5 Tips for Running a Founder Mastermind Group
TLDR: It’s harder to run a peer group than you think
Peer groups are incredibly valuable for founders of all types. Sometimes called Mastermind groups, these are mentoring groups where members support and advise each other on their challenges.
We’ve seen famous people throughout history from Benjamin Franklin with his Junto organization to Sara Blakely, founder of Spanx, with her 14 years spent in her EO peer group rise from relative obscurity to great heights with the support of their peers.
Peer groups are especially useful for founders who want reliable and trusted connections with people who get them and the challenges that they’re facing. Friends & family often operate on a completely different wavelength than you as an entrepreneur.
If you are struggling with hiring/firing decisions, co-founder disputes, whether to pivot, how to deal with a difficult customer, how to delegate effectively — these are all challenges that other founders have experience with.
And in a peer group setting, they could share their experiences openly with you and help you brainstorm, wayfind, and watch out for unforeseen hurdles.
If this sounds like exactly what you need and you’re ready to form your own peer group, that’s awesome, but it’s not as easy as it looks. I’ve seen countless peer groups either never get off the ground or sputter and stop meeting after just a few sessions.
During 2020, I chatted with dozens of peer group attendees and ran my own group for Facet. Here are my top tips on how to make a peer group successful, valuable, and lasting for all your members.
1. Curating the group
A peer group starts and ends with its members. I highly recommend getting to know people at least a bit before inviting them to join your group. In a high-functioning group, everyone lifts each other up. But groups are also as strong as their weakest link.
Make sure you have a core set of values that all the members share, just so everyone is on the same page in terms of how to behave. You don’t have to get fancy with this, some examples are: honesty, respect, timeliness, etc.
A group should be diverse yet also similar in some ways. Diversity is great because founders can get out of their own silos and learn from others who can offer out-of-the-box ideas from a different set of experiences. But you also need some common thread or founders may feel like they can’t really help each other out.
Some examples of common threads could be: software founders, bootstrapped businesses, selling direct to consumer, women CEOs with over $1M in revenue, and so forth.
You can come up with your own group theme by combining what you’re interested in as well as what resonates with others when you recruit members.
Lastly, groups need to be just the right size. I recommend between 5–8 members. This also depends on how long your sessions are and how often they meet. If you have a longer session, you could have up to 15 members. The sessions I ran were 90 minutes long and 7 members was about the upper limit that I’d recommend so everyone has a chance to participate fully.
2. Scheduling challenges
Scheduling can be incredibly difficult when you first form your peer groups. Especially if you have a large group across different time zones.
Use a group scheduling tool like Doodle to see what time slots have the greatest overlap for most of your members. You can choose a time based on those results and ask the members who didn’t choose that time to accommodate if they’d like to participate.
Or just don’t offer that many options. This leads to choice paralysis and could make it harder for you to find a time.
If you suggest a reasonable set of times and your fellow members are serious, then they should make room in their schedule for the meetings. If they don’t find the sessions valuable enough to make room, then they probably are not a great fit for the groups after all.
Once you come up with a day/time, just keep it the same and don’t change it constantly to accommodate shifting schedules. This helps with consistency because members will know that Tuesdays at 5pm, for example, are peer groups time and not to schedule anything else for that time.
3. Inside the sessions
The magic happens every time you meet, and I recommend setting a general structure for your sessions.
For my sessions, we started off with a round robin check-in where everyone got to share their progress, their hurdles, and any asks they may have of the broader group. The second half of the session was a rotating ‘hot seat’ where 1 founder would have the floor and give us a brain dump of all the context surrounding their top of mind challenge. Everyone would listen first and then ask questions to peel the layer, better understand what they’re facing, and then share their own experiences to help out that founder.
Structure is crucial, but I also recommend including some dynamic component for each session — a changing theme perhaps. Some examples are: how you handle burnout, what’s the most important lesson you’d share with yourself at the beginning of your entrepreneurial journey, and so forth. You can be creative with these themes — they really help your group get to know each other better beyond what they’re facing with their businesses at present.
