The power of a good accountability group can’t be overstated. The right team, the right coach, and the right level of peer pressure can help you discover parts of yourself that perhaps aren’t always possible by grinding alone. After running our leadership incubator for the last six years, as well as masterminds + group programs for more than ten years, I get a lot of questions about how to run them.
This is a two-part series on running group programs. The first essay covers what mastermind groups are, the history of the idea, and what they can be used for. This second essay in the series goes over the key things you need to do to set up or run your own group. Early in my career, I ran facilitated peer masterminds for free with friends. After seeing the incredible value of the groups, and the labor required for running them, I started hosting paid groups. Today, I lead The Wise Women’s Council, our paid leadership incubator for business moms, based on many of the lessons learned from running groups over the last decades.
Also, if you want to know even more after reading these two essays, check out the private podcast sessions I did for paid subscribers on running group programs and how to design, structure, and price a group program, where I cover the exact details of how I designed my programs. This two part essay series is 20+ hours of writing and 10+ years of experience documented for you to learn and build your own. I hope it helps, and thanks for reading.
10 Things To Know When Starting Your Own Mastermind Groups
I’ve been a part of mastermind groups for years, and I’ve led them professionally for groups of like-minded leaders to help them level up in their leadership and work. If you want to run your own group, here are the nuts and bolts you’ll need to create your own mastermind group: how to start one, what to consider, and what traps to avoid.
1: First, decide how big you want your mastermind to be.
My favorite size group is typically 5 to 8 people in longer sessions (90 minutes to two hours), following a more formal process. When a group gets bigger than 8 people, it can become unwieldy, and I’ll typically break it down into smaller sub-groups so that everyone has enough time to share their puzzles and journeys with the group.
For the sake of this article, I’m going to focus on a group size of 5-8 people, because it’s a size I highly recommend. If one or two people miss in a given month, you can still get quite a lot done; if everyone shows up, you can break it into two sessions as needed. More than 8 people, and scheduling becomes a nightmare; fewer than 4 people, and you don’t have enough people in the room to get at your puzzle or project with enough perspectives.
If you’re pressed for time as a parent or a CEO, I’ve also hosted mini-masterminds with fellow entrepreneurs in groups of three; this, however, requires strong attendance track records—you’ll need people to show up to 90% of the meetings or it won’t work. If you need more flexibility with attendance, go for at least 4-5 people.
2: Create an intention and a goal.
The mastermind will serve a purpose; get clear on what it is together. You’ll want to set a clear intention from the start, and you might want to do one or two gathering sessions to work through this.
Is it to help grow, develop, and shape each other?
To hold people accountable to hitting goals?
To provide a space for smart feedback?
For my masterminds, I often set a goal of honest, kind feedback for people to grow in community with each other, and we set quarterly goals to keep track of where we’re going. We meet for several months at minimum and in every session, we each do a deep dive into a puzzle or problem that we’re working on that relates to our quarterly goals.
3: Invite the right people.
Decide on the criteria for the group and what you want the shared interests to be. It's important to develop a criteria for the group so that you’re able to speak at a higher level of expertise about a particular topic.
Make sure you’re in a group of people at roughly the same growth area or level of expertise. It helps if you’re all looking at similar projects or businesses. For example, you might all be a product-based business, or perhaps you’re all leading companies. You might all be new parents or women in predominantly male-based fields. You don’t want everyone to look absolutely identical, but generally speaking, having a shared baseline is important.
Things to consider demographically: Expertise or experience, domain, industry, management experience, seniority, education, age, location, geography, time zone, diversity, equity, availability.
Things to consider psycho-graphically: Emotional maturity, kindness, empathy, values, ability to give good feedback, commitment or follow-through, level of life experience.
Write down what you’re looking for in a participant in the same document as your intention or goal.
4: Write a call for requests.
Write out a description of the type of person you’re looking for. Also know what kind of people you don’t want in your group. For example, you might be a consultant who is regularly making low six-figure business income, and you want to scale up to high-six figures or hit the seven-figure mark. It might not make sense to invite someone who is a brand-new entrepreneur or works in a corporate job, for instance. Their expertise will be elsewhere. It’s critical to get the right people in the room, because they’re going to be giving you feedback on your most important projects and ideas.
It’s critical to get the right people in the room, because they’re going to be giving you feedback on your most important projects and ideas.
This is another reason why it’s such a great growth strategy. When you create a solid group of people whose feedback you can count on, you build trust, skill, and confidence in the work that you’re doing. In contrast, unsolicited or irrelevant feedback—especially from the wrong person or at the wrong time—can really sink a project. Call it a mastermind group, a personal advisory board, or a set of trusted friendships, developing a circle of thoughtful leaders around you is a great way to accelerate your personal and professional growth.
