Strategy as search, uneven AI gains, and org design that follows the business

1️⃣ Strategy now works more like search

INSEAD’s Andrew Shipilov argues strategy has to move from annual planning to continuous search. His frame is blunt: define the goal, identify capability gaps, then decide what to build, borrow through partnerships, or change as evidence moves.

💡 Why it matters

Leaders still treat strategy as a document and execution as the real work. In volatile markets, the real work is updating assumptions, capabilities, and options before the deck goes stale.

☕ Coffee talk

Which line in the annual plan is still being defended just because it made it into the deck?

2️⃣ AI is helping the strong and hurting the rest

MIT Sloan Management Review highlighted a Kenya field experiment with 640 small business owners using a GPT-4 adviser on WhatsApp. Top performers improved revenue and profit by 15%; the bottom half saw nearly a 10% decline because judgment, not access, was the constraint.

💡 Why it matters

AI rollout is a management design problem now. Give the same tool to everyone without support and you can widen performance gaps inside the same organization.

☕ Coffee talk

Same copilot, opposite outcomes. Who on your team knows when the machine is wrong?

3️⃣ Org charts should follow the business, not the other way round

Former Square CEO Alyssa Henry argues org design should start with market reality: whether you are a pioneer or fast follower, which customer groups need different teams, and which tradeoffs the culture is meant to protect.

💡 Why it matters

Most reorganizations still start from boxes and reporting lines. The better question is what operating model your product, customers, and pace actually require.

☕ Coffee talk

Your product spans different customer worlds; why is the org chart still pretending they are one?