Four Guidelines for Offsite Planning Season

You're flying people in from all over the country (if not the world), you're spending thousands of dollars, and you're dedicating days of everyone's time, let's not wing it!

Four Guidelines for Offsite Planning Season

As offsite planning season approaches, many leaders and teams are preparing for these important gatherings and are about to spend significant time, energy, and money. Having coached leaders across industries and facilitated many offsite experiences, I know that a well-designed offsite is a powerful mechanism for building cohesion, ensuring alignment, and deepening a team’s capacity for impactful work. I also know they can be a colossal waste of resources if not done well. 

Let me paint the picture for you, it’s Q3 and I am in the last 15 minutes of a coaching session, predictably a client will ask, “Hey, we have an offsite coming up—do you have any ideas?” More often than not, we end up collaborating on the design and facilitation of their offsite. For others, a full collaboration may not be in the cards, which is why I’ve distilled some of my tried and true guidelines on how to design a successful offsite. While it’s by no means exhaustive, it’s a great starting point to ensure your offsite is impactful and effective!

1) Identify the Outputs

The first step is to clearly define what you want to accomplish at the offsite. Is it a strategic planning session for the next year? A quarterly review where everyone needs to define their big goals? Or perhaps your team simply needs face-to-face time to deepen relationships and enhance collaboration. Once these outputs are identified, everything else—structure, timing, and content—should align to support them.

2) Structure the Inputs

Now that you have 1-3 key objectives, it’s time to create the structure to support achieving them. This structure ensures that not only are the goals met, but the process is dynamic and engaging. I see two common pitfalls when this principle is overlooked:

• Teams tackle messy issues without the necessary structure to support the desired outcomes. This results in conversations feeling untethered and shallow, with everyone eventually shaking their heads, saying, *“What are we even talking about?”*

• The event is overly structured, and teams are simply herded from one activity to the next without any real depth or connection to their real-world challenges, with everyone wondering, *“Why are we even doing this?”*

To avoid these traps, I recommend using tools like SessionLab, which prompts you to define the goal for each part of the session. This keeps the flow connected to the intended outcomes and ensures the content serves the larger goals.

3) Get Real About Timing

One of the best pieces of advice I’ve received about offsite design is this: "As soon as you hear yourself saying, 'This is such a great conversation, but we need to move on,' you need to rethink your design and timing." In moments like these, you’ve likely underestimated how much time was truly needed. In my early days, I often misjudged timing, from scheduling overly long lunches to not accounting for how much time people needed to re-enter the room after breaks or context switches.

To avoid this, I suggest using SessionLab’s timing functions to visualize and adjust your design. See the example below. This way, you can set up spacious, effective sessions that don’t leave you rushing through important conversations. I also like to send people on breaks before they know they need them. It’s sort of like eating something before your blood sugar drops, you stave off nausea and people are less cranky.

4) Not Everyone is Fueled by Group Time

Not everyone thrives in large, verbally driven group settings. One of the most common mistakes I see is a schedule packed with back-to-back group sessions and verbal processing time. Great teams can burn out when there’s too much of this.

To prevent this, I build experiences with alternating solo work, small group work (dyads, triads, or quads), and larger group sessions. I also build individual work segments, where participants can immediately start applying what they’ve learned or discussed. By building in action-taking time you stave off the “camp effect” of an offsite and allow people to implement the next steps right away, reducing the likelihood that all the brilliant ideas from the offsite go to die in someone’s backlog.

If you’d like to see how I integrate these principles check out a screenshot of an offsite I ran a couple of years ago. 

I hope these principles support you as you plan your next offsite.  If you'd like help applying them, feel free to schedule a complimentary co-design session with me, message me through Substack, or email me at annalise@annalisekoltai.com. Let’s make your next offsite the best one yet!

May your outputs be achieved,  

Your inputs well-structured, 

Your design friendly to a myriad of personalities,

And your timing is exquisite!

Example of a SessionLab with these four guidelines adhered to.