Handle a Milestone Slip

Milestones don't always hit their target dates. When that happens, address it quickly: understand what happened, adjust the plan, and get back on track.

Recognizing a Slip

A milestone has slipped when:

The target date has passed but status is still In Progress (not Completed)
The owner marks the milestone as At Risk
You notice no progress updates for 2+ weeks

Your Conversation (If You're the Manager)

Step 1: Open the milestone in Mentora

Step 2: Leave a comment asking for context:

"Hi @Sarah, I notice this milestone was due on March 15 and we're now in late March. Can you give me a quick update on what's happening? I'm here to help."

Step 3: Wait for a response (24 hours)

Step 4: If they don't respond, follow up in Slack or email to schedule a quick 15-minute call

The Conversation (If You're the Employee)

If your milestone is slipping:

Step 1: Be honest early — Don't wait until after the due date

Step 2: Leave a comment explaining:

"I'm realizing this timeline was too ambitious. Production issues took 2 weeks, and now I'm about 4 weeks behind. I think we need to extend the deadline to April 15. Thoughts?"

Step 3: Propose a solution:

Extend the deadline
Reduce scope
Get additional help
Break it into smaller pieces

Step 4: Follow up with your manager directly (message or call) to discuss

Adjust the Plan

Once you've talked, take action in Mentora:

Option 1: Extend the Deadline

Click the milestone
Change the Target Date to a new, realistic date
Update the status to In Progress
Leave a comment explaining the new date

"Adjusting the deadline to April 30 based on the production delays we hit. We're still on track with this new timeline."

Option 2: Reduce Scope

Delete tasks that aren't critical
Simplify the milestone description
Adjust the target date accordingly
Leave a comment explaining what changed

"Simplifying scope. Removing the advanced features and focusing on core functionality. This gets us back on track by March 30."

Option 3: Get Help

Assign additional people to tasks
Secure mentorship or support
Keep the original deadline if possible
Comment in Mentora about the support plan

"Pairing with @James on the architecture work. This should unblock us and get us back on schedule."

Follow-Up

One week later:

Check the milestone status again
Has progress resumed?
Is the new deadline realistic?
Leave an encouraging comment

"Great to see momentum again. Let's check in next week to make sure we stay on track."

Preventing Future Slips

After handling the slip, think about prevention:

Questions to ask:

Was the timeline unrealistic? (If so, use better estimates next time)
Were there blockers we didn't anticipate? (Plan for them next time)
Did we have enough resources? (Allocate more next time)
Was there unclear acceptance criteria? (Define better next time)

Tips

Address slips early — Don't wait until 2 weeks after the due date
Be supportive, not blaming — "What got in the way?" beats "You fell behind"
Adjust, don't give up — A slip is usually fixable with a new timeline or approach
Learn from slips — Use them to improve future planning
Celebrate recovery — When you hit the new milestone, acknowledge the effort

Troubleshooting

The person won't admit the milestone is slipping

Sometimes people are embarrassed. Start with "I noticed the date has passed. Can we talk about what happened?" Make it a problem-solving conversation, not a blame conversation.

This is the second time the same milestone has slipped

That's a sign the timeline was overly optimistic or there are bigger blockers. Have a deeper conversation: "This is the second time we've extended this. What would make it realistic?"

The milestone is slipping due to priorities changing

That's okay. Leave a comment: "I know we deprioritized this because of the urgent customer work. Let's find a new slot in the schedule."