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What I Learned Co-hosting My First Small Group Retreat

This is a guest post from Kaleigh Moore. She’s a full-time freelance writer specializing in blog content for eCommerce platforms and the software that integrates with them. In her free time, she writes about retail and DTC commerce for publications like Glossy, Fast Company, and AdWeek.

Earlier this month, I co-hosted my first ever women’s business retreat with fellow writer Emma Siemasko. We called it the Domina Retreat, and for two and a half days we spent time learning, sharing, and relaxing at a beautiful Airbnb home on Lake Travis just outside Austin, Texas.

Emma and I, both working as independent consultants, had been getting together once a year to co-work and brainstorm ideas since 2016. But this year, we decided to open things up a bit and invite other women to join us for a small retreat.

It was always a highlight of the year for us to get face time with another person who truly “gets” what we do, so we figured that there must be other women out there feeling the exact same way–longing for community.

Turns out, we were right. This year, our small group included 16 female freelancers, consultants, and entrepreneurs who traveled from places as far as Japan, Hawaii, and Canada to be there.

I’d be lying if I said I wasn’t nervous going into this event. Even with a fantastic partner and lots of planning, I still worried that something would go wrong. I spent a few nights losing sleep over silly questions like:

“What if people hate the food and go hungry?”

“What if people don’t talk to each other or are bored?”

“What if someone gets hurt while they’re at the house?”

The good news is: None of those things happened. But this worrier mentality did help my partner and me think through the details and create some plans that made us both feel more secure going into the event.

Emma gathered some information about hosting successful events from Jessie Char, and I spoke with Dorie Clark who offered some great tips on planning and executing business retreats.

Tips for a polished retreat

These activities helped us come up with a few elements of the event that really made it feel more polished, such as:

  • An amenity table with travel-sized items, personal care, and office supplies for anyone who needed them
  • A big supply of drinks, including lots of bottled water and La Croix
  • A general script for our welcome speech that explained the ‘why’ behind the event, that positioned us as capable leaders, and that outlined our goals for the days ahead
  • Take-home bags with personalized, handwritten thank you notes

And guess what? From the very first night of the retreat, things went smoothly. Everyone loved the location, we ate pizza, and people introduced themselves, chatting in small groups around the house. Our location had lots of great areas for mingling both inside and out, and everyone fell in with each other naturally.

Over the next few days we had a few more structured sessions during the event:

  • Tracey Wallace shared her expertise on everything from networking to technical SEO for content writing
  • Linda Perry led a session on limiting beliefs and business growth
  • I did a session on using Twitter for networking and finding opportunities
  • Emma shared her onboarding and pitching process, then lead a goal-setting workshop
  • Emma also led our business book club discussion where we talked about The Four Tendencies by Gretchen Rubin (which was great for getting to know each others’ personality types) and business “hot seats”, wherein each person was able to present a question and gather feedback on how to solve problems within their business. Our post-event survey showed that the hot seats were one of the most-loved activities.

What worked well

So what worked well about the retreat?

1) Balanced activities

Our agenda for the retreat was focused on striking a balance between group activities and private work time, during which attendees could co-work in a shared space or go off and do their own thing (whether that was swimming, taking calls in a private room, or going back to their hotel room to work for a bit.)

We wanted there to be some autonomy around what people could do while they were there rather than scheduling everything down to the last detail, and that served us well. While it freed people up to enjoy their time at the house, it also made time for unstructured conversations and networking between attendees–which was great.

2) Time outdoors

We were fortunate to have some excellent weather while we were in Texas, so I’m glad we had a couple of outdoor activities scheduled and available during the retreat. Miranda Hanna, one of our attendees, lead an hour-long morning yoga class on the lawn one day, and the next morning a small group hiked at Mount Lakeway trail. We also took a sunset walk one night after dinner as a group, which was a relaxing way to wind down the day.

3) The group

This group of women all specialized in creative work, but specialization varied quite a bit in regard to work type: We had graphic designers, writers, coaches, consultants, and even an interior designer. The amazing thing was that despite the fact that our day-to-day work didn’t always have a ton of overlap, this group really connected well on a personality level and just naturally gelled.

