Mastermind Essentials – Tips and Tools to Make Your Group a Success

mastermind chalkboard

So you’ve read about all the benefits of being in a Mastermind Group and are ready to start your own. Here I’ll share tips, including the initial soul bearing email I sent out when starting my first Mastermind, key learnings to keep the momentum going and helpful tools to facilitate your meetups.

There are many types of Mastermind Groups (as described in this thorough 56 page PDF), so I won’t cover them all here. My experience is with a business and personal growth oriented group that puts accountability at the forefront, though these recommendations can apply to all types of groups.

Starting a Mastermind Group

Establish Core Values

Just as your personal values are guide your life, it’s essential to establish a set of core values for your Mastermind. Really quickly write down what’s important to you in your group and you’ll see how writing values down will set a tone for your group and shape who you select for your Mastermind.

For my own group, I even included values that I specifically did NOT want. This is because I’ve been to far too many networking events that I felt only served to benefit a few (typically lawyers, accountants and multi-level marketers) at the expense of more junior members, so I wanted to make it explicit that this group exists to help each other out selflessly, not to make money off each other. That may, and often does, come naturally later on.

For fun, I opened up Photoshop and created this list of values (and un-values) alongside an image from the closing party of WDS to use as a header on our group Facebook page:

Mastermind Core Values Facebook Header

Keep in mind that a Mastermind is a living thing, so these values can change and grow over time, so don’t over think it.

Who to Invite

Now that you have your core values set, it makes it easier to think about who you want to be in the group. This is the most important step and the most difficult, not only for the obvious challenge of deciding who to invite, but also because you are putting yourself out there when asking people to join, particularly since the majority of people outside of the coaching haven’t heard of a Mastermind.

Here are three tips for choosing members:

First, I’d recommend only 3 – 5 members. A Mastermind is an intimate thing. You’ll be talking about deep, personal topics, opening yourself up to your group on a regular basis. Logistically, it’s a pain to have a large group. Not only is trying to videoconference with more than five people inefficient, but try getting everyone to agree on a meeting time, especially when they’re in different time zones.

Second, everyone should get along with each other. They don’t have to have met before, but if you share common values (that’s why #1 is so important) and have similar outlooks on life, this is easier than it sounds. In fact, in my five member Mastermind, two of the members have not met the other two, but we all get along great and are looking forward to all meet in person one day.

Lastly, members should share similar interests, drive and commitment. But variety is good, as it’s beneficial for members to think differently and to continue to challenge each other.

My group are all fans of Chris Guillebeau’s work (we all attended WDS), share a love for travel and are all either currently digital nomads or have the goal to live a lifestyle other than the 9 to 5. We are also all in different stages in our life, with our age ranging by 15 years, which adds an element to our group dynamic as we have different skill sets and experience.

What if you can’t think of more than one or two people beyond your immediate network and group of friends? Ask the first few members if they can recommend someone. Ask colleague or mentors.

Is there someone’s work you admire and respect? Ask them too. Never discount the value you can provide to others. I have a friend who is training to be a life coach, and was shocked to have been contacted by a currently well known life coach with 15 years experience for a coaching call! You never know until you ask, and the worst is that they say no, but would likely be flattered by your invitation.

Still having troubles? Go to them. Join meetups, classes, TEDx Talks, Pecha Kucha nights.

How to Invite Them

Besides the obvious in person and phone invitations, I felt it necessary to write out an email, almost a manifesto of sorts describing my intentions for the group. This was partially due to the fact that my members were in different cities and that I was only acquaintances with two of them, but also because in the process of writing the email it helped me form my thoughts and deliver a clear message.

You can read the actual email I sent out here (In PDF format, feel free to re-use):
Screenshot of Initial Email to Mastermind Group - click for PDF

One confession: it was extremely nerve wracking to hit SEND on this email. It’s a similar feeling to publishing a blog post for the world to see. You’ll get the usual thoughts of rejection, worrying what people will think. Erase all that. These thoughts are normal anytime you put yourself out there. Not everyone will be on board, but that’s life, those ready and willing will be there. What’s more likely is that you’ll find people not only receptive to your idea, but 100% on board and willing to help. Within hours I was getting enthusiastic emails and comments like “I’ve wanting to do something like this for a long time!”. The positive feedback added to my excitement of starting this Mastermind, and that’s when I knew I selected the right people.

If you want it and see the need for it in your life, chances are someone else does too. I can’t think of a more win-win situation than that.


A Mastermind is like a plant that needs watering and the occasional feeding. I’ve taken what I’ve researched on the web and applied to my group, as well as tips from a member our group with previous experience in a Mastermind, and combined that with examples of what’s worked for us, and distilled it down to the following learnings:

Choose a Regular Time

Our group meets every two weeks, but choose a frequency that works for your group. Weekly can work if it makes sense logistically and the members are committed, but you may find that is not enough time for action. Monthly can work as well, but no more than that as these regular meetings will lose their effectiveness.

Our group usually meets on a Tuesday or Wednesday afternoon at 2pm Pacific Time. For those members in North America, this works out well as it gives time in the morning to get work done. We chose this time also to facilitate our members in Australia and in Thailand. It’s awfully early for them (5am).

Create a Meeting Structure

In the first meeting, someone (probably you), will have to be the facilitator / leader. After a few minutes of waiting for everyone to arrive, we give each other equal time and go one by one answering the following questions:
1. What are you working on?
2. What did you learn? (this past two weeks)
3. What do you need help with?
4. What’s your accountability item for the next meeting?

The last one is my favorite, as it pushes us to grow by setting these mini goals to report every meeting.

