Why your strategy ages badly
In most organisations, the people who know the most about customers have the least influence on strategy.
The product teams, the sales teams, the customer success teams, the customer support teams. They have the most touch points. They see the patterns before anyone else does. Typically senior leaders write the strategy and hand it down to the people who know the most. You can see the gap? Of course senior leaders need to be making the crucial choices. They need to identify the ICP and they need to decide where they will and won't play. But the best ones get as much insight from their organisation as they can.
I'm working with a CEO who wanted to improve that flow in his own organisation. The people closest to customers weren't informing strategy as much as they could. He made fixing that a deliberate focus. Focusing on this is a sign of a very smart CEO, but what stops other organisations making this step?
Why doesn't insight reach the people who need it?
The first reason is context. People in teams are focused on their outputs. Without a clear line of sight to the strategic hypothesis their work is supposed to be testing, they don't know what's worth raising. They're not withholding. They just don't have the frame. The second reason is layers. In most organisations there are several levels of management between the people closest to customers and the people setting strategy. By the time insight travels up through those layers, it has been edited. Middle managers, often unconsciously, filter what reaches the top. The third reason is structural. There is no mechanism. Insight is expected to travel upwards through goodwill and initiative. Sometimes it does. More often it doesn't, because nobody has built the conditions for it to happen reliably.
The question that changes the intent
Most check-ins ask the same question: are we on track? It sounds reasonable. But the intent it produces is narrow. Teams focus on production. Are we moving fast enough? Are we hitting the numbers? The OKR becomes a target to chase rather than a hypothesis to test. The better question is: does this still represent our best thinking? That question requires teams to keep the bigger picture in mind. It invites challenge of the thinking behind the work, not just the pace of it. It treats the OKR as something that can be revised when the evidence calls for it. The difference sounds subtle. The intent it produces is not.
What has to be true for insight to travel up
From the work I do with leadership teams, three conditions have to be in place for insight to travel up reliably.
Teams surface honestly. That means raising concerns as they emerge, not polishing the picture before it goes up. Most teams have learned, through experience, that bad news travels badly. Unlearning that takes time and requires the conditions to change first.
Leaders receive without punishing. A team that gets burned for bad news won't give bad news again. This one sits entirely with leadership. You cannot ask for honesty and then make it costly. Leadership is willing to revise. If strategy is treated as fixed once set, the upward flow produces nothing. The insight arrives and goes nowhere. Teams notice that quickly.
All three have to hold. One missing and the mechanism breaks down. An organisation without this flow isn't strategy free. It has a strategy. It just has a strategy that stops learning the moment it's written.
The leadership team makes the best call they can with what they know. Then the organisation goes to work executing it. Months pass. Customers reveal things the strategy didn't anticipate. Teams see it. Nothing changes upstream because nothing is built to carry that signal.
By the time the next strategy cycle comes around, the cost has already been paid. In wasted effort. In missed shifts. In the quiet departure of the people who tried to raise it and gave up. The CEOs who fix this don't do it because they're more open. They do it because they understand that strategy without an upward flow is strategy with a shelf life.
