The Good, Bad, and Ugly of Mastermind Groups

A quick disclaimer to help you understand the lens with which I write about this topic: I am biased in favour of Mastermind Groups as I personally facilitate such groups through my business.

I’ve also personally participated in many different mastermind groups, despite differences in individual experiences (both positive & negative), I’ve found that the overall experience has greatly benefited me and will continue to benefit me as I grow myself as an individual.

I hope to shed some light on some of the good vs. bad aspects of different mastermind groups, that you may be able to make a more informed decision when it comes to deciding if you should join one, or even if you decide to form one of your own.

First, what is a “Mastermind”?

A mastermind is a collective of individuals who have banded together for the common goal of improving the whole.

Masterminds are not a new concept, they’ve been around for a long time. They’re manifested in a variety of different ways for different purposes:

• Roundtables
• Committees
• Board of Directors
• etc.

The premise is that many minds are better than one. Individuals in the group benefit through brainstorming, education, support, and accountability.

The idea of a personal “mastermind” to help you improve yourself both through personal growth and business growth was popularized by Napoleon Hill in his book Think & Grow Rich. Some of the most successful men (and arguable women too though I struggle to find examples online) were found to have participated in groups of this sort:

• 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).

As famously said:

You are the average of the average of the 5 people you spend the most time with.

Jim Rohn

The goal with mastermind groups is to accelerate growth through a collective effort.

The Ugly

Most articles on mastermind groups elevate it on a pedestal – for obvious reasons, most of the authors are trying to further their agenda of selling their groups too (not that I’m exempted).

But let’s start by looking at some of the negatives. There are a lot of groups out there, and not many of them are done (in my opinion) in the “right” way.

1. It’s a Cult!

You don’t often see many mastermind groups that get branded as a cult, but there are some that definitely give off that cult-like vibe.

Let’s first address some common elements of cults:

Rituals

Structure is important in mastermind groups. Without structure, meetings can easily go off-topic or someone could end up dominating the conversation.

The problem is when structure is implemented without clear benefits, only for the sake of “having structure”.

Rituals on their own are not directly harmful, but they need to serve a purpose and the purpose needs to be beneficial and transparent.

A manipulative indoctrination/initiation process

Using coercive persuasion or brainwashing under the guise of “reforming” you because you aren’t “good enough”.

Leveraging cognitive dissonance to manipulate you into a false sense of value

What is cognitive dissonance and how does it look like in the indoctrination process? Some groups make joining difficult on purpose, they make you jump through loops, go through interviews, and insinuate that many people don’t qualify.

Because of this, when you do get in, you have a tendency to self-justify the value of the group even though you may perceive the value of it to be lower had it been easier to get in.

A comparable example of cognitive dissonance in practice is that of smokers – Even though they know the harmful effects of smoking, they will actively adjust their beliefs better accommodate their actions and reduce this conflict in beliefs:

• “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”

For more on cognitive dissonance, you can read about it on Wikipedia here: https://en.wikipedia.org/wiki/Cognitive_dissonance

If you want to go down an unrelated rabbit hole on the topic of cognitive dissonance, this is an interesting article on how it played out during the COVID-19 pandemic: https://www.theatlantic.com/ideas/archive/2020/07/role-cognitive-dissonance-pandemic/614074/

Watch out for this manipulative tactic, but be aware that good groups also place high importance on a good matching and admission process. It’s only harmful when it’s done without clear relevance on improving the quality of the members that get accepted.

Lack of transparency

Discouraging critical thinking, questioning, or challenging the process/authority. Good groups and facilitators should be open to evolving their groups to improve based on suggestions from members.

They should also be willing to give clear explanation & reasoning as to why specific suggestions may not work if they choose to reject them.

Making leaving a bad thing

Good groups will recognize that people will outgrow their groups eventually, and will accept that some people may have to quit with just cause due to unforeseen circumstances.

Cult-like groups ostracize & penalize people who defect.

The idolization of a leader or “guru”

While some groups are built around the reputation of a particular leader, smart members should recognize that the leader is only a small benefit and that there’s greater value through the collective peer network.

The leader should never be the person who knows all the “right” answers. There is no such thing as a right answer, different things work for different people in different situations. Good leaders/facilitators are able to recognize this and are merely guides to point out blind spots, challenge assumptions, and make suggestions on how members are approaching a particular problem.

Placing priorities of the group above priorities of the individual

To make a good member, you should not only receive but also actively contribute. That said, you should benefit just as much as an individual if everyone else is also contributing to you.

Good groups recognize that personal priorities always take precedence.

Without naming names, I participated in a personal development program once, where someone had a huge fire break out at her house.

In order to deal with it, she had to ask for permission to leave early & miss the next session – that’s a warning sign, the program is discouraging independent thinking. Of course, it’s good manners to inform people that you have to leave, but you should not need to seek permission to fulfil your personal needs in a time of crisis.

They permitted her to leave, but the response (and I kid you not) was along the lines of “Be there for your family, but if your family knows that it’s important for you to be here and be present to help you get through these times, they will excuse you for being absent”. It made her feel guilty/bad for leaving and she ended up attending the next session. While yes, it’s just as important to focus on self as you navigate and try to support others in a time of crisis, I simply can not align myself with the motives of a group that would blindly prioritize self above family.

