Step 1: Start with a legitimate reason (or don't do one at all) 💡 

Not all companies need offsites. "Our competitors do them" or "we have budget left over" are terrible reasons to plan one.

Here are the four legitimate reasons to bring your team together:

1. You're entering a pivotal moment where everyone needs to be in lockstep. Major strategy shift. New product launch. Whatever it is, the stakes are high and alignment matters.

2. You just survived hell and the team needs to unplug, unwind, and celebrate together. You made it through a brutal quarter. You hit a massive milestone. People are burnt out and need to remember why they're doing this.

3. You've been through trauma and need to unify under one mission again. Layoffs. A failed launch. Leadership turnover. The team needs healing and reconnection.

4. You just acquired a company and need to bring both teams together to meet, mingle, and build a shared future.

If your offsite doesn't fit one of these buckets, save your money.

Step 2: Hire a facilitator 🧑‍🦳 

Almost everyone should hire a facilitator. Yes, even if it costs you $10k per day.

Here's why: It's hard to be present as a participant when you're also wrangling other participants. You can't wear two hats at the same time.

A good facilitator:

• Acts as an objective third party

• Plays bad cop when needed (so you don't lose social capital)

• Pushes for uncomfortable conversations

• Guides the team to raw, vulnerable places

• Actively captures action items in real-time

Market rate for good facilitators is about $10K per day. Be willing to pay it.

And if you’re thinking, “Regina, that’s a lot of money for a single day of facilitation,” you’re right, it is. But you know what else is a lot of money? Bringing your whole team together.

Think of how much in collective time offsites cost. Think of how much you’re spending on getting everyone in the same place at the same time, working on the same problems.

Your $10k investment is insurance.

If you're a money-constrained startup and genuinely can't afford it, fine. Do it yourself. But choose the person with the best EQ/IQ skills in the company to help you build the experience. And know that it's going to be harder.

Step 3: Structure for vulnerability first, tactics second 🎯 

Here's the flow that actually works:

👉 Day 1: Break down emotional walls

Start with celebration or a vulnerability exercise. This is the time to let people see each other as humans, not just coworkers.

Good examples:

• 360 feedback for the CEO. When else are you going to tell your CEO where they're falling short? Do it here.

• "If you really knew me, you'd know..." Deep trust-building. Not performative bullshit.

• "What's your dream? Why?" Let people share what actually drives them.

After the vulnerability work, you can do high-level vision stuff. General direction. Where we're going as a company. But keep it strategic, not tactical.

👉 Day 2: Get tactical, make decisions, assign action items

Now you can get into the weeds. Who's doing what. Project-specific work. Push for decisions.

Always close with:

• Where we're going next

• Gratitude for the team

Step 4: Do things only possible IRL (or don't bother) 💡 

If you're going to fly everyone to one place, make sure you're doing things that can't happen on Zoom.

Worth the IRL time:

• Giving the CEO feedback on where they're lacking

• Deep trust exercises ("If you really knew me...")

• Vulnerability work around dreams, fears, motivations

Not worth the IRL time (keep these on Zoom):

• Reading slides about last quarter's numbers

• Reviewing next quarter's projects without action items

• Getting nitty-gritty on things that should happen during normal work hours

Step 5: Choose the venue with intention (not Instagram likes) 🏨 

The venue should serve the purpose of your offsite.

Here are examples of thoughtful choices I've seen:

One company I coached held their offsite at the location of the company they'd just acquired. Why? So the acquired team would feel heard and considered. Smart.

Another company chose Hawaii because it was the perfect balance of "relax" and "work hard." The change of scenery helped people unplug while still staying focused.

Another company's mission was helping countries devastated by natural disasters. They held their offsite in a developing country and spent part of the time volunteering together, packing boxes of supplies. The work reinforced their mission.

All of these had a clear why.

Compare that to the company who chose the fanciest location imaginable and blew what some companies spend in an entire quarter on the venue alone. Lots of Instagram pictures. Zero thoughtfulness about the company's mission.

Wrong incentives.

Step 6: Don't overstuff the agenda (give people whitespace) 📝 

The biggest mistake operators make? Trying to cram too much into one day.

Don't do it.

Give people time to relax. Time to spend with one another outside of structured sessions. Time to process.

If your agenda is back-to-back from 8am to 10pm, you've failed.

Step 7: Capture action items and follow through 💡 

A good facilitator will actively ask throughout the offsite: "Is there an action item here?"

Or: "You two should have a conversation about this separately." (And that becomes an action item.)

After the offsite, send out all action items to the team. Reference them in your next leadership meeting. Keep the momentum going.

If it's a company-wide offsite (larger than 20 people), action items are harder to assign. But you should still ride the momentum. Reference the presentations that rallied the team. Ask for progress updates toward company-wide goals.

Don't let the good feelings fade without translating them into forward motion.

And if you’re reading this - you're already ahead.

Because you know where to find the stuff that’s actually good. Like my templates and resources, and this newsletter.

Want more operational content?

Check out Coaching Founder for over a dozen free, downloadable Notion templates to use at your company, and tons of write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner, daughter, and dog, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.