If you haven’t heard of the concept of a mastermind group before, it might be best to start with this post on starting and maintaining a mastermind group.
I gave Nathan and Caleb big hugs as they loaded their bags into the back of my dad’s F-150. After grabbing dinner with my fiancé and picking up our fourth group member, we were off to the mountains of North Carolina for a weekend retreat.
Nathan Barry (NathanBarry.com & Convertkit), Caleb Wojcik (DIY Video Guy & Caleb Wojcik Films), and I have been running a mastermind group together for over 2 1/2 years. We’ve met weekly or every other week during that stretch of time, with Barron Cuadro (EffortlessGent.com) joining the group in 2014, and James Clear (JamesClear.com) dropping in on a call here and there.
I don’t drop the names of our crew publicly all that often for fear of it being obnoxious, but in this case I hope it will illustrate a point: mastermind groups are one of the very best ways to take your business to the next level. I believe the proof of that principle can be seen in the members of our group and how much their businesses and careers have grown since we started meeting.
In March 2015, we decided to step up our commitment to each other by having our first mastermind group retreat. When Barron got stuck in a blizzard in New York City, preventing him from joining us, we invited Matthew Marshall, the Atlanta up-and-comer in UX design, to fill his spot.
There we were — five guys going to a cabin in the woods for a four day weekend full of business planning, honest conversations, great food, and a bit of fun sprinkled throughout.
But why?
Masterminds are powerful, but they’re more powerful when you can regularly meet in person
There are a couple problems with mastermind groups (especially groups who meet virtually):
Meeting for an hour a week or 90 minutes every two weeks allows us to stay up to date and hold each other accountable, but it doesn’t allow for deep understanding of each other’s businesses or comprehensive business planning
The lack of physical presence can make the meetings dull over time, leading to lackluster accountability or calls that have less energy than when the group started.
But the real problem behind all of this is that humans are social animals. We thrive on community, especially once we’ve found “our people” or our “tribe.” Mastermind groups are exactly that, and without the chance to get together in person from time to time, things get stale.
After our first experience planning and executing on a mastermind group retreat, I think we all agree it will become a bi-annual event for our group. The learning and action items from the weekend were simply too valuable to ignore the opportunity going forward.
In this article, I’ll help you understand exactly how to plan an execute on an excellent mastermind retreat, based on what we learned from ours.
Key elements of a great mastermind group retreat
Even when you understand the great value of getting together in person, it can be tough to get the planning process started. The task seems all too big and it can be easy to let it slide into the future as a result. Our group talked about doing a dedicated retreat for over two years before we actually made it happen.
If you’re reading this article, then you’re the perfect person to plan the retreat, so I’d encourage you to take that responsibility head on — your fellow mastermind group members will thank you later. To make it easier on you, I’ve given you a step-by-step guide below.
Scheduling
First things first, you simply need to get a date on the calendar. This might be the hardest part of the entire process. Coordinating schedules, especially for a long weekend, can be a chore (especially when significant others and families are involved).
You’ll want to schedule 3-4 months in advance. When we planned ours, we started about four months ahead of time, when I sent out an email that looked like this:
“I’d like to propose that we put together a mid year retreat for us, at the mid point between WDS’s.
If you can swing it, I’d be more than happy to host — we could spend a long weekend (or week) at my family’s mountain house in January or February. Not a lot to do up there other than hike, enjoy the scenery, drink beer at the local brewery, and enjoy time together. It’ll probably be cold, so we may not want to spend a ton of time outside.
In order of preference, I propose:
Friday 2/6 – Monday 2/9
Friday 3/6 – Monday 3/9
Friday 1/30 – Monday 2/2
Any of those work?”
By giving a limited number of choices, I made it much easier for each member to choose what worked best for them. Asking everyone to throw out random dates they think could work is a miserable experience and I definitely wouldn’t recommend it.
When you’re thinking through length of the trip, I would plan for one day for every two members of the group. Ie: 4 group members would mean a minimum of two full days on location with a travel day on either end. We’ll chat more about why this is a good rule of thumb later.
Ideally, everyone will agree on a date that works. In the worst case, you can pick three new dates and offer them back up for consideration. Once you’ve settled on a date, it’s your job to work towards that date as if it is a sure thing — your confidence and planning will make the rest of the group remain committed to showing up.
Location
Location for your retreat will be key. In my experience planning retreats of many kinds, remote locations where everyone is removed from their home environment are best.
