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Uber’s advice for on-site planning with your leadership team

“The mindset for planning and the mindset for day-to-day work are very different muscles to exercise,” says Uber's Chief of Staff to the Chief Legal Officer Jodi Kawada Page. “The day-to-day is a checkbox exercise, and planning is more of a think-outside-the-box exercise.”

Why it matters: “Planning is not super effective over Zoom. You can get more done in half a day, in-person than multiple Zooms where everybody's doing work on the side and distracted,” Page says.

👇 Where Uber is investing:

  • “We're doing more of our in-person team get togethers later in the year and centering them around planning… We’re trying to make them compact — a two-day offsite is almost too long.”

  • “We're taking people out of their comfort zones, scheduling a team building exercise that pushes people — like improv or go-karting — then jumping into a planning session so we think differently.”

  • “We've been intentional about assigning action items after the process so everybody has a role in pulling it together, actioning what we're doing, sharing outcomes, and staying on track.”

The bottom line: Stay human, stay flexible, and it will “lead to better outcomes.” And for any essential communication management — whether it's strategic planning or day-to-day operations — clear, effective, and people-first operations win.

Go deeper: Hear more from Uber and Olive Ventures about leading a team through tough times.