I've spent years building executive onboarding programs for other people. So it was a little humbling to realize, somewhere around day 90 at my new job, that nobody was coming to check on me.
Not because the company dropped the ball. Their onboarding is genuinely great — the kind where you show up on day one with your laptop actually configured, a real sense of what you're walking into, and enough context to hit the ground running. Way above average.
But a formal 90-day conversation? Not on my manager's calendar.
So instead of waiting around, I wrote it myself. What was going well, what wasn't, and what I wanted from the relationship going forward. I sent it ahead of our next one-on-one. What followed was honestly one of the best conversations we'd had.
That experience got me thinking about something we don't talk about enough. We spend a lot of time on performance infrastructure — better managers, feedback systems, and leadership development. What we rarely discuss is what senior leaders owe to their manager relationships when they're the ones being managed. That's the gap I want to dig into.
The numbers on this are kind of alarming
The failure rate for senior leaders in new roles is remarkably consistent across every firm that studies it. McKinsey puts it somewhere between 27% and 46% of senior executives who fail or leave within two years. Executive coach Mike Ettore's take: it's rarely about capability. It's about the fact that organizations underestimate how much support these transitions actually need — and leaders underestimate how much they need to create for themselves.
Egon Zehnder studied 500+ experienced executives and found the same thing. New leaders don't usually stumble over skill gaps. They stumble over culture, politics, and relationships — specifically, not building the right ones fast enough.
Here's the kicker: only 2% of global companies offer anything close to real, structured integration support for senior leaders. Most handle the basics fine — you get a badge, some compliance training, and a lap around the office. But actually aligning expectations with your hiring manager? Only half of the companies do that. Helping you understand the culture? 29%.
Which means most of the time, you're on your own to figure it out. And most people don't realize that until too late.
So I wrote my own 90-day review
When I came in as Global CPO at a high-growth fintech, I was busy from week one. That part I expected. The harder part — the part that never really gets easier — is reading the room of a team with years of history while you're simultaneously expected to lead. Figuring out what to keep, what to change, and how to push things forward without blowing up what's already working.
My self-written review had three parts.
Wins, actually named. It's easy to assume your manager is tracking what you've built. They're probably not, or at least not all of it — they've got their own full plate. Things you don't name tend to just... disappear. Calling them out isn't bragging. It's just making sure the record is accurate.
Misses, framed honestly. There were things I got wrong in those first 90 days. Places I moved too fast. Things I underestimated. Writing them down — as lessons, not as a confession — made the conversation real in a way that formal check-ins usually aren't. It also signaled that I was safe to give feedback to, which matters more than most people realize.
A direct ask about how I wanted to work together. By 90 days, you usually have a pretty clear picture of where you can add the most value. The question is whether you say it out loud or just hope your manager figures it out. I said it. That one move changed the texture of every conversation we had after it.
Russell Reynolds interviewed a bunch of senior HR leaders about what they'd do differently in their transitions. The most common answer wasn't "build better relationships with the CEO" or "connect faster with peers." It was: be more intentional about the direct manager relationship. The regret was almost universal. Acting on it in advance, much less so.
Why senior leaders stop managing up
It happens slowly. Each promotion comes with more autonomy and less scaffolding, until eventually the assumption is that you're beyond needing structure or feedback. You're not. You've just stopped being offered it.
By the time you're at the C-suite level, the infrastructure that helps everyone else develop and integrate quietly stops applying to you. If you want it, you have to build it yourself.
Four things that actually help
Don't treat onboarding as something that happens to you. Even if your company has a great program, treat it as a starting point, not the full plan. The business cycle — budgets, reviews, promotions — runs longer than 90 days. Your integration plan should too.
Tell people what's going well before you need credit for it. Regular, specific updates early on shape how your work is understood before opinions harden. Don't wait for a formal review to make your contributions visible.
Own your mistakes before someone else names them. The leaders who build real trust quickly are the ones who show self-awareness about where they've gotten it wrong. A miss you name reads as confidence. One person's name for you reads very differently.
Say out loud where you're most valuable. Don't assume your manager knows where you can have the biggest impact. Tell them directly, framed around the business. It's one of the things organizations are worst at facilitating — which means it's usually on you.
The question nobody asks at 90 days
Most 90-day reviews, when they happen, are really just one question: Is this person working out? The leader is being evaluated. The relationship itself isn't.
The more useful question — and I rarely hear anyone ask it — is simply: how is this working for both of us?
Because the quality of that manager relationship, especially at the senior level, has an outsized effect on whether you succeed or flame out. When it's working well, everything else tends to work better too.
The review I wrote for myself wasn't really about my performance. It was about building the kind of relationship where real feedback could actually flow — in both directions. That doesn't happen automatically. You have to make it happen.
Most organizations do a decent job of getting you oriented. Almost none are built to support the longer transition — the 12 to 18 months where you're actually figuring out your leadership identity in a new context, building real influence, and learning what it takes to sustain performance here.
That part's on you. Start earlier than you think you need to.
The main shifts: shorter sentences, more direct address ("you" throughout), less formal citation of research, and a conversational opener on each section rather than a headline. The ideas are all intact — just delivered more like a talk than an article.