She had given the organization twenty years. When the person she reported to moved on, the buffer he provided went with him, and she found herself answering straight to a new chief executive who ran every meeting like an interrogation. By the time she and I began working together, her blood pressure had climbed and several of the people she relied on had already handed in their notice. Nobody had walked her into the new arrangement. There was no plan for her first ninety days, no briefing on how the man above her actually reached a decision, no recognition that the role she now held only looked like the one she had spent two decades mastering. She had been moved up a level, and the assumption was that the rest would take care of itself.
I have watched some version of this land on capable people more times than I can count, and the detail that stays with me is how ordinary the neglect is. Nobody decided to abandon her. The support simply was not there, because the organization had stopped building it somewhere below the floor she now stood on.
The care runs out on the way up
Think about how much attention a new hire gets at the bottom of the house. A graduate joining in an entry role is handed a plan for the first month and a colleague whose job includes answering their questions. The investment is real, and it is sensible, because that person is learning the work. Move up a few rungs and the same care begins to thin. By the time someone reaches a senior seat, it has all but disappeared, replaced by a belief that a title is its own set of instructions.
Russell Reynolds, a firm that studies executive transitions and, worth saying plainly, earns its living selling the coaching that steadies them, puts the danger window at the first twelve to eighteen months in a new senior role.1 What derails people there is rarely a shortage of ability. More often it is the failure to grasp how much the job itself has changed at the top of an organization, where reading the chief executive's real priorities and earning the confidence of peers who already share a long history count for more than the technical strength that earned the promotion.1
None of that is written down anywhere. It gets learned by being in the room, and a leader dropped into the room without a guide learns it the expensive way, through the mistakes that spend trust before anyone has extended much.
We put real development into the people whose mistakes are cheap, and almost none into the ones whose mistakes can cost a quarter or a career.
We already know where the gaps are
This is not a case of hidden information. In DDI's 2025 study of nearly eleven thousand leaders, run by a company that itself sells leadership development, the leaders named setting strategy and managing change as their two greatest skill gaps. Only twenty-two percent of HR teams currently prioritize those skills.2 The same work found that high-potential individual contributors are 3.7 times more likely to leave in the next year if their manager does not regularly provide opportunities to grow.2 People keep needing support as they rise. What changes is that the organization stops offering it.
So why does the scaffolding come down exactly where the fall is fatal? The honest answer sits in the culture rather than the budget. Somewhere along the way we decided that needing help at the top is evidence you should not be there. A senior leader who asks for a coach, or for an honest map of the politics, risks looking like a person promoted past their depth. The safer move is to perform certainty and absorb the strain in private, which is roughly what my client was doing when her body started sending the bill.
The role changed, and nobody said so
There is a companion piece to this I wrote earlier, on how the very strengths that carry a person into a senior role stop carrying them once they arrive. I will not relitigate it here beyond the part that matters for this argument. If the job genuinely changes at the top, and it does, then the person stepping into it is a beginner in the ways that count, however senior they look on the chart. Treating a beginner as a finished article is a design choice that the organization owns. Whatever goes wrong afterward gets filed under the individual, which is the tidiest way to avoid looking at the design.
The leaders who handle this well draw one distinction the rest miss. Onboarding is paperwork and orientation, finished in a fortnight. A transition is the year or more it takes to actually become the leader the new seat demands, and it needs structured support the whole way through.1 When a company treats the first day as the finish line, it hands its most consequential roles to people it has agreed, in advance, to leave stranded.
What it costs to keep pretending
We spent our sessions building the scaffolding the organization never did, working out how the chief executive actually reached a decision and how she might steady the people still on her team. That labor was hers to carry only because no one had carried it for her. The resignations that piled up while she found her footing were the tuition an organization pays for a lesson it keeps refusing to learn, that the top of the house needs the most support and is handed the least.
If you run a function, look honestly at your own last move into a bigger seat. Was there a plan, or was there a title and a wish of good luck? And if it was the second thing, what did that teach you about whether it was safe to admit you were still learning the job? I would like to hear how it actually went.
If the picture of a capable person set up to fail in a role no one prepared them for landed with you, the book carries a longer version of it. There is a stretch in Agile Sucks! about a client that burned through seven product owners in two and a half years, each one handed the title and none of them handed what the job actually asked for, along with what it would have taken to break the cycle. If you want to see where this pattern leads when nobody interrupts it, the read is below.
Read Agile Sucks! (When You Do It Wrong) →References
- Russell Reynolds Associates. (2025). Why C-suite transitions fail: How to set up new executives for success. https://www.russellreynolds.com/en/insights/articles/why-c-suite-transitions-fail ↩
- Development Dimensions International. (2025). Global leadership forecast 2025. DDI. (Survey of 10,796 leaders and 2,014 organizations across more than 50 countries. DDI sells leadership development, disclosed in the body. Figures cited here are from DDI's own release; the full report is gated.) https://www.ddi.com/about/media/global-leadership-forecast-2025 ↩