How To Host A Business Mastermind Retreat

How to host a business mastermind retreat

I’ve just returned from a women’s business mastermind retreat. Seven of us, all with online businesses in various genres, drove or flew from our various home towns to meet up on the Sunshine Coast and nut out our business plans together.

It was such a valuable experience that I wanted to share with you what we did, how we did it, and tips you can use to host your very own business mastermind retreat.

What is a business mastermind?

A mastermind is a group of people who come together to brainstorm or “mastermind” each other’s businesses, ideas and sometimes personal lives.

The primary purpose is to support, encourage, challenge and hold each other accountable. This might be a temporary arrangement – for example, for a weekend retreat – or a longer term one, where the participants connect regularly over a year or more.  The longer term groups are better for facilitating deeper connections and building trust, as well as truly getting to know the other participant’s businesses and goals.

In my case, we had been part of a Facebook group for more than six months, but this was the first time we all connected in person!

Why go to the effort of holding a retreat when we are regularly in contact online? Honestly, there is just no comparison in the surface level chats of Facebook, and the real-time, in-person conversations of face-to-face connection. It was the best thing our group could have done.

Tip: It’s ideal if participants are at similar levels in their businesses – for example, all solo businesswomen, or at similar income levels.

Planning the retreat

Once your group has agreed to have a retreat, survey everyone to find the right dates and location. With multiple heavy schedules to balance, this is a really tricky part. Sometimes one or two people just can’t make it, and you have to go with when the majority are available.

We decided to book a large beach house through airbnb. There was plenty of beds, multiple lounge areas for our group sessions and enough room to split off into pairs or just to have some quiet time. It was a great choice for us! You could book a hotel room, conference room, yoga studio, or host it at someone’s home.

For food, we pooled money and one of the lovely ladies went grocery shopping for the house.  It was a smart move because we could power through our brainstorming sessions with plenty of snacks and meals on hand.

Structuring the retreat

Mastermind retreats without structure do not work. Heed my warnings on this! It just turns into a fun-filled weekend away with the girls: which, while totally awesome, is not productive. People will miss out on getting the advice they need and will be disappointed.

If nobody is interested in taking the lead, it could be worth asking a third party (a friend, coach or assistant) to tag along and play the boss.

Here are a few ideas for sessions within your retreat structure:

The Hotseat

I recommend you start your retreat with hotseat sessions. A hotseat just means that one person has the floor for an allotted amount of time (choose this based on how many people you need to rotate through, and how long everyone wants to keep working for in a given day), and can discuss whatever they want within this time. Prepare beforehand by writing down a few things that have you stuck, or new ideas you’re thinking of implementing, and use your hotseat time wisely.

When it comes to your turn, offer a quick run down of your business as it stands, where you’d like to go, and present your first problem to the group. They will offer feedback, ideas, alternatives and encouragement. Try to record the session on your phone or take notes to keep track of things. Once that topic is resolved, move onto your next item.

Many people find this the most valuable part of the retreat (I did)! We spent 45 minutes per person, with lunch break factored in, and worked from 8:30am to 4:30pm.

Tip: Make sure you actually time the hotseat sessions. It’s so important to make sure the retreat runs smoothly and you’re not working into the night! Offer a ten-minute warning to the hotseat participant so they get a chance to air any remaining concerns.

Working on your business values

This is a valuable exercise to get clarity around your purpose, direction and what you consider most important in your business and life. Use a model such as Danielle LaPorte’s The Desire Map to determine a list of core values (ideally, 3-5) that drive you and encapsulate where you want to go.

Help each other by discussing your own core values, suggesting concepts or words to other participants, and talking about how you can bring those values to life through your businesses.

Hosting How-To Sessions

Take advantage of the various skill sets that participants bring to the retreat by offering each person a chance to teach a class. It could be on topics like graphic design, writing effective newsletters, SEO, accounting, hosting a workshop, social media strategy, mindset: you name it! Everyone knows something that could be of use to others.

1:1 Assistance Sessions

Similar to the how-to sessions, you may want to offer your services to the group on a one-on-one basis. Perhaps schedule a two-hour window where you are available share your expertise, and participants can come along with questions or problems to work through together.

Group Website Critiques

If you’re feeling game, get everyone to bring their laptops and take turns viewing each other’s websites. Offer honest first impressions and insights on what you think the person is offering based on their homepage. Is it clear? Strategic? Confusing? Obvious what to do next?

When it comes to our own stuff, we’ve usually got blinkers on. This is an excellent opportunity to find out what people outside your niche think when they land on your website.


Last but certainly not least, you can have a little fun! Organise dinner at a local restaurant, a pyjama party, day trips, a yoga class or a few adult beverages to wind down in the evening. Then revel in the fact you’ve created a life where this is what you call work! ;) 

Following Up

Make a plan for the weeks and months following the retreat to ensure you follow through on goals made during those planning sessions. Use a weekly check in via Skype, phone or online forum (like Facebook) to track each other's progress and hold each other accountable. You'll be making incredible progress in no time!

*Desire Map link is affiliate.