Some of my Facilitation Blunders (3 Case Studies & the tools I developed from them)

It’s true that I’m known as one of the best workshop, ritual and retreat facilitators in the industry, but what you probably don’t know is this: In my nearly 20 years of facilitating (& training others to facilitate!), I’ve made tons of mistakes. Not just little mistakes, but real biggies. The kinds that are cringe-worthy and the kinds that I’ve shed some real tears over.

But that’s how I’ve learned and that’s how I’ve developed so many of my facilitation tips and tools.

I decided it would be fun to share 3 Case Studies with you on mistakes I’ve made and the facilitation tools that came out of them.

I hope you don’t cringe at some of my blunders!

#1: Always Time Your Check Ins

I am told time and time again by my workshop & retreat participants that they are amazed at how respectful of boundaries the women who participate in my events are. It’s so rare that I have someone “take the group hostage” by speaking too much or creating emotional chaos in the circle. Here is some insight into why I am able to create this:

THE BLUNDER: I sometimes do “group check ins” when I’m facilitating more intimate retreats – I’ll use a talking stick and each woman in the circle will have an opportunity to check in, share what’s been moving through her and transforming, and how she’s feeling. When I facilitate these check ins, I also give a time limit, anywhere from 90 seconds to 4 minutes, depending on how many women are in the room and how much time we have for the exercise. It’s a wonderful exercise to help women process all they’re experiencing, get clarity on everything that’s coming up for them, concretize new ideas that are evolving, be seen, and connect with community.

One time, I was facilitating a check-in and had given a time limit of 2 minutes. But I didn’t ask anyone in the circle to be the official timekeeper (meaning, to have someone set a timer on their watch). One woman talked way past 2 minutes, and at about 3 minutes or so I asked her to bring her share to a close. Even though she stopped her share right away, I could feel energetically that she became very insulted, angry with me and shut down.


THE LESSON: Had I asked someone in the circle to time each woman and rattle a shaker when her official time came to a close, I could have avoided insulting this participant because it wouldn’t have been “arbitrary” or singling her out when I asked her to bring her share to a close. It would simply just be the easy way to follow the protocol that when the shaker was rattled, it signified that the 2 minutes were up.


BONUS TIP: We took a break right after the check-in and while I could have just let it go, knowing this participant would eventually “get over it”, I didn’t. I went straight to her and let her know I sensed that she was upset and asked if we could talk about it. It gave her the opportunity to share with me that she felt I shamed her and shut her down. And this open dialogue allowed me to apologize, and explain what went wrong (I knew right away it had to do with the absence of a timer). The most magical thing happened through our exchange – because I was so honest and upfront with her, she told me it healed the part of her that always felt others didn’t want to hear from her or wanted to shut her down. Amazing!


#2: Be Clear about Your Agreements

While I stretch my clients all the time, it is extremely rare that I will trigger someone unintentionally so that they become very angry or passive aggressive at me. The mark of a master facilitator is to be able to make your clients feel uncomfortable (in all good & stretch-y ways) without making them blindly angry. But here is an example of when this wasn’t the case:

THE BLUNDER: I was leading a 3-day retreat for a group of clients who had been working with me for a considerable amount of time. On the first evening of the retreat, I prepared a very special ritual for them offsite (it included journeying to an amazing & magical pool in the middle of the woods and each woman crowning herself as Queen in the water and then drawing down the Moon with the owls howling in the background…but that’s a story for another time). We ended the evening very late, and I told them we’d start at 9:30 am the next morning.

I was pretty tired and allowed myself to be a little slow out the door the next morning, so we didn’t start our day until 9:45 am. This really triggered one of the women in the room because she felt I wasn’t showing up with my full presence if I was showing up late.

Of course, she was right!

As a practice, I never show up late. It was a big mistake, on my part, to assume that because I had been working with these women for so long and because I had given them an extra session the night before, that it would be OK for me to show up a little late the next day.


THE LESSON: Agreements matter. If you say you are going to show up at a certain time, or break for lunch by a certain time, then honor your agreement. In line with this, if you say you are going to end the day at a certain time, don’t go over time. You may think you’re giving extra value, but it can trigger or inconvenience participants in the room.

The time agreements you make are sacred and this is part of holding the container in a tight and safe way.


BONUS TIP: While I was definitely in the wrong about showing up late, I recognized immediately that this client wouldn’t have become as triggered as she was if there wasn’t more to her story. In fact, she shared with the group that the late thing was really tough for her because her mother was always late when she was a child, and it felt to her like she was abandoned each time.

Because being a master facilitator means not only teaching your curriculum, but also helping your clients heal and transform on what comes up in between the curriculum points, the first moment I had in private, I connected with this client, looked her straight in the eyes, and let her know that I was there for her, fully, 100%. I let her know that we had an opportunity right there in that very moment to finally break her fear of abandonment in her life, and it simply needed to start with her seeing and recognizing that my being late meant nothing about how I care for her as her mentor. Big healing and magic happened with that simple exchange.

#3 – Be Intentional about how you Initiate Your Community

Clients tell me all the time that they feel so held and seen by the community I bring together, even if that community comes together for just one short retreat. Clients also tell me how connected they feel to the other women in the room, how they become trusting and vulnerable in my circles right away, and how they feel they are part of a tribe that is in full alignment with who they are. This is a sign of a strong community, and when you are able to create a strong community, your clients will experience greater transformation & results, and also invest with you over and over again.

Here’s a good example of when I made a mistake in building strong community:

THE BLUNDER: Many of my masterminds are set up so that you can continue on & re-commit each year. My clients tend to stay with me for many years, and my clients also become very close with their “sisters” in the program, so it’s not uncommon for the majority of a group to continue on together in the mastermind the following year.

The first year that this happened, something was really off at the first retreat of the cycle. It felt like the women who had been there before were staying in a tight-knit posse, and the new women were connecting a little bit, but not fully present. By the second day, I could also sense that the new women were getting caught in a lot of comparison and feelings of “not good enough”. I had to work really hard the rest of that retreat to bring the new women fully present and feeling like they were part of the community.


THE LESSON: That blunder taught me that when a circle or community is tight and you add new members to it, the new members are at risk of feeling like outsiders. That’s why now, each year at the very first retreat of a continuing program, I add in a small ritual or exercise that names and honors the women in the room who have been together already, and then I name that it’s time for a new cycle and new circle to form, and I name that new women are coming together with graduates, and we physically do something to create that new circle. This makes ALL of the difference and creates a solid community with new and old women together from the get-go.


BONUS TIP: Use the art of ritual to create any new circle (whether it’s completely new, or whether graduates or people who are already friends are there). Something as simple as using a rope that is ritually tossed from woman to woman to connect the circle, or even just having each woman consciously take the hand of the next, can create a powerful container for a community. Also, be upfront and name that it’s natural for new women to feel tentative and graduates to feel closed off and that your intention as the leader/facilitator is to bring together this powerful new circle because you know the exact right women are present. Naming resistance allows it to melt right away.


I hope these case studies were helpful for you! Would love to hear from you on what you’re learning when it comes to facilitation at our Facilitation and Coaching Mastery Facebook Group.


With love,


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