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Every team has a plan. This is how they actually run it.

How planning works at different stages of growth, and the ideas worth stealing from each.

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Chiefs of Staff VP Operations Directors of Strategy Program Management Founders Plan vs Reality PMO Leaders AI Era Chiefs of Staff VP Operations Directors of Strategy Program Management Founders Plan vs Reality PMO Leaders AI Era
About

Planning looks different at every company.

Some teams run on OKRs. Some on weekly commits. Some on a shared doc the CEO updates every Sunday. What works at 50 people breaks at 200. What works at 200 gets rebuilt at 500.

How Are We Tracking? is a podcast about how real teams actually plan, track, and adjust as they grow: the cadences, the artifacts, the workarounds, and what they'd change if they could start over.

Format

30 minutes. Conversational. No frameworks.

We talk to Chiefs of Staff, VPs of Operations, Directors of Strategy, Program Management leaders, PMO heads, founders, and executives at every stage of company growth.

The people closest to the process, talking candidly about what's working, what isn't, and what others can steal.

What we talk about.

01
How your planning actually works
Not how it's supposed to work. The real cadences, artifacts, and workarounds people actually use.
02
What changes as you grow
The specific moments when what was working stops working, and what teams build to replace it.
03
AI in the planning process
Where it's genuinely helping, where it's overhyped, and what people are quietly building on their own.
04
The one thing they'd change
Every episode ends here. The insight that took too long to learn, and that you can use tomorrow.
Be a guest

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

If you're close to how your company plans and executes and have something honest to say about it, we'd love to have you on.

Get in touch
"Our annual planning takes two months. By the end of Q1 the document is already stale."
The kind of conversation we have every episode. This is what we're here to understand.