We watch your six.
Lead your first.
Never run.™

Strategic wingman to first-time healthcare C-suites navigating the first 18 months in the seat.

• Book Your Pre-Flight Check

$1,500 · 90 minutes · Diagnostic session before any commitment

Forty years operating inside healthcare · Six C-suite seats · No theory

How we think about the work.

Five disciplines. Stoic-informed. Operationally tested. No trademarked methodology name — just the practices that hold up when the stakes are real.

Why Stoic? Why aviation?

Stoic philosophy was not built for seminar rooms. It was built for commanders, governors, and leaders under pressure. Marcus Aurelius wrote his Meditations on campaign, not in retreat. Epictetus was a slave. Seneca spent years managing an emperor who wanted him dead. The framework held because it was designed for conditions where clarity matters and composure is a professional asset.Aviation discipline adds the structural layer: pre-flight checks, debriefs, threat-and-error management. These are not metaphors. They are the actual operating cadences that keep complex systems from cascading into failure.Healthcare C-suite leadership sits at this same intersection. You inherit a team mid-flight. You manage threats with incomplete data. You debrief when the culture will allow it — or you don't, and the same failure loops. The five disciplines below were selected because they work. Not because they are elegant.

The five disciplines.

Likely / Dangerous / Deadly

Aviation threat-and-error management classifies hazards by severity, not by proximity. The thing loudest on your radar is not always the most dangerous. The thing that seems manageable is sometimes the one that cascades.In practice: every week, you surface the threats in front of you and sort them into three buckets. Likely — realistic, probable, needs attention. Dangerous — could cause significant harm if unmanaged. Deadly — if this goes wrong, the mission is over.Most first-year C-suite leaders spend their weeks in "likely" territory — the visible, the urgent, the squeaky wheel. This discipline forces you to name the "deadly" before you have to manage the wreckage.

Applied: Weekly threat triage. Typically takes 20 minutes if you're honest about it.

Control Audit

Epictetus drew a hard line: there are things within our control, and there are things that are not. The work of leadership is not to pretend this line doesn't exist. It's to know exactly where it falls.First-time C-suites frequently carry problems that belong to other people — board politics they can't resolve, physician relationships that predate their tenure, structural budget constraints that aren't their fault. Carrying problems you can't solve is not diligence. It's a drain.

Applied: Monthly. List every active problem you're spending attention on. Sort by: my call to make, collaborative, not mine at all. Aggressive deletion from the third category.

The Control Audit Doctrine — 90 seconds

View From the Balcony

The leader on the dance floor cannot see the pattern of the dance. That's not a failure of intelligence — it's a failure of positioning. The practice is simple: get above the situation before you interpret it.In healthcare, this is structurally hard. You are pulled into every crisis, every negotiation, every board concern. The bias toward action is relentless. The balcony requires you to stop, step back, and describe what you observe — not what you're experiencing.

Applied: Before major decisions, before board presentations, before difficult conversations. A structured 15-minute step back: What would I see if I were watching this from outside?

Pre-Mortem Brief

Before a mission launches, before a strategic initiative rolls out, before a leadership team change is announced — run the failure forward. Assume it went wrong. Ask: how?This is not pessimism. It is professional hygiene. The failure scenarios surfaced in a pre-mortem brief are almost always visible in advance to the people closest to the work — and almost always unspoken because the organization is invested in success theater.

Applied: Any significant initiative, hire, or structural change. Convene the direct reports. The question is not "will this work?" It is "what would cause this to fail?" Spend one hour on it. Surface the top three failure paths. Assign mitigation.

Wingman Debrief

Every mission ends with a debrief. Not a celebration. Not a retrospective that surfaces nobody's fault. A structured conversation that answers: What happened? Why? What do we carry forward?Healthcare organizations are structurally allergic to the debrief. Success is celebrated and forgotten. Failure is managed and quietly buried. The result is an organization that learns slowly and makes the same mistakes in different clothes.The Wingman Debrief is peer-level, not hierarchical. No rank in the debrief room. The question isn't who failed — it's what did we learn and how does it change the approach going forward.

Applied: After every significant event — strategic launch, leadership change, board cycle, crisis response. 60 minutes. Structured questions. Written summary. Filed.

The Pre-Flight Check is where this starts.

Ninety minutes to walk through where you stand against all five disciplines. We identify what's working, what's drifting, and what needs immediate attention.

• Book Your Pre-Flight Check — $1,500

We publish pricing because your time is valuable and we respect it. If what we offer doesn't match your budget or your stage, you'll know in 60 seconds — not after three calls.

Every tier is built around one principle: a leader should leave every engagement with more clarity, not more material.

Pre-Flight Check

$1,500 · 90 minutes · One-time engagement

A diagnostic session before any commitment. We review where you are in your first 18 months, run the five disciplines against your actual situation, and produce a clear picture of where the threats are and where your attention belongs.

What you receive:

Who this is for: Any first-time healthcare C-suite leader who wants a clear-eyed diagnostic without committing to a longer engagement. Also appropriate for search firms, boards, and Chiefs of Staff supporting a new placement.