My best suggestion is to host the first retreat within a couple hours of your hometown. Being somewhat close to home means you’re probably familiar with mountain, beach, or getaway towns nearby. Or, if you’re lucky enough to have a family retreat within 2-3 hours’ driving distance of an airport, that’s even better.
Use AirBnB or VRBO.com to check out rentals big enough for the entire group nearby the town. It might seem odd to have everyone stay in the same place, but this is non-negotiable in my book. Staying in the same house means the group will share meals and have serendipitous conversations outside of the scheduled programming.
Book a place, put down a deposit if necessary, and then let the group know you’re good to go on location, so it’s time for them to book their flights.
Menu
I’m a big believer in the power of food. I believe food provides a shared experience and point of connection amongst groups, as well as being the fuel for the energy of the group.
Conversations and drinks over meals provide a great break from the business of the retreat, in addition to generally giving the group an experience of tasty food.
Before our retreat, I was tempted to say I would take care of food and then put it off until last minute. Instead, I forced myself to create a menu for the weekend to set expectations and hold myself accountable to making it an integral part of the weekend.
Here’s the email I sent with the menu, about 4-6 weeks ahead of time:
“Hey team,
Looking forward to seeing you in three weeks. So you can plan on your own timeline, I’m sending along some details for you.
AGENDA We won’t have too much structure for the weekend, but I do want to give everyone a chance to drill down on a challenge or opportunity while we have good minds in one place.
Bring one topic — challenge, opportunity, project idea, whatever — that can serve as the basis for a 90 minute drill down session that will help your business or career. We’ll use the 90 minutes to apply the group’s know-how to whatever’s on your mind.
Each morning (Friday/Saturday/Sunday), we’ll have breakfast, then have 3ish hours of mastermind time.Then we can break for lunch, enjoy the afternoon, go hiking, check out the brewery, or whatever else we want to do. Or, if we want to flip that and do masterminding in the afternoon one day, we can always do that as well.
There is no internet at the house. If you need to print anything to make your mastermind time more valuable, do that ahead of time. We can also go into town (30 mins) if we really want/need internet.
FOOD
I’ll be cooking all weekend. Organic, gluten-free food all the way unless you have any major objections to that. If you have any other dietary restrictions or have a specific meal request, just let me know. I’ll be as frugal as possible in making purchases and we can split cost.
Here’s what I’m thinking:
Thursday
Dinner: Grab something before leaving town or on the way up
Friday
Breakfast: English breakfast of eggs, baked beans, bacon, tomato, cucumber, toast, coffee/tea
Lunch: Build your own salad or sandwich
Dinner: Grilled fish, roasted cauliflower, roasted brussel sprouts
Saturday
Breakfast: Gluten free pancakes and sausage, coffee/tea
Lunch: Build your own salad or sandwich
Dinner: Crockpot roast with veggies
Sunday
Breakfast: Poached eggs and sweet potato hash, coffee/tea
Lunch: Build your own salad or sandwich
Dinner: BBQ grilled chicken, corn on the cob, cole slaw
Monday
Breakfast: Egg + avocado toast
Lunch: Grab something on the way home
Snacks/Drinks: Chips and salsa, Kind bars, dark chocolate. Wine, beer, water.
Anything missing? Anything else you want to make sure we have/do/talk about?”
By creating a menu, you’re reinforcing your commitment to making the retreat happen, building momentum and excitement amongst the group, and giving anyone with food allergies or intolerances a chance to let you know ahead of time. You’re also making a de facto shopping list for when it’s time to hit the grocery store.
Soap box moment: whenever I host a dinner party, retreat, or other event driven by food, I go out of my way to buy high quality, healthy ingredients. For our retreat, I bought all organic produce, grass-fed or pastured meats and eggs, and there were gluten-free and dairy-free options for every meal. You don’t have to accept this dogma, but I truly believe great ingredients lead to better tasting meals with less effort… Not to mention showing you care about your friends by nourishing their bodies. Take that for what you will.
The Schedule
You’ll want to plan for a travel day on either end of the retreat. This gives everyone a chance to get in and out of town without interrupting the flow of the weekend.
On the day of arrival, it’s good to set expectations. Review the schedule, then give each person a chance to spend 15-20 minutes giving an overview of how things are going, both in their business and personal lives. This is a perfect way to ease into the weekend without diving deep on any one person’s business challenges and opportunities immediately.
