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The gap between the plan and reality.

Honest conversations with the operators navigating execution at scaling companies — in the age of AI, roadmaps, and relentless change.

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Chiefs of Staff VP Operations Directors of Strategy Execution Reality Scaling Companies Plan vs Reality AI Era Chiefs of Staff VP Operations Directors of Strategy Execution Reality Scaling Companies Plan vs Reality AI Era
About

Strategic planning wasn't built for this moment.

Roadmaps are moving faster than ever. AI is compressing execution timelines. And somewhere between the board deck and what's actually happening — there's a gap.

How Are We Tracking? is a podcast about how the smartest operators at scaling companies are rethinking the relationship between plans, execution, and reality.

Format

30 minutes. No prep. No frameworks.

We talk to Chiefs of Staff, VPs of Operations, Directors of Strategy, and the executives who rely on them at companies scaling from 300 to 1,000 people.

The people who know exactly how the sausage gets made. And exactly where it breaks down.

What we talk about.

01
The synthesis problem
How executives actually get a picture of what's happening — and how often that picture is wrong.
02
AI and execution speed
What happens to planning cadences when AI compresses execution timelines by 10x.
03
Plan vs. reality
The real stories behind how plans drift — and what operators do when they catch it early vs. late.
04
Steering at scale
How leaders make course corrections without derailing the teams executing against the original plan.
Be a guest

Your company has a plan.
How's it going?

We're looking for operators living this problem firsthand — people responsible for keeping strategy and execution aligned at scaling companies.

Chief of Staff or VP Operations at a 300–1,000 person company
Director of Strategy, Planning, or Operations
Executive with a strong point of view on where planning is headed
Get in touch
"Every time the CPO asks where an OKR stands, someone manually pulls from Tableau, Jira, wherever the data lives. Nobody has a current picture."
The kind of conversation we have every episode. This is what we're here to understand.