What Went Wrong Before Anyone Noticed

When things go wrong, there’s a moment everyone remembers. The room goes quiet. The expressions shift. Someone says what everyone is thinking.

But that’s not when it went wrong. It went wrong earlier. Usually months earlier, in a moment no one remembers because it didn’t feel like a decision at all.

Here’s one of mine:

It was an average Thursday in October. Biweekly product-sales sync. Sales was riding a wave. They’d moved up-market from our typical small-and-medium sized clients, closing four enterprise deals with January start dates. The differentiator was a feature called “job costing.” Think of it as the ability to track costs against specific projects or business units. Big deal for enterprise clients. Sales wanted a status update from Product.

Product jumped in with their “org units” update (a system that mapped those same projects and/or business units inside our platform). More complex than expected, but they felt good about a December launch.

Then I asked: “Just confirming... the org units MVP is going to cover what the enterprise clients need, right?”

Wrong.

Org units was phase one. Job costing was phase two. Sales had sold the complete capability. Engineering was building the foundation. Both teams had been meeting for months, using the same words, meaning different things.

The room shifted. Confusion, then recognition, then something close to panic. We’d sold something we couldn’t deliver. We were screwed.

I’ll come back to how this played out. But first, the pattern underneath it.

The Pattern

It would be easy to call this a communication breakdown. It wasn’t. The communication was constant. The problem was that nobody paused long enough to check whether everyone had the same understanding.

This repeats across organizations, and it has a consistent structure: pressure to move forward, different functions solving different problems in parallel, and the window for sorting out the handoffs closes before anyone realizes it was open.

Two examples:

• A product initiative gets approved during annual planning. The VP of Product greenlights it based on customer demand and revenue projections. Six weeks later, the infrastructure team escalates tradeoffs nobody consulted them on. The database can’t support the proposed design without a migration that adds three months. The commitment was locked before the people who understood the technical cost were in the room.

• Finance needs to know which engineering work qualifies as a capitalizable asset. Engineering works iteratively, in ways that don’t map neatly to those categories. Without a shared way to bridge the gap, engineers end up filling out timesheets as compliance paperwork rather than as a reflection of what they’re actually building. Both teams are doing their jobs. Neither is solving the same problem.

Both follow the same shape. Someone needed to slow down and ask “do we actually mean the same thing?” No one did. Everything felt like it was moving in the right direction.

It’s like building a house with four different contractors who each have their own blueprints. The electrician wires based on one floor plan. The plumber runs pipes based on another. Everyone’s working hard. The work is competent. But when you flip the switch, nothing connects. No one stopped to confirm they were building the same house.

That’s what happens at the seams between functions. Engineering thinks in dependencies. Product thinks in priorities. Sales thinks in timelines. Finance thinks in constraints. Each one fills gaps in their understanding with assumptions. The misalignment only surfaces after contracts are signed, commitments have cascaded, and undoing any of it is expensive.

What Actually Happened

The decision to promise job costing by January wasn’t made by one person. It was a company decision, embedded in revenue forecasts, implementation timelines, and customer contracts before anyone realized the underlying build wasn’t going to support it.

The shortcut was treating “job costing” and “org units” as interchangeable. They weren’t. Org units came first; job costing came second. But that distinction got lost. Sales heard customer needs and relayed them as requirements. Engineering decomposed the technical work and built from there. Product scoped based on level of effort.

Nobody stopped to ask “wait, are we talking about the same functionality?” The moment for that came and went without anyone noticing.

By the time we found the gap, reversing the commitment was more expensive than living with it. Engineering accelerated the org units build. Sales stopped selling job costing. Operations built workarounds for the four clients already committed. It took twelve months to deliver what clients expected in ten weeks.

AI Compresses What’s Already Fragile

Organizations have always struggled with the gap between exploring an idea and committing to it. AI didn’t create that problem, but it makes the gap harder to see.

A leader can pose a question to their LLM of choice, receive a polished and confident answer, and move straight to a decision. Without recognizing that the messy, necessary work of figuring out what they actually mean never happened.

The AI doesn’t know what it doesn’t know about your organization. It can’t flag that your sales team and your engineering team are defining the same term differently. It just builds on whatever you give it.

So, when the underlying thinking is sound, AI accelerates good work. When it’s not, AI makes the problems harder to spot. The output looks clean even when the inputs were unresolved.

The failure isn’t the technology. It’s the unresolved thinking the technology inherits.

Welcome to Call It Early

I’m Clare Hawthorne. I’ve spent my career working across engineering, finance, product, and operations. Usually in rooms exactly like the one I just described, trying to figure out why decisions that seemed sound created problems no one anticipated.

What I’ve found: most organizational failures start between functions, in the phase before commitment. Not in the execution. Not in the people. In the moment when thinking that should still be open gets treated as settled. Sometimes that looks like two teams using the same word to mean different things. Sometimes it looks like a roadmap that locks in a bet before anyone pressure-tested it. Sometimes it looks like a leader handing off authority without defining what comes with it. We all talk about alignment, but that’s the step that gets skipped when everyone’s under pressure to move. And almost nobody notices until it’s too late.

Call It Early is about that moment. Timing, judgment, and the structural conditions that shape decisions before they become irreversible. If you’ve been sensing a pattern you can’t quite name yet, you’re probably right. And you’re probably not looking early enough.

What looks like momentum is often premature closure. Call It Early is about learning to spot it before it hardens.