of your career, who or what can you point to as artifacts and evidence of success?
  • Are you being valued?
  • Are you doing work that aligns with your values?
  • What is your Unique Ability? (from Strategic Coach)
  • What are 3 new resume bullets you want to add by the end of the year?
  • How can you be a higher contribution to your company? Clients? Colleagues?
  • What is your superhero name?
  • What do you want to say in your retirement speech?

Business Mastermind Group Questions

  • What is your end game for the business?
  • How do you measure your success besides profit?
  • If you had the cure to cancer in your hand right now, would you market it in the same way you are marketing your product or service?
  • Who is your tribe? How would you describe or name your ideal customer?
  • What would happen to your income and business if you had jury duty for 1 month? 3 months? 6 months? 1 year?
  • What problem do you really solve?
  • What business are you really in?

Financial Questions for your Mastermind Group

  • How do you measure you wealth? Savings? Income? Cashflow? Assets? Passive income?
  • When you think of rich, what number comes to mind?
  • How much is enough?
  • If you were CEO of the company you work for, how much would you honestly pay yourself? Could you go earn that independently as a consultant within the next year? So how do you justify your value?
  • If you got a $250,000 windfall today, what would you do with it?

Family Mastermind Group Questions

  • What important family events have you missed that you regret? And why did you miss them?
  • What kind of _________(e.g. husband, wife, daughter, uncle, sister) do you want to be?
  • What would __________(e.g. wife, son) say about your presence? Are you happy with that?

Social Mastermind Group Questions

  • Who is in your network up (e.g. mentors, your personal board of directors)?
  • If you were starting a Presidential campaign, who would you call on? When is the last time you called them? How can you connect more often?
  • What does fun look like for you today?

Benjamin Franklin’s Junto Mastermind Group Questions

On Wikipedia, I found some great question that Benjamin Franklin devised for his Junto, covering a range of intellectual, personal, business, and community topics. These questions were used as a springboard for discussion and community action and can also be found in Franklin’s papers, dated 1728, and included in some editions of his autobiography):

  1. Have you met with any thing in the author you last read, remarkable, or suitable to be communicated to the Junto? particularly in history, morality, poetry,physics, travels, mechanic arts, or other parts of knowledge?
  2. What new story have you lately heard agreeable for telling in conversation?
  3. Has any citizen in your knowledge failed in his business lately, and what have you heard of the cause?
  4. Have you lately heard of any citizen’s thriving well, and by what means?
  5. Have you lately heard how any present rich man, here or elsewhere, got his estate?
  6. Do you know of any fellow citizen, who has lately done a worthy action, deserving praise and imitation? or who has committed an error proper for us to be warned against and avoid?
  7. What unhappy effects of intemperance have you lately observed or heard? of imprudence? of passion? or of any other vice or folly?
  8. What happy effects of temperance? of prudence? of moderation? or of any other virtue?
  9. Have you or any of your acquaintance been lately sick or wounded? If so, what remedies were used, and what were their effects?
  10. Who do you know that are shortly going [on] voyages or journeys, if one should have occasion to send by them?
  11. Do you think of any thing at present, in which the Junto may be serviceable to mankind? to their country, to their friends, or to themselves?
  12. Hath any deserving stranger arrived in town since last meeting, that you heard of? and what have you heard or observed of his character or merits? and whether think you, it lies in the power of the Junto to oblige him, or encourage him as he deserves?
  13. Do you know of any deserving young beginner lately set up, whom it lies in the power of the Junto any way to encourage?
  14. Have you lately observed any defect in the laws, of which it would be proper to move the legislature an amendment? Or do you know of any beneficial law that is wanting?
  15. Have you lately observed any encroachment on the just liberties of the people?
  16. Hath any body attacked your reputation lately? and what can the Junto do towards securing it?
  17. Is there any man whose friendship you want, and which the Junto, or any of them, can procure for you?
  18. Have you lately heard any member’s character attacked, and how have you defended it?
  19. Hath any man injured you, from whom it is in the power of the Junto to procure redress?
  20. In what manner can the Junto, or any of them, assist you in any of your honourable designs?
  21. Have you any weighty affair in hand, in which you think the advice of the Junto may be of service?
  22. What benefits have you lately received from any man not present?
  23. Is there any difficulty in matters of opinion, of justice, and injustice, which you would gladly have discussed at this time?
  24. Do you see any thing amiss in the present customs or proceedings of the Junto, which might be amended?
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