25 questions to ask when planning a coaching retreat - Coaching Blueprint - marketing for life coaches

So you’re thinking of planning a coaching retreat, hmm? Fabulous! As someone who has run a few of my own (in Iceland and Peru) I can tell you from first-hand experience that they can be profound and transformative experiences for both the participants and you. They can also be complete stress-bag nightmares.

As with all things in online business, we only see the highlight reel of what others are doing. We see smiley photos full of glowing faces on retreat with a sublime sunset background. But not many people talk about the work that goes into to planning, prep, and execution of a large (often international) event. It’s even less often that you hear any mention of the dark side of the retreat business.

Personally, I’m not interested so much in what went really well…there are tons of tips and advice out there on how to make sure your event is a huge success.

What I’m fascinated with – and what I’m sharing with you today – is everything you need to know or put in place to ensure things don’t go sideways.

Trust me; problems with accepting international payments, having a high drama diva on your retreat causing headaches to the other participants, or mismatched expectations causing problems between you and your retreat co-leader are all things you want to avoid at all costs.

Retreats are wonderful but they do require a lot of emotional energy. Set yourself up for success from the beginning, and the rest takes care of itself.

What do I wish I’d considered before running my first retreat? Here are 25 ideas:

1) Do I like being responsible for the happiness of a group of 8-15 people I don’t know well (or at all?)

2) What is my ideal guest for this retreat? What type of person are they? What are they currently craving in life? And importantly, who are they NOT?

3) Where will it be held? Does the time of year need to be taken into consideration? (Both for retreat location – rainy season vs dry season for example – and also for participants home countries – March break anyone?)

4) Will there be an option for people to have their own room and if not what’s the policy for people who decide they don’t like their roommate?

5) What’s included in the price? (retreat only? meals? international airfare? travel insurance?)

6) How will it all be insured?

7) How can I legally accept payments for a retreat in my state/province if I am not a travel agent?

8) In the event of a medical emergency, how will it be handled?

9) What are my deposit, payment, and refund policies?

10) Will I have an application process and if so, how will that be handled? also: how will I reject applications nicely?

11) How will I price the retreat in order to ensure profit?

12) Who will book the venue and any extracurricular activities? Who will follow up with those vendors to make sure everything is in order close to the retreat date?

13) What kind of information do I need to include in the information packet? (if not provided by the venue)

14) How will retreat guests get to and from the airport to the retreat location – what parts of travel to and from am I responsible for?

15) Do I want to collaborate with another person? If so, why? Does it feel less intimidating than doing it alone? What if they don’t pull their weight or there are tensions between us? Will I have a partnership contract in place and who will put that together?

16) Who is responsible for the marketing of the retreat? Me alone? 50/50 between my partner and I? The retreat venue?

17) What is the minimum viable attendance in order to split even? What’s the ideal number in order for it to be profitable?

18) What is a price point that I know my audience would be willing and able to pay?

19) Many retreat venues require a non-refundable deposit to hold the place for your event. Where will I get that funding?

20) What will happen if some people sign up and make a deposit (which I use to make a down payment at the retreat centre) but not enough to make the retreat viable? How will I refund their money?

21) What kind of contract will retreat guests need to sign? And medical form?

22) What is my contingency plan if I end up with a “problem guest“? i.e.; a diva who’s making other retreat guests miserable.

23) How much downtime will guests have? How much of each day will be full of activities?

24) What is the mix of activities I am going to offer? Think mix of physical activities like yoga or zip lining through a Costa Rican rainforest, coaching exercises that require guests to go deep and use a lot of emotional or mental energy, etc.

25) What is the theme of my retreat? What can people expect to do, be, or receive after it all over by having been a part of it?

As you can imagine, this list is really a jumping-off point. Next steps are writing down all of the other questions that these questions bring up, and making a list of everything you don’t know and need to find out. Then go out there and ROCK your retreat like an old pro.

Heather Thorkelson is an small business strategist for location independent entrepreneurs over at the Republic of Freedom. She’s a firm believer that it’s entirely possible to live as we dream, and spends her days proving it. Currently in Sweden, Heather can often be found in Peru and sometimes in the Polar Regions. Get her regular tips over on Instagram and say howdy over on Facebook or Twitter.