HIGHLAND
Highland is a device-free expedition for an intact executive team of six to ten, held on Root Astro's seven private acres in the Catskills, 90 minutes from New York City. There is no keynote and no trust fall. There is a physical and strategy reset the team faces together, the honest conversations that follow it, and a 90-Day Bearing the team writes as one document before they leave. What changes is not the offsite photo. It is what the team does the Monday after.
41.4739° N 74.5401° W
ELV 840 FT POLARIS ALT 41°
DESCEND
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STRENGTH · ROOT ASTROLABE SPECTRUM
Highland is strength. Real terrain, real weather, real consequences for poor communication. The mountains do not care about your org chart. That is the point.
THE PROMISE
Highland doesn’t fix teams. It reveals them. Through shared physical challenge and facilitated dialogue, the unspoken tensions surface, the real dynamics emerge, and the team discovers what they’re actually capable of when the conference room walls fall away.
Before you arrive, every team member sits for a confidential interview. Your facilitator synthesizes what they hear into a single Highland brief, surfacing what's unspoken so the team can finally address it. This pre-work is what separates Highland from every team offsite you've endured.
Three days that test how your team actually leads under pressure.
Devices surrendered. The Highland perspective is shared. For the first time, the team hears what everyone has been thinking but no one has said.
The team starts here, not at the trailhead.
A guided field exercise that demands real teamwork. Not a ropes course. Not a trust fall. Real terrain, real weather, real consequences for poor communication.
The mountain doesn't care about your org chart. That's the point.
Facilitated conversations that connect the physical experience to your real leadership challenges. What broke on the trail is usually what's breaking in the boardroom.
What broke on the trail is what's breaking in the boardroom.
The team builds shared agreements for how they'll lead differently. Not abstract values. Specific behaviors, accountabilities, and a follow-up cadence that outlasts the adrenaline.
Adrenaline fades. Operating agreements stay.
WHO THIS IS FOR
Highland is for senior leadership teams of 6–10 people. You're the team that runs the company, but you've never been in a room, or on a mountain, where the real conversations happen. Your offsites produce slide decks. Highland produces truth.
This is not team building. It's team revealing — the moments under pressure where you see how your team actually thinks, who steps up, who gets quiet, and where the trust holds. If your team is ready for that, for the kind of honesty that only shared adversity can unlock, Highland is where it begins.
A three-day expedition for one leadership team. Higher elevation, harder terrain, real consequences for poor communication.
SHAWANGUNK RIDGE · DUSK OVER THE VALLEY · ELV 840 FT
Researchers Norton, Mochon, and Ariely found something now called the IKEA effect: people value what they build with their own hands far more than the identical thing handed to them, because the effort itself creates the value. The 90-Day Bearing your team leaves with is not a takeaway packet. Your team writes it, together, before anyone leaves the land, which is exactly why it survives the drive home.
Bringing a group takes planning most people start months early. Start here.
Highland begins with a confidential conversation about your team. No sales pitch. Just an honest assessment of whether this is the right experience for where your team is now.
Start the Conversation
