Career Transition Diagnostic
The Career
Compass Scan.
A rapid diagnostic for leaders navigating career transition — crossing sectors, ready to advance, or actively between positions.
Ten focused questions. No file uploads. An honest initial read of where you are, what you distinctively bring, and what may be standing in your way — followed by a clear path forward.
Ready to take your reading?
01 — Your Situation
Where Are You Right Now?
Select the one that fits most closely.
Crossing the Divide
Moving between for-profit and non-profit sectors
Anchored in Place
Ready to advance but feeling blocked
Open Water
Actively between positions
02 — Career Stage & Direction
Where You Stand
and Where You're Headed.
Career Stage
Emerging Leader
Building toward senior individual contributor or first management role
Mid-Career Leader
Director / VP / senior manager, established track record
Executive
C-suite, ED, CEO, or equivalent organizational leadership
Senior Executive / Board
Multi-org executive, board director, or sector leader
Sector Journey
Coming from
Moving toward
03 — What You Bring
Strengths and
What Gives You Energy.
Core Strength Domains
Select up to 3
Strategy & Vision
People & Culture
Fundraising & Development
Operations & Systems
Communications & Narrative
Partnerships & BD
Governance & Boards
Advocacy & Policy
Finance & Sustainability
Program Design & Delivery
What Energizes You
Select up to 2
Mission-driven work
Building something new
Developing people
Solving complex problems
External-facing leadership
Shaping organizational culture
Having a public voice
Changing systems
04 — What's in the Way
Barriers and
Your Timeline.
Primary Barriers
Select up to 2
Unclear personal narrative
Thin network in target sector
Credentialing or perceived qualification gap
Unfamiliar with how target sector works
Confidence or self-doubt
Compensation expectations misaligned
Low visibility or profile
Lack of clarity on direction itself
Timeline & Urgency
Urgent
I need to move within the next 60 days
Active
Actively searching, 3–6 month horizon
Strategic
Not urgent — building toward a deliberate move
Exploring
Still discerning — no fixed timeline
05 — In Your Own Words
Two Final Questions.
Be Brief. Be Honest.
Your Next Right Role
In two or three sentences — what does it look like?
0 characters
One Thing You Need Clarity On
What is the single question you most need answered right now?
How Did You Find Us?
LinkedIn
Waypoints Newsletter
Referred by someone
Web search
Other
Your responses stay with you unless you choose to share them when booking a Compass Call — in which case Jamie will arrive prepared, not cold.
Reading Your Signals
Analyzing your responses. This takes a moment.
Compass Reading
Your Initial Reading
This reading is directional, not definitive — shaped by what you have shared here. Treat it as a starting point for the conversation, not a final verdict.
Three Things Worth Naming
The Leader’s Guide · Career Compass Scan