To gauge if an executive is a true 'builder' with customer empathy, ask them to design a new feature for a product they use daily. Their ability to solve a problem for themselves reveals their capacity to be empathetic to new customers.
A simple litmus test for an executive team's health is to ask members, 'What team are you on?' If they say 'marketing' or 'engineering,' it's a collection of functional heads. A truly aligned team will identify the executive team as their primary team.
The defining challenge for executives in hypergrowth is adaptability. You must operate with the assumption that any current process, like how DoorDash launched cities, is guaranteed to break. The key is building the next, more scalable model in parallel.
Instead of letting go of underperforming employees, adopt the philosophy that their failure is your failure first as a manager. This forces you to re-evaluate if you've provided the right goals, context, and support, which can often unlock their potential.
Unlike purely digital ('Bits') businesses where finance is simpler, physical ('Adams') businesses like DoorDash require executives to obsessively manage unit economics from the start. They are often initially unprofitable, so making the math work is paramount.
Senior executives must retain the ability to dive into a granular user-level problem (e.g., a missing ciabatta), generalize it with data to confirm it’s a real issue, and then drive a systemic solution (e.g., implementing store planograms).
Bottom-up goal setting often leads to conservative, achievable targets. Instead, leaders should set an ambitious top-down goal with a resource constraint ('achieve X with Y people'). This forces teams to rethink their approach, not just incrementally improve.
To scale nationally, first 'crawl' by perfecting operations and unit economics in a single market. Then 'walk' by adapting the model to a few different market types (e.g., city vs. suburb). Only then can you 'run' by creating a playbook for rapid expansion.
When launching new initiatives ('S-curves'), a leader's primary role is protection. The core business will inevitably try to absorb their resources for the main thing. The battle is lost if you're debating which is 'more important.'
To manage a complex business, use the 'plate spinning' metaphor. Let stable areas run with light guidance, but each quarter, free up capacity to go deep on 2-3 struggling initiatives, acting as a team member to solve problems directly.
The path from VP to C-suite is blocked for those who remain specialists. Aspiring leaders must take calculated risks, moving into unfamiliar functions (e.g., finance controller moving to strategy) to build the generalist perspective required at the top.
While data is crucial, leaders must teach teams to use judgment and not over-analyze obvious problems. The impulse to A/B test cleaning a milk spill versus restocking shelves is a sign of a culture that has lost its connection to practical reality.