The Good, Bad, and Ugly of Mastermind Groups

First, what is a “Mastermind”?

  • Roundtables
  • Committees
  • Board of Directors
  • etc.
  • The Vagabonds: Henry Ford, Thomas Edison, Warren G. Harding, Harvey Firestone.
  • The Inklings: CS Lewis, JRR Tolkien, Charles Williams, and Owen Barfield.
  • THRIVE: A mastermind group for female artists (that I’ve been supporting through my previous engagement at Spring).

The Ugly

1. It’s a Cult!

  • “Smoking helps relieve my stress”
  • “Smoking helps me concentrate”
  • “Smoking is not any more risky than many other things we do in life like driving”

2. Members lack Commitment

  • People not showing up for meetings/being late.
  • Members who don’t contribute and are only in it for personal gain.

3. The group lacks an objective/goals

4. It’s a gossip/complaint table

  • Members of a mastermind may be matched based on their industry, and there’s always a tendency to gossip & speculate when you know many common connections in the same field.
  • There’s no point in meeting if it’s just social chitchat. Mastermind groups are groups with a purpose.
  • You’re meeting and constantly raising some of your challenges/problems in meetings, there’s a tendency to focus on the negative without emphasizing
  • What you will do to address it.
  • Gratuity for what IS working/who has supported you.
  1. Weren’t listening when people provided suggestions.
  2. Didn’t take any action on the previously suggested feedback.

The Bad

1. Paid vs. Free groups

  • Needing to pay to join helps weed out freeloaders who aren’t serious about committing (both to the group, and to their own development).
  • Those that join paid groups are typically more committed & engaged.
  • Paid groups can usually afford a dedicated facilitator. I’ll go more into the benefits of having a facilitator and what makes a good facilitator below.
  • Free groups can have facilitators too but often rotate the role of facilitators between members for each meeting.

2. Group coaching/mentoring

3. Referral groups

4. Lack of structure

  • Collecting your thoughts on updates you wish to share — helps prevent you from ranting & keeps you efficient with your time.
  • Defining your challenges and factors+limitations that influence them.
  • Preparing necessary information your peers may need to consider in order to provide quality feedback/suggestions.
  • Preparation should also not be too rigid or done too far in advance. Challenges/opportunities can present themselves at any time and you need to be flexible enough to address them.
  • A good practice is to prepare a week prior to the meeting, and review 24 hours prior.

5. Bad matching

  • Matching people who are “similar” together.
  • When people who are too similar, there is a tendency to fall into groupthink.
  • Diversity encourages different perspectives and allows you to come up with innovative solutions to problems/opportunities.
  • I’m going a little off-topic here, but it’s similar to how you shouldn’t hire people based on “fit”, centred only around likeability.
  • Members in the group having too big a gap in experience/skills
  • While diversity is good, you should also “mind the gap”. Members who differ too greatly in experience/skills may also be in very different places in their lives and face different problems/opportunities.
  • This isn’t always the case with every group. It is a little trickier to navigate and depends a lot on how you theme your mastermind groups around specific niches/objectives.
  • Not accounting for personalities/mindset/attitude when matching.
  • True, you shouldn’t just match people who are likeable together. But it’s still important to ensure that members can get along well with each other.
  • The most common manifestation of this is having an imbalance between introverts and extroverts. If there are too many extroverts in a group, introverts will unconsciously share less. If there are too many introverts, the extroverts will tend to dominate the group.
  • Members who share a common mission will face similar problems/opportunities and work best to support each other.
  • Mission can be for a greater cause, or even for a simple objective. e.g. Reduce pollution, get to $20k in MRR, become an amazing public speaker.
  • If mission is the WHY, values are the HOW.
  • Members who share the same values will align better, they will feel that other members better “get” their situation and have similar philosophies and ethics when it comes to addressing problems/opportunities.

6. Exclusive groups (and inclusion)

  • Different genders, sexes, or sexual orientations.
  • Different races or nationalities.
  • Different “social standings”.
  • Different ages.

7. Unaccountable

The Good

1. Dedicated facilitator vs. Rotating facilitators

  • Experience with and ability to match the right people who are a fit together.
  • Accountability and continuity. By having 1 person in charge of facilitating, that person is put in a better position to notice overall trends and patterns in both the groups and on an individual level.
  • Reduces distraction & ensures that everyone gets to fully participate.
  • Facilitation itself is a heavy role. If you’re in-charge of facilitating a particular meeting, you’ll find it hard to reflect & digest on how everything shared could be applied in your personal situation while balancing the duties of a good facilitator.
  • They create a safe & encouraging space for sharing.
  • They listen between the lines and tease out underlying assumptions, beliefs, biases, misconceptions, unspoken fears and uncertainties, and identify if problems are really a symptom of a much larger underlying problem or a root cause.
  • They are experienced enough to point out bad feedback/suggestions or elaborate on limitations/considerations if those suggestions are acted upon.
  • They ensure that everyone has a voice.
  • They are not afraid to also share their own expertise and experiences where it applies.
  • They recognize they don’t have all the answers and aren’t preoccupied with always “being right” or “looking good” as the leader.
  • They should never dominate the group.

2. The lonely journey gets a little less lonely 🙂




Startup go-to-market and sales specialist, father, avid packrafter

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Chang Chin Hing

Chang Chin Hing

Startup go-to-market and sales specialist, father, avid packrafter

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