Why Most Engineering Reorgs Fail

I've lived through seven engineering reorgs. Led three of them. Two of the three I led failed. Here's what I learned from the failures that I wouldn't have learned from the successes.

A "failed reorg" means the org ended up no better than before, just disoriented. People lost context. Productivity dropped for months. Some good people left because they lost trust in leadership. And within 18 months, another reorg happened because the first one didn't achieve its goals.

That's the pattern. Reorg, disruption, disappointment, repeat. Most engineering orgs are stuck in this loop.

# Why Reorgs Happen (And Why the Reason Is Usually Wrong)

Every reorg starts with a real problem. Communication is slow. Teams are stepping on each other. Nobody owns a critical system. The product strategy changed and the team structure doesn't match.

These are legitimate problems. But a reorg is rarely the right solution. It's just the most visible one.

Here's the uncomfortable truth: most engineering reorgs are a substitute for making hard decisions. It's easier to rearrange the org chart than to fire the underperforming director, fix the broken process, or have the difficult conversation about ownership.

# The Contrarian Take: Reorgs Are Leadership Failure

A reorg is an admission that the current structure can't solve its problems. Sometimes that's genuinely true. Most of the time, it means leadership didn't address the problems early enough, and now the only option is to blow up the structure and start over.

The best engineering orgs I've worked with reorg rarely, maybe once every 3-4 years during genuine strategic shifts. They solve structural problems incrementally: adjusting team boundaries, moving individual engineers, creating temporary working groups.

If you're reorging more than once every 2 years, the reorg isn't the solution. It's a symptom.

# The Five Failure Modes

# Failure Mode 1: The Org Chart Obsession

The leader redesigns the org chart in isolation, announces it, and expects everything to work. They moved boxes on a slide but didn't change how work actually flows.

I did this my first time. Spent three weeks designing the "perfect" team structure. Presented it at an all-hands. Engineers nodded politely. Nothing changed. The same communication problems persisted because I'd reorganized people, not processes.

Fix: Define how work flows before you define how people are grouped. Map the value stream: how does a user request become a shipped feature? Wherever the value stream crosses team boundaries, you'll find your coordination problems. Structure teams to minimize those crossings.

# Failure Mode 2: The Big Bang

Everything changes at once. New teams, new managers, new processes, new tools, new sprint cadences. Engineers wake up on Monday with a completely new world.

The cognitive load of absorbing all these changes simultaneously tanks productivity for 2-4 months. Engineers lose context on the codebases they've been working with. New teams go through the full forming-storming-norming cycle. Institutional knowledge evaporates.

Fix: Phase the changes. Move teams first. Let them stabilize for 4-6 weeks. Then adjust processes. Then introduce new tools. Each change should be absorbed before the next one arrives.

# Failure Mode 3: Ignoring the Informal Network

Every org has two structures: the formal one on the org chart and the informal one that actually gets things done. The engineer who always knows the answer. The manager who mediates every cross-team dispute. The architect whose opinion carries weight across all teams.

Reorgs disrupt the informal network. The engineer who knew everything about the payments system gets moved to the growth team. The informal dispute resolution channel disappears. Nobody realizes it happened until things start breaking.

Fix: Map the informal network before you reorg. Ask managers: "When your team has a question about system X, who do they ask?" When you see the same names appearing across multiple teams, those are your keystone people. Plan around them. Either keep them where they are or explicitly create new channels for the knowledge they provide.

# Failure Mode 4: No Success Criteria

Most reorg announcements sound like: "We're restructuring to improve velocity and alignment." What does that mean? How will you know if it worked?

Without specific success criteria, the reorg is unfalsifiable. If things get better, it was because of the reorg. If things get worse, it's "transition pains" that will resolve with time. Leadership never has to admit the reorg failed.

Fix: Before the reorg, define 3-4 specific, measurable outcomes you expect:

• Cross-team blockers decrease from 8/sprint to 2/sprint within 90 days
• Deployment frequency for the payments domain increases from weekly to daily within 60 days
• Developer satisfaction score on the quarterly survey improves from 6.2 to 7.5 within two quarters

If these targets aren't met, the reorg failed. Commit to that publicly.

# Failure Mode 5: Communication Vacuum

The worst thing about most reorgs isn't the structural change. It's the uncertainty before, during, and after the announcement.

Rumors spread. People assume the worst. By the time the reorg is announced, half the team has already updated their LinkedIn profiles. Even after the announcement, engineers don't understand why decisions were made. They assume political motivations even when the reasons were sound.

Fix: Overcommunicate. Before the announcement, signal that changes are coming and explain why. During the announcement, explain the reasoning behind every major decision. After the announcement, hold small-group Q&A sessions (not just an all-hands) where people can ask hard questions.

I now budget 30% of my time for communication in the month surrounding a reorg. That sounds like a lot. It isn't enough.

# When a Reorg Is Actually Necessary

Sometimes a reorg is the right call. Here's when:

• The company strategy fundamentally changed. You pivoted from B2C to B2B. Your team structure was built for the old strategy. It won't serve the new one.
• You acquired a company and need to integrate engineering teams.
• You've grown past a structural threshold. Going from 20 to 60 engineers usually requires restructuring because the communication patterns that worked at 20 collapse at 60.
• You have a clear ownership gap that can't be solved by adjusting existing team boundaries.

In all other cases, try incremental changes first.

# The Stealable Framework: The ORBIT Checklist

Before committing to a reorg, run through ORBIT:

O - Outcome defined? Do you have 3-4 measurable success criteria? If not, stop. Define them.

R - Root cause identified? Is the problem structural, or is it a people problem, a process problem, or a communication problem wearing a structural disguise?

B - Blast radius estimated? How many teams are affected? How much context will be lost? How many reporting relationships change? Minimize all three.

I - Incremental option explored? Can you solve the problem by moving 2-3 people instead of reorging the whole department? Can you create a working group instead of a new team?

T - Timeline and transition planned? Do you have a phased rollout with stabilization periods? Have you planned the communication cadence?

If you can't check all five boxes, you're not ready to reorg.

Most reorgs fail not because the target structure is wrong, but because the transition is handled badly. Plan the transition as carefully as you plan the destination. That's the difference between a reorg that works and one that just rearranges the dysfunction.