1. What is Your Experience Level?

Find out if the others in this group are at a similar experience level to you. A step ahead or behind is acceptable, but more than that usually doesn’t work out well for anyone.

Some examples: Is everyone in the group fresh out of college? Is everyone in the group 10-20 years into a career and they’re starting a business on the side? Is this everyone’s first business or just another in a portfolio of businesses?

2. When are You Available to Meet?

Make sure the people in your group are available when you’re available. See my checklist of online scheduling tools that can help compare schedules and narrow down a common meeting time.

Ask about their time zone. It’s not uncommon to meet someone at a conference, strike up a conversation, and not realize they live halfway around the world from you.

Ask them what days of week are ideal for a meeting of this kind. Make sure they can find a few days in their schedule so they can be flexible in case of scheduling conflicts that arise from time to time.

Find out what times of day they’re thinking of having a mastermind call. Some people shut their brains off at 4:59pm every day. Other people are night owls, and are ready to make progress in their business at midnight. This is something you need to know, up front, before you go any further.

3. Do You Have Time Available to Make Progress?

Make sure that all the members of the group have a similar expectation of how much time they can spend between meetings working toward their stated goals.

When someone commits to accomplishing a goal in a meeting, they must also have a corresponding pool of time in their lives set aside to work on those goals. If not, frustration quickly builds, week after week.

4. Do we all speak the same language?

Make sure all members are conversant in a common language. With the rise of virtual mastermind meetings, it’s common for someone in Berlin to be meeting with someone in Morocco, so make sure you’re all able to understand one another!

5. What is your Business Model?

Successful mastermind groups have members that are all striving for common goals. Critical to this is making sure all the members of the business mastermind group are pursuing similar business models.

For example, is your group comprised of ebook authors looking to achieve their first sale in the Kindle book store, or is it mostly freelance software developers looking to streamline client work?

Are your members all SaaS founders looking for funding, or are they starting self-funded Amazon eCommerce stores?

While it’s helpful to have a homogenous business model trend in the group, it can be beneficial when those members are in a variety of niches.

For example, I know of a successful mastermind group with SaaS founders. But, they’re not all pursuing the same customer: one’s product is a budgeting app, one is on-page analytics, another an email template provider , and another sells a leading learning management system. All are in different niches, but they’re all confronted with similar problems and milestones as SaaS founders. All SaaS founders, differing markets.

In a mastermind group of book authors, ask specific questions about the age level and genre of the books they’re writing. All authors, differing niches.

In a mastermind group of freelance graphic designers, one can be a vector illustrator, one can be a UI/UX professional, another can be a specialist in banner ads, another can be focused on posters and print media. All designers, different niches.

6. What is your Funding Model?

You must know if the member businesses will be primarily self-funded/bootstrapped, or if they will be venture-backed, investor-funded companies. You should try to never mix the two into the same group.

In my experience with MastermindJam.com, when I’ve mixed venture-funded founders into mastermind groups with self-funded founders, the two often aren’t speaking the same language. Venture-backed companies and startups have divergent goals and often use dramatically different tactics to reach those goals.

The lesson we’ve learned is that it’s just not appropriate to mix founders of funded companies into a mastermind group with founders of bootstrapped companies (your mileage may vary).

7. What is your Revenue?

It’s crucial that members in the group be of similar revenue levels. This is the #1 most difficult question to ask, but it’s arguably the most important question of all.

Beginners who are still seeking their first dollar in their business shouldn’t be matched with a business owner who has just passed the ten thousand a month mark growing his consulting business, and neither should be in a group with the founder of a company that is pulling in millions each year.

At every revenue level in business, there are hurdles and milestones. But those hurdles and milestones look different at each level.

To get the most out of any business-focused mastermind group, revenue levels must be fairly close among the members. This parity ensures that information flows in all directions in the meetings, and all members get their unique needs met most efficiently.

You may be thinking: “If I’m in a group of people just like me, at my revenue and experience level, won’t this lead to a ‘blind-leading-the-blind’ situation?”

The answer is No (and the reason may surprise you). I’ll address that common question and a few others in a future article I’m working on. Sign up with your best email address at MastermindJam.com to be notified when that article goes live.

8. Do You Have a Day Job

In the mastermind group, are they going to be discussing a side hustle, or their full-time business? We ask about day job to get an idea for the immovable time commitments in their lives.

If this is their primary job, are they a founder or co-founder in the business, or in an executive role where they can take the suggestions made in the group and apply them directly in their business?

If they’re not in a role where they can effect change in your business, give this some extra thought. Non-founders can benefit from mastermind groups, for sure, but they shouldn’t be mingled into a group with founders.

9. Do You Have a Family and Kids?

You need to find out about family and kids to gauge where their heart lies, where their priorities are.

The topic of family and kids is 100% (a million percent, even!) germane to this discussion. Don’t shy away from this. You need to know for the success of the group, or its just a waste of everyone’s time.

10. What Do You Need Help With Today?

Be sure to ask exactly what the prospective mastermind group member is hoping to receive from the group. Make sure what the person is looking for can actually be achieved in the group, and be sure their goals and needs are in alignment with the core strengths and weaknesses of the group and its members.

11. What Skills & Expertise Do You Bring To The Group?

In this question, you're turning the tables and asking what they're bringing into the group that can be of benefit to others. Every person in the mastermind group must be able and willing to help other members in some way. 

EXTRA CREDIT 1: Watch Body Language and Unspoken Cues

When you’re asking these questions, while the answers do matter, the way that the answers are given is important as well.

Being observant to body language will help you discern achievers from excuse-makers.

If a person expresses frustration, and they roll their eyes when talking about how busy they are (or how swamped they are, or how things are always encroaching on their time), you can be pretty sure they will not be successful in a mastermind group with you unless you’re in a similar phase of your life.

If you’re in a similar position, you can help each other stay on track and stay accountable, but if you’re focused on making steady progress, and their life is constant distractions and never-ending excuses, you’ll only find yourself facing a hard decision a few weeks down the line.

EXTRA CREDIT 2: Homogenous Priorities

If everyone in the group has similar commitments in their life, then they’ll make similar progress toward their goals and will get more out of the experience.

People with family commitments should be in groups with people with families. Likewise, single folks should be in groups with single folks.

It doesn’t just stop with family commitments…

Someone single but studying for their MBA will not have as much time as a single college dropout building a startup in their parent’s basement, regardless of if they’re both single.

This is not to say that there are people that can’t benefit from a mastermind group; I absolutely know that there is a mastermind group match possible for everyone.

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