How It Works
Serious development. Very little theater.
The structure is rigorous. Your participation within it is self-directed.
Four dimensions. Each one earns its place.
Self-Care, Awareness, Influence, Learning — the architecture behind this leadership development program, and every SAIL pathway. Choose a letter; the work behind it unfolds.
Self-Care · Awareness · Influence · Learning
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Self-Care
This is not superficial corporate wellness. Energy, capacity, recovery, boundaries, attention, decision fatigue, sustainability, and identity outside productivity.
"Who are you when usefulness isn't required of you?"
Eight private sessions with one of the country's most sought-after executive coaches.
Private executive coaching, start to finish. Not a rotating bench of associates — you work directly with the coach who built this work, before you board, while you sail, and after you come home.
"You don't get a curriculum. You get a coach who's done this at the highest level — and the room is yours."
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Before the voyage
25 min each
Intake & calibration
Your story, your context, and what's genuinely at stake.
Assessment read-through
We walk through your CrowsNest360™ and Periscope results together.
Goal architecture
Two or three behavioral outcomes worth committing to, named precisely.
Your SAIL pathway
What the voyage is for you, written before you board.
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Aboard
30 min each
What's surfacing
Live patterns, observed in real time, named out loud.
In motion
Small experiments — aboard, on shore, in the conversation you've been avoiding.
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After you come home
25 min each
The decisions you came back with
Behavioral commitments, made deliberately.
30 / 60 / 90
Accountability, the path forward, and where to go next.
One-on-one, every time
Every session is private. No group coaching, no shared airtime.
Built around you
Your goals, your assessment, your pathway — not a template.
Confidential by design
Nothing moves without your direction. Ever.
Five phases. Before, aboard, and after.
The arc is fixed. What happens inside each phase belongs to you.
Before the voyage
Discover
A conversation about what you actually want from the experience — both the leadership work and the voyage itself.
01 · DiscoverHow you lead. How others experience you. What you want to work on.
Two proprietary instruments — CrowsNest360 and the Periscope Leadership Profile — surface what you can't see on your own. Your executive coaching and your leadership retreat are then built around what we learn.
Nothing is shared without your direction.
What you can't see on your own
The SAIL app supports the work. It isn't the work.
Five things it can help you do — Think. Try. Notice. Do. Nothing. The fifth is the point. It carries your development work from pre-voyage into the voyage and home again.
Questions, answered
The short answers.
How does the SAIL program work?
SAIL moves through five phases: Discover (a fit conversation), Assess (CrowsNest360 and the Periscope Leadership Profile), Coach (four private pre-voyage sessions), Sail (a four-to-five-night intensive with two onboard coaching sessions), and Integrate (two post-voyage sessions and a 30/60/90-day plan).
How many coaching sessions are included in SAIL?
Eight private one-on-one coaching sessions: four pre-voyage, two aboard the ship, and two post-voyage integration sessions.
What assessments does SAIL use?
Two proprietary instruments: CrowsNest360, a behavioral 360 gathered from people you choose, and the Periscope Leadership Profile. Both are calibrated with your coach to your specific situation, and nothing is shared without your direction.
Is participation mandatory aboard a SAIL voyage?
No. The structure is rigorous but nothing is mandatory. You choose how much SAIL curates for you — almost everything, some things, or very little — and the rest is intentional space.
Ready when you are