How to Run a Successful Mastermind Group

How to Be an Evil Mastermind … I mean, How to Run a Successful Mastermind.

Working on a business or new project can be lonely. Your family and friends support your efforts, but they don’t really understand the details of what you are trying to do or what exactly you are going through. Projects are difficult and the long hours can make you feel isolated, frustrated or overwhelmed - but don’t let that kill your morale or progress.

What if you found a small group of people that knew what you were going through?

People on a similar similar path and with similar successes who understand where you are, where you are going and what you are struggling with. You could meet regularly, either virtually or in real life, to discuss your goals, challenges and recent “wins” and “fails”. Since they’ve been through it or are facing it themselves, they could offer real advice, not just platitudes.

This is a mastermind group.

“A friendly alliance with one or more persons who will encourage one to follow through with both plan and purpose.” - Napoleon Hill, Think and Grow Rich

Masterminds can be extremely useful for any project or endeavor such as a business, learning a new skill, or self improvement (for example, going to the gym). The benefits include:

  • Having a sounding board - the group understands the ideas you are working on better than most people.
  • Accountability - the group will help you keep track of your goals and progress.
  • Encouragement - the group will celebrate your wins at each meeting.
  • Focus - there’s someone to help you stay on track with your stated goals.
  • Inspiration - hearing and helping others with similar goals is motivating.
  • Outside feedback - disinterested honest opinions will give you new perspective.
“If you want to go quickly, go alone. If you want to go far, go together.” - African Proverb

I am currently starting a mastermind for a startup software business, and will use the rest of the article to describe some of the issues and questions I’ve tackled in the process, assuming that you are doing the same.

Who should your fellow group members be?

Before you’re asked to join a group or decide to create a new one, be sure to think through what you would like from your group and fellow members. Ideally others in the group should have similar objectives and values to you and be slightly ahead of you on their path.

They should be open to accepting advice and be able to give kind, considerate, and honest advice in a way that can be accepted by others and not be perceived as an attack. Of course, you yourself should be open to criticism and accept it as positive input.

It can be useful if the other group members are running somewhat similar businesses but a variety of niches can improve diversity and minimize competition.

Also, be prepared to discuss the rules you expect the group to operate by. For example, decide what to do if a member starts missing meetings or is not participating. It is especially important to discuss the expectation of confidentiality. What is said in the group stays in the group.

What if you don’t know of any groups you could join?

Masterminds may be new to you but many people swear by them. However the hardest part of joining a mastermind is actually finding one. The best way to find one is to think of the people you meet at industry and tech events. When you meet someone you admire, tell them about mastermind groups, make sure they know what they are (not everyone does) and let them know you are interested in joining one. They may know of one, may be interested in forming one with you or may know of someone you should talk to.

There are also services like MastermindJam that can help match you up with others looking to form a mastermind.

If you can’t find one, don’t waste too much time: just start one yourself. Leading the group is not that difficult. It may mean that you need to do a little bit more work, but it will be worth it to build a healthy, successful group.

First off, you’re probably looking for 3–5 people total in the group. A two-person conversation can be really useful but there may not be enough variety and experience. More than five people can be hard to coordinate, and members won’t get enough attention unless the meetings are extra long.

Since you’ve already thought about the purpose of the group and the type of members you’d like to see, start asking people who might be a good fit. Then, as you find others, you can refine:

  1. The purpose of the group
  2. The type of members it should have
  3. The expectations of the group and the members
  4. The logistics of meeting and communicating

How often to meet

Choose a fixed start time, duration, place and frequency. The common choices are weekly, every other week, monthly, quarterly and yearly. For most startup-style masterminds, weekly might be too frequent. People will eventually not be able to prioritize showing up weekly and you won’t have enough time to implement many ideas and suggestions and get results in just one week.

However, monthly may not be frequent enough to keep momentum and continuity. There seems to be a sweet spot at every other week, every three weeks or twice a month.

Choose where/how to meet

Basically there are three options for how and where to meet
  1. In real life. You pick a time and place and everyone physically goes there. You get great face-to-face time and build a sense of community. However, travel and commitment are a challenge and you limit yourself to the people in your immediate area.
  2. Virtually in real time. You use the phone or an online chat or conferencing system to hold the meeting. No travel involved and members can participate from anywhere in the world. You lose some of the intimacy and scheduling is still a challenge.
  3. Virtually asynchronously. You use a forum, persistent chat channel, or social media group. Pick a rough day or time when members should check in and write up what they’ve been up to. Discussions are not limited to preset meeting times and can even be effectively continual. With this option it’s probably the hardest to build rapport and easiest to lose focus.
Of course you can do a combination of any of these. A regular Skype call and a perpetual Slack channel seems like a powerful combination.

Plus you can always be in more than one mastermind, maybe a local in-person one with good people who are not a perfect fit and a virtual one with people from all over the world who are your ideal members.

Meeting format options

Hot Seat

With a rotating hot seat format, the group spends most of its time on focusing on one specific member’s business. The benefit is that periodically your business will get a lot of attention. A drawback is that there will be a long gap before you can discuss your business again.

Round Robin

Divide the time up evenly and everyone gets a turn. This way each business is visited during each meeting and you don’t have to wait too long to get help. The drawback is that sometimes useful, productive conversations need to be cut short to be fair to others and stick to the schedule.

Short Hot Seat

This is a combination of the other two, where the person on the hot seat gets more time than the others but not majority of the meeting. There’s no big gap between the times you can discuss your business and no single business dominates the entire meeting.


Having a standard list of questions or topics for your group can really be productive. It gives the group structure for the reports and helps you avoid missing important topics. Every group is going to have a format that works best for them, but here are some common questions or sections that others have used.

Sample questions / agenda items

  • Share wins - starts you off on a positive note.
  • What did you do well that you should repeat?
  • What did you do less well that you should reduce?
  • What did/didn’t work from last time?
  • Why/how is the product better for your customers than it was last week?
  • What have you done to acquire new customers?
  • What do you hope to do by next time?
  • How’s your business doing (MRR)?
  • What do you need help with?
Also, decide if someone is going to take notes, who it’s going to be, and how you are going to share them. If you’re in a forum, everyone can create their own updates or one person can create them in a Google doc.

Start today

If you’re interested in being part of a mastermind I hope you don’t delay in finding or starting one today. If there aren’t any organizations in your area that can help, call a friend who fits your group profile, tell them what you are interested in, and ask them if they want to take part or know anyone who might.

Let me know if you have any questions or if there is anyway I can help.


Much of this article is based on information gleamed from these resources:

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