Take action: Write out a “job description” for the type of people you’re looking for, and circle it with a few people that you’d like to join you, or people who might be able to give you recommendations.
Tip: Tell people that you’re considering the idea and interviewing people in an informal process, but don’t guarantee them a spot right away. In fact, I like to not even tell people that I’m interviewing them, and instead set up a casual chat where I ask them about their work, their goals, what they’re up to, and how it’s going.
5: Set a start date and an end date.
Many peer-led groups fizzle out because there’s no clear end date. I find at least six months is good, and doing a series for twelve months (and then stopping) works really well. Be clear about both the start date and the end date.
6: Commit to a regular, recurring frequency.
I find a lot of success with meeting every other week. Every week can be hard to schedule into an already-full calendar. Alternatively, once a month can be a good rhythm for longer-running masterminds. To save scheduling headache, try to pick a recurring time rather than a new time every month.
Some scheduling examples:
Every other week — The first and third week of the month, or second and fourth week of the month. Note that a lot of holidays fall on Mondays and Fridays, so picking a mid-week day can be better.
Monthly live, mid-month check-in — Do a live session once a month, with a halfway check-in that’s specified (e.g. we’ll all check in on our projects in our group chat / WhatsApp / Slack room by Friday the third week of the month).
Monthly — meet once a month for around 90 minutes.
Quarterly deep dives with monthly check-ins — Once a quarter or semi-annually, do a longer planning and deep-dive session with folks (plan on 20-30 minutes per person), with a shorter monthly check-in (10-15 minutes per person).
7: Require attendance at a high level.
Masterminds often fail when people don’t show up or repeatedly miss meetings. For this reason, many groups have an attendance policy: if you miss more than 2 meetings, or attend fewer than 80% of the meetings, then you’re put on the wait list or you’re automatically out. It’s strict, but worth it. It shows that you’re taking the work seriously, and you’re taking yourself seriously.
We live in a world that allows for flaking, ghosting, cancelling, and more. Having a strict attendance policy can feel abrupt but it’s an important practice, and it shows that you’re taking the work seriously. It’s best to decide on it in advance, together. In a planning session with members, put this on your agenda: “What should our attendance policy, and how many times should you be allowed to miss before we move on without you?”
Why attendance matters. Remember, if you’re in a group with 8 people, and you miss three meetings, you’re missing 21 updates from folks, and 21 chances to get feedback and support on your project or idea. We know that life happens, so this isn’t a punishment. If you’re unable to attend because of illness or chaos, then the group can put you on the waiting list until you’re able to attend again in the future.'
8: Decide on the technology and structure in advance.
How and where will you meet? Decide if it’s phone calls, video calls, in person, or another medium and stick to it. I have a Zoom account I use and I set up a recurring calendar invitation with a link to the room for everyone to join.
How long will the session be? Don’t pick the session length first, decide on the structure and then determine the length. For example, if you want 10 minutes for a group check-in, and 15 minutes for each person, plus a midway break and 10 minutes to wrap up — then for a group of eight people, you’re going to need a 2.5 hour meeting.
Quick sidebar: I have a personal dislike of 60-minute meetings. They’re the opposite of Goldilocks — they’re too long for a quick discussion that could be 20 minutes, and create bloat on people’s calendars. They’re too short for depth. It’s like picking the number seven on a NPS rating (don’t do it!). You have my strong encouragement to pick 30 minutes, 90 minutes, or two-and-a-half hours. (But a caveat — sixty minutes is a good time length when it’s a group of four.
Create a structure for the calls and bring a timer. Ad-hoc is not a great way to run a meeting. There are lots of ways to set up meetings. I like using “Rose, Bud, Thorn” and give everyone 15 minutes to chat about their progress or a specific puzzle they want to work through. A ‘rose’ is something that’s going really well, a ‘bud’ is something on the horizon, and a ‘thorn’ is something that’s not working well.
Tips for dividing the time: Always give yourself an extra 1-minute buffer for each person and an extra 1-minute allowance for transitioning to the next person. Bring a timer and have it ring loudly in the group when they have one minute left. Learn how to interrupt and cut people off.
Sample structure for a 90-minute call:
Have everyone submit a 3-question check in & focus area at least 24 hours before.
0-10 minutes: welcome folks to the room and have them put updates in the chat. Do a 1-minute energetic check in for each person.
Starting at 10 minutes: use 60-70 minutes to divide the time:
If eight people: you can each do an eight-minute check-in using the rose, bud, and thorn. Have people share updates, what they’re doing next, and an ask they have for the group. Set your timer for six minutes.
