File 02 · Leadership
Two to four days away for the people who set the direction. The Renewal Office plans leadership retreats, executive offsites and board retreats around what your leaders need to decide, and who they need to become to carry it.
At a glance
Why a leadership retreat
Most executive offsites fix the plan and skip the team. Two days of slides, a dinner, and by Wednesday everyone is back to how they worked before. The decisions were fine. The way the team makes and keeps them never changed.
We design for both. Every leadership retreat we plan has hard strategy work in the morning and the human work around it: how each leader is wired, where the team gets stuck, what trust actually looks like in practice.
Place does half the work. A hilltop inn in Ojai or a desert estate in Indian Wells changes how people talk to each other. You choose the place, and we help match it to the conversation you need to have, not the ballroom you can fill.
We bring leadership teams away when the next year depends on them deciding together, and meaning it.
Five ways in
Every one is built around a goal your leaders name, then designed on the TRO Six Pillars.
WhenAnnual or quarterly planning for the leadership team. Strategy sessions, set somewhere that clears their heads.
OutcomeA clear plan they’re all bought into.
4 to 20 · 2 to 3 daysWhenAn executive team that needs to strengthen how it works together, not just plan. Honest feedback, how decisions really get made, and what each leader needs from the others.
OutcomeLeaders who communicate and decide better as a group.
4 to 15 · 2 to 3 daysWhenNew managers, rising leaders or a leadership cohort. Coaching, reflection, group equine-assisted learning and honest feedback, so leaders see how they lead.
OutcomeLeaders who know how they lead, and lead better for it.
6 to 30 · 3 to 4 daysWhenA founder or CEO passing the company to the next leader. The outgoing leader honored, the incoming leader welcomed, and the team aligned behind them.
OutcomeA clean handoff, with the team’s trust carried across.
5 to 25 · 2 to 3 daysWhenCompany, foundation and nonprofit boards. Strategy, succession and trust, with a neutral outside facilitator holding the space.
OutcomeA board that agrees on where it’s going, and trusts each other to get there.
3 to 25 · 1 to 2 daysTell us the decision your leaders need to make. We’ll tell you the format.
Open a fileLeadership retreat or executive offsite?
An executive offsite settles the plan. A leadership retreat changes the people holding it. We build every leadership file to do both, every day you’re away.
Leadership retreat ideas
Pulled from the sessions we run most, tagged by the TRO pillar they serve. Turn a card to read it.
Outcome
A shared language for how each leader works.
Each leader’s wiring mapped on one wheel, so the team sees where it overlaps and where it clashes.
Knowing
Outcome
Honest feedback on how the team actually leads.
A ground session with horses, no riding. They mirror how a group communicates and leads, fast.
Knowing
Outcome
Risks named early, while they are still cheap to fix.
Imagine it’s next December and the plan failed. Write down why. Then fix those things now.
Guiding Star
Outcome
Three decisions made, each with an owner.
Not twenty priorities. The three decisions the year depends on, made on site.
Guiding Star
Outcome
Clear heads before the hard sessions begin.
Phones in a basket, a trail at first light. The best conversations of the week usually start here.
Renewal
Outcome
A calmer team, and conversations that go deeper.
An hour of nothing to fix, then the honest talk that only happens after dark.
Renewal
Outcome
Leaders who know each other beyond the title.
A long-table chef dinner where every course comes with a question worth answering.
The World
Outcome
The why behind the company, heard firsthand.
The people who built the company tell how it really started. New leaders inherit the why.
The World
Outcome
Trust tested in real time, then talked through.
Ropes, puzzles or a relay, then the real work: who led, who waited, and why.
Transcend
Outcome
Every leader heard, one conversation at a time.
Paired walks with a single prompt. Leaders who rarely talk alone get forty minutes together.
Transcend
Outcome
Promises in writing, with names and dates.
Owners, dates and what changes on Monday, signed before anyone gets in the car.
The Offsite
Outcome
Decisions still alive a quarter later.
