Tip
Chandra Janakiraman talks about strategy work: “Whether it’s big S or small S, these are incredibly satisfying processes to go through in the end. But they have a ton of challenge, frustration, and dead ends while you go through it where you kind of get a lot of self-doubt like, ‘Hey, will you ever reach the end?’ I just want to sort of normalize that. That’s actually normal.”
Turns out AI strategy development works the same way.
You’re three weeks into developing your AI strategy. You’ve interviewed stakeholders, gathered competitive analysis, mapped out problems, analyzed use cases… and it’s a mess. Nothing’s converging. Your product lead is frustrated: “We’ve spent three weeks and we don’t have an answer yet.” The engineering director wants clarity on what to build. The team wants to just pick something and move on.
Younger leaders panic when things feel messy. They equate “feels uncertain” with “process is broken.” They haven’t seen enough strategy processes play out to know that week 3 always feels like chaos before week 4 brings clarity. They abandon rigorous process for speed, pick something superficial, and end up with strategies that don’t hold up.
You’ve seen this movie before. In 2015, you led the mobile strategy process—same frustration at week 3, then breakthrough at week 4 when patterns emerged. In 2019, cloud migration strategy felt completely lost until week 5, then everything clicked. You know the pattern: good strategy work feels uncomfortable in the middle. The discomfort isn’t a bug, it’s a feature. It means you’re wrestling with real complexity instead of accepting easy answers.
This judgment—knowing the difference between productive uncertainty (lots of data, competing frameworks, hard choices) versus unproductive uncertainty (no data, no frameworks, no criteria)—comes from watching enough strategy processes reach the end. You can tell when your team is making progress through complexity versus when they’re stuck. That pattern recognition lets you coach the team through the discomfort, defend the timeline to leadership, and persist to insights that competitors who gave up at week 3 will never find.
Context
Chandra Janakiraman is former Director of Product Management at Meta, ex-VP of Product at Headspace, and currently CPO at VRChat. He developed a structured 5-stage process for product strategy after watching teams struggle with strategic clarity.
His key insight: rigorous strategy work always feels frustrating in the middle—lots of dead ends, self-doubt, competing frameworks. For experienced executives leading AI strategy development, this pattern recognition is critical—you’ve watched enough strategy processes complete to know that discomfort in the middle is normal, not a sign of failure.
That comes from seeing the full arc repeatedly.