Boss: If the client asks when this work will be delivered, what should I tell them?
Me: Today’s the first, so tell them the end of the month. We might be ready a week sooner, but it always pays to have some extra time in case of unforeseen issues, scope changes, etc.
Boss: Brilliant, I’ll let them know.
1 week later, 3 weeks before the proposed delivery date.
Boss: How are things coming along? Are we on track for completion next week?
Me: Next week? Currently, we’re 3 weeks away from the due date we discussed last week. Has something changed that I should be aware of?
Boss: What do you mean 3 weeks away? I told the client this would be ready next week. You’ve put me in a really awkward position now. I’ll have to phone them and tell them the bad news.
Myself and the dev team worked out a plan involving significant overtime, and eventually deliver 2.5 weeks into the project (that’s a whole 1.5 weeks earlier than scheduled). Boss not happy, client not happy, and to this day, our boss still believes we let him down.