Planning a Winning Staff Retreat: Expert Strategies for the Weary Leader

Your team needs an IRL off-site, but you’re too darn tired to plan it.

Use our expert strategies for a stress-free team retreat.

 

Off-sites. Staff Retreats. Staff Gatherings. Team Building. Call it what you will—your team needs the time to “be off” from work but still share meaningful experiences. They need permission to pause and time and space for the “in-person” magic that happens when you share physical space. Your team needs time to celebrate their successes and learn from their failures. They need to learn together. They need to build deeper relationships with one another. They need to reflect on their goals and consider what their focus will be in the new year. And, dare I say it…they need to have shared experiences that are straight-up FUN!

Yes, your team needs a beginning-of-the-year staff retreat. All humans operate on a calendar rhythm, and your team’s work rhythm is calling out for a gathering with purpose. And you know it, but you’re too darn tired to plan it for them.

So what do you do?

We have three answers for you. None of our answers include postponing the retreat or pushing it to the spring when you have more bandwidth to plan it. You can do something of value soon—your team needs it.

So again, we ask, what do you do?

 
  1. Hand It Over to the Professionals

I’ll cut to the (Chevy) chase: You need to hire a pro to do the planning and facilitate it for you.

You can hire professional facilitators, like us at The Group Forward, to help you design a world-class staff retreat experience. And after we design it with you—we’ll facilitate it!

Professional facilitators are skilled at designing meaningful gatherings and can breathe fresh energy into your team retreat. They know how to:

  • Build customized sessions for the time you have.

  • Establish frameworks based on your staff retreat objectives.

  • Create content that speaks to your team.

  • Deliver extensive toolkits of activities and exercises to facilitate a session your team will remember.

Not only do facilitators help you plan meaningful experiences for teams of people, they also allow YOU—the leader of the team—to fully participate. You don’t have to be the cruise director and first mate to make sure retreat objectives are met. And yes, of course, you are capable of running a staff retreat. But that doesn’t mean that you have to. Wouldn’t it be nice to get strategic help to design a meaningful experience for the team so you can focus on your day-to-day responsibilities? Sometimes it’s nice to pay someone else to do one thing really well instead of adding one more thing to your list.

And when it’s all said and done, your team feels the intentionality of the retreat design deep in their bones.

They’ll say, “this felt different.”

Well-designed and facilitated retreats result in a deep feeling of appreciation and being “taken care of,” which is important everywhere, especially in remote or hybrid work cultures. A staff retreat done well boosts employee satisfaction, which directly links to staff retention and performance.

As facilitators, we draw from a deep well of helpful and practical tools, frameworks, models, and processes to help you navigate even the most challenging team dynamics. Heck, we revel in the opportunity to help teams achieve their goals. All you have to do is bring us in.

 

2. Get a Professional Assist

You don’t have to be a Prius (or a Tesla) to go hybrid. You can still get the benefit of professional expertise without going all-in on pro design and facilitation. If you’re not sure you have the budget (let’s talk!) to bring in an outside facilitator, you can still get an assist. We can help you design a world-class staff retreat experience that meets your goals and sets the stage for a powerful, productive new year. Then you—along with your team—can facilitate the retreat.

In some ways, this is the best of both worlds: You still get the expertise of a professionally-designed staff retreat, and you get to utilize your team as facilitators. Including the team in delivering exercises and activities delivers its own form of bonding, growth, and inspiration.

 
 

3. Design Your Own DIY Staff Retreat—Exhaustion Be Damned!

If we can’t bring your vision for a staff retreat to life, we can at least make it easier for you, the overworked (let’s just admit it, tired) leaders out there. Whether bringing in outside help isn’t in the budget right now (again, we should talk before you rule this out!), or you’re unsure about hiring a professional facilitator, we’ve got a few tangible suggestions to get you started on your own, DIY staff retreat.

DIY IRL Staff Retreat Ideas

We looked at three of the most common staff retreat goals we’ve seen from our clients, and put together actionable tips to help you realize each goal at your own team retreat.

To get your creative planning juices flowing, here are three staff retreat and off-site activities to help you quickly pull together a meaningful day for your team.


Staff Retreat Goal 1: “We need our team to get to know one another better and to build relationships outside of the day-to-day work relationships.”

Solve for Goal 1: Team-Building Exercises

Confession: I love team-building exercises in all their forms; very few make me cringe. I realize I might be in the minority with this perspective, but I stand by it. The science behind team-building exercises says we need to find ways to have shared experiences and build mutual understanding in order to build a strong social fabric. Here are two ways to turn your staff into fans of team-building, too!

  • Meaningful Meals: This exercise combines two of our favorite things: food and chit-chat. Plan an intentional team meal where you rotate seating at specific moments throughout. After everyone rotation, provide question prompts to encourage conversation. Consider question prompts that aren’t just about work. Include prompts that get people talking about the things they care about—passion projects, the people (and animals) they love, and stories they don’t usually get to tell.

