How to Write Milestones Your Reps — and the AI — Will Understand
Overview
This guide is for admins setting up or editing conversation milestones for their team. Milestones have two parts, and most customization issues come down to one of them being unclear. This article explains what each part does and how to write them so the AI evaluates your reps the way you intend.
How Milestones Work
Each milestone has two fields:
- Summary — the short milestone name your reps see (e.g., "Transition to Big Picture")
- Note — the completion requirement the AI uses to decide if the milestone was passed
These two fields serve different audiences. The summary is written for your rep. The note is written for the AI. The most common reason a milestone doesn't behave as expected is that the note was written like a summary — short, human-friendly, and open to interpretation.
The AI evaluates the note literally. It won't read between the lines or assume what you meant. If the note is vague, the AI will make its own judgment about what passing looks like — and that may not match yours.
How to Write a Good Note
A good note answers one question: what does a rep actually need to say or do for this milestone to be complete?
Be specific about the observable behavior. If two different reps read the note, they should both attempt the milestone in roughly the same way.
Common Mistakes
1. The note just restates the summary
This is the most frequent issue. When the note and summary say the same thing, the AI has no additional information to work with and has to guess what passing looks like.
| Summary | Weak Note | Strong Note |
|---|---|---|
| Build Rapport | Build rapport with the prospect. |
Ask the prospect at least one personal or professional question and acknowledge their answer before moving on. |
| Confirm Next Steps | Confirm next steps. | State a specific next step — including a date, time, or clear action — before ending the conversation. |
2. Too many requirements packed into one note
When a note asks the AI to confirm three or four things at once — especially using "and" — it struggles to evaluate all of them reliably. If you find yourself writing "and" more than once, consider whether this should be split into separate milestones.
| Too much in one note | Better approach |
|---|---|
| Ask about the prospect's budget, confirm their timeline, identify the decision maker, and establish whether they've looked at competitors. | Split into separate milestones: "Ask about budget," "Confirm timeline," "Identify decision maker." |
| Introduce yourself, explain the purpose of the call, and ask if now is a good time to talk. | Three small actions — split them, or pick the one that matters most to track. |
3. The milestone is written around what the prospect does, not the rep
The AI only evaluates the rep's messages. If the note describes something the prospect needs to say or agree to, the milestone may never pass — regardless of how well the rep performs.
| Evaluating the wrong person | Rewritten for the rep |
|---|---|
| The prospect agrees to a follow-up meeting. | Ask the prospect to commit to a specific follow-up date or next step. |
| The prospect shares their current challenges. | Ask the prospect an open-ended question about their current challenges and listen without interrupting. |
| The prospect expresses interest in the product. | Present at least one specific benefit tied to something the prospect has already shared. |
4. Subjective qualifiers the AI can't measure
Words like "naturally," "confidently," "effectively," or "genuinely" sound meaningful but give the AI nothing concrete to evaluate. Replace them with observable behavior.
| Subjective | Observable |
|---|---|
| Confidently handle the objection. | Respond to the objection by restating the prospect's concern and connecting it to a specific product benefit. |
| Naturally transition to the next topic. | Signal the topic change by summarizing what was just discussed before introducing the new topic. |
| Genuinely engage with the prospect's concerns. | Repeat or paraphrase the prospect's concern before responding to it. |
5. Telling the AI what the rep should NOT do
Negative instructions are harder for the AI to evaluate consistently. It's much easier to confirm that something happened than to confirm that something didn't.
| Negative instruction | Rewritten positively |
|---|---|
| Don't rush past objections. | Pause on each objection and respond before moving forward. |
| Don't pitch the product before asking discovery questions. | Ask at least two discovery questions before introducing the product. |
| Don't end the call without confirming next steps. | State a specific next step before closing the conversation. |
6. Conditional language that may never apply
If a note says "if the prospect raises an objection, handle it" — and the prospect never raises one — the milestone is impossible to pass. Write notes around what the rep should proactively do, not around scenarios that may or may not occur.
| Conditional | Proactive |
|---|---|
| If the prospect mentions price, address the concern. | Proactively address the value of the product relative to cost before the prospect asks. |
| If the prospect seems hesitant, ask what's holding them back. | Check in with the prospect about any hesitations or concerns before moving to the next topic. |
When to Revisit a Milestone
If your reps are consistently failing a milestone despite clearly attempting it, the note is usually the place to look — not the system. A few signals that a milestone needs updating:
- Multiple reps are failing the same milestone in similar ways — if the pattern is consistent, the note likely doesn't match how your team naturally approaches that moment in the conversation
- A rep attempts the milestone several times and can't pass — this often means the note is ambiguous enough that the AI and the rep are interpreting it differently
- Reps pass too easily or too early — a note that's too broad may be passing before the behavior you actually care about has happened
In most of these cases, the fix is a small edit to the note — either adding specificity, narrowing the behavior, or clarifying what does and doesn't count as passing. If you're not sure where the disconnect is, compare what your reps are actually saying to what the note describes. If they're doing something reasonable that the note doesn't clearly capture, that's your answer.
Tips
One behavior, one milestone. If the note requires more than one distinct action, consider splitting it.
Read it as a checklist. Before saving, ask: "If I watched a recording and used this note as my only criteria, would I know exactly when to check it off?" If the answer is no, keep editing.
If something doesn't count as passing, say so. For example: "Simply asking for permission to transition is not sufficient — the rep must begin explaining the topic." This is especially useful when reps tend to attempt a milestone in a way that looks like completion but isn't.
Related Articles
- How to set up a conversation context
- Understanding the Target Milestone
- Why is my rep's score lower than expected?
Last updated: February 2026