Enhancing Your Career with a Mastermind Group

February 8, 2019

In 2011, I did something pretty out of character - I quit my job. Mind you, I didn't do it because I had another job lined up. Nope. I quit my job to go out on my own as a business owner. On top of this, I had a newborn at home and no guarentee that the income would be flowing every two weeks.

The first year of running a business was eye opening. It's hard! You have to learn a lot of lessons the hard way.

I was lucky and accidentally found myself a group of folks locally who were in the same boat. We all worked for ourselves. This was my first introduction to the wonderful world of Mastermind groups.

What is a Mastermind Group?

My personal definition of a Mastermind Group is a "group of mutual improvement".

In 1925, Napolean Hill coined the term "Mastermind" in his book The Law of Success.

Hill expands on the definition by calling it a "friendly alliancea among people to support each other with their plans".

This is a powerful statement. Hill continues to explain: "The group helps to organize useful knowledge, creating a virtual encyclopedia from which each member can draw information".

Let's put this into better terms... we're stronger as a team than we are as individuals. Hill suggests that as a group matures, the individual experiences of members will help build a virtual encyclopedia is knowledge that others can build off of.

Have you ever had a problema ailing you for hours or days? And when you explain it to someone their response is "oh, I've seen that before! Try this...".

That's the virtual encyclopedia in action.

There is much more to what makes up a Mastermind group. But we'll get to that.

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Historical context

In the regular talk I do on this topic, I like to discuss historical evidence that this concept is sound. Not to bore you with history, I'll mention my favorite example.

Many years ago, I read Benjamin Franklin: An American Life by Walter Issacson. In it, Issacson discusses how Franklin created a series of groups called

. These groups consisted of "ingenious men" who'd discuss local politics, art, science, and more.

The group aimed for not just mutual improvement, but improving the world around them.

What is the makeup of a Mastermind Group?

Okay! Let's discuss the informal makeup of a Mastermind group. Note: I'm generalizing. There isn't a manual or council that dicates the official rules for what makes a Mastermind a Mastermind.

Number of partipants

This is the most common question I get (outside of "how do I find a Mastermind group?"). How many people should be involved in your group?

Like a good software technologist - it depends.

I find a good number is between 3-5 people. This is because we need to remember that the group is meant to be for mutual improvement. There is a massive amount of trust that goes into these relationships. As the group grows, it is difficult to become intimately knowledgable about the lives and business of my fellow members. That knowledge base is necessary for me to provide good, honest feedback.

I have seen many groups that consist of a dozen or two members. The format of their meetings are much different though. Larger groups need better structure, or else the feedback will become noise. And noise is not benefical to anyone.

How often are meetings?

My most active Mastermind group meets every 2 weeks. Monday at noon. That's on the calendar.

Another group meets weekly on Wednesdays - noonish, but maybe 2pm if that's better.

Freqency of the meetings, again, isn't a hard-fast rule. But it needs to be mutally agreed upon by the entire group. Attendance is MANDATORY.

Sidebar. When I say mandatory, I mean you better have a really good excuse for missing the meetings. And do not miss consecutive meetings. This is a group of mutual improvement. Your absence is not helping anyone - and I'd suggest if you miss multiple meetings without reason, the group is within its right to remove you.

"Without reason" is subjective. Life happens, I know. Just don't try to make it a habit. Take a leave of absence if you know you'll have to miss multiple meetings for a period of time.

Are meetings in person or virtual?

The members of my Mastermind live up and down the coast. Alabama, North Carolina, Maryland, Virginia... it is impossible for us to meet in person.

Our meetings are always via Zoom - and used to be Google Hangouts. Virtual is great. However, push for video calls. Video will greatly enhance the experience and the relationships.

Common Formats

During my talk, this is the section that gets the most questions and prompts the most discussion. Let's imagine you have a group. How do you structure the conversation?

This is not meant to be a set of hard-fast rules. You do you. However, if you don't have any outline or guideance, feel free to use my list here.

