Tip
Brian Chesky talks about how founders waste time reacting: “A lot of founders spend their time based on reacting. So people will email them and they’ll wake up and they’ll respond to emails, and suddenly their email sets the agenda. People ask for meetings, and suddenly the meetings they take are based on the people who email them. Versus here’s my strategy and then over the next year, what are the relationships I need to have and the meetings I need to take to be able to execute this strategy?”
Then he adds: “If my life were to end in a year or in 10 years… who are the people I would’ve wanted to make sure I spent time with? And if you imagine that your life is finite, because it is, and you imagine you’re not going to be here as long as you thought you would be, because it’s possible, it would completely change how you prioritize your time.”
Turns out AI strategy decisions work the same way.
Your calendar fills with “AI strategy meetings” - vendors pitching tools, consultants offering frameworks, internal teams requesting input on pilots. You’re reacting. Meeting with whoever emails you. The squeaky wheel gets your time.
But when you step back and ask: if you only had 12 months to position the company for AI, who would you NEED to spend time with? Suddenly it’s clear. You need deep conversations with three customers about their actual workflows. You need to understand what your best engineer thinks is technically feasible. You need strategic alignment with your CFO on budget trade-offs. You need to rebuild trust with the product leader after six months of tension.
Those aren’t the people emailing you. They’re the people you need to proactively reach out to.
Younger managers don’t know which relationships are load-bearing yet - they haven’t lived through enough critical transitions to recognize the pattern. You have. You’ve watched companies successfully navigate platform shifts, and it always came down to a handful of key relationships being strong. The rest was noise.
That judgment—knowing which 5-10 relationships actually move the strategic needle versus which 50 feel urgent but don’t matter—comes from seeing enough transitions to know what predicts success. You can distinguish between “this person is reaching out” and “this person is critical.”
Context
Brian Chesky, co-founder and CEO of Airbnb, discusses how he shifted from reactive to proactive time management after years of letting his inbox and meeting requests drive his calendar. The insight about imagining finite time as a prioritization tool only works if you’ve lived long enough to know what actually matters.
For experienced leaders navigating AI transformation, this pattern recognition is the advantage—you’ve seen enough strategic shifts to know which relationships are truly load-bearing versus which just feel urgent.