Have you ever considered joining a mastermind or higher-level coaching program, but you’re not sure how to decide if it’s for you? These are usually a bigger investment than a course or membership, so it’s vital that you understand what to look for and how to decide if it’s right for you.

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Over the past several years, I’ve participated in 4 different mastermind programs. I’ve also invested in other coaching programs as well. So I want to share with you some of the lessons I’ve learned from my own experience of participating in, as well as running, a mastermind or higher-level coaching program.

There are many other types of programs besides masterminds that can help you grow your business. such as courses, group coaching, memberships. In episode 28, I dove into determining which type of investment is right for you, so be sure to check that one out if you want a broader look at the options available to you.

But today, I want to specifically look at deciding whether you should join a mastermind or not. I’ll share what a mastermind is, what to look for, as well as some steps to determining if a program is right for you.


What is a mastermind?

The term mastermind can be used in a variety of ways, and often it is not necessarily referring to the exact same kind of program.

In most cases that I have come across in the online space, the term ‘mastermind’ refers to a higher level program for entrepreneurs… It’s generally led by a coach and includes some level of access to that coach.

It also includes the network or community of people in the group (i.e. the mastermind piece). And it may include some level of training – live training, access to the coach’s courses, etc. It can also involve in-person events or meetups to provide additional connection and growth within the group.

Strictly speaking, a mastermind is intended to be a peer based group where there is not necessarily one primary coach but rather the group is providing thoughts and feedback. However in the course of my  7 years online, I have only seen one paid mastermind program actually operate like that with the leader acting only as a facilitator and not also as a coach.

Side note: this is partly why I call my upLIFT program a ‘mentormind’… because it is a combination of coaching and mentoring from me, masterminding with the others in the group, and ongoing training and support.

Often a mastermind type program is made up of a group of people at a similar level of business. There may be an income level required to join the program, or there may be a certain number of years in business needed. This is not about being mean or exclusive. It’s more about making sure that the group can support one another. If you’re in a group where the levels of business are all over the place, it can be challenging to refer business to one another and/or to discuss certain issues in your business.

One more note about masterminds: There can be peer masterminds and paid masterminds. In peer masterminds, it’s a group of business colleagues who create a self-managed mastermind. This means there is not one leader of the group but rather it’s more of a chance to connect, collaborate, and support one another. This can work well and it can also be challenging… more on that another time.
In this episode, I’m focusing on the paid masterminds you might consider joining.

How do you know if you are ready for a mastermind?

Masterminds work best once you have already gotten established in your business to a certain level. You’ve probably gone through some courses to help you get your biz off the ground or you may have worked with a 1:1 business coach to help you. At this point, you’re ready to expand what you have going on and you want to grow or scale.

What to look for in a mastermind type program:

Look into the person running the program.

Do you resonate with his or her style? Do you like their approach?

If you’re not sure yet… start listening to their podcast, watching videos, following ons social media.

It is SUPER important if you are going to invest at this level that you like the person you are investing with. Of course you may not always agree with them 100%, but you should feel good about their approach and style.

Are there any red flags? Anything you don’t feel good about? Pay attention to that.

Do your values align?

If faith is something that is super important to you, then find out if that’s an aspect of their program and/or of their life.

A lot of entrepreneurs give lip service to God, but they don’t actually incorporate faith into their business or program at all. So that’s key to remember.

Look into the delivery of their programs.

Have you ever purchased something from them? If so, what was that experience like? How did they deliver on their promises?

How involved are they in the delivery of their programs? Are they hands off? Do they get really invested in their clients’ success?

How organized is the content or call schedule? How good is the communication about what is being offered?

It’s really valuable to get an idea of how the leader shows up, what their strengths are, and what the overall experience is like in one of their programs.

Of course, it’s usually the case that a mastermind is going to be their highest level of support, so don’t necessarily think that if they are not super present in a lower level course that it will be the same for their mastermind program.

But generally speaking, you can get a sense of the quality of their content and programs if you consume some of their free and/or lower priced options before joining the mastermind.

Side note: some people are really great at marketing, but less so at follow through and delivery. And you can often figure this out based on what they do in their lower priced programs.

Look into the specifics of what you will be getting in this program.

At this point, I want you to spend a bit of time figuring out 2 things:

  1. What are you wanting to get out of joining a mastermind type program?
  2. What does the program offer that you are looking to join, and does it align with your needs?


Sometimes you might be tempted to join a program based on the recommendation of someone else. And often this is a really good way to determine the quality of the program. BUT it’s key that you know what YOU are looking for.

Here are a few of the things I have looked for in programs that I have joined in the past:

  • Experience and expertise in the area of my business that I’m looking to grow (i.e. the coach or leader is further ahead of me in business overall and/or has a specific area of expertise that I need help in)
  • Connection with other people in business who have similar goals and values – a safe place to share wins and challenges
  • A faith component so that I know the coach is leading from a place of similar values and incorporates that into their views on business
  • Training or growth that is going to help me at the level of business you are at

So before you join a program, I want you to sit down and really think about what you are personally needing right now in your business. What are your goals for the next 6-12 months? What is most important to you in a program like this?

Then, you need to look at the program you are considering joining to figure out if what they are offering will meet your needs.

You should be able to get the details of what’s involved in the program and how they can help you reach your goals. This might look like a sales page, a webinar or info session, or a call with the program leader. Or, it could be a combination of some of those elements.

Keep in mind that the program may have some elements you don’t need, and that’s okay. It’s more important to ensure that the program has the elements you do need, and if there’s extras, that’s just a bonus.

Should You Join a Mastermind?

Once you’ve looked at the person running the program, the way they deliver, and the specifics of what you’ll be getting in the program, it’s time to decide if you want to move forward.

Often there will be an application process and sometimes there may be a phone call to make sure that you are a right fit for the program.

After this step, there may be a deposit required and/or you may simply be accepted into the program and need to make your payment and sign your contract to join.

Once again, just like with dealing with failure in your business which we talked about a couple weeks ago… this decision about joining a program should be accompanied with prayer and allowing the Holy Spirit to guide you.

It’s likely to feel scary because often it’s going to be a bigger investment than you are used to making. At the same time, it’s often these higher level investments that will actually get you to the level of business you want to be at and it will put you in a room with people that may become amazing referral partners and collaborations.

Before You Join A Mastermind

Now maybe you’re thinking: Okay this was great, Esther, but I still don’t know exactly what to do next.

I have 2 things for you to do before you join a mastermind type program. First, I’m offering you a free resource to help you determine whether a mastermind type program is right for you. It’s a guide that will help you identify what you are looking for and 10 questions to ask as you are looking at a program.

Secondly, I’d love for you to consider my upLIFT Mentormind. The program is open to apply at any time, but since I know you might be someone who wants to get all the details and hear directly from me about it, I’m offering an info session to give you the lowdown on the program.

Just go to upliftmentormind.com/info to sign up for the free Info Session coming up on March 17th. You’ll be able to get all the details and determine if this program is right for you.

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