We had hundreds of people tell us they really wanted to go to Hustlers’ Retreat. But it was either too expensive or their business was wayyy too early.  

We still believe a retreat like this would be SO powerful for startups at all stages–pre-seed to public cos. But if you can’t make it this year for whatever reason, we still want to help. 😊

So here’s a sneak peek of our playbook on how to organize your own team offsite. There are two main parts to hosting a great retreat.

1. Logistics: food, venue, lodging, transportation
2. Programming: agenda, facilitation, sessions, fun

Let’s start with #1.

Get the logistics running smoothly

Somebody needs to own the logistics hat because it is a BIG role. This person needs to coordinate everything to make the retreat actually happen.

The founder is often the leader here, especially in early-stage startups. There are a LOT of small details that go into designing a world-class experience. But if this is your first time, focus on getting the basics right.

• Pick dates: Find a weekend or set aside 4-5 days if you have the time. Block off those dates in the team calendar in advance so your team can make the accommodations they need (finding daycare, coordinating responsibilities with their partner, shifting work project timelines).
  
  
• Book a venue: You can find an office space for the daytime through services like Breather. But it can be hard to find new and different ideas in these typical workspaces. We recommend going somewhere in nature (like what we’re doing at Hustlers’ Retreat) to switch things up, breathe fresh air, and give your mind a different mode for thinking.
  
  
• Find lodging: In our past offsites, we’ve booked a few Airbnbs within walking distance of each other so our team can be close together. Availability can book up quickly so make sure your lodging options are available before you book your venue.
  
  
• Coordinate transportation: If your offsite is far away, you need to coordinate everything from flights to rental cars or rideshares to the Airbnbs. If you’re flying, make your team check their passports are not close to expiring. Try to coordinate arrival times so your team can carpool together to the venue or where you’re staying.
  

• Provide food and drinks: Get everyone’s dietary restrictions in advance. Plan out all meals for breakfast, lunch, and dinner. If you plan to make food at your Airbnb, coordinate who’s on cooking and cleaning duty. If you plan to go to restaurants, make reservations ahead of time to ensure your spot. Don’t forget about having healthy snacks and drinks to keep your team energized throughout the week.  

Plan the programming

OK so everyone has successfully made it to the team retreat. Yay! Now what should you all do?

The more thought you put into the experience design, the better your team retreat will be. Here’s where to start.

• Understand your WHY: Every gathering must have a clear purpose. Before you all meet, get clear on what “success” looks like for your team retreat. Is it about aligning your team’s highest priorities? Working through long-term issues? Connecting with each other on a deeper, emotional level?
  
  Once you understand why you’re all meeting together, only then can you build your agenda to support your WHY.
  
  
• Designate a facilitator: You need to have someone facilitate the offsite to help the team stay focused. This person will ensure the agenda is followed through, everyone’s voices are heard, take notes on key discussions, and ensure everyone’s having a great experience. This is often a full-time role which removes the facilitator from being present in the conversations and experience.
  
  At Hustlers’ Retreat, our Hustle Fund team facilitates the entire experience so everyone can be present. But if you’re doing it on your own, designate someone to be a facilitator and switch roles in the next retreat to share the load.
  
  
• Prepare the sessions and discussions: Offsites often have learning sessions and key discussions on critical elements of the business. Each person who will present needs to be prepared to teach or facilitate the conversation. And topics need to be finalized ahead of time so that team members could think about and prepare notes for the discussion.
  
  This can surprisingly be a lot of work but it’s important for each person to adequately prepare before you all meet.
  
  
• Spark joy: An underrated feature of team offsites is doing fun things with each other. Fun activities and play connect the team emotionally, makes everyone happier, and more inclined to engage when it’s time to work.
  
  Set aside ample time to do something fun: go for a hike, play volleyball, taste wine, tell ghost stories together (things we’re all doing at Hustlers’ Retreat). Your team will be much better off because of it!

There’s so much more but if you do these basic things for your retreat, you’ll be well on your way to creating a great experience for your team. 🙂

At Hustlers’ Retreat, we’re doing the hard work in designing and facilitating the entire experience. So you have a live product and are ready to scale, join us in person next month, August 20-24.

Use promo code “HUSTLE” to get you the best deal. ⛰️