When Technical Success Isn’t Enough

Looking back, the disconnect wasn’t buried in the requirements doc. We’d implemented everything that was “needed.” Where I missed was farther upstream. I hadn’t dug into what people expected the work to actually achieve.

Here’s where the wires crossed. Leadership had quietly prioritized scalability to support future growth and pictured this release as a springboard. The business stakeholders? They wanted something yesterday, not next quarter. Meanwhile, our team defaulted to building something robust enough to never page us after midnight. Everyone got something, but no one got what they needed most.

Success starts when you define success criteria before coding, not with what you build. It’s about who you align with before you build it.

Most of the friction didn’t show up until the project was standing in production. By then every hour of “clarification” meant rework and bruised trust. The worst feedback is after you ship. It always costs more to fix, and that after-the-fact scramble is avoidable. A little upfront alignment—on what outcomes matter most, where you’re willing to trade, and who needs to sign off—turns the wild west of delivery into a predictable, low-drama process. That’s the shift that actually builds confidence, both for your work and your relationships.

Why Requirements Alone Miss the Mark: Define Success Criteria Before Coding

Requirements tell you what to build—features, APIs, buttons, flows—but they don’t align stakeholder expectations. But expectations? Those spell out why you’re building it, and how everyone plans to judge whether you succeeded. It’s easy to think listing out the “whats” in a doc is enough, but I’ve learned the hard way. Unless you name success out loud before you start, you’re just guessing what matters to everyone else. That’s how teams end up with solid deliverables that quietly miss the real win.

Some of this comes down to whose scoreboard you’re playing on. Leadership cares about long-term scalability and future-proofing. Product wants results fast. Time-to-value is how they’ll call a project successful. End users just want something that works easily. These aren’t just different; they fight each other. I’ve been in those meetings where what feels like a triumph for one side is a letdown for another.

Making tradeoffs isn’t just a theoretical exercise; it’s the heart of delivery. Fast delivery usually equals more technical debt, while building for massive scalability almost always takes longer. When we only chase speed, we’re kicking a can down the road that someone (usually us) will trip over later. To be honest, I still struggle sometimes with knowing when to flag the tradeoff explicitly and when to let it slide. I know I should call it out…but sometimes I still think, “We’ll figure it out.” Doesn’t always go well.

I’ve seen it again and again. What derails projects isn’t missed features, but the expectations that were never surfaced upfront. By the time they bubble up, you’re deep into fixes—or worse, repairing relationships. Get these things on the table while it’s still early and cheap to change them.

That’s why I now use a simple alignment framework to define success criteria before coding, long before any code gets written. Here’s how we turn a pile of requirements into real predictability—and avoid those last-minute surprises.

Five Agreements That Make Alignment Predictable

Start with shared success metrics. Every project kickoff, I bring leaders, product owners, and actual users—not just the loudest voices—into the room, or into a shared async space (Slack, Loom, or just a Google Doc). The goal is simple. Co-create what “done” and “good” actually mean for everyone. It doesn’t have to be a two-hour meeting. Sometimes posting three bullet points and letting folks react clarifies more than a phone call.

The trick is insisting on specifics: “API latency under 300ms in production,” “first orders complete with two clicks,” “no repeat tickets for issue X.” Here’s why this matters. Success criteria need to be concrete and measurable—these principles set clear standards for what satisfies all parties, which is why defining them together matters. This upfront precision makes real conversation possible and shrinks misunderstandings to almost zero. By the time we delivered that last backend service, I wished I’d pushed for specificity before anyone committed code.

But don’t stop at features. Define tradeoffs upfront. The move here is to say, in plain terms, “We’ll ship in four weeks, but scalability will come later.” If someone expects “future-proof,” make it explicit that the MVP is optimized for speed, not for huge volume. You don’t have to dance around this. Being upfront helps you and partners focus on what really matters now, not what could matter six months down the line.

For timelines, skip the fantasy dates. Build a calendar that calls out the actual risks—dependencies on other teams, unclear requirements, holidays, anything that might derail the plan. I’ve spent whole days trying to bend a timeline to someone’s wish, but if you tag the big unknowns early, the delivery date actually means something. Sometimes I say, “We think it’s three weeks, unless the third-party API changes. If they do, we could lose a week.” People respect real talk more than optimism.

Set a feedback cadence from the jump. Weekly standups? Milestone reviews at half-way and pre-launch? Whatever the rhythm, make it regular and visible. The idea is to catch drift long before the final sign-off, not wait for launch day. I go back to this every single project. If you make room for bad news early, it turns into small course corrections, not emergency rebuilds. If you’re thinking, “Won’t this slow us down?”—give it one try and you’ll see, the time recouped from fewer rewrites is worth it.

