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We Don't Know What We're Signing Up For (And That's Why Everything Goes Sideways)

Look, I need to tell you something uncomfortable.

Most of the initiatives your organization approves are doomed before they start. Not because the ideas are bad, or the teams are incompetent, or the strategy is wrong.

They're doomed because nobody actually knows what they've committed to.

I see this pattern everywhere. A product manager pitches a "simple integration." Leadership nods and says yes. Three months later, the project is over budget, behind schedule, and requiring involvement from five teams that were never consulted.

What happened? Nobody asked the hard questions upfront. Nobody mapped the dependencies. Nobody defined what "done" actually looked like.

The initiative got greenlit based on a PowerPoint slide and a prayer.

 

The Illusion of Clarity

Here's the thing about most project proposals: they sound clear until you try to build them.

"We need to improve the user onboarding experience." Sounds straightforward, right? But what does "improve" mean? Which part of onboarding? For which user types? What's the success metric? Who owns the content? What about the technical dependencies? The compliance requirements? The impact on existing workflows?

Suddenly, your "simple" project has tentacles reaching into six different departments and touching systems you forgot existed.

This isn't incompetence. It's human nature. When we're excited about an idea, we focus on the outcome and gloss over the complexity. We assume the details will sort themselves out.

They never do.

 

The Hidden Cost of Unclear Scope

The real damage isn't just blown timelines or budget overruns. It's the erosion of trust.

When initiatives consistently surprise teams with hidden complexity, people stop believing in the roadmap. They start padding estimates. They become defensive about commitments. Planning becomes an exercise in creative fiction rather than realistic forecasting.

I worked with a SaaS company where this pattern had become so entrenched that engineering automatically doubled every timeline estimate. Not because they were lazy, but because they'd been burned so many times by "simple" projects turning into multi-quarter nightmares.

The product team would estimate two weeks. Engineering would hear "at least a month." Leadership would plan for two weeks. And everyone would blame everyone else when reality hit.

 

Why This Keeps Happening

The problem isn't malicious. It's structural.

Most organizations treat initiative approval like a pitch meeting. Someone presents an idea, leadership decides if it sounds good, and if it does, work begins. There's no systematic way to surface assumptions, map dependencies, or stress-test feasibility.

The approval process focuses on whether we should do something, not on what doing it actually entails.

Executive Excitement Override – Senior leaders fall in love with an idea and want it started immediately. The urgency bypasses proper scoping because "we'll figure it out as we go."

Optimism Bias in Estimates – Teams consistently underestimate complexity because they focus on the happy path. Edge cases, integrations, and unexpected dependencies get discovered mid-flight.

Scope Creep by Committee – Different stakeholders have different mental models of what the project includes. These differences only surface after work has begun.

The result? Every project becomes an archeological dig, uncovering buried requirements and forgotten constraints.

 

The Solution: A Proper Readiness Review

The answer isn't to slow down decision-making. It's to front-load the hard questions so you can move fast with confidence.

Before any initiative gets approved, it should pass through what I call a "Green Light Checklist" – a systematic review that forces clarity on what you're actually committing to.

Define the Objective Precisely – Not "improve user experience" but "reduce time-to-first-value for new enterprise customers from 14 days to 7 days, as measured by first successful login."

Name the Owner and Stakeholders – Who's accountable for delivery? Who needs to be involved? Who gets to make trade-off decisions when things get complicated?

Map the Scope Boundaries – What's included? More importantly, what's explicitly excluded? Document the "what this isn't" section to prevent assumption creep later.

Estimate Effort and Dependencies – Not just "how long will this take" but "what other work does this depend on" and "who else needs to be involved."

Assess Confidence and Risk – Require teams to give a confidence score on their understanding. If it's low, the initiative isn't ready for approval.

 

Making It Real: The Cross-Functional Readiness Review

Here's where most organizations go wrong: they let one person or team answer all these questions in isolation.

Instead, bring together representatives from every function that will be impacted. Run through the checklist together. Let people poke holes. Surface assumptions. Flag risks.

This isn't about creating bureaucracy. It's about creating shared understanding before you commit resources.

I've seen 30-minute readiness reviews save organizations months of confusion, rework, and political fallout. Because it's much easier to clarify scope upfront than to renegotiate it when you're already behind schedule.

 

The Cultural Shift

Implementing this kind of discipline requires a cultural shift. You're moving from "figure it out as we go" to "figure it out before we commit."

Some people will resist this. They'll say it slows things down. They'll argue that you can't know everything upfront.

They're partially right. You can't know everything. But you can know enough to make smart commitments and realistic plans.

The goal isn't perfect information. It's sufficient clarity to avoid predictable disasters.

 

Document What You Decide

Once you've gone through the readiness review, document what was agreed. Not just the high-level objective, but the specific conditions: deadlines, owners, funding, success criteria, and scope boundaries.

This becomes your baseline. When scope creep inevitably tries to sneak in, you have something to point back to. When timelines get questioned, you have the original assumptions documented.

It's not about blame. It's about maintaining alignment in a world that constantly tries to push you off course.

 

The Payoff

Organizations that adopt this kind of upfront discipline don't move slower. They move steadier. Their estimates become more accurate. Their teams become more confident. Their stakeholders stop getting surprised.

Most importantly, they stop signing up for things they don't understand. And that might be the difference between a roadmap that actually delivers and one that's just expensive theater.

Look, I know this sounds like more process in a world that already feels over-processed. But unclear commitments aren't faster. They're just chaotic. And chaos, disguised as speed, is still chaos.

The best teams don't wing it. They plan it. And they do it before the stakes get high.

Want the complete framework for turning unclear ideas into rock-solid commitments your teams can actually deliver?

Download our free guide: Survive and Thrive – 7 Critical Moves for On-Time Delivery Without Burning Out Your Team 👉 www.techleaderadvance.com/thrive

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