Everyone was kind and respectful, and because they were there for the right reasons (and had paid to be there), they were open communicators who showed true interest in learning from and listening to the other women they met there. Emma and I worried a bit that we’d need to lead a lot of the conversations to avoid awkward silences, but we didn’t have to do this one bit. It was amazing to sit back and see the group sharing with each other all on their own. It seemed to us like everyone made the most of their time and squeezed as much value as possible out of the days we spent together.

What we’ll improve for next time

Were there some things we could improve upon? Of course.

1) Smaller food orders

Emma and I wanted to be sure we had plenty of snacks and drinks for everyone, and we also provided breakfast for everyone on two of the days, so we went to Costco and really loaded up. We did end up having quite a bit left over, but thankfully we were able to send some of it home with a few women who lived in Austin or were staying in the area.

Our meals had quite a bit of excess as well, but I guess it’s better to have too much rather than not enough. Next time we’ll know to cut down our orders a bit and maybe skip Costco, going for a regular grocery store rather than Costco-sized portions on everything instead.

2) Offsite overnights

One thing Emma and I agreed on was that next time, we’ll probably opt for offsite overnight lodging outside of full bedrooms located in our home base. We offered the downstairs bunks as a more cost-effective option for a few attendees this time, but felt like after an all-day event like this one was, it’s nice to have a private room with a door that can close so you can fully decompress at the end of the day. While we didn’t have complaints about this from those who went the bunk route, we both agreed this would probably improve the overall experience.

Emma and I also agreed that, as event coordinators, this change would give us the chance to regroup at the end of the day to talk about what was working well, any snafus, and what needed to be done for the next day logistically. With this setup, we didn’t really have time or space to do that.

3) Transportation

We discovered Uber wasn’t very reliable in the area where our Airbnb was the week before the event. It was out of our control, but it would’ve been nice if we had anticipated this ahead of time. That way, we would’ve been able to share the transportation details ahead of time, which would’ve eased some anxiety. I ended up getting an extra rental car for us to have on hand through Turo, but fortunately most people had their own cars and/or figured out carpool options with other people coming to the event. We also offered a shuttle to the airport on the last day, which helped simplify logistical concerns for folks as things wrapped up.

The value of having partners and sponsors

We wouldn’t have been able to pull off this event without some incredible partners who came to the table ready to support this smart, talented group of women.

These partnerships came from existing relationships I had with founders and CEOs–some from ongoing Twitter conversations, some from my reporting work. I reached out, explained what we were doing and why it was important, and made a modest ask. All of them immediately said, “Yes, this is great! How can we help?” (Ah, the power of online friendships.)

Coywolf and Noko were our meal sponsors, and the lovely folks behind these two companies stepped up to provide dinners for our guests (authentic Texas BBQ one night and a chef-made meal the next.) Both were delicious.

Along with those lovely meals, we also had a variety of ice cream pints delivered to the house from our friends at Jeni’s Splendid Ice Creams and a some champagne and gin sent over from Taster’s Club. Yum!

Creative Class and Freelance Mastermind both provided a diversity and inclusion ticket, so we were able to bring in two extra attendees from under-represented communities and had those valuable perspectives at the event.

Two people in particular were extra crucial: Becca Matimba stepped in as our event coordinator, handling lots of logistical to-do list items and generally was the behind-the-scenes wizard that made everything go smoothly. Tanialee Gonzalez was our event photographer, and she got some amazing photos plus offered to take headshots for anyone who was interested.

Takeaways (literally!)

We also had a take-home bag for each and every attendee, which included fantastic things like:

I also have to give MAJOR kudos to my retreat planning partner Emma, who was nearing her third trimester in her pregnancy during this event but was full of energy. High five to her for being up for this–she never complained once! A great leader and entertainer, she was the perfect person to partner with for this as our skills and work styles were (and still are!) very complementary.

In the end…

Overall, the retreat wasn’t a big money-maker for us, but we both went in expecting a low margin and really just wanted the chance to bring some smart women together that we could learn from. This was both of our first experience hosting an event, and I’m extremely proud of how it turned out.

The biggest thing I walked away with from our first-ever retreat was, aside from a sense of accomplishment, a real appreciation for the group of women who came together. Not only did I learn some valuable lessons and set goals for my business, but I also made new friends. As corny as that sounds, that’s hands-down the best thing I’ve done for my business in my nearly six years of running it.

Here’s to hoping we’ll do another retreat in the next year or two.