We book the follow-up before the retreat ends, so the decisions don’t fade by Wednesday.
The OffsiteFrom our files · Case file 001
“The programming put us on a different playing field, and we saw the vision for what comes next, together.”
Brad Krefman, Founder of BKID
Featured · Company retreat
Reconnect the team around BKID's future and deepen relationships. Explore Palm Springs as an expanding part of the firm, and leave with ownership, momentum and excitement.
Open the case file
Day 02 of a four-day leadership retreat, printed and handed out on arrival
Sample agenda · 4 days
Every guest gets the plan in hand, with their room, their dietary notes and the day ahead. No app to download, no hunting through email.
The outcomeThree decisions made together, owners named, and a leadership team that knows how each of them works.
More sample retreatsNapa, Palm Springs, Tahoe and Ojai, day by day
→Where we take leaders
Sixty places across eight regions, picked for the conversation, not the ballroom. Tap a region on the map to see every place there.
See all 60 destinations
OjaiQuiet valley, hilltop inns, room to think.
Indian WellsSensei Porcupine Creek and desert stillness.
Napa ValleyLong tables and serious meeting space.
Big SurCoast, cliffs and no signal, on purpose.
Marin CountyCavallo Point and Spirit Rock, minutes from SF.
TucsonMiraval Arizona, with equine work on site.
Palm SpringsMidcentury buyouts ten minutes from the airport.
Los AngelesBel-Air quiet or a Santa Monica beach house.How to plan a leadership retreat
Six steps every leadership file runs through, from the first call to the follow-up. See our full process →
Before a venue, before a date: what does this team need to leave with? We start every file with a 45-minute call on exactly that.
Map the Year, Reset, Retreat, Handoff or Board. Then size: four leaders in a private house, or thirty in a resort with breakouts.
Three places matched to the goal, with real rates and dates. A buyout for privacy, a resort for scale, a city for easy flights.
Strategy in the mornings, the human work around it, built on the TRO Six Pillars and checked against the decision you named.
Short pre-work, a few confidential interviews, and an archetype read, so day one starts at depth instead of small talk.
We hold the space and handle everything else. Then a 30-60-90 check-in so the decisions survive the first busy week.
What a leadership retreat costs
Lodging, food and programming, before flights, October 2026. Every TRO budget is built line by line for your group.
Questions
Six answers we give on almost every first call.
A leadership retreat takes a leadership team, rising leaders or a board away for two to four days to plan, decide and grow as leaders. An executive offsite is mostly about the plan; a leadership retreat is also about the people making it. Most of our leadership files do both.
Two to three days for an executive team, three to four for a leadership cohort, and one or two focused days for a board. Plan three to six months out for the best places and dates; we can turn around a focused offsite in about six weeks.
Lodging, food and programming usually run from about $1,700 to $3,900 per person, per day, depending on the place and season, before flights. We build every budget line by line, and you get a real number on the first call.
Either. We bring facilitators, coaches and practitioners for every session, or design around your own executive coach or board facilitator.
Yes. Welcome packets, top performer awards and thank-you gifts are designed and delivered by the same team planning your retreat, so there is one less vendor to manage. See corporate gifting →
Commitments go on paper with owners and dates before anyone leaves, and we book a 30-60-90 day check-in with the team during the retreat itself.
Open a file
Share the basics and the office will reply personally with next steps. You’ll usually hear back within a few hours. We’re pretty fast. No pitch deck gauntlet, no pressure.
hello@therenewaloffice.com (415) 475-0510It's on the desk.
The office will reply personally, usually within a few hours.
Newsletter
One note a month on gathering, leadership and the work. Grounded, never a funnel.
Details from the property, checked October 2026. Tro confirms rates, space and dates for every proposal.
Free · Field guide
The four best windows of 2027 and the places we would book for each, matched to the objective. Two pages, ready to forward.
Plus Notes from the Office, a few times a year. No spam.
It is yours. Open the 2027 shortlist (PDF) →
