How to Choose the Right Business Mastermind

loyb podcast mastermind Feb 22, 2022

If you believe the quote that you are the average of the 5 people you spend the most time with, are you currently surrounding yourself with the right people to help you get to the next level? 

In a recent post, I talked about identity evolution and how one of the fastest and most effective ways to get to the next level is to join a mastermind or group where you surround yourself with people already at that next level or aligned around a common scaling goal. 

To build off of that, let's break down my top tips for knowing if joining a mastermind is the right step for you right now and how to choose one that is a great fit for both you and your business. 

In episode 60 of the Lean Out Your Business Podcast, I share:

  • The top benefits of joining a mastermind
  • Which of the 5 stages of business best align with joining a mastermind
  • 4 criteria to decide if now is the right time to join a mastermind group
  • What you should plan to invest in a 12-month mastermind
  • The top 10 things you should consider when choosing a business mastermind that's the best fit for you
  • How to get the real inside scoop on what a mastermind is like before you commit to joining
  • My surprising experience in a mastermind and what you should watch out for to ensure it doesn't happen to you
  • Sneak peek into how our Change Maker 500 Mastermind is structured and why 


Tune into Episode 60 of the Lean Out Your Business Podcast or keep reading below.


As I shared in E58 of the Lean Out Your Business Podcast on Next Level Identity, being a part of masterminds has been a key part of my growth and scaling strategy for my businesses and something I regularly invest in.

The first thing to note is that all masterminds are different, so it is important to be clear on what you want, what you are looking to get out of it, and what you are willing to contribute when narrowing down the best mastermind for you. 

While there are some common elements that make a mastermind a mastermind, each one can be structured a bit differently. 

First, let's explore how to know if it's the right time for you to be considering joining a mastermind. 


How to Know If Joining a Mastermind Is Right For You

Having the support and accountability of a group of like-minded entrepreneurs is invaluable at every stage of business.  There are different options to find this support, from communities, to group coaching and mentorship programs, to masterminds.

We see there being 5 stages of business - launch, emerge, grow, scale, and influence. 

During launch and emerge, you are typically in a place where your focus is more on learning with how-to information and step-by-step guidance and training.  If this is your focus, a group coaching or mentorship program around your specific topic of interest is usually going to provide what you need and get you to a place where you are focused on growing your business.

When you move into grow, then scale, and ultimately influence, there is still learning that occurs because you never stop learning as an entrepreneur, but your focus shifts.  At each stage you level up to, it becomes less about training and curriculum and more about forming deep relationships with trusted peers and leaders.  Having a group you can brainstorm with, gain and provide feedback and insight with, and potentially even collaborate with. 

You want to surround yourself with people who challenge you to grow as a leader, push through limiting beliefs, see new possibilities, and level up your business. 

If that is the place you are at in your business, this is where participating in a mastermind is most valuable. 

Additional criteria to know it's the right time to find a mastermind:

1. You can commit to showing up and giving as much as you get. 

  • Leverage the 80/20 rule.  You practically may not be able to be at every single meeting and event, but can you commit to be there for 80%+ of them?  And not only be there physically, but also be fully present, engaged, and providing as much value as you are asking for from the group?

  • If your schedule won't allow for you to fully commit and show up, it's either not the right time to join a mastermind, or it's time to change up your schedule.

2. You are open to receiving and providing feedback and advice.

  • Sometimes you'll receive some tough love from the group, and other times, you'll be the one who has to give it. It's all about helping one another and that comes from being willing to be open, honest, and vulnerable, both when providing and receiving feedback. 

  •  It's not about showing up with an agenda, trying to "sell" to other members, or having to be the smartest person in the room.  In fact, if you are the smartest person in the room, it's time to find a different mastermind. 

