Let’s Plan an Offsite (One You’ll Actually Enjoy, I Promise!)

Okay, let’s be real.

End-of-year planning can sometimes feel like one long to-do list. But I’m here to make it a little less painful and actually kinda fun—like that first time I planned an offsite. Picture this: Big Bear, California. We rented out an entire hostel (yes, a hostel) because we were cash-poor but rich in ideas. It was scrappy, but it became legendary in our company folklore.

We had each team member do a mini-TED talk on a subject of their choice. We dove deep into business strategy, vision, and some... questionable karaoke. To this day, it’s still one of the most talked-about events at our company.

So, what’s stopping you from planning your own legendary offsite? I’ve got a quick guide on how to make it happen—everything from choosing the right location to prepping the team.

Let’s get ahead of the chaos and make your offsite one for the books. No hostels required (unless you’re feeling nostalgic like I was).

Step 1: Set the Vibe (Theme and Objectives)

No one likes a random gathering. Before everyone hops on a plane or Zoom, get clear on the purpose. Is it strategic planning, culture-building, or deciding how to overthrow Greg from finance? (Just kidding, Greg’s not that bad... except when he brings up his PowerPoint addiction). Decide why you’re meeting, then craft the agenda to reflect that purpose. No fluff, just focused time to tackle what really matters.

Step 2: Prep Like a Boss

Use a solid framework to organize your thoughts and keep the team on track:

1. The '5 Why’s' Method:
Dive deep into core challenges by asking 'Why?' five times to uncover the root cause. Get ready to unravel issues you didn’t even know were there.

2. OKR Setting (Objectives & Key Results):
Break down your goals into measurable outcomes. Each leader should bring their top 3-5 OKRs to the table. This will make follow-through post-offsite seamless.

Step 3: Why Bring in a 3rd Party Facilitator?

Let’s be honest: You might be a genius, but sometimes, bringing in an outside voice can take the session from good to next-level. Here’s why:

• Objectivity: A third-party can see things without the internal bias and politics, which often muddy conversations. They can ask the tough questions no one else will.

• Bias Reduction: Bringing in an external facilitator helps reduce confirmation bias, making sure you’re not just hearing what you want to hear.

• Diversity of Thought: A fresh perspective is invaluable. You’ll benefit from someone who’s seen it all across industries and teams, adding new approaches to your mix.

• Unlock Stalemates: Got that one decision no one can agree on? A neutral facilitator helps unblock stubborn team dynamics, cutting through the noise and getting to solutions.

Step 4: Choose Your Format (Virtual vs. Remote)

Deciding between Zoom or some remote cabin in the woods? Here’s the scoop:

Virtual (Zoom, Teams, etc.)

• Pros:

  • No travel headaches (TSA who?)

  • Easy to schedule, and great for keeping costs low.

  • Everyone can mute themselves when Greg starts talking (Just kidding, Greg).

• Cons:

  • Harder to connect on a deeper level.

  • You might lose people to distractions (emails, Slack, that adorable puppy filter).

  • Tech issues WILL happen. That’s a promise.

In-Person (Remote Location)

• Pros:

  • Team bonding magic happens here. You can’t replicate those random late-night talks over a campfire.

  • Full attention. No Slack pings to distract the crew.

  • Energizing change of scenery. People show up differently when they aren’t stuck in their same old cubicles.

• Cons:

  • Logistics can get messy. Do you really want to be in charge of booking 12 people’s flights?

  • Less flexibility if someone cancels last minute.

Step 5: Agenda = Your Secret Weapon

Have a solid game plan. Break it down:

• Day 1: Big picture strategy, vision alignment, team-building (icebreaker optional, but let’s be real, people secretly love ‘em).

• Day 2: Tactical work—key decisions, OKRs, next steps. Leave time for reflection and course corrections.

• Day 3: Wrap it up with action items and accountability. Make sure no one leaves without knowing their next steps (including Greg).

Step 6: Pre-Work for the Win

Get your leaders to show up prepared. Assign some light reading, a pre-offsite survey, or specific questions to make sure everyone is on the same page from minute one. Bonus: It keeps the chatty ones busy so you can start on time.

Pro Tips (For When You’re About to Lose It):

1. Leave Time for Fun: A little social activity goes a long way in strengthening team bonds. Just don’t make it too competitive, unless you want a full-blown dodgeball war.

2. Mix Breaks with Brilliance: Don’t force 8 hours of decision-making in one sitting. Schedule breaks so people can recharge.

3. Appoint a Timekeeper: The most crucial role of the day. Otherwise, you’ll be listening to Greg’s unsolicited TED Talk on nothing (kidding, but not really).

Want to chat about leadership offsites?

Need help with frameworks, pre-planning, or thinking about what it looks like to bring in a 3rd party?

Call me. Free planning call. No pressure, no BS, pure value.