Round Robin

The Round Robin format works well with smaller groups, maybe 2-5 people. The reason for this is that each member of the group is going to have the opportunity to speak. Assume that if each person talks for 15-20 minutes, these meetings could take a significant amount of time.

In my group, we do Round Robin. Each session requires that each member answers the following list of questions:

What was your personal win for the week?
An important part of growing professionally is recongizing the wins in your life. We start with personal wins, because it is easy to get caught up in the day-to-day minutue of WORK.

This might be the hardest question for you to answer.

But in reality, it's because you're not practiced in finding the small victories.

I took my son for a bike ride, and we rode over the big bridge.

YES! That is awesome on several fronts. Quality time with your family is a win.

Your win might be Marie Kondo-ing the house. Your win might be not eating out for seven consectutive days. Your win might be paying off a credit card.

If it's a win in your book, that's awesome.

What was your business win for the week?
This question is usually easier to answer. Personal wins are personal, but how did your business do this week? And if your Mastermind isn't focused on business, maybe replace it with professional win.

I signed a new client.

I wrapped up a contract.

I finished phase one of my SAAS idea and shipped it.

Anything that proactively pushes your business forward is a win!

Did you hit your accountability goal?
Okay, we're going to talk about accountability at great lengths in a few minutes. But for now, let's assume you made a promise to your group that you'd accomplishment ONE thing before this meeting.

I will have the landing page completed for my new SAAS.

This question is the moment of truth. YES or NO. Did you or did you not meet your accountability?

Talk more about your accountability... what's going on in your business?
Based off the answer to the previous questions, you will want to go into more detail with your group.

Yes! I got the page finished and it's ready for review at [some url].


No... I got caught up playing Nintendo and didn't have the time.

This is your moment to get the constructive feedback you need from your group. If you meet your accountability, ask for feedback. Maybe you need someone to walk through a workflow. Maybe you want another set of eyes on a email sequence. Maybe you need beta testers for an app.

We've done this several times in my Mastermind group. One of my friends, Sean, asked us to sign up for and review his latest SAAS offering. Not as a "maybe later", but as a "right now!". The group was able to give Sean immediate feedback, and helped him determine what he could work on next.

Sometimes you won't hit your accountability. That's okay, with reason. General laziness shouldn't be tolerated. Maybe the accountability was too much for the time? Were there obstacles outside of your control? Use your time to discuss WHY the accountability didn't get done. Sometimes failure can be as helpful as success.

Remember - this group is a virtual encyclopedia. You're helping add to the general knowledge base, good or bad.

What do you need help with?
I love this question. Your Mastermind group is for mutual improvement. We want to help each other succeed in anyway possible.

This might be reviewing a landing page. It might be retweeting something on Twitter or promoting something in general.

Don't be afraid to ask for help here.

What is your accountability goal for next time?
We're going to talk about accountability in a lot more depth in a moment. However, to wrap up your session, each member of the group needs to commit to a single accountability goal for the next session.

Hot Seat

This isn't "Who Wants To Be A Millionaire?"... but wait, actually it is. Okay okay...

If you have a large group, let's say 5 or more, it can be generally difficult to do Round Robin every week or two. This is where Hot Seat comes into play.

Every member of the group is required to give a quick status update. However, instead of giving equal time to every member of the group, time is then dedicated to one or two people in particular.

This opportunity allows the group to insanely focus on helping ONE person at a time. How can "we" help? The group might ask hard and uncomfortable questions.

Generally, you will know when it your turn on the hot seat. One member of the group should take the role of manager, and manage the schedule for when people are on the hotseat to guarentee fairness.

When it is your turn on the hot seat though, you need to have your act together. Come with a completely detailed list of what you're working on and what you want to discuss.


I told you we'd get back to this subject.

You are accountabie to your group. They are accountable to you.

Every session, you are REQUIRED to provide your group with a committment or accountability goal. This is something you are saying you'll have completed before the next session.

In general, accountability goals should be S.M.A.R.T goals. You've probably have seen that acronymn before, but in case you haven't.

