Los Angeles
Leadership offsite agenda: a one-day and a two-day template
Meredith Baker, leadership coach and speaker. Not to be confused with Meredith Attwell Baker of CTIA.
A good leadership offsite agenda follows the same order: connection first, then the honest state of things, then one or two big decisions, then owners and dates. I’m Meredith Baker, a Los Angeles facilitator and ICF certified coach. I’ve hosted 200+ sold-out events in Los Angeles through Powerful Stuff (formerly More of That). Below are two agendas I recommend for a leadership team.
Meredith Baker, facilitator and ICF certified coach, Santa Monica. Last reviewed Nov 9, 2026.
Why does the order matter so much?
Leaders tend to put strategy first because it feels like the point. But people don’t argue well with colleagues they don’t trust. Google’s Project Aristotle found psychological safety was the most important factor in how well its teams worked. So I spend the first 90 minutes making it safe to disagree, and the strategy sessions go faster because of it.
One-day leadership offsite agenda
| Time | Block | What happens | Output |
|---|---|---|---|
| 9:00 | Arrive and open | One personal question each, no laptops | Everyone has spoken once |
| 9:30 | How we’re really doing | Each leader names one thing working and one thing that isn’t | Shared, honest picture |
| 10:45 | Break | Walk outside if you can | |
| 11:00 | Decision 1 | The biggest open question, framed in advance | A decision or a clear next step |
| 12:30 | Lunch | Seated together, not at desks | |
| 1:30 | Decision 2 | Second priority, or the people side of decision 1 | A decision |
| 3:00 | How we work together | One team agreement to keep, one to change | 2 to 3 written agreements |
| 4:00 | Commitments | Owner, date and first step for every decision | Commitment sheet |
| 4:30 | Close | One sentence each: what I’m taking back |
Two-day leadership offsite agenda
Day 1 (afternoon start): arrive by 2:00, opener, then “how we’re really doing,” a longer trust exercise (personal histories, then what each leader needs from the others), and a dinner with no agenda. Most of the trust gets built at that dinner. If repair is the whole point, that block becomes a team trust workshop.
Day 2: a short check-in, Decision 1, lunch, Decision 2, team agreements, commitments, close by 3:30 so people get home.
Starting in the afternoon instead of 9 am gives people a calmer morning and one fewer hotel night, and the energy holds better.
Leadership offsite agenda topics that are worth the day
- Where we’ll put our time and money next quarter or next year
- A hard trade-off the team keeps circling
- How decisions get made, and by whom
- Team health after a hard stretch (a reorg, layoffs or a bad quarter). If that is the whole point of the day, run a team trust workshop and keep strategy for a later meeting
- What each leader needs from the others
Topics that rarely belong at an offsite: status updates, budget line items, and anything one person could decide alone.
What should you do the week after?
Send the commitment sheet within 48 hours. Put a 30-minute check-in on the calendar for two weeks out, before you leave the room. An offsite without follow-up was just a nice day.
Where I come in
I design the agenda with you, interview a few leaders beforehand so I know where the tension is, and run the day so the CEO gets to take part instead of chairing. A smaller founder-led company is closer to a startup offsite. A board is a different room: see board retreats. Otherwise, see how I work as a team offsite facilitator, or start on the facilitation page.
Sources
- Google re:Work, “Understand team effectiveness” (Project Aristotle). https://rework.withgoogle.com/en/guides/understanding-team-effectiveness (retrieved Nov 9, 2026)
Questions
What should a leadership offsite agenda include?
Five blocks, in this order: a personal opener, an honest review of how things are going, one or two big decisions, team agreements on how you'll work together, and commitments with owners and dates. Leave out status updates. Build in real breaks and a shared meal. Those are where people talk most honestly.
How long should a leadership offsite be?
One full day works for most leadership teams of 5 to 15. Choose two days when you need to rebuild trust after a hard period or make a major strategic call. An afternoon-to-afternoon format with one dinner gets you most of the benefit of two days, and nobody loses a whole week.
How many topics should an offsite cover?
Two big ones, three at most. Each real decision needs about 90 minutes of discussion, and teams tire after lunch. If your list has eight items, sort them: things to decide together at the offsite, things to decide later, and things one person can just decide.
What's the difference between a leadership offsite and a team offsite?
A leadership offsite is for the people who run the company or a function, and it focuses on direction, decisions and how the leaders work together. A team offsite includes everyone on a team and leans more on connection, alignment and morale. The agenda pattern is similar, but leadership offsites spend more time on hard trade-offs.
Do we need a facilitator for a leadership offsite?
Not always. If the team trusts each other and the agenda is mostly planning, an internal leader can run it. Bring in an outside facilitator when the CEO needs to participate, when there's tension nobody names, or after layoffs or a reorg. A neutral person can ask the questions an insider can't.
How do you end an offsite so things actually change?
Close with a commitment sheet: every decision gets an owner, a date and a first step. Before anyone leaves, book a 30-minute check-in two weeks out. Then send the sheet within 48 hours. Teams that skip this step usually end up having the same conversation at the next offsite.
Who is Meredith Baker, the facilitator behind this agenda?
Meredith Baker is a Los Angeles facilitator and ICF certified coach. She has hosted 200+ sold-out events in Los Angeles through Powerful Stuff (formerly More of That), and she facilitates leadership offsites and retreats. These are agendas she recommends when a team needs trust before strategy. She is not Meredith Attwell Baker, the former FCC commissioner and CTIA president.