3. You have a mindset of abundance and not scarcity.

  • We all hit bumps in the road along our entrepreneurial journey, and a mastermind group can be incredible to help you move through them and come out the other side quickly.  But that being said, you don't want to join a mastermind if you are at a place where you're feeling desperate, playing the blame game, or stuck in a scarcity rut.  You won't have a great experience and it will ruin the experience of other members. 

  • We vet those who apply for our mastermind very carefully to ensure they are joining with a mindset of abundance and generosity. If you don't feel like that's how you can show up for the group today, do the inner work before joining a mastermind.

4. You can financially commit to a mastermind.

  • Joining a good mastermind is a financial commitment.  Although there are masterminds at every investment level, you can expect to invest $20k - $50k+ for a good 12-month business mastermind.  Some are as much as $100k.

  • My recommendation is to look at it as an investment and not an expense.  If you meet the other criteria above - you are in the grow, scale or influence stage of business, can commit to showing up and being open to both give and receive feedback, have a mindset of abundance and generosity, AND you take consistent action, you will see an ROI.

  • If finances are a concern or you tend to be risk adverse when it comes to investing, look for a mastermind that helps you make back your investment quickly.  For example, in our Change Maker 500 Mastermind, and even in our group mentorship programs, we do a $25k Challenge to help members make back more than their investment within the first 90 days.  

So, if you are confident that a mastermind is exactly what you need to level up your business and as the leader of your business, the next step is choosing the best mastermind for you. 

How to Know If Joining a Mastermind Is Right For You. Click To Tweet.


Top 10 Things to Consider When Choosing the Best Mastermind to Join for Your Business

1. Commitment Required

If one of the criteria to being ready to join a mastermind is being committed to showing up, be sure to pick a mastermind that aligns with your availability and how often you'd like to meet.

Some masterminds meet multiple times a week, some meet once per month.  Some have in-person events that require travel, some have virtual events, and some don't include events.

Before joining, be sure to understand the frequency of meetings and events and get clear on when everything occurs so you can ensure you can be there.

Also understand the rules and guidelines for the mastermind to ensure it is a good fit.

2. Open or Closed Enrollment 

Some masterminds have a defined enrollment period and then close their doors so you are with the same group of people for the duration of the mastermind.  Others have open enrollment and add new members all the time.  Others welcome new members at specific points of time such as quarterly.

If groups naturally go through the stages of forming, storming, norming, performing, a group who is consistent and together for the entire duration of the mastermind will form deep bonds, really get to know each other's businesses, and experience a level of comfort and transparency in a way that's different from groups that have members joining and leaving all the time.

Looking at it from another view, consistently infusing the group with new people, perspectives, and business models can sometimes refresh and re-energize a group, and each new member is an opportunity for a lifelong business relationship or even collaboration partner.  

There are pros and cons to each scenario as a member of the mastermind.  Give some consideration to which style aligns best for you.

Some enjoy having members onboard and offboard regularly, others find it very disruptive and overwhelming to consistently be learning about a new business and making a new connection. 

3. Size of the Group

Understand the size of the mastermind and how it is structured.  The more people, the less time each individual gets to ask questions or share feedback and ideas.  This can sometimes lead to an increased number of calls or calls that are longer in duration and 90 or 120 minutes instead of 60 minutes.

Some masterminds put a cap on the number of members, typically somewhere between 6 - 15, and keep everyone together as one group.

Other masterminds will have a high or unlimited number of total members but they break larger groups into smaller sub-groups or pods so you are together with a more intimate group of 6 - 12. 

Ensure you choose a group whose size and structure aligns with your expectations and where you will get the amount of support that you are looking for. 

4. Access to the Leader

Be sure to understand how much access you get to the leader and in what format.  Some masterminds have peer mastermind calls where the leader is not present.  In others, all mastermind calls are facilitated by the leader. 

Some masterminds include private coaching or strategy sessions with the leader, but many don't. 

You'll need to assess how important it is to you that you have 1-on-1 access to the person who leads the mastermind, or how much access you get to them in a group setting. 

