1:1 coaching for senior leaders
The skills that got you here won’t get you there.
Executive Ready is one-on-one coaching for directors and senior managers stepping into — or just starting — their first executive role. It’s built around the five shifts that separate strong operators from effective executives, with AI woven into how you think, decide, and lead.
Not sure you’re ready? The readiness check shows where you stand. Or see the five shifts
Coached by a current executive who successfully went from being an individual contributor to executive in just a few years — and has made the jump more than once, across multiple industries.
The problem
Most new executives prepare by doing more of what already worked.
It rarely works, because the job itself has changed. As a manager, you’re valued for having the answers. As an executive, you’re measured by what you can build, delegate, and see coming.
The framework
Five shifts. The core of the program.
Executive Ready coaching goes deep into every shift.
Stop solving the problem yourself. Design the system that solves it without you.
Your peers become your most important team — and the hardest one to lead.
You’ll rarely have all the facts. Your job is to make the path legible to everyone else.
Being the smartest person in the room stops being the point. Making the room smarter is.
Performing well is table stakes. Holding steady when the stakes are highest is the key.
Which shift is your growth edge? The readiness check takes three minutes and points to where we’d start.
Take the readiness check →Who it’s for
Directors and senior managers stepping into — or just starting — their first executive role.
A strong fit if you are…
- A director or senior manager being considered for a VP or executive role
- Newly promoted and inside your first six months
- Told you’re “almost ready” — without anyone saying what that means
- Strong at execution, and starting to feel its limits
Probably not a fit if you want…
- Résumé writing or job-search coaching
- A generic leadership course with a certificate at the end
- Someone to tell you what you want to hear
Not sure which side you’re on? Take the 3-minute readiness check, or skip straight to a conversation.
How it works
Built around where you actually are — not a generic curriculum.
1
Readiness check and call
Start with the three-minute readiness check, then a free 15-minute call about the role you’re heading into and whether this is the right fit.
2
Diagnostic intake
An 18-question diagnostic maps where you stand on each of the five shifts before we begin.
3
Sessions on what’s live
The decision you’re stuck on. The conversation you’re avoiding. The team you’re not sure you’re leading yet.
4
Work between calls
A companion workbook and your own AI thinking partner keep the work moving, so each session starts further along than the last.
AI-first by design
The next generation of executives are leading with AI. We will leverage the best tools available to maximize your impact.
AI isn’t a separate module bolted on at the end. It’s woven into every session, so you build the leadership skills and the AI fluency your next role demands, at the same time.
Operator → Architect
Build your executive operating system
Set up AI workflows for briefing prep, decision memos, and synthesis — so your hours go to the work only you can do.
Between sessions
A thinking partner on demand
A personal AI assistant set up around your goals, your diagnostic, and the five shifts. Use it to pressure-test a decision or rehearse a hard conversation the night before.
Expert → Multiplier
Lead your team’s AI shift
Learn to set direction on AI, ask the right questions of the people building with it, and model adoption your organization will follow.
Judgment stays human. AI makes you faster and sharper; it doesn’t replace your judgment, your relationships, or your presence in the room. Every coaching session is one-on-one with me, and we work only within the AI tools your employer approves.
Program Overview
Any program can be customized to meet you where you are.
Engagements start at $1,500/month. Every tier includes the diagnostic intake, the five-shift framework, the client workbook, and your personal AI toolkit. Monthly, no long-term contract.
Core
Steady support through a known transition.
- Two 1:1 sessions per month
- Diagnostic intake and custom plan
- Client workbook
Accelerator
Weekly momentum for a role that’s already moving.
- Weekly 1:1 sessions
- Diagnostic intake and custom plan
- Client workbook
Executive Intensive
For high-stakes first months in the seat.
- Weekly 1:1 sessions
- On-call support between sessions
- Diagnostic intake, custom plan, and workbook
Not sure which tier fits? The readiness check helps us figure out the right cadence before we talk.
Take the readiness check →Coaching often qualifies for employer professional-development budgets. I’m happy to provide an invoice and a program summary for your L&D team.
Your coach
I’ve made this jump myself. More than once.
I went from entry-level individual contributor to executive in just a few years — through law, brand strategy, corporate strategy, and operations. My experience is firsthand, not studied from the outside.
I coach the way I wish I’d been coached: directly, without the performance, and with a genuine stake in whether you get there.
— David
Questions
Before you book.
How is this different from a leadership program?
Programs teach a curriculum to a cohort. This is one-on-one work on your actual role, your actual team, and the decisions in front of you this week — organized by a framework, not limited by one.
I haven’t been promoted yet. Is it too early?
It’s the best time. The shifts are easier to start before the title arrives — and practicing them is often what gets you the title. If you’re unsure, take the 3-minute readiness check.
Do I need to be good with AI already?
No. We start wherever you are — from never having opened an AI tool to using one every day. The goal isn’t to make you technical; it’s to make AI a natural part of how you prepare, decide, and lead.
Can I change tiers?
Yes. Many clients scale up around a promotion or a hard quarter, then back down. The work stays the same; only the cadence changes.
Is what we discuss confidential?
Completely — including when your employer is paying. Sponsors receive only what you choose to share. And we never put confidential company information into AI tools your employer hasn’t approved.
You’re about to be measured differently. Start preparing now.
Take the three-minute readiness check, or go straight to a free 15-minute conversation about the role ahead. No pitch deck, no pressure.
Limited founding-client spots available — ask on the call.