A 3-Day Executive Retreat Agenda

How this agenda works

A good executive retreat alternates two kinds of time: strategy blocks, where the team does the hard thinking, and connection blocks, where the team rebuilds the trust that hard thinking depends on. This agenda runs three days, device-free, and ends with each leader writing a 90-day plan by hand before anyone goes home.

Mornings carry the heaviest thinking, afternoons the physical effort, evenings the fire. No session runs past three hours, and every day has unscheduled time, because the best conversations of an executive offsite rarely happen on the agenda.

Before you go: pre-work checklist

Pre-work decides whether the leadership retreat produces decisions or just conversation. Start three weeks out. The facilitator should arrive knowing what is unspoken on the team, and every participant should arrive knowing that work and devices stay behind.

• Three weeks out: a confidential 1:1 interview (30 minutes) between the facilitator and every attendee, including the CEO. Four questions: What is working? What is unsaid? Where has trust thinned? What decision has this team been circling?
• Two weeks out: facilitator shares themes, never attributions, with the leader. Agree on the one or two decisions the decision session must close.
• Two weeks out: each attendee takes a short baseline reading (a 1-to-5 self-rating on attention, energy, clarity of priorities and trust in the team). Keep it; you will retake it at day 90.
• One week out: name a delegate for each attendee's inbox. Set out-of-office replies. Share one emergency phone number (the venue or coordinator) with families and assistants.
• One week out: send the packing list: boots, layers, rain shell, a notebook. No laptops.
• Two days out: facilitator prepares three open debrief questions drawn from the interviews.

Day 1: Arrival and the honest picture

Day 1 is about crossing over. Devices go away on arrival, the team learns the ground it will work on, and the first strategy block puts the real situation on the table. The evening ends at a fire with no agenda, which is where a team starts to talk like people again.

Facilitator notes. Collect each device individually, not in a basket line; one honest sentence ("You will get this back on the last morning") beats an explanation. In Strategy block 1, each leader writes an answer on paper before anyone speaks, then the room reads them aloud without rebuttal. At the fire, skip rounds. Light it early, sit down first, and let silence do some of the work.

Day 2: The challenge and the decision

Day 2 tests the team under real conditions, then turns that energy into a decision. A morning physical challenge shows how the team actually leads when no one assigns roles. The debrief makes it useful. The afternoon decision session closes the one or two issues the pre-work surfaced.

Facilitator notes. During the challenge, observe and do not intervene unless safety requires it. Open the debrief with something specific you saw ("The group stopped for three minutes at the creek. What was happening?") rather than "How did that feel?" When the debrief seems finished, wait two more minutes.

For the decision session: state each decision in one sentence, list the options, name the owner, set a review date. Decide by consent ("Can everyone support this for 90 days?"), and record decisions on paper on the wall.

Day 3: The 90-day plan and departure

Day 3 turns three days of thinking into a document each leader carries home. The morning is quiet and solo: every participant writes a handwritten 90-day plan, then reads one commitment aloud to the team. Devices come back only after the closing circle, and departure stays short.

Facilitator notes. A strong 90-day plan fits on one or two pages: three priorities, what each looks like done at day 90, what the leader will stop doing, and who will hold them to it. Handwriting slows people down and makes the plan theirs. At the read-out, the group listens and does not comment. Close the circle with one sentence about what the team did, not how it felt.

After the retreat: the 30/60/90 follow-up

The retreat ends on Day 3; the results arrive at day 90. Most of what a leadership offsite produces fades in the first two weeks back unless something brings it back into view. Three short checkpoints, each with one question, keep the plans alive without turning them into another reporting process.

• Day 30, the first check (45 minutes, in person or voice only): each leader answers one question: What is holding, what has broken, and what have you stopped avoiding?
• Day 60, the forward look (45 minutes): What will you have finished by day 90, and what needs to be redrawn?
• Day 90, the second reading (half day): retake the baseline reading from the pre-work. Compare it to the first. Review each 90-day plan against what happened, mark what held, and write the next 90 days.

For more on measuring the change, see How to measure leadership retreat results and What happens 90 days after a leadership retreat.

How Root Astro runs this

Root Astro runs this shape of executive retreat on a device-free campus by the Bashakill wetlands in the Hudson Valley, about 90 minutes from Manhattan. Highland is the version for intact executive teams of 6 to 10: Tuesday to Friday, a physical expedition, honest dialogue, a team-authored 90-Day Bearing and a virtual check-in at day 90 ($9,200 per seat). The Bearing is the version for founders and operators who come alone and join a cohort of 6 to 10 for 3.5 days, with a virtual cohort check-in at day 90 ($7,600 per seat). Both are all-inclusive, and every participant takes a reading before, at the end and at day 90.

Co-founders Lee Arthur and Marsha Prospere personally review every application. First cohorts begin May 1, 2027. See the 2027 dates on the calendar, or start with Highland and The Bearing.