5. Variety of Businesses 

I often see people give advice to join a mastermind that only includes others in your industry and I completely disagree. 

If you are looking to be around only others who are very similar to your business, a group coaching program or mentorship program is typically better aligned than a mastermind experience.

Do you want to be in a mastermind group where everyone is doing and selling the same things, in the same ways, to the same people, and who think and act like one another... or do you want to be in a group where people think different, have different business models, different customers, and different offers? 

There is power in everyone being aligned around a common goal - which is typically business growth related - but I can share from personal experience that you will get far more out of your experience if there are a variety of different businesses and perspectives.  That will challenge you to grow and think outside the box of your industry and can really accelerate your results.  It becomes about finding inspiration and innovation instead of copying and following the leader. 

Plus, it's nice to be in a space where you don't feel like you have direct competitors.  It makes it easier to share transparently and confidentially, and easier to collaborate with one another and refer each other business.  

Some masterminds let anyone in including people who do very similar things and would be considered a direct competitor.  Others carefully vet each member to provide a diverse group that can support one another without direct competition.

If not having direct competitors in your mastermind is important to you, be sure to ask about other members before you join and ask how they select members.

Things To Consider When Choosing The Right Business Mastermind. Click To Tweet.



6. Level of Business

Ensure that the mastermind you are joining is aligned with the next level you want to take your business to.  You don't want to be the only 7 figure business owner in a room full of newbies just like you don't want to be the only newbie in a room full of 7 figure business owners. It is a frustrating experience for everyone involved when that happens.

While it is hugely beneficial to have a diversity in types of businesses, you want to be around people at a similar enough level (typically at your level, or a mix of those at a level or 2 above and below where you are at).  Level could be related to revenue or experience or other factors. 

For example, you could have a relatively new business that hasn't broken 6 figures yet, but you could be a great fit for a higher-level mastermind if you are a seasoned serial entrepreneur with a track record of experience and success at that higher level and are ready for next level conversations instead of newer-business related conversations.

It could also be a group that is striving towards a common goal which is what we do with our Change Maker 500 Mastermind.  You probably guessed it from the title... everyone is striving to scale to $500k in revenue as their next business milestone.  We also carefully curate a group that is not only aligned around a common goal but that also has proven that they have a scalable offer in their business. This allows us to have high impact conversations around accelerated and sustainable scaling of their offer and keeps everyone laser focused on achieving their goal in the simplest and most direct path possible. 

When businesses are at a similar level, or aligned around a common goal, there is a huge opportunity for accelerated learning and results, plus great opportunities for collaboration.

If you notice that a mastermind allows people at a wide variety of levels in, check to see if they create sub-groups and pods based on level.  

7. Trust and Integrity

Do you know, like, and trust the person who is leading the mastermind?  Do they walk their talk?  Are they someone who's feedback and advice you would value (and listen to)?  Do you feel they can help you level up themselves or do you trust them to curate a group of mastermind members who can?

Are they truly committed to helping you achieve a transformation or are they just in it for the transaction?

Here are some tips to vet if a leader is the right mastermind leader for you. 

If they have a podcast, listen to a few episodes if you aren't already a regular listener.  Look at what they talk about and look at who they interview.  Many podcast hosts will interview their clients as guests.  About 80% of the guests on the Lean Out Your Business Podcast are active or former clients.  This can give you great insight into the type of people they work with.

Check out their website and social media for behind-the-scenes pictures and insights into what the mastermind is about, and to see who is a member.  Most leaders tag their members in retreat photos, and most sales pages have testimonials with the client's name listed.

Review the testimonials and don't be afraid to ask if you can reach out to members to hear about their experience. Unless it is a mastermind where members names are kept confidential, which is rare, most are willing to share. 

Finally, look at their communities, especially their private communities.  While you are always going to get a broader range of people in a free group, you can see still get valuable insight into the type of person they work with.


