Short answer: Deadlines stick when the person doing the work agrees to them, the date and time are specific, and the deadline is visible to everyone involved.
Why deadlines slip
They were imposed, not agreed.
They were vague, like “end of week”.
Priorities changed but the date didn’t.
Nobody noticed until it was late.
Five rules for deadlines that hold
Ask, don’t tell: “Can you do this by Thursday 15:00?”
Use a date and time, not a word like “soon”.
Leave a buffer for anything client-facing.
Move the date openly when priorities change.
Make overdue work visible without anyone having to ask.
What to do when a deadline is missed
Talk about the specific task, not the person. Ask what got in the way and fix that, whether it’s workload, unclear instructions or a missing part.
Frequently asked questions
Should every task have a deadline?
Yes. A task without a deadline is a wish. Even “by end of month” is better than nothing.
Try it with your team
Agree a deadline on every task you send this week. Please Do It is free for 30 days, with no credit card required.