How to Plan and Run a Team Retreat


The Bossed Up team is quite small, but for leaders and direct contributors at any level at any organization of any size, I’ve got some strategies you can deploy to plan a retreat for your team.

Here are the four key strategies that really helped make our team retreat effective, productive, and fun.


1. Set Clear Objectives (well ahead of time)

I’m sure you’ve heard this before, but at the risk of stating the obvious, create clear objectives as a team. I didn’t want to just set the agenda and decide what we needed to learn about, so we started talking about our team retreat a month-and-a-half before it happened. This gave us a fluid list of things we needed to figure out as a team. By starting the conversation early, we could co-create objectives.

Our retreat objectives included: clarifying our road maps for the six months ahead, clarifying roles and responsibilities, making sure we’re clear on our vision, values, and bigger picture of why we do this work, and bond as a team.

We specifically put on the agenda that we wanted to bond because we haven’t seen each other for so long. This is much harder to do if your entire team is remote, but bonding was on the goals of the retreat list.

So clarify early on and co-create with your team the concrete learning objectives, discussion objectives, or just team development objectives that you want to meet on during your retreat is top priority.


2. Co-create the Agenda

Create that agenda. Not only should you develop an agenda with your team, but make sure as you keep adding extra items and discussion topics to that agenda that you double check as you go. Does this agenda meet the objectives and are there any objectives that are not met based on what we have realistically scheduled on this agenda?

Resist the temptation of aspirational planning. Don’t try to do too much. Don’t try to over-estimate what you can accomplish in a 30-minute block or one hour block. Write a name for a focused conversation and try to be realistic and over-estimate how much time it will take to discuss and explore the things you need to discuss. Do this weeks in advance so that you can continue to talk about things, plan strategically, and add to the agenda as needed.

Another thing to mention is to make sure to give everyone a piece of ownership over the team retreat. We had an entire portion focused explicitly on brand identity which Elie, our Creative Director, took the lead on. Similarly, we had a 90-minute marketing brainstorm that Kirby, our Marketing Director, led. Giving true ownership and agency to our collaborators, our contributors, and our teams is the best thing we as leaders can do.

This is the first time that a good portion, like half of the team retreat was led by myself and half was led by my team. That was really eye-opening. I think it gives everyone on the team more skin in the game – more responsibility, more desire to contribute, to take ownership of their their contributions, which is a beautiful thing


3. Leave plenty of room

Leave plenty of room plenty of room for rest for breaks to step back rest. I’ve really come to value introvert needs and building in time in your retreat agenda for introverts to just chill is so important.

We also need that time and being on 24 hours a day is just too much. We left room from 4pm to 6pm to relax before we had dinner together and a structured activity in the evening.

Creating plenty of room for personal solo time, for regular work time. and for structured bonding activities really works. It helps balance time that we didn’t spend in structured strategic planning mode, which you just can’t do for so long.


4. Change up your location

I think the interpersonal bonding that happens outside the conference agenda is part of what makes these retreats so important hat my final take away is to change up your location.

We rented a big gorgeous Airbnb that had room for everybody to stretch out on their own and enjoy space physically, mentally, and psychologically – which was really important. I’m so glad that we went with something a little more spacious despite the higher cost because it gave us some breathing room.

We had beautiful, gorgeous mountains around us an inspiring environment to leave us feeling creative, so that we could contribute new ideas. I think having a new location makes you think differently. It is something to keep in mind, especially for teams doing any kind of virtual retreat, because people need to change their perspective to have new ideas.

So even if there is a virtual component of the retreat, we as leaders need to create spaces that are both accessible and inspiring. So you’ve got to get out of the office or out of your regular day-to-day routine by changing things up and restructuring your team’s environment to create out-of-the-box thinking.


How have you created time and space to think big picture?

I cannot tell you how important it is and how refreshing it felt to zoom-out collectively as a team to say, ‘Okay, the email inbox can be dealt with later. How can we think big right now? How can we come from a place of abundance and unbridled ambition and inspiration to remind us why we work so damn hard?’

It was definitely intense. It was a bit exhausting but I feel a new sense of hope on the horizon and I think thats what we all need right now.

I encourage you to change your space, to change your perspective, and let me know if these tips and strategies help you.

If you found today’s blog helpful, share it with the world including those friends of yours. In the meantime, take care of yourself. I know it’s hard out there. Give yourself a gift of boundaries right now. Spacious freedom to think big and keep the hope that things are going to get better. Let’s keep bossin’ in pursuit of our purpose and together, we’ll lift as we climb.






Your email address will not be published. Required fields are marked *