If six people: you can each do a ten-minute check-in. Set your timer for eight minutes.
If four people: you can each do a fifteen-minute check in. Set your timer for 13 minutes.
Give people five minutes at the end to write down their action items, accountability needs, and asks in a shared group doc.
Also, I have a lot more meeting templates and structures that I can put into a downloadable format. If you’d like to borrow all of my meeting templates, leave a note in the comments so I know that you’re interested!
9: Allow it to iterate.
It might take a few rounds to really get into a rhythm. People may come and go—I’ve started with a group of four, built to six, and then had one person take leave for personal reasons. It can ebb and flow until the right mix comes along. You’ll know within a few months if it’s working, and if it’s not, scrap it and try again.
When you scrap it, however—or when you successfully run a program—there’s one final thing to make sure you also do…
10: Create an intentional ending.
Things that fizzle out or end with a whimper leave a sour taste in our mouths. For everything we don’t finish, for everything that doesn’t quite work, there’s a trail of could-have/would-have/should-have that creates detritus in the brain. When we end things clearly and with a bit of celebration or reflection, we honor what happened, regardless if it worked or not.
Honor the end date. Appreciate the process. Thank people for the time. Clearly wrap everything up.
If it doesn’t work: “Thanks everyone, for giving this a try! I really appreciate your energy and time. After doing this for three months, I’m going to close this down and call it a wrap. I’ve learned a lot about how to structure a group, what we need, etc … and I’ll be taking these lessons with me as I iterate in the future. I’ve also learned so much from each of you, and I want to wish you the best success for your projects going forward. Please keep in touch with me by sending me a note when you hit a big project milestone! I’d love to hear about it.”
If it works: “What a beautiful year we’ve had together. I can’t believe how much we’ve done. I loved this so much, and learned so much from all of you. We’re at our agreed-upon end point, and so I want to give everyone the chance to complete their time here. I am hoping to start another group kicking off in a month. If you’d like to join me for another year, or you’re satisfied with your work here and the things you’ve accomplished, send me a DM and let me know what you’re interested in doing for next year.”
Organizing, managing, and leading a group is an investment—but it can be incredibly rewarding and useful.
Facilitating and managing the organization of any group is a fair amount of work. Know that if you’re starting the group, you’ll probably put in a lot more energy and time corralling and organizing everyone (as well as the design of the process), but the up-front investment and curation of the right group can create a wonderful container for growth.
One of my biggest lessons from running a mastermind for my friends is how much work it truly takes to organize it. A well-run group is not an accident. If you’re benefiting from someone else’s organization, know that the person running it is doing a lot of work.
Creating your own groups can be incredibly rewarding. If you’re short on time, or you don’t want to run it after reading this, then consider a paid mastermind group.
Joining a paid group can sometimes be more effective and better than running your own groups. When people pay for a group, they take the commitment more seriously — more people will flake on free commitments than paid investments. For me, I realized that it would take less time and cost less, to pay to join a group. After a while, the opportunity cost of taking my time to organize groups was more expensive than paying for a facilitator.
Also, many paid masterminds offer value beyond what they you can construct yourself. The network effect of tapping into a group that’s already well-connected can have a huge rate of return: what’s the value of joining a group that introduces you to your next agent, client, or partnership? Your time and energy might be better spent paying someone else to organize it rather than trying to bring everyone together, depending on where you are in your life and business.
Erin Kelly, co-founder of Member Vault (a company she started while pregnant and on the road, living in a trailer with her partner) said that masterminds have been instrumental in her business, especially because she spent so much time on the road:
“The biggest thing for me was participating in a paid Mastermind full of women that stretched me — I stayed connected throughout the week with them through Slack, and we have biweekly calls and in-person retreats. The connections I’ve made there directly have been huge and they have then rippled into their own networks. Having a place to show up, and be accountable with people you respect is crucial to avoid the PJs covered in crumbs downfall of working from home!”
If the price of a paid program is beyond you, however, especially in the early days of your startup, then use the tools in this article to build your own group with your elbow grease, your current network, and a bit of grit.
The structure is all here for you to steal (like an artist).
It’ll be worth it.
— Sarah Peck
CEO & Founder
Startup Parent
Leave a note in the comments:
Have you ever been part of a mastermind? What worked well? What didn’t?
Also, is there anything else you’d like to know about running or leading group programs?
So many gems in this post, thank you Sarah for sharing! I'll be bookmarking this for a time when I have the headspace to lead a group. I appreciate the way you walk through how, specifically, you facilitate these calls. Also useful in a corporate environment! Thanks again!