The idea that bad news doesn’t age well is likely obvious to everyone — if you’re a parent, you want your kids to share the failed test ASAP, and not a month later.

“Bad news isn’t wine. It does not enhance with age” – Colin Powell

But in a professional environment, it’s sometimes a tough balancing act between not rushing to your boss to bring the problem with any analysis/recommendations to them (see the HBR article Who’s got the Monkey?) and over-engineering the analysis and recommendations.

As a leader, establish the culture that bad news should be shared (you won’t “shoot the messenger”, and teach your employees to analyze and bring recommendations). People early in their leadership journey often jump in too quickly to try to solve problems that should be solved at a lower level on the org chart, so they can focus on more strategic activities.

On the proactive side of this balancing act, don’t surprise your boss with a big presentation that they haven’t had the opportunity to give you preliminary feedback on. That doesn’t mean sending them a long presentation before a meeting and asking them to read the entire thing. Instead, that means investing energy in finding ways to efficiently validate your assumptions, such as asking a few questions during a 1-on-1 conversation with your boss to confirm the direction you’re moving with the presentation or sharing a key slide or two and asking for preliminary feedback, such as a slide with key milestones or overall conceptual vision.