Why I Insist on a Roadmap Before Starting Any AI Project.
- Introduction
- The Symptoms of an Unstructured AI Project
- How a Roadmap Creates Predictability and Focus
- From Hopeful Experiment to Engineering Investment
Introduction
In the early stages of an AI project, the inherent uncertainty can make ‘playing it by ear’ feel like the right move. In their desire to verify a project’s feasibility, teams often over-focus on the initial proof-of-concept at the expense of long-term planning. While this approach may feel productive at first, it becomes a major liability as the project matures.
I learned this lesson on an engagement where this ‘play it by ear’ approach led to a cycle of promising starts but no finished milestones. We’d make a breakthrough on one front, only to have priorities shift to a new, exciting idea. This cost us focus and burned valuable time. Progress became increasingly difficult to measure, and communicating a clear project status to stakeholders became nearly impossible.
This experience taught me that a well-defined roadmap isn’t about bureaucracy or stifling creativity. It’s what separates a speculative experiment from a predictable, manageable engineering effort.
The Symptoms of an Unstructured AI Project
An AI project without a roadmap doesn’t fail all at once. It slowly bleeds resources and momentum, exhibiting a few predictable symptoms.
1. Constant Context Switching
On my engagement, we’d make a significant breakthrough on one part of the project, only to have the client, excited by the progress, immediately shift priorities elsewhere. This “project hopping” was incredibly costly, leaving a trail of half-finished work. Every time we jumped between tasks, we burned valuable time just re-familiarizing ourselves with the previous context.
Worse, it squanders the most critical moments. A breakthrough isn’t a signal to move on. It’s a signal to follow through with the disciplined cycle of real-world testing, failure analysis, and improvement that forges a truly robust solution.
2. Generating Zero Business Value
A roadmap is a tool for delivering value. Without it, my client contact struggled to provide clear progress updates to their leadership, eroding stakeholder confidence. But the problem is deeper than communication. As David Guttman argues in his book, The Superstruct Manifesto, a project has zero value until it is shipped.
Without a roadmap relentlessly focused on getting one thing to the finish line, a team can appear busy for months while generating zero actual business value: no user feedback, no analytics, and no revenue. Progress becomes a measure of activity, not achievement.
3. Uncontrolled “Sideways” Scope Creep
A roadmap provides a framework for saying “not yet.” Without one, a project’s scope inevitably expands. In our case, the scope didn’t just expand with new features. It crept sideways. Unexpected requests, like suddenly needing to support entirely new production environments before we had even validated the first one, were treated with the same urgency as core project goals.
Because we hadn’t defined and agreed upon a fixed set of milestones, it was impossible to effectively prioritize these new tasks or explain the trade-offs of diverting resources. My attempts to correct this by creating a roadmap partway through the project were unsuccessful, as the unstructured habits were already too entrenched.
How a Roadmap Creates Predictability and Focus
It may be tempting to view roadmaps as rigid plans set in stone. On the contrary, they’re a strategic alignment tool for keeping teams focused on a shared definition of success, even as the technical details evolve. Here’s how it solves the problems of an unstructured project.
1. It Defines “Done” and Delivers Value Incrementally
The most critical function of a roadmap is to break a large, vaguely defined objective into a series of distinct and, most importantly, demo-able milestones. This is a direct antidote to the “zero value until shipped” problem. Completing each milestone delivers real, tangible value. It proves the core concept, provides a concrete demo for stakeholders, and builds the foundation for the next milestone.
2. It Forces Prioritization and Controls Scope
Creating a roadmap forces the difficult but essential conversations about what matters most right now. It provides a powerful, neutral framework for managing new ideas and requests.
When unexpected requests come up, a roadmap helps prevent an immediate and disruptive diversion by facilitating strategic discussion. It turns a potential conflict into a collaborative planning session and protects the project’s momentum.
3. It Serves as a Powerful Communication Tool
A roadmap is the single best tool for managing stakeholder expectations. Instead of my client contact having to give a vague verbal update, a roadmap would have empowered them to present a simple visual summary. They would have been able to clearly communicate which milestones are complete, which one is in progress, and whether or not it’s on-track.
That level of clarity builds trust and makes it far easier to justify the project’s continued investment. It transforms the project’s status from a mystery into a transparent, shared reality. This transparency in turn helps leadership know exactly what they can show to potential customers and when.
From Hopeful Experiment to Engineering Investment
My experience has made roadmaps a non-negotiable part of my consulting practice. Insisting on one after an initial discovery phase isn’t about being rigid. It’s about respecting the client’s investment. It is the professional discipline required to navigate the inherent uncertainty of AI development and turn an ambitious idea into a real-world solution.
Ultimately, the choice is a simple one. An AI project without a roadmap is a hopeful experiment. An AI project with a roadmap is an engineering investment.
I’m Christian Mills, an Applied AI Consultant and Educator.
Whether I’m writing an in-depth tutorial or sharing detailed notes, my goal is the same: to bring clarity to complex topics and find practical, valuable insights.
If you need a strategic partner who brings this level of depth and systematic thinking to your AI project, I’m here to help. Let’s talk about de-risking your roadmap and building a real-world solution.
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