8. Retreats and Events

How important are in person events and retreats to you?  Many masterminds include retreats and events, virtual and/or in person, but some don't. 

If your mastermind has retreats, do you care about where the retreats are?  Do you want a tropical and dreamy destination, or do you not care where you are as long as you are connecting with other members and upleveling your business?

While some masterminds do include luxury locations for at least one of their in-person events, many are not held in sexy locations.  Instead, they are held somewhere convenient for the leader, typically close to their home. 

So, you'll need to determine how important retreats and events are to you and how much location matters. 

9. Structure

Some masterminds are 100% about connection and discussion and provide zero access to digital programs, curriculum, or templates / tools / resources.  

Others have curriculum and / or resources specific to the mastermind, although it is typically more lightweight since robust curriculum tends to be more of a group mentorship experience than a mastermind experience. 

Others provide access to the leader's other relevant programs when you join their mastermind. 

For example, when someone joins our Change Maker 500 Mastermind, they get access to our full Simplify to Scale Business Accelerator.  It is at their discretion how much or how little they leverage that program but it is included because the content, templates, SOPs, adaptable systems, and next level resources that are included will enhance a member's experience in the mastermind.  Other Lean Out Method programs are not included because they have no direct relevance to the mastermind. 


10. Application Process

Finally, I highly recommend choosing a mastermind that has an application process.  And although a lengthy or in-depth application can feel like a total p.i.t.a. when you are the applicant, it shows the leader's level of commitment to curating right-fit members. 

Our application process for the Change Maker 500 Mastermind is robust and takes about 15 - 20 minutes to complete.  And while that probably does stop some people from applying, it doesn't deter the people who are truly serious and interested.  It also increases the likelihood that they will join the mastermind if invited to do so because they took the time to really think through why they want to join and confirm it was a good fit.

So don't let an application process deter you. Instead let it give you that one final bit of confidence that a mastermind is the right fit for you if each of the other items checks out.

If a mastermind has no application process and everyone is approved, I would seriously consider if that is the group you want to be a part of.  


Things To Consider When Choosing The Right Business Mastermind. Click To Tweet.

In Summary:

After having participated in masterminds, hosting my own masterminds, and helping my clients build and launch theirs, the best piece of advice I can give is to get clear on what you want to get out of it and find one that's in alignment because they are all a bit different.  

Ensure you align with the commitment that is required and that you can be present and give as much as you get. 

Get clear on what's most important to you and what's a would-be-nice vs. show stopper such as whether the mastermind lets in new members at any time or if you are with the same group of people throughout the duration of the mastermind, the size of the group, how much access you get to the leader, the variety of businesses included and whether they allow direct competitors. 

Ensure the level of other businesses aligns with what you are looking for and that the structure including retreats and events is what you want.

And finally, be sure that you trust the leader to curate a mastermind experience that will lead to the results you want if you show up and do the work and that they are invested in transformation over transaction. 

If you have a target to hit $500k in the next 18 months, I invite you to apply for our Change Maker 500 Mastermind.  It is a 9-month small circle mastermind exclusively for impact-driven and passion-fueled entrepreneurs ready to scale to $500k, on their way to 7+ figures. If you are ready to take your big bold vision, goals, and revenue targets and fast track making them a reality in 2022, without the hustle, then you’re invited to apply for the Change Maker 500 Mastermind.


References Mentioned 

Ready to simplify and streamline how you scale your business?



by Crista Grasso

Crista Grasso is the go-to strategic planning expert for leading global businesses and online entrepreneurs when they want to scale.  Known as the "Business Optimizer", Crista has the ability to quickly cut through noise and focus on optimizing the core things that will make the biggest impact to scale a business simply and sustainably. She specializes in helping businesses gain clarity on the most important things that will drive maximum value for their clients and maximum profits for their business.  She is the creator of the Lean Out Method, 90 Day Lean Out Planner, and host of the Lean Out Your Business Podcast. 


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