We all eat. Breaking bread matters to humans. Hosting an intentional dining experience that asks people to enjoy food and lean into conversation topics that reveal new insights about one another can do wonders for team connection.

  • Item from Home: As a short homework assignment, ask everyone to “bring an item from home that helps your colleagues learn something new about you.” As people arrive at your retreat, collect and hide the items under a blanket. To start the activity, remove the blanket and ask team members to guess who brought each item. Once everyone guesses, the rightful owner of the item shares why they brought it and what they want their colleagues to know about them that they didn’t know before.

I have run this activity with technology executives, grassroots leaders, and media moguls. No matter the group, people walk away from this activity with a deeper sense of their colleagues’ interests, passions, and background—the things we don’t always get to share during a work day.

Staff Retreat Goal 2: “We need time to slow down, to celebrate what’s been going well, and to honestly explore what’s not going well in a safe and productive way. Work is so go-go-go with back to back meetings and deadlines. We need permission to reflect and make sense of shared experiences at work.”


Solve for Goal 2: Team-Wide Reflection Activities

You know who has a lot of experience and perspective but often doesn’t get a chance to reflect? YOUR TEAM! Give your team the gift of time and space to surface key reflections on important topics in your work. Ask them what their experience has taught them and find ways to surface these learnings and insights together.

You can run end-of-year or new year Retrospectives (here’s a step-by-step guide). Start with individual reflection time, then move to smaller group discussions, and finally expand to larger group ‘sense-making’ conversations to allow for more participation across the team.

We also encourage you to get creative with reflective activities. Here’s an example from an organization in the travel industry. Imagine asking your team to reflect and consider what they’ve learned in four categories:

  • Reflection Category 1: “Free Flight” - When did we surprise and delight our customers this year? How did we make our customers happy?

  • Reflection Category 2: “Lost Baggage” - When did we frustrate our customers most this year? Where did we ‘lose the bag’ in our work?

  • Reflection Category 3: “Top 5 Hidden Secrets in Travel” - What are the key learnings and insights we gained from our work this year? What learnings are uniquely ours to explore further?

  • Reflection Category 4: “Bucket List Destination” - What are we excited to do next year? What would make us proud to cross off our bucket list as a company/team? What do we need to gear up to do in order to meet this bucket list goal?


Staff Retreat Goal 3: “We need our team to collaborate more. They don’t go to one another to help troubleshoot their challenges. Maybe if they saw one another as thought partners, we could build a healthier team dynamic.”

Solve for Goal 3: Peer Problem-Solving with a Coaching Protocol

Does your team need a deeper understanding of one another’s work? Use this activity to help them empathize with one another’s work context.

The basic premise is that each person gets a chance in the “help me seat” and when they aren’t in “help me seat,” they support whomever is. They listen. They ask questions. The team shares ideas to help teammates solve their challenges in a way they want to solve them.

We all eat. Breaking bread matters to humans. Hosting an intentional dining experience that asks people to enjoy food and lean into conversation topics that reveal new insights about one another can do wonders for team connection.

At 10-minutes, rotate to the next person.


Pro Tips:

  • Rounds: You can do more than 10 minutes per round, but don’t go longer than 15 minutes or the group will lose energy. Make sure that whatever time you commit to as a group, each person gets the same amount of time in the “help me seat.” You can do these in 90 minute bursts to keep the energy high, then take meaningful breaks between coaching sessions.

  • Timer: Use a timer—like a loud and obnoxious buzzer—and designate a timekeeper. This way when the buzzer goes off, the timekeeper isn’t the bad guy, they’re just the person resetting the next timer for the protocol. You can switch this role each time you rotate to a new “help me seat.”

  • Note-taking: Ask someone to take notes so that the person in the “help me seat” can fully engage and listen to the coaching their teammates are providing. Rotate note-taking responsibilities.

This protocol is engaging, energizing, fun, and easy. Every time I run it with a group, people walk away with new ideas, a sense of empathy for their colleagues’ lived working realities, AND the feeling that they were of service to someone else. This is the magic of peer problem-solving coaching, 10 minutes at a time.

 

Bringing It All Together

You could take any of these activity offerings as inspiration and run with them. And we hope you do! Or, you could use all three for a day-long staff retreat agenda.

WHAT NOW?

So, now you get it: At The Group Forward, we firmly believe that meaningful gatherings for organizations—ones that are intentional, thoughtful, and well-designed—can build goodwill and much-needed connection across your team. Especially in a remote-first or hybrid work context, great staff retreats can help folks feel more positive about their work life and colleagues, resulting in better work output and retention.

We love this stuff, so if you want to riff with organizational development and team culture nerds like us, we would revel in the opportunity to be your thought partner in this important work. And if you just needed a nudge of inspiration, we hope that the nuggets we gave you help you do even more great work as a team lead.

NEXT STEP

Let’s talk about how The Group Forward can help you design and facilitate a much needed staff retreat experience for your team where you leave energized too!