The Reorg Delusion

Mathias and I released episode two of our podcast this week, and the topic is about reorgs. I've been through more of them than I can count, some I led, most I didn't. What I didn't expect was how quickly the conversation turned into something closer to group therapy. By the end of our podcast conversation we were both laughing in that specific way you laugh when something has genuinely hurt you more than once.

Here's the number that stopped me while I was prepping: something like 70-to-80 percent of reorgs fail. Not "have some rough edges." Fail. And almost nobody agrees on what failure even means here, which might be the real story. If you can't say what success looks like going in, you can't really claim failure coming out either. You just have a tree that fell in a forest and a whole company quietly wondering if anyone heard it.

I want to write about why that number doesn't surprise me at all, and about the five or six patterns I've watched play out over and over, in companies of very different sizes and very different cultures, that turn a reorg from a structural adjustment into a trust-eroding event.

The reorg as a magic button

The pitch for a reorg almost always sounds clean. New structure, more speed, better clarity, cost savings. It's a spreadsheet exercise on the surface: names in boxes, lines connecting the boxes. Push the button, get the new org chart, everyone snaps into their new roles and productivity resumes on schedule.

I lived through a version of this that still makes me laugh, not the good kind of laugh. Leadership announced a major reorg mid-sprint and told the team that the current sprint would absorb the transition and the next sprint would be fully back to normal, new teams, new focus, full output. As if a person could be told on Tuesday that their manager, their teammates, and their scope of work were all changing, and then show up Monday and ship code at their usual pace. That's not how humans work. That's not how trust works. That sprint, and the one after it, and often the one after that, all take a hit, and pretending otherwise just adds a credibility problem on top of a structural one.

Reorgs get treated like a reset button because a reset button is a much more comfortable story than the truth, which is that you're asking a group of people to unlearn how they work together and relearn it, on a timeline that has nothing to do with how long that actually takes.

Forming, storming, norming, performing, again

There's a framework we talk about in the book: teams have to move through forming, storming, and norming before they get anywhere near performing. That sequence isn't optional and it doesn't skip steps because leadership is in a hurry. Every reorg resets that clock, sometimes for one team, sometimes for a whole department's worth of teams that all touch each other.

I've watched entire functions get moved wholesale from one part of an org to another. Product analytics moved under finance because the work was framed as being about metrics and KPIs. On paper, the team itself stayed intact. In practice, every single team that depended on product analytics now had a different way of working with them, a different set of priorities shaping their work, a different chain of approvals. Nobody's job title changed. The whole relationship changed anyway.

The word "reorg" is doing a lot of hiding

Mathias made a comment in the recording that I haven't stopped thinking about: it's easier to give something a non-human name. We're not moving people, we're moving resources. Said with an eyebrow raised, but it's true, and it's exactly why the language around reorgs stays so abstract. Org chart, structure, resourcing, synergy. All words that let you avoid saying the actual sentence, which is: your manager is changing, your team is changing, and the work you've spent years getting good at may no longer be what anyone wants from you.

I think about an employee I worked with who had been on the same manager's team for years, and was, by every read she and her manager had, close to a promotion her manager had been building the case for. A reorg moved her to a new manager with none of that context. She wasn't laid off. Her title didn't change. But she described it, accurately, as starting over. All that invisible groundwork, the track record, the trust, the case already half built, gone in a way that showed up nowhere on the org chart.

That's the part a spreadsheet can't capture. The human cost of a reorg isn't measured in headcount moves. It's measured in how much invisible infrastructure, trust, context, momentum, gets thrown away in service of a cleaner box-and-line diagram.

Middle management gets stuck holding the bag

One of the worst patterns I've seen, and Mathias put his finger on exactly why it happens: leadership announces a big vision-forward change, and the managers who actually have to explain it to their teams weren't brought into the reasoning early enough to explain it well. They're rolling their eyes right alongside their reports, except now they also have to stand in front of a room and defend a decision they don't fully understand, absorbing questions they have no good answers for.

If you want a reorg to land, the people delivering the message need more than a script. They need the actual reasoning, well before the announcement, in enough detail that when someone in their 1:1 asks "wait, why is this happening," they have something honest to say. Not corporate speak. An actual answer.

Avoiding surprise as a metric

If there's one operating principle from this conversation I'd want every leader to walk away with, it's this: treat avoiding surprise as a real, trackable goal, not a nice-to-have. Get ahead of the rumor mill. Map out who hears what, in what sequence, individually versus at the team level versus company-wide, and what channel each message goes out on. That planning takes real time and real care, and skipping it is exactly how you end up with a team that finds out about their new reporting line from a Slack message instead of a conversation.

This connects directly to what we talked about in our difficult conversations episode. Preparation is the whole game. The plan for a reorg rollout deserves the same rigor as any other hard conversation, because that's what it is, just multiplied across dozens or hundreds of people at once.

What I'd actually ask before doing this again

Gary Klein has a line in his book "Sources of Power", about organizations reorganizing for efficiency with no real evidence the new structure will be better, adopting change for the sake of motivation without proof it'll work. It landed hard for both of us, because it names the thing under all of this: a lot of reorgs are magical thinking dressed up as strategy.

So here's what I'd want any leader, myself included, to sit with before pulling the reorg lever:

What specifically isn't working right now, in concrete terms, not vibes? What is the actual goal of this change, stated clearly enough that you could tell in three months whether you hit it? How many people does this touch, directly and at the edges, and does your communication plan match that scope? Have the managers delivering this message been given the real reasoning, early enough to actually explain it? And what is this going to cost the people involved, not just in disruption, but in the trust and context they've built that doesn't show up on any org chart?

Reorgs aren't inherently wrong. Sometimes the strategy genuinely shifts, the team genuinely outgrows its structure, and change is the right call. But treating it as a clean, fast reset instead of a slow, human process is where most of them go to die. The 70 to 80 percent failure rate isn't a mystery. It's just what happens when you optimize the boxes and lines and forget there are people standing inside them.

Mathias and I get into all of this, plus a fair amount of shared cynicism, in episode two of The Intentional Organization Podcast. Give it a listen if you're in the middle of one of these right now, or bracing for one.