2. Members lack Commitment

While over-commitment results in a cult-like environment, under-commitment is also equally harmful.

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

A good group will truly care about you, if you’re surrounded by people who aren’t committed – both to the group and to their own personal growth, you will find the meetings lacking in value.

3. The group lacks an objective/goals

Personal development never ends, but it’s important to set objectives & goals, both on an individual level, but also on a collective level. Groups that don’t set goals & objectives will remain stagnant – and that defeats your objective of joining a group to begin with – to grow.

4. It’s a gossip/complaint table

If not led by an experienced facilitator, some groups may accidentally evolve into this. It’s common because:

• 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.

Never raise the same problem twice. It shows that you either

1. Weren’t listening when people provided suggestions.
2. Didn’t take any action on the previously suggested feedback.

The problem may not have gone away from what you’ve implemented or tried, but smart people will share what they’ve learned and how the problem has evolved after implementing some changes.

The Bad

The points here are not exactly harmful but depend strongly on how they’re executed and manifested:

1. Paid vs. Free groups

Yes, free groups CAN work and can be amazing if done correctly. However, from my experience, there are some clear benefits to joining a paid group.

• 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

Good mastermind groups will maximize the value of each member contributing instead of relying on the expertise of a specific leader/facilitator.

Yes, the leader/facilitator could add immense value if they are experienced and “successful”, but the best groups are groups where everyone wants to help each other instead of only relying on value from a solitary figurehead (he/she can only do so much for so many people).

Group mentoring/coaching in itself is valuable and has its own time and place, but true mastermind groups aren’t these in the guise of a “mastermind”.

3. Referral groups

While the act of soliciting and encouraging referrals in itself is beneficial, referrals for the sake of referrals creates unwanted pressure and damages relationships.

Good groups and facilitators will guide members on how to appropriately leverage each other’s networks. People should make referrals because they earnestly believe that the referral will benefit both parties.

4. Lack of structure

You can still get a good experience from being in a group that lacks structure IF you are surrounded by amazing members and a capable facilitator. But this is the exception to the norm.

Structure helps ensure that meetings deliver on their objectives and that everyone has an equal opportunity to be heard. That said, good facilitators are also flexible and able to recognize when it’s appropriate to deviate from rigid structures and create space for the right type of sharing given what’s happening with their groups.

Not preparing in advance of meetings

Closely related to structure is the common problem where you have lots of members just show-up to sessions and “winging it”. Good structure should also help prompt members to prepare in advance of the sessions to make the most out of them.

What “preparation” is needed?

• 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

This is the most obvious point, but what makes a good match and a bad match?

Properly matching members is something that is equally important to BOTH paid & free groups. I’ve had a few people ask “Is it better to join a free group that aligns with your values or join a paid group with individuals who are willing to commit”

They’re not mutually exclusive.

Bad Matches

• 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.

Good Matches

Instead, you should match people based on values & mission.

• 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)

Very closely related to matching is how certain mastermind groups require that you meet certain criteria before joining.

Again, having criteria itself is not a bad thing. The right criteria can help reduce the gap in differences and better qualify members depending on how you theme/structure your groups.

Criteria become harmful when it unconsciously reduces diversity and creates an environment of exclusivity instead of inclusivity.

Here are some things that you should ensure your group is inclusive for and doesn’t unconsciously filter out:

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

Diversity on these elements create a rich environment where you benefit from different perspectives, it exposes blind spots, it fosters creativity.

7. Unaccountable

Accountability is a difficult area for many people. No one wants to come across as naggy or overbearing.

But you should know this yourself. One of the reasons you’re joining a group is to get people to hold you accountable and push you (healthily of course) to achieve your goals.

Facilitators and members need to be comfortable with holding the group and every individual accountable, while also being flexible as things evolve (but be wary of confusing flexibility with excuses).

The Good

1. Dedicated facilitator vs. Rotating facilitators

All groups will have a facilitator for each meeting. Groups that don’t have dedicated facilitators will have different members take-turns playing the facilitator for each meeting.

The clear benefits of having a dedicated experienced facilitator include:

• 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.

What makes 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 🙂

Most mastermind groups are designed around entrepreneurs because they are naturally more driven and self-motivated to grow & develop themselves as leaders.

Yes, entrepreneurship is a lonely journey. Your friends & family will never truly understand what you’re going through and it’s hard to relate and get support from them.

But even if you’re not an “entrepreneur”, if you’re a lifelong learner who’s hungry for growth, you’ll notice that you’re an exception to the crowd. Most would rather remain ignorant & content with what they have.

Your journey to self-enlightenment & development is often a very personal and solitary experience. Groups like this help not only by providing the resources, education, & support, but also give you the mental strength to achieve your mission.

That’s a lot of advice. All in, most groups will not be perfect at first, and I don’t claim that I’m an expert or that my groups are perfect too. But awareness is the first step to improvement.

It’s much better to join a group (almost any group) than to try to do everything on your own.

Even if you don’t end up joining my group or some other group, I strongly encourage you to form your own and begin surrounding yourself with people who can help you achieve your goals.

What has your experience been with joining/facilitating groups? If you have other best practices/observations, would love to hear from you too.

Curious to learn more about our soft-skills & personal development masterminds?