• Book Your Pre-Flight Check — $1,500

Payment collected at booking via Stripe. 2.9% + 30¢ transaction fee applies.

Wingman Program

$24,000 · 6 months · 1:1 coaching

The primary engagement. Structured around your calendar, not a generic program. We meet regularly, run the five disciplines against your real decisions, and build the operating cadence that serves you for the rest of your career — not just the first year.

What you receive:

Who this is for: First-time healthcare C-suite leaders who want consistent, peer-level support through the full first 18 months. Typically begins at or before the 90-day mark.

• Start the Wingman Program

Formation Flight

$75,000–$125,000 · 12 months · Executive + team engagement

Leadership coaching for the executive plus structured work with the direct reports who execute strategy. The gap between leadership intent and team behavior is where most first-year failures live. This tier closes it.

What you receive:

Scope variable: Pricing varies by team size, geographic distribution, and engagement depth. The range is $75,000–$125,000. Every engagement is scoped from a direct conversation.

Who this is for: Health systems, foundations, and physician groups where the new C-suite leader has identified that team alignment is a constraint on execution.

• Request a conversation

Custom Advisory

From $6,000/month · Ongoing retainer

Continuous access. For leaders who want a trusted peer available across the full range of leadership challenges — not just scheduled sessions. Board prep. Off-cycle crises. Succession decisions. Culture interventions. Available when you need it.

What you receive:

Who this is for: C-suite leaders post-first-year who want ongoing, senior advisory support without the overhead of a consulting firm. Also appropriate for executives managing multiple leadership transitions simultaneously (e.g., a CEO managing a CNO transition while onboarding a new CFO).

• Request a conversation

Enterprise & Board Engagement

Proposal / custom scope

Multi-site, multi-executive engagements. Board advisory. Governance and leadership transition support at the health system level. Built entirely from a direct conversation — no standard package applies.

Typical engagements include:

• Request a conversation

Email directly: [email protected] — no Calendly for enterprise and board inquiries.

Start with the Pre-Flight Check. If the longer engagement is right, we'll know after ninety minutes.

• Book Your Pre-Flight Check — $1,500

Chip Flinn, MBA, LFACHE.

Thirty-plus years inside healthcare operations. Now in independent practice — working with a small number of first-time C-suite leaders at a time.

The bio in plain language.

I have spent more than three decades running healthcare operations — hospitals, emergency departments, compliance, patient flow, and the leadership structures that hold those systems together or fail.t

I have been the first-time executive. I know what it costs to walk into a room where you hold the title but haven't yet earned the room's trust. I know what it's like to make the call before the data is clean, to manage a board relationship that was complicated before you arrived, to try to build a team culture while the organization watches to see what you're made of.

I am not a therapist and I am not a consultant who produces decks. I am a peer who has been in the seat, and I fly wing.

Every engagement I take is chosen carefully. I work with a small number of leaders at a time — because this work requires genuine attention, not a scalable product.

Credentials:

Why a wingman.

In aviation, a wingman does not fly the lead position. The wingman clears the airspace, watches for threats the lead pilot cannot see from the front, and communicates what's real — not what the lead pilot hopes is true.

That is the role. Not a cheerleader. Not an accountability partner in the pop-psychology sense. A peer who will tell you what you need to hear, disagree with you when the stakes warrant it, and stay in the aircraft through the hard parts.

The Stoic framework underneath the work is not an affectation. It is practical philosophy — developed by leaders who managed empires, armies, and courts under conditions that would break most people. The practices are old because they work. They work because they were tested in conditions where failure was not abstract.

I use these disciplines in my own practice. I teach them because they changed how I operate. That is the only honest reason to teach anything.

A few things worth knowing.

I keep engagements small by design. At any given time, I work with fewer than ten leaders. That is not a scarcity play. It is because the work I do requires genuine presence — and you cannot be genuinely present for twenty clients simultaneously.

Every engagement is confidential. I do not reference clients. I do not use client situations as case studies, even sanitized ones. Your organization's leadership dynamics are not my content.

I do not offer a free discovery call. The Pre-Flight Check is the front door — a $1,500, 90-minute session that is a complete engagement in itself. If a longer engagement follows, it follows because it is warranted. If it doesn't, you leave with something genuinely useful.

I am not the right fit for every leader. If you are looking for a coach who will affirm your instincts, I am not that. If you are looking for someone who will tell you hard things clearly and help you build the operational clarity to act on them, call.

Insights.

Short briefs and field notes from the practice — the kind of thinking that gets shared with clients and worth making public. Writing happens when there's something worth saying. No newsletter cadence, no content calendar.

When briefs go live, you'll be able to subscribe by email — no marketing, no automation, just the writing.

Get in touch.

The Pre-Flight Check is the fastest way to start. Ninety minutes, $1,500, fully refundable if we're not the right fit. Book directly below — payment processed securely at the time of booking.

Pre-launch note: Pre-Flight Check bookings are by invitation through April 30. Public booking opens May 1, 2026.

Other ways to reach me.

For enterprise, board, or press inquiries, email directly: [email protected]