My Learnings from a Turnaround

When I first wrote about how I helped an organization get unstuck, I focused on the play-by-play: the moves I made, the decisions I executed. In this post, I want to flip the lens and share what I actually learned along the way—moments I could have handled better, lessons that only became clear in hindsight.

Making decisive calls without hesitation. I knew early on that two senior leaders were poisoning the culture. They were cynical, resistant to change, and—frankly—made me wrinkle my nose the way you do when you read really sloppy code. I can either wrestle with their negativity or cut them loose and start fresh. I worried that, even though they felt indispensable, they would sabotage any changes I wanted to implement. My executive coach put it bluntly: “You already know the right choice. Stop convincing me and just do it.” She was spot-on. Once I let them go, the team initially bristled—after all, they were losing friends—but they gradually came around. The hard truth: recognize when someone is actively blocking progress, make the call, and move on to the next problem. Waffling only costs time and morale.

Standing firm against flashy consultants. The business pressured me to hand our broken app over to a well-reviewed consultancy that bragged about pushing 10,000 lines of UI code every day and rebuilding systems from scratch faster than our own team could finish features. That should have been a red flag. Massive PRs mean massive maintenance headaches—and plenty of opportunity for things to go sideways. Under duress, I relented. Big mistake. They delivered about 65% of what they promised, threatened to pull their team unless I approved payment, and even tried to go over my head to strong-arm approval. I had spotted the warning signs—a bloated codebase, empty promises—but I let politeness cloud my judgment. Lesson learned: be ready to say no, and if a vendor or partner fails to deliver, don’t keep funneling money into a sinking ship. Protect your leverage and your budget.

Finding simplicity buried under complexity. Technically speaking, the existing system was a monstrosity: a distributed monolith chewing through cash, forcing us to vertically scale, and prone to random outages. But underneath all that chaos was something that could fit on a thumb drive and run from my laptop. Early on, I struggled to see past the tangled architecture. Only later did a consultant’s offhand remark resonate: “It’s just a few apps.” Once I understood that, the path forward became obvious. No one needs 27 microservices if three well-structured modules will serve the same purpose and cost a fraction as much. Simplicity is powerful and—paradoxically—often hidden under layers of complexity. Don’t assume a giant codebase is inherently valuable; sometimes it’s just an inflated liability.

Managing expectations for large projects. When I pitched a ground-up rewrite, I knew the company needed it—our existing codebase simply wouldn’t survive production. But I also knew that projects of this scope often die under their own weight. History showed me that lengthy rewrites make executives nervous; they tend to pull the plug if they don’t see tangible progress fast enough. I tried to protect the project by back-channeling for weeks to shore up support—but in my absence, they deployed the half-finished product while I was on vacation. They wanted to preempt my objections. Returning to an environment where my carefully laid plans had been overridden was a harsh wake-up call: understand your organization’s appetite for big bets. I probably should have broken the rewrite into smaller, incremental milestones, even though that was almost impossible given how intertwined the underlying problems were. Next time, I’ll slice the work into bite-sized chunks and manage expectations at every step.

Recognizing that deadlines don’t always win you credit. In my notes, I found that one senior stakeholder labeled the entire project a failure—not because it collapsed technically, but because it wasn’t delivered three weeks early. That person wielded significant influence, and I never saw that “deadline obsession” coming. Looking back, someone higher up had overpromised a timeline they couldn’t possibly meet, then tried to dodge accountability by pointing fingers at the implementation team. The result: we were forced to cut corners chasing an impossible date, which ultimately slowed us down. Clear agreements and documented milestones helped me defend myself against that hindsight rewriting of history, but it was still a painful lesson: when promises get made above your pay grade, insist on realistic timelines, document every commitment, and be prepared to push back if top-level expectations become disconnected from engineering reality.

Tuning in to unspoken signals. I’ve written before about the importance of body language and emotional cues—and nothing brought that lesson home like watching two people in a senior leadership meeting exchange a glance that said, “Yeah, that’s bullshit.” The executives were rallying everyone to believe we could hit a new deadline, but I saw skepticism flicker in my teammates’ eyes. When I asked them afterward, they confirmed my read. That deadline never had a chance. If someone higher up had noticed those silent exchanges, we might have recalibrated expectations or adjusted our strategy. Instead, they plowed ahead unaware. Lesson: watch for the unspoken “truth” in the room. When the water cooler whispers contradict the marching orders, it’s time to dig deeper, address real concerns, and calibrate the plan to what the team actually believes is possible.

In the moment, I was so busy fighting fires that I barely registered these lessons. Hindsight sharpened them. If I could go back, I’d move faster on personnel decisions, refuse to let flashy consultants off the hook, relentlessly pursue simplicity, slice big projects into manageable increments, demand accountability for unrealistic deadlines, and pay closer attention to the unspoken doubts in the room. Those are the lessons I carry forward—none of which appear on a Gantt chart, but all of which make the difference between a turnaround that endures and one that simply grinds to a halt.