Based on my experience, facilitation is also critical to the success of peer groups.
This can come in several forms — peer-led, dedicated/trained facilitators, etc. But the function of facilitation needs to be well defined because it keeps the engine of the group running smoothly.
Here‘s what facilitators can do for a peer group:
- Keep the group on track so they don’t go off on a long tangent
- Make sure that participation is balanced and not dominated by 1–2 members
- Gently steer the discussion to go deeper rather than just touching on the surface-level questions
- Help the group build trust faster if they are more experienced with psychology and group dynamics
- Improve continuity across sessions by noting and bringing up points from previous sessions
Personally, I recommend getting a dedicated outside facilitator for your sessions. Members could definitely do this themselves but usually one person ends up being the de-facto facilitator anyways and may feel undue pressure. If you rotate instead, some members may not be as good at facilitating as others, degrading the overall experience.
If you do get a dedicated facilitator though, it is important for them to be trusted and respected by all the group members. Ideally they also have some form of entrepreneurial experience so they can relate with group members at some level and speak their language.
Ultimately, sessions need to build trust between group members. The more trust, the deeper they can go in their discussions, and the more value everyone gets. And a good facilitator helps build trust much faster.
Lastly just start and end each session on time. Be respectful of founders’ busy schedules and run your sessions with a sense of professionalism.
4. Post-session energy
Right after each session, your minds are racing with the deep discussion you just had and everyone is filled with energy and enthusiasm.
It’s great to be able to capture this on a chat platform like Slack (that’s what we use) and members can continue 1-on-1 discussions afterwards on topics that were brought up during the session.
For my groups, I saw a flurry of activity after each session on Slack that would continue throughout the week. It’s definitely great to see members help each other out and take an interest in each other’s progress.
5. Long term consistency
Getting peer groups started may not be that difficult, but maintaining them properly for the long haul can be quite challenging.
First and foremost, sessions shouldn’t be free. Set at least a small membership fee because that serves as a great commitment mechanism.
It also weeds out the people who may come a couple of times and leave. That would be terrible for group dynamics because people may wonder what’s going on if you have a revolving door of members coming in/out. As for what to do with the fee, you could use it to pay the organizer/facilitator for their time operating the group.
It’s also important to build relationships and familiarity between group members as quickly as possible. It’s much harder for someone to flake on the group if they know/like their other members and don’t want to let them down.
Lastly, just as an additional safeguard, I recommend setting a threshold for the number of sessions each member can miss per some period of time. It could be 1 session per quarter for example. And if they cross that threshold, they should step away from the group.
We all have things come up that’s out of our control for sure. But missing too many sessions is a sign of deeper problems. It’s not fair to the other members nor people waiting in the wing to join your group for someone to miss too many sessions.
Don’t feel like managing your own groups?
Come check out Facet! We’re a network for founders and entrepreneurs, centered around small peer groups.
We curate, schedule, facilitate and maintain peer groups for you. All you need to do is show up and participate fully.
We’re primarily designed for bootstrapped founders with some consistent revenue, not looking to raise VC funding, and want to expand the team beyond just themselves.
These are not strict requirements, but essentially we want people who are very serious about their business and won’t quit after a few months if they hit a roadblock or aren’t able to raise funding.
Our peer groups are 90 minutes, every other week, virtual, and facilitated. We also curate topic-specific breakout sessions, office hours with experts, and 1-on-1 introductions.
What we’re tackling is the shallow connections and one-off advice that we see all over the place these days within other founder apps/groups. Rachel and I hated that as indie entrepreneurs, so we want to build the opposite experience for founders just like us.
If you want to form your own peer groups then I hope the tips I shared above help you make a successful one. But if you just want to join a high-functioning group ASAP then you should apply to Facet!
P.S. We’re accepting 100 founding members right now for a January 2021 kick-off and at a $55/month price. Come join us.
