You know how the story ends before it starts.
A senior leader told me recently about a digital modernization effort at his company. It had everything a big bet is supposed to have. It came from leadership. It had a cool name. Every senior leader was involved. Eighteen months after it took off, he gave me the review in one line:
It was doomed from the start.
He is not the first person to say that to me. He will not be the last. And the part that stuck with me is that nobody involved was surprised.
A platform leader at a multimillion-dollar logistics company gave me the phrase I now use for this: execution reality. It is his framing for his own work: where the resources are actually going, and whether that work lines up with what leadership said mattered.
Leadership announces the future. Sometimes it is a digital transformation or a modernization. Sometimes it is a totally new, innovative product, which is even harder, because you are building a whole new business at the same time. The room rallies. Everyone agrees this is the turnaround.
Then everyone goes back to work. And everyone involved already had a full-time job.
Execution reality is what is actually getting done on the ground, measured against the plan leadership thinks it assigned. There is often a huge gap between the two. When you start looking at the real data from both sides, the gap is bigger than the Grand Canyon.
Different company. Same ending.
A friend of mine helps lead corporate development at a large financial company. On a call a few weeks ago, he told me about their big technology modernization program, and we ended up laughing about it together. Not because it was funny, exactly. Because of how familiar it was.
His words for the program: it is the least surprise of surprises.
The most unfortunate version of this story is when the thing that happens is the thing everyone knew was going to happen, and afterward everyone stands around asking how it could have happened. His answer to that, and mine: we all just pretend it is not going to happen.
Then he told me about the lessons learned slide he had seen. One of the official lessons from the program: this was harder than anticipated, and we should have planned more up front.
We all knew that slide was coming.
By the time he and I first talked, that train had already left the station. There was nothing either of us could have done to change the outcome. The decisions that decided it were made at the start, which is exactly when nobody wanted to hear them. He made the point that matters for the next one, though: catch an initiative at the beginning and its ending is still negotiable. Catch it after it has left the station and you are a passenger.
Back to the first story. By his count, a million hours went into that modernization effort over 18 months.
Sit with that number for a second. A million hours is real time from real people. The hours are only part of the cost, though. The rest is the work that never happened because the hours went there.
It is the same pattern that shows up when you audit the work directly: only about 30% of roadmap work matching the plan the teams agreed to. The other 70% is real work. It just is not the work anyone chose.
And the outcome was visible early to anyone who wanted to look. He said it plainly: we all knew it would go that way. Funny thing is, when he started telling me the story, I said the same thing back to him. I knew how this one was going to end. You probably did too, a few paragraphs ago.
We all know how these stories end. We keep starting them anyway.
When we talked through why, it came down to questions that were never answered at the start. Was the thing actually feasible? Was the capacity really available, from people who already had full-time jobs? Was the level of effort ever validated, and did anyone line up the partners the work would need? Were the right resources ever dedicated to it?
None of that analysis got done. The resources were never properly assigned. So the plan said one thing, the calendar said another, and the work followed the calendar. I keep seeing the same shape everywhere: the strategy gets approved, and the capacity never got the memo.
The research says this is the base rate, not bad luck. Bent Flyvbjerg and Alexander Budzier studied 1,471 IT projects for Harvard Business Review and found one in six became a black swan, with cost overruns averaging 200 percent. Those projects did not lack talent. They lacked an honest answer, at the start, about what the work would actually take.
Some of this is just the nature of building. Growing, building, and launching something takes time. You are going to learn. It is never quite what you expected. That part is fine, and it is priced into any honest plan.
The problem is skipping the question that decides whether the effort has a chance: how could you possibly focus the time needed to get this to market while still getting everything else done? If that question has no answer, the ending is already written, and the lessons learned slide is already drafted. It just has not been presented yet.
Before the next big bet gets a name and a kickoff, ask one question in the room: where are the people and the hours actually going to come from, and what stops to make room?
If the room can answer it with real names, real capacity, and real trade-offs, the bet has a chance. If the room goes quiet, you have just heard the ending of the story, 18 months early, while there is still time to write a different one.
That is the view I wanted when I built Iteright. You have built the strategy. Iteright helps you actually run it: the decisions, the people, and the money in one view, so the gap shows up in week one instead of month eighteen.
