The Compass

Insights for the altitude you just stepped into.

Essays for newly-promoted senior leaders on the operational realities of leadership at altitude. Identity, decisions, transformation, and what successful executives actually do differently in the first 90 days and beyond.

Identity & Altitude

The Identity Shift: Why Becoming a Senior Leader Requires Grieving Your Old Self

Most newly-promoted senior leaders treat their transition as a skill problem. They look for new techniques, new frameworks, new approaches. They attend trainings. They read leadership books. They...

May 6, 2026 6 min read
Leading at Scale

Why Most Organizational Transformations Fail (And What Senior Leaders Can Do)

Industry studies consistently report that 60 to 70 percent of organizational transformations fail to deliver the outcomes they were designed for. The standard explanations (bad strategy, wrong...

April 29, 2026 8 min read
Operating System

Building an Operating Cadence: The Five Forums Every Senior Leader Needs

Most newly-promoted senior leaders inherit broken meeting structures and try to operate within them. They attend the meetings their predecessor attended. They keep the cadences they were given. They...

April 15, 2026 7 min read
Operating System

Executive Presence Is Not What You Think It Is

Search any leadership development library and you'll find executive presence treated as something performative. Stand up straight. Speak with conviction. Wear the right thing. Modulate your voice....

April 1, 2026 6 min read
Operating System

Leading Through Ambiguity: A Senior Leader's Guide to Operating Without Certainty

Most leadership content treats ambiguity as a problem to be solved. Get more data. Run more analysis. Wait until the picture clears. Decide when you know.

March 17, 2026 7 min read
Operating System

How to Manage Former Peers After a Promotion: The Conversation You Have to Have

Internal promotions carry a specific challenge that external hires don't face.

March 10, 2026 6 min read
Operating System

Decision Altitude: How to Know What Level of Decisions You Should Be Making

Most newly-promoted senior leaders spend 60 to 70 percent of their time making decisions one or two altitudes below their pay grade. They don't know they're doing it. The decisions feel important....

February 24, 2026 7 min read
Identity & Altitude

Are You Still Operating as a Senior IC? Seven Signs to Look For

You're operating as a senior individual contributor inside a leader's title.

February 3, 2026 8 min read
Operating System

The First 90 Days as a Senior Leader (What Actually Matters)

The 90 days aren't a transition. They're the calibration window, and what happens in them sets the pattern for the next two years of your tenure. I want to walk through what that means in practice.

January 20, 2026 7 min read
Identity & Altitude

The Promotion Paradox: Why the Skills That Got You Promoted Will Disqualify You

Here's what it looks like.

January 7, 2026 6 min read