You know you have a good boss when you can take a project you own that isn’t going as well as it should, bring its status to their attention, and get this kind of response.
“Things aren’t going well. I’ve got a late-breaking blocking issue. Even if/when that’s resolved, the results of this work are likely to fall short of our hopes and expectations. I’m sure I can knock down this specific barrier given a little more time, but needed to catch you up where things stand.”
* I understand the challenges you’re facing.
* Some projects generate big returns on investment; others take time and are less fruitful.
* You’ve learned a lot during this process so it was worthwhile regardless.
* Take your time fixing the late-breaking issue you uncovered; time pressure only makes it harder to solve problems, so just focus on solving it, I’ll handle others’ expectations.
* Don’t forget you can still look forward to the next [more fun] project when this one is done.
I also think it says a lot about your boss if they engender the kind of mutual trust and respect that make bringing up bad news a naturally met obligation. Everybody wins.
Struggling with something at work? Tell your boss.
(If you don’t, you’re harming an important relationship and missing an opportunity to strengthen it.)
And it will probably make things better.
(If it doesn’t, maybe you should find a better boss.)