Mark Cuban’s weekly format:
The format is easy
I want all bad news first
Challenges and issues you need my help with second
For a strong relationship with high levels of trust and connection, this sounds great, especially when both people are very experienced and short on time. If more time is available, the relationship is newer or either person is newer in that job, I’d add a “good news” item up front to build connection.
Bad news is critical for actually solving the problem. “Thinking positive” or whatever else we do to try to please people hides what’s really going on and is thus counter-productive.
“You need my help with” is highly focused both on action and on what the superior can actually do to help, plus emphasizes desire to help.