How a mastermind group can take your freelancing to the next level

How To Start a Freelance Mastermind Group
Freelancing can be very lonely. It’s highly likely that, early in your freelance career, no one in your social circles is running a business or even doing the same sort of work you do. This makes it hard to know whether the hundreds of little decisions and the two or three bigger decisions you make in an average week are good ones.

This is how I started out. I was on an island, doing my best to move my business in the right direction and having no clue which direction that was or how to get there. Things started getting better as I began doing more face-to-face networking with other entrepreneurs and business owners, but what really changed the way I work was joining my first mastermind group.

What is a mastermind group?

A mastermind group is a small group of people who share common goals. You’ll meet with your mastermind group on a regular basis and take an interest in the success of the others in your group. It’s a simple concept, but, executed properly, your mastermind group can be one of your most valuable resources for growing your business.

Although there are no hard and fast rules for setting up a mastermind, it works better if it has some structure. Here are my rules for a great mastermind group:

  1. Your group should consist of 3-4 businesses/freelancers. You can find other people locally or online. Skype and Google Hangouts are great for these sort of meetings. You could always do a text-only chat, but it really helps to see the faces of your members. You really want to get to know these people well.
  2. Find members with enough common ground that you will be facing many of the same struggles. You’ll also want to be different enough that you’re not in conflict or afraid of sharing something.
  3. Your members should be at similar levels in the development of their businesses. You don’t want a Fortune 500 CEO in a group with some fresh-out-of-school freelance designers. This will make the group less valuable for all parties. You can make a group work with very different businesses and goals as long as their businesses are at roughly the same level.
  4. Speaking of sharing things, you have to be able to share everything about your business with your mastermind. Pricing, strategy, sales, and income numbers… everything is fair game during your mastermind meeting.
  5. Since everyone is going to be very open, you must keep this information in strict confidence.
  6. Set the starting and ending times for your meetings and stick to them. Your members are busy and will appreciate this.
  7. In general, divide the meeting time as equally as possible. Each person in your group has problems and struggles and deserves an opportunity to get help and input from the group.
  8. Meet every week or two for 1-2 hours. You can adjust this as you go depending on the needs of your group. Some groups will find their businesses are moving too fast to meet for only a single meeting per week. If your group is full of moonlighters, you may find your businesses don’t change enough in a week to justify the weekly schedule.
  9. If someone needs to exit the group for any reason, make sure they can do so smoothly and without judgment.

Now that you have a foundational structure, it’s time to explore the nuts and bolts of running a mastermind group.

What are the first steps?

In your first meeting, you’ll want to talk about the 8 “rules” of a mastermind group, introduce everyone, and tell about what you do. Answering these eight questions will help your other members better understand your business and how they can help:

  1. Who am I?
  2. What do I do?
  3. Who do I do it for?
  4. Who can I sell through? or Who knows my customers before I do?
  5. Where do most of my leads come from? (This answer may be the same or similar to number 3.)
  6. What are my goals for my business moving forward?
  7. What is my greatest struggle?
  8. What do you want to get out of the mastermind?

The first two questions establish the very basics. The next three questions give your other members the opportunity to give you referrals. They may know people who are like your ideal customer or the people who can help you sell. These will be valuable contacts for you. The last few questions tell your members about the other ways they might be able to help you move forward.

Pick someone to start. That person has the spotlight. Let them answer all the questions and provide whatever other information they feel is pertinent. Move around the table until everyone has had a chance to speak.

How does the mastermind work?

At each meeting, you’ll come together to answer a few questions:

  1. What did I accomplish?
  2. What am I working on?
  3. What’s coming up?
  4. What are my current challenges?

In your meetings, you’ll take turns just as before. Just like your first meeting, let one person answer all the questions before you move to someone else. Keep in mind, this is not like school; you can talk when it’s someone else’s turn, but be judicious in doing so. This is not an opportunity to turn the spotlight to you. It’s a chance to offer value to the person who has the spotlight.

