After 20 years inside some of the world’s most iconic companies, the moment I stepped out, what both sides were missing became unmistakably clear. As an executive, pitches never stop. Everyone believes they’ve cracked your problem — they just need a moment of your time to prove it. Each conversation starts with the same confidence: that they’ve discovered a capability you were oblivious to, one that will unlock what your own organization somehow failed to see.
After two decades on the inside — 13 years at Moët Hennessy and Diageo, six at Maersk, and four at Google — I crossed the line for the first time. I went from the inside to the outside and it was a huge wake-up call.
On the inside, people are not blind to opportunity., but they are managing a dense web of commitments, history, habits, and risk. What looks like resistance or a gap from the outside often masks careful sequencing, resource constraints, and competing promises — all invisible unless you’ve lived them.
We talk endlessly about AI replacing jobs. But inside any organization, few people ever say: “Let’s cut 20% of my department because we’ve become 20% more effective.” Efficiency is easy to celebrate in principle; much harder to act on when it means reassigning people, reshaping budgets, or renegotiating board expectations. In many organizations, incentives quietly reward footprint growing larger teams, bigger budgets, broader scope. Those signals tend to carry more clout than focus or simplicity. This creates a subtle tension: the choices that would streamline work often sit at odds with what many cultures implicitly encourage to grow.