S - Specific

Your goal needs to be very specific as to what you're going to get done. For example, I was working on developing a new course for Swift Kick, and the first step of that was to have a well defined outline.

So I promised my group that I would "develop a full outline for the new course". And I met it!

M - Measurable

Sometimes your goal will be a yes or no whether you met it. You promised to do an action, and you either did it or did not.

Other goals can be qualitative. For example, Sean had the goal to sell 10 copies of his book. In the bootstrapped product business, this is hard to do! Sean missed his mark, but it wasn't for lack of trying. As a group, we were able to discuss potential ways that Sean could succeed better in the future.

A - Achievable

A goal should be realistic and something you can actually achieve by the next session. Let's use the previous example with Sean. If Sean said, "I will sell 1,000 copies of my book by next session", that is probably not going to happen.

Like I said, 10 was HARD - but realistic. Trying to get 1,000 is aiming a bit too high. And I'm talking about this particular situation. If Sean had a larger audience, and maybe 2 or 3 products under his belt, then 1,000 copies wouldn't be a huge undertaking.

R - Relevant

One of our members, Jason, had the vision of moving into the education space with a product idea. What is a good accountability goal for such vision?

Jason said he was going to finish a book he had on his shelf. A book that was unrelated to his vision.

The group rejected the accountability goal because it wasn't helping Jason move forward towards what he wanted to accomplish. Instead, the group helped Jason realized there were better goals to pursue.

When choosing an accountability goal, it is important that the goal is helping you move forward. Does your goal benefit the greater good?

T - Time Limited

Lastly, you need to be able to complete a goal in the limited time before your next session. Don't set a goal that takes 3 months to complete. If you find yourself falling into this trap, take a step back and break the problem down into smaller bits.

Most likely you'll see there is a series of goals that need to be hit before the BIG goal is acheived. What are they? Can one of the goals be accomplished BEFORE the next meeting occurs? When the answer is yes- that's a good goal for your accountability.


No matter what type of group you find yourself in, there are a couple key rules you'll have to mind by.

First, be honest. The group you surround yourself with is a trusted collection of individuals. Their goal is to help you and each other move forward - however that sound be accomplished. If you cannot be honest with this group, how can you expect them to give you advice and direction.

Be open about everything. At the end of 2018, I opened up my Balance Sheet and Profit/Loss sheets for the group and did an analysis for how much money came into the business. Outside of my accountant, I do not disclose that much information to ANY individual. In order for your group to give honest, criticial feedback - you need to be open about everything. As soon as someone tries to assume, the usefulness of your advice will diminish.

Be supportive and be non-judgemental. This is hard to remember, because the first thing you might want to say during a conversation is "that is the stupidest thing I've ever heard."

Yup - don't do that. Reserve yourself. Consider your words. Remember that people might be the thinking the same about you. Use the reaction time to think about a better, more constructive way to guide the conversation. More times than not, your understanding might be wrong or you might have a piece of collective wisdom to instill on the group.

Finding a Mastermind Group

As you adventure out into the world, watering holes will being to show themselves. Where do you go to meet like minded people in software dev? Maybe a user group? Maybe a conference?

General networking practices apply here. Are you active on Twitter, LinkedIn, or Reddit? Pick a place, and ask someone there if they'd be interested in jumping on a call every week or two. All my Mastermind groups have started this way? If you're not being invited, do the inviting!

Some services, like ~Mastermind Hunt~, exist to help make this easier for you too. Mastermind Hunt is a marketplace for people looking for groups, and aims to make it happen organically. Use code

for a free month and see if you find a group there.

Wrapping up

Whatever you do, don't buy into a Mastermind group. There are a series of "gurus" on the internet who will promise you the world by joining their "mastermind group" for the low price of XYZ dollars a year. These are scams, and glorified Facebook Groups. You will not get value out of these relationsships.

I hope this overview has been enlightening, and given you something to think about. I credit all of the major victories in my career and business to the advice I've received from different Mastermind Groups.

Find yourself a group - and let's takeover the world!