Why a Staff Retreat is Brilliant Business - What Would Arlene Say?

7 min read
January 25, 2018

One of my favorite clients just had a retreat to launch her venture from a solo practice to an ensemble of staff and a junior advisor. She decided from the first moment the team started working together she wanted to create a winning dynamic. We worked though the steps to introduce the junior advisor to clients, and now the retreat has laid the foundation for a fantastic team atmosphere. In financial planning do you find it is more fulfilling to plan than to fix errors your clients make? In that same vein, I enjoy coaching proactively rather than reactively. Planning this retreat was a blast. It is exhilarating to move forward and watch a team grow so positively.

When Worlds Collide - Generational Differences & Succession Planning

The advisor population is aging. The time has come to assure that the next generation of advisors is in place so that aging advisors can retire knowing they have left clients in good hands.  I know Baby Boomers and Gen Xers don’t have a lock on generational differences, but technology advances and economic life experiences have drawn some stark differences between the generations in this millennium. Successful succession planning means addressing all of the joys and concerns that come with mixing multiple generations in the office.

The Why & How Of Amazing Staff Retreats

Ah, the elusive concept of the perfect staff retreat. There are so many questions surrounding the idea of planning a staff retreat, and when they go unanswered businesses tend to shy away from hosting them. Will they be a good use of time? Will the retreat have long term positive impact? Does your team really need to attend an off-site retreat?

Let’s dive in so you can fully understand the why and how of staff retreats (and start implementing them to improve your business!).

Building a Team - Act or React

We all hope for the best when we begin a new phase. No one hires a new team member assuming things will go badly, and yet sometimes things do. Your choice as you move your team forward is to act or react. A staff retreat is one way you can be proactive. Get a jump start on potential issues such as communication styles and employer/employee expectations. You can talk about fears and concerns from the outset as well as learning about generational differences so that you are prepared for, and preferably avoid, irritations and miscommunications. Regardless of the exact contents of your agenda, you are reaching out to set the stage for success.

Why Are Staff Retreats Brilliant Business?

Staff retreats help build your business – big or small – in so many ways. Even if we focus on the high level of what staff retreats accomplish, the truth is you get so much done. Way more than you’d get done during a routine team meeting. I’ve had clients plan their marketing initiatives for the year, how they want to scale their company growth, and some of them have walked away from their staff retreat with a five and ten-year plan. That’s a lot of actionable planning that’s getting knocked out!

While staff retreats are great for accomplishing tangible goals, like future planning, collaborating on big projects, and brainstorming ideas that will help you move your business forward, they also help your team connect on a deeper level outside the traditional workplace. For some, the work environment is a natural stressor. They suffer from impostor syndrome, they view it as an aspect of their life where there is no enjoyment, or they’re naturally anxious about their own work performance.

A staff retreat gives these people a chance to connect with coworkers outside of that environment and take time to truly understand one another, as well as their purpose within the grand scheme of your business. This connection helps you to align your team’s goals, boost morale, and ultimately improve productivity at work when your team returns with renewed inspiration and energy.

Can’t we just have a meeting?

Setting aside time for a retreat takes you all away to a neutral location, reduces participants’ stress, and levels the playing field. A facilitator further helps to maintain neutrality and aid team building. You don’t have to go to an exotic locale, but getting away from the office sends a clear message that this is worth taking the time to take the best path forward. Annual retreats tell your staff that it is a special time to get the business revved up for another great year.

No retreat looks quite like any other. Create a schedule that covers your goals and concerns. Some things you may consider are generational communications, work ethic and styles, processes and workflows – especially if you are a one person show hiring your first staff. Discuss client relationships, career paths, performance expectations or take time to do some strategic planning. . Allowing for some time in the evening to socialize gives people time to relax, create great memories and connections. It may seem to be down time, but those connections will be strong when stress rises back at the office and you all need to pull together. The agenda is limited only by your imagination. Let your facilitator help you brainstorm ideas and build the schedule to suit your team and your needs.

Who Should Have A Staff Retreat?

Everyone. One of the reason staff retreats are so amazing is that they’re inclusive. You have the flexibility to invite your close team, an entire office, or the two or three people in your firm. And if you’re a solopreneur? You’re not excluded from having staff retreats for yourself! In fact, it can be even more important for a solopreneur to take a step back and invest time in solidifying their business vision and plans.

