Executive Team Retreats · Boulder or On Site
Most executive teams are chasing AI tactics.Wise teams start with vision and strategy.
The Summit is a two-day retreat for your executive team, built around your organization. You leave with a written AI strategy, the governance to hold it, and an implementation plan with names, dates, and a budget — decided together, in one room, with two coaches.
Two days. Two coaches. One team that leaves aligned.
Scheduled around your team’s calendarWhisper Ranch, Boulder, Colorado — or at your location
Outcomes, Not Features
Three things your team carries out of the room.
1
A written AI strategy your whole team built.
Vision, priorities, what AI is for in your organization and what it is not for. The document your executive team agreed on in the room — not a deck one person wrote and the rest nodded at. You can hand it to your board on Monday.
2
Governance decided, not deferred.
Who decides what. What is off-limits. How you handle data, risk, and the questions about people that everyone is quietly carrying. Written down and signed off by the people who will have to hold the line.
3
An implementation plan with names, dates, and a budget.
Who owns each move. What starts first, and when. What it costs, and what you stop doing to pay for it. Not a wish list. A plan your team can begin the week you get home.
The Shape of the Two Days
Two days. From what your organization is for, to a plan that’s yours.
This is the standard arc. Before the retreat we talk with you about your team and your situation, and shape the two days around what you actually need to decide.
Day one · Morning · Essence → Vision
Start with what you’re for.
The reframe that sets up both days, one live demo of what is actually possible now, and the move from your organization’s essence to its AI vision. The team gets on the same page about what you are trying to protect and what you are trying to build.
Day one · Afternoon · The reckoning
The honest reckoning.
A tool-discernment lab, the hard adoption conversation, and the reckoning most teams avoid: what to greenlight, what to kill, and what it means for your people. We close the day over dinner with a fireside on faith and technology.
Day two · Strategy → Governance → Plan
Write it, decide it, commission it.
Draft the strategy together. Make the governance decisions. Build the implementation plan — who owns what, what starts when, what it costs. We commission the climb together and your team leaves with the documents in hand.
The Summit commissions the climb — your team leaves with the plan and the first moves, not a 90-day deployment.
Two days at Whisper Ranch — or at your place.
Most teams gather at Whisper Ranch in Boulder, Colorado, co-founded by Jeff and Mindy Caliguire. A long table, a great room that opens onto the Flatirons, and a full day’s distance from the office.
Getting away is part of the work. Your team gets focused attention from two coaches on the hardest questions you are carrying, with nothing else on the calendar. The input you get here is the kind that would have taken months back at the office — or never come at all.
If travel is not realistic for your team, we come to you. Same two days, same two coaches, in a room of your choosing.
Your hardest question, on the table
Two coaches and your own team on the decision you keep postponing. Come away with it made, and with the reasoning written down.
Pressure-tested by the people who carry it
Your strategy gets sharpened in the room by the executives who will have to live with it — before it meets your board or your staff.
Room to breathe
Great food, wide views, a walk in the foothills if you want one. The kind of days that remind a team why the work matters in the first place.
A Tight Perimeter
Built for one executive team at a time.
This Is For
An executive team — the CEO and the people who report to them — that has to make its AI decisions together and is done waiting for someone else to make them. Founder-led companies, publishers, and organizations of consequence whose leaders want a plan they all own, and two coaches who won’t waste their time.
This Is Not For
A single leader looking for a peer cohort — that is what Base Camp is for. A team that wants a tools demo or a how-to on prompts. Anyone who wants a strategy delivered to them rather than built with them.
We work with one team at a time because the plan has to be yours. Every person in the room changes what the room can decide.
Investment
Scoped to your team. Quoted after a conversation.
The Summit
One engagement, one executive team.
Priced by team size, location, and the preparation your situation needs.
- ✓A scoping conversation with the CEO or sponsor before we quote
- ✓The two-day retreat, at Whisper Ranch or on site
- ✓Two coaches in the room for both days
- ✓The strategy, governance decisions, and implementation plan your team built
- ✓Meals on site at the Ranch
For retreats at the Ranch, travel and lodging are paid by your team — see our recommendations below.
Tell us about your team →You already know what a bad AI decision costs at your level. You know what it costs when the executive team is not aligned and every department decides for itself.
This is what it costs to decide together. The question is what it costs to keep deciding apart.
Plan Your Retreat
Tell us about your team.
A few facts about your team is all we need to start. Jeff and Jason read every inquiry personally and reply within two business days to set up a short conversation — not a sales call, a real conversation about whether this is the right two days for your team.
- 01
You tell us who is in the room
Your team, your timing, and the decision you are facing.
- 02
We talk
A short call with the CEO or sponsor. We shape the two days around what you actually need to decide.
- 03
You get a proposal
Dates, location, and price for your team. Then we book the room.
Prefer email? [email protected] reaches both of us.
Getting to the Ranch
Travel and lodging, without the guesswork.
For retreats at Whisper Ranch. The Ranch sits on Marshall Road in south Boulder — about 45 minutes from Denver International Airport and 15 minutes from downtown Boulder. Travel and lodging are paid by your team. Here’s what we recommend.
Where to Stay
St Julien Hotel & Spa ↗
Downtown Boulder · ~15 min to the Ranch
Boulder’s flagship luxury hotel — full-service spa, Flatirons views, and Pearl Street a block away. The classic executive choice.
Hotel Boulderado ↗
Downtown Boulder · ~15 min to the Ranch
A Boulder landmark since 1909, one block off Pearl Street. Historic rooms under a stained-glass atrium, with some of the best bars and restaurants in town under one roof.
Limelight Boulder ↗
University & Broadway · ~15 min to the Ranch
Boulder’s newest hotel, from the team behind Aspen’s Limelight properties. Modern rooms, mountain views, and an easy walk to Pearl Street.
Omni Interlocken Hotel ↗
Broomfield · ~10 min to the Ranch
A resort-style option just off US-36 — golf, spa, and the shortest morning drive to the Ranch. Convenient if your team is heading straight back to the airport after we wrap.
To & From Denver International (DEN)
Rent a car — our recommendation.
Every major agency operates at DEN, and the drive to Boulder runs about 45 minutes via E-470 and US-36. A car makes the short morning drives to the Ranch simple and keeps your evenings flexible.
Uber or Lyft.
Plentiful at DEN — expect roughly $70–100 each way to Boulder. Rideshare works for the Ranch too; just schedule your return pickup in advance, since Marshall Road sits outside the busiest pickup zones.
Private car service.
Several Boulder-area services run private sedans and SUVs between DEN and Boulder, with your driver meeting you at arrivals. Book ahead — especially for early flights out.
RTD SkyRide (Route AB1).
The public express bus between DEN and Downtown Boulder Station — about 90 minutes for around $10. Simple and reliable, though you’ll still want a car or rideshare to reach the Ranch.
Once your retreat is booked we send arrival details and the full schedule. Questions about logistics? Email us.
Questions People Ask
What teams ask about the Summit.
Climbing on your own for now? Most leaders start at Base Camp →