How to run a mastermind retreat

5 minutes reading time

Last week I spent a few days in East Sussex for our annual mastermind retreat. It was a pretty intense few days. I learned lots and, most importantly, got clarity on where I’m heading with my business over the next few months. I highly recommend it.

As I was sitting reflecting on my retreat, I thought it would be useful for others if I wrote up how we planned and organised ours.

What is a mastermind?

If you’re not familiar with the concept of a mastermind group, Marc Jenkins, one of my mastermind confreres, wrote an excellent primer on the subject.

What’s the value in a retreat?

The regular calls you have with your mastermind group are great, but usually, they’re held virtually for an hour to ninety-minutes every week or two. Over time you get to know each other and each other’s businesses. However, it’s easy to become a bit blasé, the energy of the group can falter, and letting the accountability slip.

A retreat where you’re all together physically for a much lengthier period of time boosts that. You get to be surrounded by a group of smart, like-minded peers who have a common goal of propelling their businesses forward.

Coming together with a group of smart, like-minded peers in an inspiring location away, from the day-to-day distractions of running your businesses is a great way to be inspired and get fired-up to propel yourself and your business forward. It also gives you the space to create a more comprehensive plan of action.

I think of it as a quarterly or annual review on steroids. You should already be taking the time to review your business and your goals on a regular basis. The benefit of doing this as a group means you get constructive criticism from people who know you and who you trust, and you can have extended, more in-depth conversations than your regular meetings can allow for. Further, you have time to reflect on those conversations, clarify your thoughts and get some accountability for taking action.

Set dates and budget

It needn’t take a lot of work to organise a retreat. We started thinking and planning ours about 6 months in advance. First, get buy-in from your group, suggest some dates and agree on a budget so you can start to find somewhere to stay.

For a group of about 4-6 people, we’ve found that planning for a 3-night stay works well. We arrive on a Tuesday afternoon, and leave on Friday morning. This gives everyone chance to unwind before two full days.

We use Airbnb to shortlist properties that are large enough for everyone, and somewhat inspiring. We’ve looked for places that are quiet and secluded, so there’s space to sit quietly to think or reflect or go for walks. You’ll also want to ensure there are plenty of places to work. A big dining table for the group sessions is ideal, as well as some nooks and crannies.


Once you’ve got your venue booked and you’re about a month or so out from the retreat dates, it’s time to start thinking about how your retreat will be structured so you can all make the most of your time together.

It’s critical that you each know what you want to try and achieve while you’re there. We created a shared document that we added to over the weeks leading up to the retreat. We used it to plan the group agenda, our personal aims as well as the more general logistics for catering and so on.


This could be the stickiest part if you have fussy eaters. We’ve been lucky in that we’re all pretty flexible and we all eat most things. Unless you’re going all-out and hiring a private chef to take care of all your nutrition, then you’ll want to agree on how to handle food. The format that follows has worked well for us.

Find a local pub or restaurant to eat on the first night. People will likely have travelled a distance and part of the aim is to get to know each other on a more social level. Going out for a meal solves these nicely. Shortlist a few places in the surrounding area, get recommendations if possible and then book a table ahead of time, so you know it’s sorted; it’s one less decision to make on the day.

For the primary two days of the retreat, take it in turns to cook meals for the whole group. We have plenty of people in our group who like cooking, and so we took it in turns to prepare meals for the primary two days of the retreat. We chose a few recipes and ordered the ingredients via Gousto. (Make sure you’re aware of allergies or preferences such as vegetarianism or veganism.) If one or two members of your group are happy to cook all the meals, then everyone else should handle washing and cleaning up.

Create a shopping list for essentials like tea, coffee, and snacks and nibbles to keep you going. Either agree that everyone will handle their own breakfasts and lunches and add everything to the shared list or decide on the specific meals and who’ll cater them. Again, add these details to the planning document. Either nominate someone to go shopping on the way or just have it delivered to the venue.

Aim and Sessions

Set some “homework” to have everyone think about what they want to achieve during the retreat and prepare accordingly.

The format we used is simple. We scheduled a session each hour starting at 9am. Each person had about 45 minutes where the focus was on them. The remaining 15 minutes allowed for the conversation to finish and time for a brief break before the next session. We had a break for lunch and continued in the afternoon. Once all the sessions were over, the rest of the afternoon was free to do whatever you wanted. Think, relax, work on your business.

The pattern repeats the following day. To make it easy, we randomly selected the order of the sessions and then reversed it for the next morning.

In our planning document, we have a section where everyone writes out their aim for the retreat and what they wanted to focus on during the first session along with any background information necessary. The second session was more open since it likely depended on the outcome from the first.


There’s as much value in the other conversations that naturally happen between members while cooking, walking or shooting the breeze so don’t be too rigid with the schedule. If you find you need to break it on the day, do so. Don’t let a fixed program control the day.

Bring cards and board games — it’s not all about work. Make time for fun and casual conversations. At this last retreat, we had lots of interesting discussions ranging from the environment to parenting. In the end, we didn’t actually play the games.


Most venues will want you to be out by mid-morning, so we suggest finding a local cafe for breakfast and use it as an end to the retreat, wrapping up what you each learned and your next actions.


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