The When, Why, and How of Planning Your Staff Retreat

Don’t let the word “retreat” put you off. Staff retreats are hugely productive – and are critical for steering your organization in the right direction. They’re a way to get your team aligned with your vision and mission, and an opportunity to reconnect away from the keyboard. Newer team members or remote/hybrid workers will also get the opportunity to put faces to names, building camaraderie and organizational buy-in.

Technically, a staff retreat can happen whenever it’s convenient for your calendar. But there are certain times of the year that will return the most value. A year-end date is great for reflecting on the previous year’s efforts and for redirecting team energy into the next year. Meanwhile, a mid-year date can galvanize your team to push forward and give their all for the remainder of the year. Retreats can also double as rewards for finishing a major project, or can help refocus and reorient the organization in the wake of major organizational change. Be mindful to plan your retreat around popular holiday breaks – and avoid overlapping important religious or cultural events. 

Organizing a staff retreat involves many moving parts. For best results, make the process collaborative and inclusive. For example:

• Use Doodle Polls or Calendly to choose a date. Shortlist a few dates and invite team input to see what works best for your team. Depending on the size and make-up of your organization, it might make sense to book multiple days. Think mid-year, end-of-year, or even around key events or milestones in your organizational calendar. Polls are also vital for identifying dietary needs and other accommodations.
• Decide on in-person or virtual format. In-person gatherings are ideal, but whether this is a viable option depends on the distribution of your organization. If your team is scattered across the country, offer to fly everyone to a central destination, or piggyback your meeting off an industry conference or event. For smaller budgets, a strategic partner’s conference room or a coworking space can be an affordable way to get people out of the office. (If you opt for a virtual get-together, here’s how to make it a success.)
• Know your goals and plan accordingly. Retreats aren’t one-size-fits-all. Identify what you want to achieve with your retreat, and build out your itinerary to suit. Set objectives, break into groups, invest in facilitation and visual note-taking services, and follow up with post-retreat material that your team can incorporate into their day-to-day.