And if you’re reading this thinking, “I don’t need a staff retreat – my team gets along great, business is running smoothly,” you’re probably wrong. That sounds harsh, but it’s accurate. The less you believe you need a staff retreat, the more you probably do to make sure you’re in touch with your team and what’s going on with their workplace engagement.

Staff retreats allow for a safe space to share ideas and express any reservations, which all team members have at one point or another. Rather than try and gauge if and when you need to host a retreat, try to commit to hosting one annually. That way it’s on the calendar, and there isn’t any guesswork.

Plan Ahead

The first key to a successful staff retreat is to plan ahead. Start with building an agenda to make sure all the business planning, idea brainstorming, and teamwork exercises you want to accomplish get put on the schedule. Planning ahead and deciding how you’ll use your time is the best way to make sure your retreat is the best possible use of both your and your team’s time.

While you can definitely put together your own retreat, sometimes the planning step is where people get stuck – and then the retreat never happens. That’s why it can be extra handy to involve a facilitator like me to help guide you through the process. Facilitators take the pressure off the leader by helping to uncover key points you want to touch on, brainstorm helpful team building events, and build your agenda.

Depending on what your team needs, you and your facilitator can plan in one of two ways. You can choose to involve your team. Sometimes a team that already tends to be collaborative enjoys being a part of putting together the agenda, and their ideas and enthusiasm can help guide the tone of the retreat. Alternatively, there may be some teamwork issues that your team is facing. This isn’t uncommon, but if you feel that someone might have a concern that wouldn’t be voiced in a team-planning session, host private meetings with each of your staff to ensure that everyone’s concerns and ideas are addressed.

When you’re planning your retreat, making it an offsite event is a key factor. This creates a neutral ground where all your team, not just the vocal few, will feel like they can voice their ideas and opinions. Remember, the loudest voices don’t always have the best ideas. If possible, schedule your retreat overnight. There’s something exceptional that happens when people sleep on the work they’ve done and the progress they’ve made, and wake up as a team to keep pushing forward.

This may sound overwhelming – and that’s okay. Planning a retreat can be a bit of a bear whether you’re a first timer or a seasoned retreat veteran. Having a coach ensures that you’ll stay on track during the planning process without falling behind on your daily work duties (because those are important, too). A coach can also be involved during the actual retreat, making sure voices are heard, guiding the team to stick to the agenda, and tracking ideas that you may want to revisit later so that you, as the boss or team leader, can be fully engaged with your team.

Appreciate Your Team

Finally, as much as a staff retreat is about planning, team building, and making progress, it’s also about appreciating your team. They’ve done great work for you, and they’re doing even more great work here at your team’s retreat. It’s a simple gesture, but start the retreat with some comfort food or treats. Donuts, coffee, bagels – whatever floats your boat. This sets the tone of appreciation early. Continue to show your appreciation by scheduling time for fun lunches and dinners, maybe head out to a wine tasting, or incorporate another enjoyable event at the end of the day. You’re getting amazing things done, but taking time to bond and have fun is equally important.

Showing your team appreciation in these small ways improves your overall connection – nobody likes to go unacknowledged. However, that doesn’t necessarily mean that everyone is going to want to be 100% involved the entire duration of the retreat. Give your team permission to unplug. Staff retreats, while amazingly productive, can also be amazingly exhausting. The introverts on your team will appreciate optional events – even if they opt to head up to their room and read a book with a pizza instead of tagging along.


Staff retreats are so fun because not one of them is exactly alike. They can be tailored to your team and your business needs, located anywhere you can imagine, and with a schedule that is unique to what you want to accomplish. I’d love to help you set up your staff retreat, or answer any lingering questions you might have. Please, contact me for a free first consultation. I’m looking forward to hearing from you and your team!


About Arlene Moss, Executive Coach

Arlene gets a kick out of helping financial advisors get over being overwhelmed and take on their frustrations so their businesses soar. Arlene works to ensure XYPN members are able to help their clients prosper while creating a sustainable business model. Through XYPN Academy and one-on-one coaching, members get the support they need to grow their businesses and overcome the challenges that come their way.

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