Building and Maintaining Competitive AI Products
Milestone planning is the work of building a plan that moves a product from its current state toward those measurable targets.
A Demo That Looks Almost Finished
Imagine a team that has just built a prototype AI feature in a short amount of time. It works, it impresses the people who see it, and everyone can see the effort that went into it. It is tempting to conclude that the product is most of the way finished. This article follows a team from a measurable goal to a plan for reaching it, and shows why that conclusion is often wrong.
What do you think happens?
A team's goal is to have an AI system handle 60% of customer support tickets automatically. An off-the-shelf model they are evaluating can already handle 30% of them with no custom work. How much of the gap is still left to close?
Reveal answer
Half of the gap is still left. The model already covers 30 of the 60 percentage points the goal requires, so 30 percentage points remain.
The model already covers half of the target, which is what makes the gap look small. The remaining 30 points are still work that has to be done, and that is what milestone planning organizes.
From a Measurable Goal to a Route
Once a team has defined measurable goals for an AI product, the next question is how to reach them. Milestone planning is the work of building a plan that moves a product from its current state toward those measurable targets. A milestone is an intermediate target along the way, so milestone planning turns one goal into a sequence of smaller checkpoints.
Milestone planning turns a measurable goal into a sequence of intermediate targets, and the right sequence depends on where the team starts.
Milestone planning follows goal-setting because it cannot begin until the goal is measurable. A goal such as handling a share of support tickets automatically can be checked against a number. Without that measurement, there is no way to say which intermediate target has been reached. The plan is also not written in the abstract. The route depends on the starting point, and the starting point is usually a set of existing models whose abilities can be measured before any custom work begins.
How a Starting Model Shapes the Route
Evaluating existing models is how a team learns its starting point. The evaluation shows what the models can already do, which makes the effort needed to reach each goal visible. The principle is direct: the stronger the off-the-shelf models are, the less work the team has to perform, and weak baselines mean more building.
A Checkpoint That Can End the Project
Evaluation does more than measure progress. It can also change the goal itself. Suppose the work needed to bring an application up to the level where it is useful turns out to cost more than the value the application could return. In that case, the team may decide not to pursue the product at all. For this reason, milestone planning includes a checkpoint where the goal is revisited, not only a schedule for reaching it.
Why an Impressive Demo Misleads
A very common belief holds that if a prototype already looks impressive after a short build, the product must be most of the way finished. The reasoning feels sensible. When effort is visible and results are visible, people tend to assume the remaining distance is proportional to what has already been done. The source gives two reasons this pattern appears. Foundation models already have impressive base capabilities, so a convincing demo can be built quickly. But that speed hides the work of refining behavior, and the source names product kinks and hallucinations as areas that consumed a large share of the time.
Common mistake Treating a fast demo as a measure of how much work remains
What it looks likeA prototype built in a short time handles typical cases well, so the team assumes the product is nearly complete.
Why it failsThe speed of the demo reflects the strong base capabilities of the model, not the work still needed to refine behavior across all cases.
Do this insteadMeasure the existing models against the goal and define milestones before estimating how close the product is.
Common mistake Assuming remaining effort is proportional to completed effort
What it looks likeHalf the visible effort is spent, so the team expects to be about halfway to the goal.
Why it failsThe last stretch of product development is often far harder than the first, so early progress is an unreliable guide to total effort.
Do this insteadPlan for the harder final stretch explicitly, with its own milestones and checks.
Common mistake Skipping the checkpoint that asks whether the goal is still worth pursuing
Why Progress Slows Near the Finish
The central pattern is that the last mile of quality often takes far longer than the first stretch of progress. Early on, a team can move a product a long way with a strong existing model and a small amount of work. Near the final quality level, each further improvement tends to require much more effort. This is why early success can mislead: the first stretch looks like the whole story when it is only the beginning of the route.
Reading the Gap in the Support Ticket Goal
A team's goal is to have an AI system handle 60% of customer support tickets automatically. An off-the-shelf model can already handle 30% of them with no custom work. How much of the goal is covered, and how much remains?
- 1Identify the goal
The measurable target is 60% of tickets handled automatically.
- 2Identify the starting point
The existing model is evaluated and already handles 30% of tickets, with no custom work.
- 3Compare the two
The model covers 30 of the 60 percentage points the goal requires, which is half of the target.
- 4Name the remaining work
The remaining 30 percentage points are the gap that custom work and milestones must close, and the harder final stretch is likely to be where much of the effort falls.
Half of the target is covered by the starting model, and 30 percentage points remain. Because the last stretch is typically the hardest, the remaining half of the goal should not be assumed to take half the effort.
Practice Planning a Route
A team evaluates two existing models against the same quality goal. Model A already reaches a large share of the goal, while Model B reaches only a small share. Describe how the milestone sequence for each team would differ, and name one checkpoint each team should include.
Hints
- Start by asking what the evaluation of each existing model reveals about the effort ahead.
- Think about which milestones are already met before custom work begins for the stronger model.
- The checkpoint asks whether the goal is still worth pursuing, not just whether the schedule is on track.
Key Takeaways for Milestone Planning
- 1Milestone planning turns a measurable goal into a sequence of intermediate targets, and it follows goal-setting because the goal must be measurable before milestones can be checked.
- 2Evaluating existing models reveals the baseline. A stronger baseline means less custom work is needed to reach the goal, and a weak baseline means more building.
- 3An early impressive demo can mislead, because foundation models make early progress fast while the last mile of quality often takes far longer than the first stretch.
- 4A good plan includes a checkpoint for reconsidering the goal, since evaluation can show that reaching the goal is no longer worth the cost.
At a glance
- Milestone planning turns a measurable goal into a sequence of intermediate targets, and the right sequence depends on where the team starts.
- Evaluating existing models reveals the baseline, and a stronger baseline means less custom work is needed to reach the goal.
- Early success can mislead, because the last mile of quality often takes far longer than the first stretch of progress.
- A good plan includes a checkpoint for reconsidering whether the product is still worth pursuing.