I advise Gen Z professionals. I want to make sure I’m giving them the best possible advice. So, I asked 25 senior leaders what they wish they had known earlier. I am distilling the information from those interviews here.

The second in this series: “Learn how to bring a problem to your boss.”

It sounds simple. But behind that statement is a complex skill set—one that early-career employees often fumble, and seasoned professionals learned the hard way. Knowing how and when to bring up a problem can change the way your boss sees you, and even your future trajectory.

Here’s what that advice really means:

Problems are not like fine wine—they don’t get better with age.

When something starts to go wrong at work, many early-career folks hesitate to speak up. Sometimes it’s fear—”I’ll look incompetent.” Sometimes it’s pride—”I should be able to fix this myself.” Sometimes it’s just not wanting to be the bearer of bad news.

I was lucky.  One of my first bosses said: “Everyone screws up. Let me know right away; waiting never helps.”

The longer you delay, the more likely the issue gets bigger, more expensive, and harder to fix. And if you hide, it looks like you either didn’t notice or didn’t care.

The instinct to stay silent has a name: it’s called the “mum effect.” It refers to our tendency to avoid sharing bad news with people in power. While it may feel protective in the short run, it undermines trust.

So, the first rule: Don’t wait. Speak up early. Don’t escalate everything, but if something is going off course, your boss needs to hear about it sooner than later.

Don’t show up empty-handed.

Just because you flag something early doesn’t mean you dump it at your manager’s feet and back away.

Unless it’s an emergency, don’t just identify a problem. Bring your proposed next steps too. You don’t have to have the answer. But come with at least one possible move. It could be a full solution, or just a suggestion for the next few steps.

Think of it like this: bringing just the issue turns your boss into the lone problem-solver. Bringing your thinking makes you collaborators. You’re showing initiative, judgment, and a desire to help. According to recent research, managers respond more positively to team members who not only raise concerns, but propose thoughtful ways forward.

My interviewee offered a framework:
Describe the issue; accept responsibility; identify next steps; ask for input and help.

Don’t be afraid to enlist your boss in the solution.

Your boss has access to people, systems, or information that you don’t. Part of their job is to help remove roadblocks. So, after you bring the issue and your initial thoughts, ask for guidance and support for the fix.

Maybe you need a cross-functional partner to weigh in. Maybe you need to elevate a request outside your chain of command. Or maybe you just need a sanity check before you move forward. When you treat your manager like a resource instead of your judge, you build a different kind of relationship. One rooted in trust and shared purpose.

Doing this well will actually make your manager more confident—not less. That’s how you get known as someone who brings value—not just noise.

The Bottom Line: “Don’t panic. Don’t wait. Figure out next steps. Then go get help.”