How to Plan for a Productive Team Retreat

Planning a Successful Retreat

I love rolling from my bed to my desk in sweatpants and glasses each morning. That’s the main reason I decided I wanted a work-from-home job! Getting dressed felt like a waste of time.

But there are some important benefits to getting out of my routine (or, more accurately, my NON-routine) and meeting with my team in person.

The first is obvious: It forces me to get dressed and put on some makeup for once in my life. I always forget how good it feels to look like a human being! And I always say, “I’m going to do this even when I work from home!” And, as you can imagine, I never do. But I digress…

The other is that there are ideas and feelings and criticisms and celebrations that can only truly be realized when we’re all in the same room together, addressing the same problems, and feeling the same fears.

You see, as much as my stubborn self always thought I could run this small business alone, it’s not a viable option. I’ve got too many important clients, too many talented team members, and too big of a vision to be limited by the number of hours in a day. Teamwork makes the dream work, after all.

And so, at Don’t Panic, we prioritize our retreats each year. We don’t always relax at a gorgeous spa, or hit the downtown of a big city, or embark on a foodie adventure. Every year is a different location with different priorities. But no matter where we end up or what extracurricular activities we engage in, one thing remains constant: We get A LOT done. How? With some planning and preparation, of course!

There are some questions we like to ask ourselves prior to our retreat that help put us in the mindset to work hard and be efficient with our time. Since we are a fully remote team, getting together for 3 days is never enough, but we try to make the most of it. Use these questions to guide you in the weeks and months leading up to your retreat. And remember: you’re not trying to solve anything yet, you’re only reflecting, listing, and identifying during this preparation phase.

Who Do You Love?

It’s helpful to start with the WHO of the company. For us, this includes both team members and clients. If you’re running a software company or a leggings manufacturing business, it might be employees and customers. No matter what kind of business you have, your people are your everything. Without them you don’t have anyone to make the things you’re selling. You don’t have anyone to buy what you’re making.

We always use a red, yellow, green system (like a stoplight) to rate each client and each team member every month. Green means everything is going great and we aren’t having any issues. Yellow means there’s a problem that we need to or have already addressed and it’s in the works. Red means things are on the verge of breaking and need to be addressed immediately.

This ranking exercise is fun when things are going well, and painful when they’re not, but either way it’s important. It gives us a record to look back on when the year is over. We can compare out gut feelings about each person with our actual ranking month over month.

We rank everyone on two different factors: Work Product and Culture.

Work Product is all about our professional relationship. Do they give clear directions and deadlines? Do they give constructive feedback? Do they show up to our weekly meetings? On the VA side, do they complete all projects on time? Are they easy to communicate with?

Culture is all about the mushy stuff, the things in the relationship that are less tangible. Are they respectful, responsive, and communicative?

We try to avoid working with anyone that we don’t think is going to be a good fit on the professional side, of course, because that’s our bread and butter. But we also like to look at the less tangible qualities of a relationship because while work product can often be ameliorated, culture isn’t something that we can always teach. Both are important to the success of our relationships with our clients and team members.

What’s Right?

It’s always nice to ease into a team meeting with some happy feels. Thinking through what went really well over the past 12 months gets our wheels turning as we reminisce on our wins. It’s useful to ask each team member to write at least one thing down that they feel like they did a great job at and one thing they think the company as a whole did a great job at. Then, when we get together, we can compare the obvious wins with the not-so-obvious and figure out what we can do more of in the future.

In addition to the celebration element of this exercise, it also helps you, as a leader, see what part of their work your team feels best about. This allows you to know what makes them tick and then reward them for a job well done, which builds morale and encourages retention.

What’s Wrong?

Discussing all the mishaps, headaches, and mistakes from the past year was always my forte during our retreats. For some reason, it’s easier for me to remember the losses than the wins. Don’t worry, I’m working on that!

Initially, when the “what’s wrong?” question came up, I remember thinking, “Well, everything! That’s why we’re on a retreat! To fix all the things!” Over the years, the things that were truly “wrong” have become more subtle and more specific, which is what we want. We never want to be trying to solve the same darn issue year after year. The word “wrong” can also seem a bit strong, so if that rubs you the wrong way you can simply think of it as things that aren’t quite right.

These might include lost revenue due to a mistake or production error, poor retention among employees, or people forgetting to take vacation time. Whatever it is, remember that it’s not important to SOLVE these wrong right now, but more to think about and list them to be discussed later during the retreat.

What’s Missing?

Reviewing the wins and losses from the year only scratches the surface. Your business can be as big as you want it to be, so there are certainly things that you can start doing that you’ve never done before. Now, you don’t want to get carried away here. The “missing” categories might be a little more squishy. For example, maybe you’re missing a useful system for providing feedback to your team. Or maybe you’re missing a fair compensation policy.

Hopefully you’re not missing something enormous, because that could mean your business is in trouble. And remember, these are not blatant “wrongs” but rather things that could be created or improved for the good of the business. Encourage honesty among your team here so that you can get to the core of what they feel could be better.

What’s Confused?

Maybe you have a vacation policy but people don’t know how to use it. Perhaps there’s reimbursement for childcare but no one knows how much. Or maybe you’re promising certain services to clients but they’re telling you that they’re not seeing the value.

These are all issues that aren’t necessarily wrong or missing, but definitely need to be clarified. You might ask your team to list these in the form of questions. This could make them easier to identify. In fact, you may not even want to ask the question, “What’s confused about our business?” but rather, “What are YOU confused about?” Then they can answer with things like, “I’m confused about why we bill on the 1st instead of the 30th,” or, “I’m confused about when I can take vacation days,” or, “I’m confused about why we use this partner instead of another, better quality partner.”

Again, try to make sure your team feels comfortable sharing the things they feel confused about. This isn’t going to happen by saying, “I want you to feel comfortable sharing!” It takes months and years to build up that kind of trust. But learning how to be the type of leader that encourages that mutual respect and comfort is another blog topic for another day.

Meet With Determination

You’ll notice that none of these questions are related to goals or outcomes. That’s because your preparation and planning time shouldn’t be spent thinking about what you’re going to get out of your team’s time together. Why not? Because all of the questions above are certain to bring up conversations that you never imagined. Your team has more ideas combined than you could ever have alone. That’s part of the beauty of meeting in person, fostering open communications, and asking questions, not seeking answers. Your biggest, solvable problems will become clear as you move through discussions about these questions and then, and only then, can you create goals and initiatives for the year to come.

In my next post, I’ll explore more about how we actually run our retreats (from coffee to cocktails!) and how we set our project and task lists for the year. In the meantime, I’m curious: Do you plan annual retreats with your team? How do you plan for them? Let me know in the comments below!

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Jess Tyson, CEO & Director of Calm

Jess is the founder and proud Director of Calm at Don’t Panic Management. (And yes, she invented that title because that’s what you do when you’re the boss!) She wrote the book on how building a successful relationship with a virtual assistant can make all the difference in helping business owners get to the next level. Her life is often a whirlwind of wrangling her toddler, speaking at conferences (virtual and beyond!), researching productivity hacks, and meticulously making matches between overworked entrepreneurs and focused virtual assistants. Jess's first book, Panic Proof: How the Right Virtual Assistant Can Save Your Sanity and Grow Your Business is available now: panicproofbook.com

  • Current location: Redding, CT
  • Go-to Karaoke song: “Hand in My Pocket” by Alanis Morissette
  • Favorite kind of cheese: Aged Goat Gouda
  • Beverage of choice: Champagne
  • Pronouns: She/Her/Hers
  • Superpower: Delivering miracles, especially when all hope is lost.

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