From 2016-19, I (and a very talented team) tackled one of the most complicated projects in LinkedIn’s history: Migrating every customer from to a brand new product, LinkedIn Learning, following LinkedIn’s acquisition of for $1.5 billion.

This project was, for lack of a better term, one of ‘nightmare’ complexity. It involved 10,000+ customers who weren’t all eager to move (migrations are painful), migrating millions of rows of sensitive customer data, building a new product in parallel, & more.

It took us over three years. And during that time, our team went from what felt like ‘headless chicken’ to ‘well-oiled machine.’ Ultimately, the project was a success, but we made plenty of mistakes.

These are the top five things I learned.

Who’s in Your One-pizza Team?

Reference (for us, “one-pizza” worked better.)

Avoid a ‘too many cooks’ situation by defining your team and RAPID. They represent their function. It’s their #1 priority. You’ll have a committed meeting cadence, and no flaking or “sorry, I have a conflict” responses are allowed.

Things Will Break, but They Can’t Break the Team

Plan, but also focus on making sure your team knows how to respond to the unexpected with urgency. Get good at being agile. Your team should be prepared to drop everything else to course correct. We embraced “expect the unexpected” and came to consider reacting effectively to be as crucial as planning effectively.

Above All Else, Plan for What You Can’t Outwork

We learned to obsessively plan where there isn’t a 1:1 relationship between time invested and rapidly solving an issue – issues where you can’t fix oversights with a few late nights. People take time to hire; infrastructure takes time to build and test; other teams won’t share your priorities.  These are the “20” in the 80/20 of planning.

A Target Will Unite & Empower

Your target—even if it feels “made up”—will help your team rally around a single goal, and prioritize and make the right decisions independently. Even an inaccurate target is exponentially better than no target. Move forward, even if the target is “best guess.”

Teams Fail When They Lose Control of the Narrative

Rumors and speculation can’t define your project. You’re the expert. Focus on creating clarity. You must have the loudest and most transparent voice. Over-communicate up, out, & down. When there’s a communication vacuum at the “top,” people creatively fill in the blanks themselves. If you’re not sick of saying it, you’re not saying it enough.