The Chief of Staff's Guide to Planning a Company Offsite

"Can you plan the offsite?" usually lands on the Chief of Staff's desk with little more than a date and a headcount. It isn't in the job description, but it's one of the most visible things you'll do all year. Done well, the offsite moves the company forward. Done badly, it's three expensive days of presentations nobody remembers.

This guide isn't a step-by-step corporate retreat planning checklist. It's about your role: what a Chief of Staff should own, what to delegate, and how to work with your CEO and leadership team before, during and after a company offsite.

Key Takeaways

• Think of yourself as the offsite's architect, not its event planner. Own the goals, the agenda and the executives, and delegate the logistics.
• Start by agreeing on two or three outcomes with your CEO. Every other decision follows from them.
• Talk to each executive one-on-one before the offsite, so tensions and decisions come up early rather than in the room.
• During the offsite, keep a live log of decisions and owners, and watch the room so you can adjust the agenda.
• Send a recap within a week and follow up at 30, 60 and 90 days. That's where the offsite pays off.

Your role: architect, not event planner

The most common mistake is trying to do everything yourself. Offsite's founder, Jared Kleinert, has described the Chief of Staff's job here as architecting the experience while others handle the logistics. In practice, that split looks like this:

Logistics can go to an executive assistant, an operations lead or an outside partner. Working with an experienced corporate retreat planner can take most of that list off your plate.

Before the offsite

Set the goals with your CEO

Start with a working session with your CEO. Five questions to ask:

1. What should be different after the offsite?
2. Which decisions must be made while everyone is in the room?
3. What tension or topic do we need to address openly?
4. Who needs to be there, and who doesn't?
5. How will we know it worked 90 days from now?

Turn the answers into two or three outcomes in writing. Share them with the leadership team before you build anything else.

Set the budget

Agree on a per-person budget early. A fly-in team offsite of 2 days and 3 nights typically runs about $2,700–$3,000 per person in 2027, based on current team offsite costs, and most company offsites fall within $2,000–$4,000+ per person including travel. Set limits on the big trade-offs, such as destination, length and venue tier, and let your logistics partner work within them.

Pre-wire the executives

Whether it's a company-wide gathering or an executive offsite, the best offsites are mostly decided before anyone arrives. Two to three weeks ahead:

• Meet each executive one-on-one. Ask what they want from the offsite, what worries them and where they disagree with peers.
• Share a short pre-read with goals, the agenda and the data everyone needs, at least three days before.
• Settle what you can in advance. Use the offsite for decisions that need everyone together, not updates that could be an email.

The same principles apply whether it's a company-wide offsite or a smaller leadership retreat.

Own the agenda

Build the agenda around the outcomes, not around who wants stage time:

• Decide who leads each session. The CEO usually opens and closes; executives lead their topics.
• Protect discussion time. Short presentations, long conversations.
• Plan for energy. Put the hardest decisions in the morning, and schedule real breaks and time outside.
• Bring in a neutral facilitator for strategy sessions when the CEO needs to take part rather than lead.

During the offsite

Your job on the day is to keep the offsite on course while the CEO and executives do the work.

• Keep a live decision log. Record each decision, its owner and its deadline on a shared screen, so everyone leaves with the same list.
• Watch the room. If energy drops or a discussion stalls, adjust the agenda. A shorter session that ends in a decision beats a full one that doesn't.
• Manage time without being the timekeeper everyone resents. Agree with the CEO in advance on how you'll signal when to move on.
• Hold a parking lot. Capture off-topic issues with an owner, so they don't derail the session.
• Check in with the CEO at each break. Two minutes to confirm what's working and what to change.

After the offsite

The offsite pays off in the weeks after it, and that part is usually the Chief of Staff's.

• Send a recap within a week. Decisions, owners, deadlines and open questions, on one page.
• Plan what the rest of the company hears. Agree with the CEO on what to share, when and how, ideally at the next all-hands.
• Follow up at 30, 60 and 90 days. Review progress on each decision with its owner and flag anything that's stalled.
• Run a short retrospective. What worked, what didn't and what to change next time.

Common pitfalls for Chiefs of Staff

• Doing everything yourself. If you're booking shuttles, you're not watching the room.
• An agenda built on presentations. Updates belong in a document. The offsite is for decisions and connection.
• No decision log. Without one, people leave with different memories of what was agreed.
• Skipping the one-on-ones. Tensions you don't hear about beforehand tend to surface in the middle of the most important session.
• Letting follow-up slide. The offsite is only as good as what happens in the 90 days after it.

Conclusion

As Chief of Staff, your value at an offsite isn't in the logistics; it's in the design. Agree on two or three outcomes with your CEO, pre-wire each executive, own the agenda and the decision log, and delegate everything else. Then make sure the follow-up happens, because that's where the offsite pays off. Offsite can handle the venue, travel and on-site logistics, so you can focus on the parts only you can do.