And for fun, our group added a fifth question: “What did you do that you’ve never done before?”. This doesn’t have to be on topic, it can be as simple as a blog post, signing up for a coding class, taking ukulele lessons, meditating for five minutes a day, or even seeing a sunrise.

No One Owns It, Everyone Owns It

Small groups like this work best when everyone owns it. I learned this from the life coach that started a men’s group that I was part of (more about that in a future post).

Although it helps to have one facilitator to create the calendar meetings, everyone has an equal voice. Everyone wants this to work as much as I do, so we find it easy to find times that work for all of us, even though it’s harder for some members in different time zones (try driving at 5am to the local 24 hour coworking space).

Also, although attendance should be as high a priority as a business meeting, sometimes life prevents you from making a meeting. So by having every member take ownership, members will keep the Mastermind at the tops of their lists.

Start on Time, End on Time

We’re all busy people in this hyperconnected world, so we’ve set our meetings to a maximum of one hour. I say maximum because if the meeting goes longer, no one is obliged to stay. One member meets us before driving to work in the morning.

By establishing this early on, it encourages us to be brief and to the point. If the conversation starts veering off topic, which often happens when sharing inspiration and especially when sharing links, sometimes the facilitator needs to interrupt and suggest the conversation to go offline. In fact, it’s encouraged for members to talk outside of the regular meeting times.

And sometimes when there is little to report, like during holidays, everyone has had their say in only half an hour so we end it then, but someone usually sticks around just to chat because we like talking to each other. 🙂


As a freelancer or solopreneur, there is always work to do. Getting lost in the day to day transactional work and feeling “busy” is common, which is where Masterminds can help the most. There’s so much evidence that saying out loud what you will do actually pushes you to do it.

After the meetings, members post their accountability items that were discussed in the meeting. We do this in a Facebook group.

Capture It

Any links and meeting notes are captured in an ever growing basic Google Doc. It only takes a minute to update as it’s a simple copy and paste from our Google Hangouts with any verbal notes added, but I’ve found it’s saved many emails of the “what was that link again?” variety.


Encourage interactions outside of the regular meetings. We keep our Facebook group fresh with links to inspirational, on topic articles or videos. It’s great to have a group to post this to as not everyone is comfortable with posting certain topics on their personal Facebook page or Twitter.

Also, meet up in person! This may seem obvious, but it’s like that good friend you only see once a year that you always have amazing conversations with when you finally do meetup, with both of you ending with “why don’t we do this more often?”. Take the initiative and make an effort to get people together. I dream that our group will all meet in Chiang Mai or Medellin in the near future. 🙂

Challenge Each Other and Have Fun!

Masterminds are intended to be challenging, to push each other and to learn, but don’t take things to seriously.

There is always the productivity versus presence argument (which Maria Popova distills down masterfully in this piece on, but as with life, don’t take things too seriously and have fun with it!

Recommended Tools

I’m a big GTD (Getting Things Done) fan, so if it takes me an hour to learn something that will save me ten down the road, I’m all on board

Here tools that help facilitate our Mastermind group:

Google Hangouts

Skype doesn’t have free multi-person video conference, so the free Google Hangouts works very well for us. It’s in your browser, and I like how it focuses on the person who is speaking.

Google Calendar

I use GCal for everything. Once it’s setup right, you can sync your phone, desktop and tablet and you’ll never miss a meeting.

One awesome feature is that video calls are integrated in every Google Calendar event. After creating your even, click the link “Add Video Call” (More details on Google’s Support page). Now everyone who receives the meeting request will have a link to the video conference, saving an email!

Another headache it solves is time zones. I’m used to working in different times, but I don’t know what I’d do without Google Calendar. Some countries don’t have Daylight Savings Time, so this has prevented that awful feeling when you’re the only one on the call and you realize you got the time wrong. We have five members in five time zones, sometimes crossing the International Date Line, so this has been a lifesaver.

Another GCal tip: you can show two different time zones in Google Calendar (Ecuador is on Eastern Time, except it doesn’t practice Daylight Savings). Under “Settings”, add an additional time zone and check the box “Display all time zones”. Read Google’s support article on scheduling across time zones.


We try to meet at a regular time, but sometimes that doesn’t always work out. Doodle is a great free tool to reduce the number of emails back and forth to set a time that works for everyone, using a voting system.

Simply load recommended meeting times, enter member’s emails, and Doodle will send a link to a poll showing everyone’s chosen preferences.

After trial and error, what’s even more effective for our group is to decide on the next meeting time at the end of our meetings, while everyone is online.

Facebook Groups or Google Groups

We needed a forum to share notes and get feedback. Since all of our members were on Facebook, Facebook groups worked best and kept our email inboxes lean.

If you’re all into the Google products, Google Groups can work as well.

Bounce App

We want everyone in our group to feel that it’s a safe place to post drafts, mockups and ideas at anytime. For instance, we all have blog posts, and some of us have written epic posts (like Dan’s post, I’m Quitting Drinking… For Life).

But we don’t have editors, and you are the worst editor of your own work, so using an annotation tool like Bounce allows for quick feedback. Google Drive can also work, but I like how with Bounce you can draw boxes, versus in Google you can only add comments in the margins.

I love having the support of a Mastermind group and the safe forum that it provides. Knowing that someone is there for you when you need it is a great feeling. Knowing FOUR people are there for you in a safe forum is even better.

Don’t lose momentum, start your Mastermind today! And please use these tips and share what works for you. I’d love to hear about your experiences. After all, it’s all about learning!

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