This is definitely a multi-stage process. It begins the very first day of working together, when you establish the ground rules of engagement. How often do you review? How does your boss like to be kept up-to-date? If managed pro-actively bad news hardly ever comes as a surprise, for example when expectations are set correctly. It is also important to flag concerns at the earliest opportunity.
Now - however hard you try, now and then it will all go wrong. Un-foreseen circumstances or, heaven forbid, a mistake you or your team made, will lead you to the point where you have to break bad news unexpectedly.
Before you communicate - think! Get all the facts right and avoid over-reacting or un-necessary dramatisation.
If you made a mistake - own up. No boss worth a penny will hold a fully-fledged mistake against you (meaning you tried to do the right thing but it did not work out). Of course, you cannot make the same mistake twice without consequences.
Come with solutions - not just problems. Most bosses hate it when their team members only come with problems and give no indication that they have put effort into fixing the problem themselves.
Don't dress up and/or confuse your message. - it's the same as for giving feedback. Don't mix good and bad (the infamous s**t sandwich), because the good won't be remembered anyhow in that context.
Most importantly - don't delay. Problems tend by their nature to get worse. The sooner all the facts are known and everybody is on the same page, a path to resolution can be defined and executed.
Most importantly - don't delay. Problems tend by their nature to get worse. The sooner all the facts are known and everybody is on the same page, a path to resolution can be defined and executed.
And - everybody who is a boss already (or will be in the future), should also think about this. Firstly bosses usually have bosses themselves, but secondly.... remember how it felt!
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