Spend the evening of the arrival day enjoying time together, catching up, and having a hearty meal (plus drinks, if you’re into that kind of thing) to set the tone for the weekend. An added bonus that’s easier said than done: let everyone get to bed early so you don’t start the first full day with lazy
Each full day thereafter, here’s a sample agenda that worked very well for us:
9am: Breakfast
10am: Mastermind session #1 (90 minutes)
11:30am: 30 minute break
12:00pm: Mastermind session #2 (90 minutes)
1:30pm: Lunch
2:30pm: Outdoor or group activity (hiking, rafting, beach volleyball, visiting a brewery, etc)
7:30pm: Dinner
Evening: Drinks, movies, chats, work sessions, etc
You might also consider flipping the day with group activities and/or independent work sessions in the mornings and then mastermind sessions after lunch. Key principles I would stick to: two mastermind sessions per day + some kind of activity to get everyone out of the house.
Refereeing sessions: 90 minutes
The structure of your mastermind sessions will affect how productive they are, just like the structure of a regular mastermind call affects the outcome there. Each member should have one 90 minute session, and the group should have two sessions scheduled per day.
Here’s a structure we used successfully during our mastermind sessions:
15 minutes: Overview of the business situation and key challenges or opportunities for discussion
15 minutes: Clarifying questions from the group to make sure they have a full understanding of the business context and challenges/opportunities at hand
30 minutes: Group discussion on how they’ve seen similar challenges or opportunities approached in the past, either in their own businesses or by others
30 minutes: Group discussion about how the person on the hot seat should approach the problem or opportunity, given their unique business situation and personality.
Feel free to adapt this outline to what you’ve learned as a group over time. I just want to give you a place to start so you don’t flounder. Again, the key principle is to have structure to the conversation and limit mastermind sessions to two per day. This keeps everyone fresh and ensure no one gets screwed because the group is tired.
Have fun and allow for serendipity
Beyond the schedule and mastermind sessions themselves, be sure to leave time for fun and serendipity. Some of the best conversations we had as a group were not planned.
We stopped by a brewery near the mountain house to play cornhole one afternoon. We took a hike to check out a waterfall nearby. We did a design review of one of the members’ websites since there were designers in the room. We did a one off session for 15 minutes to talk about the direction of my writing on this site (which was outside of the challenges/opportunities in my main mastermind session).
We also had plenty of time to enjoy meals, talk about our personal lives, and explore ideas completely unrelated to business. We had drinks each evening and reserved time to chat about whatever was on our minds.
In other words, leave some time free to just be there with one another and enjoy the company. The time goes fast and retreats will probably only happen a couple times a year. Enjoy it.
The last session: unsolicited feedback
My last recommendation for your mastermind retreat is a closing session. We came up with this on the fly during our retreat, and it turned out to be the most valuable session by far.
We called the closing session, “Unsolicited Feedback.” During the session, the group spent 15 minutes giving each person unsolicited, unfiltered constructive criticism on their business and work product.
The subject of the conversation was not allowed to respond to any comments. Instead, they simply sat quietly as a passive observer, taking notes for themselves. Meanwhile, the rest of the group’s mission was to speak about the person as if they weren’t in the room.
Our goal in hosting this final session was to say all of the things that are hard to say directly to a person. To give the kind of feedback we all wish we could receive on a regular basis. But it’s hard to give direct feedback everyday, and it’s hard to receive that feedback objectively. This session avoided both of those challenges by making it ok, and by forcing every person to sit back and be vulnerable.
There has to be a very clear shared understanding for this to work: it’s about the work, not the person. And everything that’s said is said out of love and respect, not out of animosity or the desire to demean.
My key takeaway from my session: “I have questioned many time whether Barrett will be able to contribute to group conversations I’ve been part of with him because he simply hasn’t “achieved” as much as some of our other friends… And then I’m consistently blown away by the quality of his advice. He is much better at giving advice that’s spot on, than applying the same advice to his own work. That makes him a great coach. I’d like to see him apply that level of business understanding to his own projects.”
Wow. I never would have received that feedback if we hadn’t been open to the vulnerability of listening with an open mind. Instead, it’s changed my perspective on my ability to do great work and help others do the same.
Moral of the story: Mastermind groups are made infinitely more powerful by adding an annual or biannual retreat
The moral of the story is simple.
First, have a mastermind group. If you don’t already meet with a group regularly, get started on finding one now. I’ve written a detailed article on how to start and sustain your own mastermind group here.
Second, while a regular cadence of weekly or every-other-week meetings is great, having an annual or bi-annual mastermind retreat takes the group to new heights.
I hope you’ll take action on this article today. Tweet me and let me know if you do.