Leaders Mistake Bad Strategy for Communication Failure

A leader stands in front of her board and says it plainly. We had a great strategy, but we couldn't execute it.

The room nods. Everyone knows execution is hard.

Rather than examine whether the original decision was flawed, the leader blamed the gap between intention and outcome on communication failures. This diagnosis is almost never rigorous. The entire argument rests on an assumption that leaders can accurately separate a bad strategy from bad execution. But organizational practice shows they almost never do.

They default to blaming communication because it's less threatening than admitting the strategy itself was unexecutable from the start. Mark Bertolini faced exactly this at Oscar Health, the insurance startup built to challenge incumbents. He inherited a company that had bet aggressively on technology, scale. A particular vision of how healthcare could be disrupted. When the numbers didn't move, the instinct was to clarify messaging, tighten the org chart, get people aligned on the vision. Yet nobody seemed to ask whether the vision itself was built on false assumptions about speed to profitability, regulatory complexity, or the actual behavior of the market.

The strategy and the communication became impossible to untangle because the leader had already decided which one was the problem. This creates a trap. If you've already concluded the strategy was sound, then any failure looks like execution. You'll keep pouring energy into communication fixes while the structural constraints that made execution impossible remain untouched. You'll get very good at articulating something that was broken from conception.

The real diagnosis requires a different kind of listening. Not to clarify the message. To question whether you ever had clarity about what the world actually is.