If they are working on something you have experience with, you might say, “I tried that a few months back. I’m happy to help you with it or tell you about how it went for me.” If someone mentions they’re having trouble with marketing, you might offer, “I have a friend who works in marketing. I’ll see if she’d be willing to help you out with that.”

It’s crucially important that your members be invested. Each person needs to be willing to lay everything out on the table and willing to offer up whatever resources they have access to. If someone is holding back, the entire group will suffer as a result. If you feel your group as a whole is holding back, help break the ice. Bring in a story about a recent failure or share some revenue numbers. Your other members will feel compelled to reciprocate by sharing as well. Even though it may hurt a bit, this small sacrifice could be enough to jumpstart your group.

Of equal importance is that your meetings are interactive. It’s easy to take a list of questions like those I’ve provided above and look at them as tiny to-do lists. Once I tick all the boxes, I’m done. The mastermind doesn’t work that way. It’s value comes from finding ways you can help the members of your group by actively listening and making the other members’ problems your own.

Be ready to give and take constructive criticism

Although your mastermind session should be generally positive and optimistic, constructive criticism is a necessary part of the process. If another member discusses an idea that sounds like it will fail, you should let them know this and convey why you think this is the case. Present this in a way that shows the member you are providing this feedback because you are on their side not because you are against them. In general, your group exists to encourage one another to meet your goals, but this does not translate to being positive about each and every idea that comes up. If you feel an idea will fail, better to hash that out when the idea is presented than to let a member devote time and resources to a strategy you knew would fail. With constructive criticism, members can improve upon their ideas and scrap those that are half-baked before they cause problems.

The flip-side of constructive criticism is being thick-skinned enough to take it. When you come to your meeting with an idea you think is great, it stings when others are not entirely on board. Once you feel that sting, it’s easy to get defensive. First, you need to understand this is happening to you and employ your willpower to suppress that reaction. Take a step back and realize that your mastermind wants to help. If they feel this way, your customers may as well. You’re better off fixing the idea now than having to scramble later to make it work after you have already put it into practice.

How do we remain accountable?

Another important aspect of your mastermind group is that you keep one another accountable. If someone mentions an idea or a project and doesn’t bring it up again in subsequent weeks, check up on them and see where the project is. They may have forgotten to mention it. It may be going poorly (and you may be able to help). They could have dumped the project. All these are common ways to progress with a project, but it’s best to keep these things out in the open. Your project’s problem may have a simple solution you hadn’t considered.

If you’re like me, it’s impossible to keep track of previously mentioned projects without a written record of what has happened. Designate a note-taker and an alternate for your sessions. The note-taker will take notes when the others talk. Your alternate will step in if the note-taker is out and while the note-taker is talking.

Paper notes are great (and most people prefer taking notes on paper), but they’re difficult to share. I recommend using Google Drive or Evernote. These services will let you make the notes once and share them with everyone easily. I use Google Drive. Before a session, I make a copy of the notes for the previous session. This gives me a template to use for the current session and a reference of what we discussed previously.

Accountability makes it a bit harder to drop ideas and projects now that you know you’ll need to explain those decisions to your mastermind. It will help your business be more stable if you are forced to be able to explain your decisions.

Great! How do I get started?

The hardest part of any new habit is starting, and, as I mentioned previously, it may be that you don’t know any people who have similar goals. Fortunately for you, we here at Your Freelance Career do know loads of people who are going through the same things you are!

First, grab the resources I’ve provided here:

Mastermind Reference Sheet
Mastermind Reference Sheet PDF
Mastermind Session Notes
Mastermind Session Notes – Google Drive template

Second, post in the comments if you’d like to start your own mastermind group online. This is a fast way to start reaping the benefits of a small team of like-minded individuals who help you become more successful. See if you can find an existing thread which is a good match for you. If not, start your own thread.

Provide a few pieces of information to be sure you get a good match: your name, your preferred time to meet (converted to GMT), what you do, how long you’ve been doing it, and your Skype and/or Google Hangouts username. Once you have a group of three or four, take the conversation to IM to work out all the details. You’re on your way to making better decisions for your business!

If you enjoyed this article and the resources provided, please take one second to share on your favorite social media site. It really helps and is much appreciated!