The 8 Things Your Retreat Needs

Company retreats serve many purposes:

• It brings all of your staff together into a room that isn't virtual, an uncommon occurrence for hybrid companies like ours.
• It provides a space for goal-setting, encouraging everyone on your team to align with a vision for the organization.
• It's fun. (Enough said.)

At Online Optimism, we plan year-round for our retreat. It truly ends up feeling like the culmination of a year of work, as well as a celebration of all we accomplished. This year's retreat felt particularly successful, so I wanted to share elements that we include so others could adapt for their own organization.

1. Pick a Good Location

This year, we held our retreat in New Orleans, a city known for its ability to host anyone and everyone. Roughly half our staff lives in the city, which means that we coordinated travel (flights, hotels, Lyfts) for the other half. You want to make plans as early as possible, particularly if your company retreat occurs around the holidays so that individuals can adjust any family vacation times they want to take.

Tip: schedule the flights early in the day since they're less likely to be delayed. Your first event of any retreat is going to be a welcome, and it's important to have your whole team there from the start.

2. Start with an Orientation

Yes, you're going to have to do some icebreakers.

Companies change, and there's going to be a number of staff that have never met each other. It's important to keep it informal so folks don't become overly cautious in sharing, but don't expect deep, emotional answers. Anyone who traveled in may be jet-lagged, and simply want to get the welcome over so they can go take a shower. We've found brief (15-30 minute) questions about themselves and their work at Online Optimism, followed by an optional longer welcome event (typically for those who live here) works great.

Tip: Optional events are great to include throughout your retreat. You might want staff to do everything you planned, but people have different energy levels and will want different experiences. It's best to have at least one event each day be optional, so your introverted staff don't burn out.

3. Support Your Community

We always try to set aside some time to work in the Retreat's community to give back. This year, we dedicated our time to Culture AID NOLA, an amazing organization that provides free food in New Orleans, acting as a no-barrier, no-stigma (meaning no ID, no proof of income, and no questions asked) organization.

Tip: Looking for an organization to volunteer with? If you need some inspiration, you can find a year's worth of Online Optimism donations here, all worthy causes.

4. Include Something Unique

No, that's not a placeholder I forgot to change. Your retreat should include something different and unique that other organizations don't do. This gives your staff an interesting thing they get to share with others when talking about your retreat, and also helps you stand out from the cookie-cutter retreat you may be planning after reading a LinkedIn blog post about how to plan retreats.

At Online Optimism, our "something unique" is an activity related to public health each year. (Yes, this was inspired by dating and then marrying someone with a Masters in Public Health.) It goes well with one of our company values: Support Our Community, but it also helps folks feel like they're leaving our retreat a better, more invested individual than they arrived.

Last year, we did the Red Cross' CPR Certification and this year we brought in Trystereo to provide harm reduction and Naloxone training. For one to two hours, we stopped working together on digital marketing and instead gained skills and knowledge that helps our staff be better members of their community.

Tip: Consider a harm-reduction course for your team. It's not something that many companies consider - we were told after our training that we're the first non-healthcare organization to ask for it - but everyone learned something from the historical lesson on the history of harm reduction, and it could even save a life.

5. Take A Celebratory Look Back

A retreat shouldn't be all hard work and no play.

As you might expect if you know our agency, we're good at celebrating. Our annual end-of-year party named the OOies in honor of The Office's Dundies celebrates the big wins of the year. Over the course of the evening, we make speeches and celebrate every member of our team's hard work, calling out the clients they launched, campaigns that succeeded, and the tireless work that in the end of the day actually pays for all this fun stuff. Everyone dresses up in black tie, or the closest you can with green accents.

I've been told that after our OOies there's a tradition of Karaoke'ing as well, but I politely excuse myself after the formal festivities end so our staff can enjoy themselves without the boss around.

Tip: If you're providing alcohol at your retreat (as we do,) make sure your staff are provided with company Lyft or Uber accounts. Our staff knows, and is reminded, that if they have any drinks that they're expected to use those accounts to get themselves home safe.

6. Set Your Goals

On the last day of our agency's retreat, we've dedicated time to goal-setting for the new year. This includes:

• Agency goals, created by our company leadership.
• Department goals, created by the departments themselves.

All of these goals are shared with the team. Following the retreat, we build dashboards and other tools that hold us accountable to our team (more on accountability shortly).

Tip: Your goals should be SMART goals: Smart, Measured, Actionable, Relevant, and Time-Bound.

7. Request Feedback

The retreat isn't over after you all wave goodbye. For our Operations team, they shift immediately into planning next year's retreat. The first step of that process is asking for feedback on how things went.

We ask a number of questions about each event, as well as items that individuals want to do again, or never repeat.

This year, we scored 9.00 out of 10 on the main question: "Generally speaking, how satisfied were you with our retreat?" Pretty great results!

Tip: Make feedback required. It's better to get everyone's voices heard, and the only one to do that is to make it mandatory.

8. Take Action

Lastly, you don't want to fall into the common retreat trap: Everyone has a great time, sets lofty goals, and then immediately gets swept back into the swing of things (after all you just missed two days of work) leaving your dreams of a more focused company in the dust.

Provide time for your staff in the weeks following to actually cement the plans that they created during the retreat, including setting up those goals for their departments to keep you all accountable.

Tip: Before the retreat begins, your follow-up time should already be blocked off on your calendar so it's not forgotten.

My Final Thoughts

These are some of the elements that we've found to be successful, but it's not all of them. In addition to what's described above, our 2023 retreat included axe throwing, present-giving, donuts & tacos, a DISC-assessment, and our annual State of the Agency.

I left the retreat with a feeling that all retreats should end with: Optimism toward your company's future.