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Hi Reader,

Have you ever thought about hosting your own mastermind retreat?

A mastermind group is a group of people who come together to share ideas, solve problems, and help each other grow. An ideal group has people who are at similar levels in their career or business. While members are typically in similar industries, each should have a different specialization and bring a complementary skill set.

Even if you meet regularly with your mastermind group, there’s nothing quite like getting away for a few days to a new location and unplugging from work to brainstorm.

Dedicating time to planning and strategizing for your business is one thing, but when you mix it with likeminded people and a change of scenery, you’re bound to get inspired and experience breakthroughs.

Why host a mastermind retreat?

You’ll find that getting in person for just a few days will help you go deeper, and get to know people better, than you would in half a year or more of virtual meetings.

Though we often try to find focus by closing our office door, putting on a pair of headphones, or toggling Do Not Disturb mode, we still can’t simulate the kind of immersion that comes from getting away for a few days. When you’re in your regular place of work and doing usual business, your focus just isn’t the same.

There’s also something about the energy you experience in person with people that makes everyone feel more comfortable about sharing genuine, honest feedback. You’ll find people are willing to share more and be more vulnerable after spending a few days together in person than they would online.

What is a good mastermind group size?

A mastermind group could be as small as three or four people, but right around six seems to be the sweet spot in terms of getting enough different perspectives while still having enough time to talk to everyone.

But while your mastermind retreat will benefit from having people who already know each other, that doesn’t mean you can’t invite people who are new to the group. You can host a retreat with people who might make a great group but don’t otherwise meet regularly. You could also invite an extra person or two to your usual mastermind group just for the purposes of attending this retreat.

Whether it’s your usual mastermind group or a bespoke group, avoid having more than eight people at your retreat. It becomes a logistical problem with having enough time for sessions and it also becomes difficult to have meaningful conversations with everyone. It’s better to have a smaller group where no one feels rushed.

How often should you host a retreat?

Once or twice a year is a good cadence for hosting a mastermind retreat. Having a retreat more frequently than twice a year yields diminishing returns. You need time between events to implement the things you learned and said you would do. However, any less than once per year, and your group is likely to drift apart. You need to meet regularly enough to keep the group together.

How often you host a retreat also depends on the nature of the group itself. Different groups will have members with different needs and capacities to meet.

For instance, individuals who run solo businesses and live in the same city will probably find it easier to meet more frequently. Whereas a mastermind group of CEOs may be hard pressed for time and find annual retreats to be more suitable.

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Location, lodging & logistics

Choose a location that isn’t any member’s hometown. Everyone should get to experience a change of scenery. Switch it up each time, and take turns planning the logistics.

Relatively quiet and reflective places are a good choice for a retreat. Mountains, trees, and great views are a plus. Of course, you can try different locations, but generally avoid places with lots of noise and distractions.

Everyone should stay at the same place. Some of the most important conversations you’ll have will be serendipitous, and those conversations won’t happen if you’re staying in different buildings or lodges.

I like to grab an Airbnb for a few days. You can also ask people you know who’ve hosted their own retreats if they have favorite places they’d recommend.

Food

You might be tempted to treat food as an afterthought, but food can be a huge part of the overall experience. A great meal will bring people together—and it’s even better if you don’t have to make it yourself.

Though someone in the group might be a great cook, resist the temptation to assign them to meal duty. They’re here for the retreat too, and cooking and cleaning for a group can quickly become a full-time job.

It’s a much better idea to hire a chef and incorporate the expense into the overall retreat budget (or simply go out to eat for dinners). Not only will it elevate everyone’s experience, but it will free you up from distractions and let you focus on the reasons you attended the event in the first place.

If the budget is limited, have a chef cook just the dinners. You can arrange simpler options for breakfast and lunch. Do an initial grocery run before you arrive to pick up any miscellaneous items you may need (snacks, coffee, etc.). This can include breakfast and lunch ingredients if you’re only having a chef make dinners.

Schedule

Four days is just the right amount of time for a mastermind retreat. Thursday through Sunday works well.

The first and fourth days are largely going to be travel days. While some people may live closer to the retreat location and have less travel time, others may need to take multiple flights to reach the destination. Even if there are no connections or delays, consider that people aren’t going to have much energy to jump into deep sessions after a day of travel anyway.

You’ll have two full days in the middle for sessions and deep conversations.

DAY 1: TRAVEL (ARRIVE)

• Afternoon — People arrive
• Dinner — Prepared by chef

DAY 2: SESSIONS

• Morning to early afternoon — Mastermind sessions
• Mid to late afternoon — Group activity
• Dinner — Prepared by chef
• Evening — Drinks, conversations

DAY 3: SESSIONS

• Morning to early afternoon — Mastermind sessions
• Mid to late afternoon — Group activity
• Dinner — Prepared by chef
• Evening — Unsolicited feedback

DAY 4: TRAVEL (DEPART)

• Morning — Pack up, head home

“Hot seat” session format

Designate a chair to be the “hot seat”. Each attendee takes a turn in the hot seat and gets to share a bit about their business, what they’re working on, and any things they need help with.