Finally, document sign-off. Get actual stakeholder names on paper (or in Notion, Confluence, or JIRA). Treat this like a recipe. You wouldn’t start cooking without checking what’s in the pantry. Contracts exist so everyone knows what’s being promised and what isn’t. Documenting tradeoffs and agreements upfront isn’t just CYA—it’s how you turn “but I assumed…” into “we all saw this coming.”

I should say, sometimes alignment feels like extra process. But I haven’t found a better shortcut. Every time I skip it, something goes sideways, and we wind up doing the alignment work anyway—just messier, under more pressure, with less goodwill.

Turning Alignment Into a Ritual That Actually Works

Here’s what I do now, every time we kick off a multi-team project—engineering alignment best practices in action. I block an hour (60 minutes, not more) for a live or async alignment ritual. The structure is simple. First, set out the measurable outcomes, then talk tradeoffs, lay out the timeline and risks, lock in a feedback cadence, and wrap with sign-off from everyone who matters. We capture the agreements in a lightweight doc—two pages in Google Docs or Notion, nothing fancy. You don’t need procurement to bless it; you need everyone to read and nod. A simple agenda like this makes sure nobody’s guessing what counts as success or how bumpy the ride might be.

If you’ve got stakeholders with packed calendars—what PM doesn’t?—don’t get stuck chasing meetings. I’ll often post our draft doc in Slack or record a Loom summary, call out the big choices, and ask for feedback or a “thumbs up.” Quiet folks or execs can reply in their own time, and their comments go straight into the next version. Honestly, admitting that live meetings aren’t always possible frees you from chasing perfect attendance. This works better than expecting everyone to download requirements asynchronously. Association is direct and questions surface fast.

Let’s look at how this plays out in an AI/ML context. Say you’re shipping a new model for fraud detection: together you define success as “latency under 500ms and accuracy above 95%, keeping cloud costs under $100/day.” You talk tradeoffs—maybe you agree to skip secondary features to hit those performance goals, knowing it won’t scale for global traffic yet. Timeline? Set a four-week pilot, with risks flagged (like missing labeled data or vendor rate limits) so people see what might slow you down. Four weeks later, everyone knows if you hit the mark or what needs tuning.

If you want to make these conversations repeatable, use templates. You don’t need a wiki full of documents—just a handful of high-impact forms. Try building an outcome brief (summary of what success looks like), a tradeoff ledger (choices you’re making and what you’re leaving out), a risks and unknowns register (what could derail things and what you simply don’t know yet), a cadence calendar (feedback checkpoints), and a sign-off page listing everyone who agrees. Having these visible isn’t overhead—it keeps alignment out in the open, so no one can say, “Wait, I thought we were building X.” If you’re skeptical, treat the templates as checklists: five boxes to tick before you commit code. It turns high-stakes guessing into shared predictability.

Run this once, and you’ll see. The time you spend upfront isn’t bureaucracy. It’s insurance against every painful surprise downstream. Alignment isn’t about slowing you down; it’s what lets teams ship with confidence, knowing that what goes into production is what stakeholders actually wanted.

Alignment Isn’t Overhead—It’s the Shortcut to Predictable Delivery

I hear it all the time. “But if we slow down to align everyone upfront, won’t our velocity take a hit?” Actually, moving fast without alignment is what drags you down. The real time killer is rolling the dice and doubling back for late feedback or last-minute pivots. Every missed expectation means a costly reset—and those can turn weeks of work into cycles of rework. If you want speed, invest in fewer surprises. That’s how you get to done with minimal detours. It doesn’t feel as quick at the start, but it pays you back triple when launch rolls around and you aren’t scrambling.

Here’s another one I hear: “Aren’t detailed PRDs enough?” A PRD spells out what gets built but keeps space for new insights and mid-course feedback, which means you still need separate expectation alignment. I’ll admit, I’ve leaned on well-written PRDs hoping they’d cover the bases—only to realize the features list isn’t the finish line. Unless you co-create success criteria upfront, you’re betting someone else will guess what matters. Spoiler: they almost never do.

So here’s your playbook. Before you start building, define measurable outcomes (stuff you can point to and say “that’s done”). Decide on tradeoffs—speed or scalability, now or later. Set realistic timelines that call out actual risks and unknowns. Agree on a regular feedback cadence so nobody drifts off-course. Finally, get clear stakeholder sign-off (names, not just roles). With these boxes checked, you know what you’re aiming at. And so does everyone else.

Make this a habit. Align early, ship predictably, and skip the delivery-day surprise. Next time you roll out a release, everyone knows what ‘good’ should look like before you hit deploy.

I’ve yet to figure out how to make every stakeholder excited for the kickoff doc. Some will always see it as “extra paperwork.” Maybe that tension never goes away. But if alignment means the difference between predictable delivery and project chaos, I’m keeping it in the routine. Even if it means answering the same questions twice.