Jack Skellington leads a technical team at a large, multibillion-dollar enterprise. Last year, his company named a top priority: fix the company's internal search, with AI, by the end of the following year. One of the executive team's top three priorities, with funding secured. Executive attention, real money, a mandate everyone in the building could repeat.
Jack was excited, and he should have been. This is the project you want to be handed in your career. An important problem, a funded team, the newest tech, and a company saying out loud that it matters.
Then the calendar did what enterprise calendars do. The priority was set in the fall. The direction reached Jack in February. Procurement wrapped up in May. The delivery date never moved. Nobody decided to shortchange the project. The months just left, one handoff at a time.
What Jack did not know: by the time the work finally reached his team, the executives had already moved on to other things. He found that out much later.
He and his team built it anyway. Shipped the first version, kept improving it, lived and breathed this project for 12 straight months while users changed what they wanted from it. The work was good. Hard in places, frustrating in others, like any real build.
Six months in, Jack was asking the question nobody wants to ask about a top priority: what are we even building here? Is there even a real plan? You can write requirements all day. When the why goes missing, the work gets heavy, for the lead and for every person on the team.
Jack calls himself a feedback guy. Autonomy was never his problem. What he wanted was confidence. Someone in leadership checking the roadmap now and then and saying: yes, those are still the right things. Move this one up. Park that one. We still care about this. Proof the work still mattered to somebody above him.
It never came, because agendas do not work that way. Executives cannot keep the same item at the top for the year-plus that enterprise delivery takes. The meetings move on. New priorities show up, shinier and closer. As Jack put it, the care goes where the agenda shuffles around.
Silence does not stop good teams. It sends them off on their own. His team started building things nobody asked for. Useful things, some of them. Talented people will not sit idle. Months later, leadership surfaced with the obvious question: why are you working on this?
Then the project delivered. It landed in silence. The priority that launched it was no longer a priority, no longer important, no longer the thing anyone asked about in reviews. Before long, the question in the room was why money was still being spent on it at all. Two years in, they shut the program down.
If you have carried a team through something like this, you know the feeling, and it is hard to explain to anyone who has not. You did the job. You delivered the thing. And somehow you end up standing in a room defending the work as if it failed. Your team watched all of it happen. They learned the lesson you never wanted to teach them: around here, priorities are weather. Wait long enough, and they change. Next time the company announces a top three, they will smile in the meeting and pace themselves in private. That cynicism is the real cost. It never shows up in a budget. It shows up in every project that comes after.
Jack's story is not rare, and his company is not unusually broken. When Donald Sull and his coauthors studied strategy execution for Harvard Business Review, they found that two-thirds to three-quarters of large organizations struggle to execute their strategies, and that about half of C-suite executives cannot connect the dots between their own company's strategic priorities. In related research, 60% of companies that execute poorly never link their strategy to their budget at all. The plan and the money live in different documents, so the plan quietly starves.
We keep meeting the same mechanics from the other side. When we matched 10,000 Jira tickets against an approved plan, 23% of the work lined up with the plan. Another count found only about 30% of roadmap work matching the plan it came from. The people are working. The hours are real. What fails is the connection between the priority, the plan, the money, and the daily work, because keeping those tied together is nobody's job while the year runs. I have called that gap the canyon between strategy and execution. It is where good projects go to be forgotten. AI compresses the building now, so the same waste arrives in months instead of years. It does not fix a room that has already moved on.
There is a quieter cost underneath. When the questions finally came, nobody could reconstruct the story. Why was this funded? What did we spend? What did it produce? The decisions had happened in meetings, two years earlier, and meetings do not keep records. So the team was not just defending the work. They were defending it without evidence, against a question that sounded perfectly reasonable: if this mattered, why can nobody show me?
What Jack needed was not complicated, and it was not more process. He needed the priority to stay alive for as long as the work did. He needed changes recorded when they happened, with what they displaced, instead of discovered years later. He needed leadership's attention to leave a trail his team could see. And when the work finally landed, he needed a room that still remembered why it mattered, with an honest account of what the investment had produced. A plan that stays connected to the work. Decisions you can still read years later. That is the whole wish list.
That is the problem we built Iteright to solve. Iteright keeps strategy, execution, and outcomes connected in one place, so leaders can decide what deserves investment, keep the work aligned while the year runs, and prove the impact when it lands. Priorities can still change. They should change when the world changes. But the change gets recorded, the displaced work gets named, and the team building the thing never has to guess whether it still matters. Jack's team deserved that. So does yours.
Have you been in this position?