Depending on the size of your group, set the individual hot seat time to either 60 or 90 minutes. Assign someone to be the time keeper. Have them start a timer at the beginning of each session and give a warning when there are only 15 minutes left. Make sure to follow the timer and stop on time! It can be tempting to ignore the timer and go long, but you’ll find your entire schedule will quickly get off track if you do.

Aim to have no more than 4 or 5 hours per day of sessions. Though it seems like you’re just sitting around talking, you’ll use a lot of mental capacity which can be draining. Save some energy for the serendipitous conversations later as those are where you’ll get a lot of breakthroughs.

If you have six people in your group, you can do the first three sessions on Day 1 and the remaining three sessions on Day 2. You could go up to 90 minutes per session if you want.

If you have eight people in your group, you’ll want to limit sessions to 60 minutes. Do the first four sessions on Day 1 and the remaining four sessions on Day 2.

If you start at nine in the morning, and take a break for lunch, you’ll have all of your sessions finished by early afternoon. This will give you some time to relax or do a group activity.

Here’s a format you can use for each hot seat session (the times are just estimates and don’t need to be strictly enforced):

CONTEXT (15 MINUTES)

• Where are you at right now? Tell us a bit about your business and give us the necessary context to be able to help with any issues.

CHALLENGES (10 MINUTES)

• What is your biggest struggle right now? What are some of the primary problems you’re facing, and where are you feeling stuck?

CONVERSATION (30 MINUTES)

• Before offering advice, ask clarifying questions. Allow the person in the hot seat to follow up with any relevant details. It can be easy to jump to solutions, but if people give advice before getting the full picture, it can do more harm than good.

COMMITMENT (5 MINUTES)

• What are you going to do? Tell the group what your plan is moving forward. Where do you hope to be by the next time we meet?

Group activity

After a morning of intense sessions, it’s a good idea to get outside to move your body and clear your mind. This could be as simple as a walk to enjoy the scenery, or a trip into town to visit some of the local shops.

Look into what unique opportunities your particular location might afford. Consider activities that may be novel or uncommon in other areas, and try to do the kind of things you could only do here.

Alternatively, play a game, sit on the porch, walk on the beach, go on a hike, do a tour, take some photos, or just enjoy one another’s company.

Unsolicited feedback

On a hike along the river at my first mastermind retreat years ago, the group I was with started talking about our mutual friend. He wasn’t with us, but we all shared what we thought he should do with his business.

At first, I felt a little guilty like we were gossiping. But it’s not like we were saying negative things. It was all good advice and feedback. If I were him, I’d want to know.

This is how unsolicited feedback was born.

We all have thoughts about what other people are doing, but we don’t share those thoughts out of politeness. But sometimes, that advice can be super valuable.

We decided we set aside time where we’d make a point to talk about someone as if they weren’t in the room—only they were in the room. They just weren’t allowed to speak. All they could do is listen and take notes.

The rules are simple:

1. Sessions last 15 minutes per person
2. The subject cannot speak, they can only take notes
3. Everyone else talks about them as if they aren’t there

We’ve adapted to allowing the subject 5 minutes at the end to make any comments, but the idea isn’t to rebut or defend. Rather to share any insights. They can always go further in depth with others later in the night in one-on-one conversations.

Though you might think the advice would be largely critical, participants often leave the session feeling respected and valued by their peers.

At 15 minutes per person, with another 5 minutes for comments added at the end (totaling 20 minutes), you can complete an unsolicited feedback session for a group of six in 2 hours.

The best time to have your unsolicited feedback session is after dinner at the end of Day 3. By this time, you’ve heard from everyone and likely had many conversations over the days. This provides enough context to make the unsolicited feedback useful (even if some of the attendees only met each other a couple days ago).

Takeaways

• Get in person with your mastermind group. It really makes a difference.
• Keep the group to 6–8 people. More people makes planning and connecting difficult.
• Host a retreat once a year to keep the group together. More than twice per year tends to be too often.
• Choose a location that isn’t anyone’s hometown.
• Hire a chef. If there’s not enough budget for all meals, just do dinners.
• Schedule four days for the retreat.
• Allow 60–90 minutes for “hot seats”.
• Use this session format: context, challenges, conversation, commitment.
• Plan a group activity for the afternoons. Choose something you can only do in this location if possible.
• End the retreat with unsolicited feedback at the end of Day 3.

Hope this helps!

—Nathan

P.S.

I published a new episode on my podcast this week with our Head of Deliverability at ConvertKit, Alyssa Dulin. It covers what professional creators need to know about email deliverability, how the industry actually works, and the semi-secret organizations that exist behind the scenes.

Watch or listen to the episode »