How to tell your boss you might miss a deadline

Short answer: say “We're at risk of missing Friday. I'll know by Wednesday and confirm then.”

DON'T SAY
“We might miss the deadline, not sure yet.”
SAY THIS
“We're at risk of missing Friday. I'll know by Wednesday and confirm then.”
An early, specific warning earns trust. A late surprise loses it.

When to use it

Use it as soon as you see a real chance of slipping. Name the deadline, say when you'll know for sure, and commit to confirming then. An early warning gives your manager time to adjust plans; a late one leaves them scrambling.

Example

You: “Heads-up: we're at risk of missing Friday. I'll know by Wednesday and confirm then.”

Manager: “Thanks for flagging. What would help?”

You: “If design can review Tuesday, we can still make it.”

In an email or Slack message

In Slack or email: “Flagging early: Friday's deadline is at risk because the data import is slow. I'll confirm by Wednesday. If it slips, the new date would be Tuesday.”

Quick drill

When you need a decision or input from someone busy.

Which sounds more confident?

Practice 10 more →

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