Context
While working with a CEO at an early-stage company, I initially leaned into an operating rhythm that had worked well for me with other leaders.
It was familiar, efficient, and — on paper — reasonable.
What I noticed (and missed at first)
My early diagnosis was that the team needed to become more effective at communicating upward.
The thinking was straightforward: if the team could distill their thinking more clearly — surfacing options, framing tradeoffs, and bringing concise decision prompts — the cognitive load on the CEO would be reduced. That, in turn, would allow her to engage more efficiently with the highest-leverage problems.
This approach reflected how I had worked successfully with other leaders: don’t bring me all the detail — bring me something I can react to and decide on.
The signals were there early that this cadence wasn’t quite landing. But I didn’t slow down soon enough to fully understand how she actually processed information and context.
What I eventually realized was that the issue wasn’t clarity — it was mismatch.
The pattern
This CEO didn’t want less detail. She needed more — but structured consistently and predictably.
Without sufficient context, she wasn’t being freed up; she was being put at a disadvantage. Decisions were harder, not easier, because the mental model she relied on wasn’t being honored.
In trying to make engagement “lighter,” we were inadvertently making it more difficult.
Once that became clear, the work shifted. Instead of pushing the team to abstract more aggressively, we focused on establishing consistent structures for detailed information, helping the team understand what kind of context mattered, and coaching toward patterns that supported how decisions were actually made.
It took multiple iterations. It wasn’t easy on the organization, and it required patience on all sides.
But once the rhythm aligned with her way of thinking, momentum followed quickly.
Why it matters
There is no universal “right” operating cadence.
Best practices around executive communication often assume that abstraction and distillation are always the goal. In reality, effectiveness depends on how a leader consumes, processes, and trusts information.
When teams optimize for an assumed preference instead of a real one, friction shows up as stalled decisions, misread engagement, or a sense that leadership is “hard to work with.”
In many cases, the problem isn’t execution or capability — it’s rhythm.
Learning to recognize and adapt to that rhythm isn’t a soft skill. It’s a form of operational clarity — and one that compounds quickly once it’s in place.