Following up on Mark's admission that he dreads collaboration, whether it's with peers or employees, Jesse discusses one way the leadership team at YNAB has fostered collaboration. They call it the strategic council, and it's a two(ish) day meeting with all the functions at YNAB presenting the challenges and opportunities for growth in each function. The meeting is tightly structured, with desginated time slots for each team to present and field questions. This is critical to keep things moving and keep the focus on getting started with solving problems. It's not a time to fully solve problems and implement strategies, it's simply a time to get everything everyone is working on out in the open, so that everyone is aware of the challenges and no one is caught by surprise.
Mark points out that this type of meeting has the potential to become toxic if teams are concerned about protecting their own reputations rather than being open with their challenges, and thereby use the meeting time to deflect problems and shift blame. To Jesse, this kind of meeting can only happen productively with high trust teams, who are all aligned with the idea that the presentations are a way to make the company better. In a low trust environment, the collaborative aspect of the strategic council falls apart quickly.
Mark and Jesse end on a discussion of collaboration as a way of buying back your time. Jesse explains how his personal assistant has not only saved him time by taking care of mundane problems for him, but has shored up the "mental leaks" that occur when your focus is distracted by competing priorities. Mark shares that despite his preference to use software over humans to free up his time and mental capacity, he has found an employee with high initiative and drive to solve problems on their own to be very useful.
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