Welcome to Work Tip Wednesday, where every Wednesday I get ready and share one lesson I've learned about career, leadership, and success from working at some of the world's biggest brands.
One of my bosses used to say that business has peaks and valleys. Sooner or later you land in a valley, and you have to bring tough news to your boss. Learning to do that well is part of growing and taking real ownership, and it is one of the clearest signs of someone ready for more responsibility. Here are two approaches I lean on when the news is hard.
The Real Challenge
The instinct when something goes wrong is to wait. You want to gather every fact, find the fix, and walk in with the problem already solved so you look like you had it handled the whole time. That instinct usually makes things worse, because it costs your manager the one thing they need most, which is time to react.
A manager who hears about a slipping deadline three weeks out has options. The same manager who hears about it the day it slips has none. So the skill is learning to bring hard news in a way that gives them room to act, and to do it without pretending things are better than they are. The two approaches below are how you get there.
1. Tell Them Early and Be Direct
You do not need every answer before you speak up. Waiting until you have the complete picture often means waiting until it is too late to change the outcome, which defeats the entire point of the conversation.
Flag it as soon as you can see it coming, in plain language. Try something like: "I want to flag something now so we have time to respond. We're at risk of missing the deadline because of X. Here's what I know, and here's what I'm going to do next." That framing does a lot of work at once. It names the risk directly, it shows you are already moving on it, and it brings your manager in early enough that there are no surprises later.
Being direct is a kindness here, even though it rarely feels like one. A softened, hedged version of bad news forces your manager to work out how bad it actually is before they can help, and that delay is exactly what you cannot afford when something is going wrong. Say the real thing clearly, and say it early.
2. Bring a Recommendation, Even If You Need Their Input
Bringing your manager a problem with no proposed path puts all the weight back on them. Even when you genuinely need their decision, come with a recommendation and your reasoning attached.
Something like: "I see two options. I recommend we do A because it protects our biggest priority, but I'd like your perspective on the tradeoff." You are still inviting their input, and you are showing that you have already thought it through rather than handing them a fire to put out alone. Naming the second option and the tradeoff matters too, because it proves you looked at more than one path.
So much of rising in your career is anticipating the questions coming next. When you walk in having already asked yourself what the options are, which one protects the priority that matters most, and what the cost of each is, you turn a bad-news conversation into a decision conversation. That shift, from reporting a problem to steering through it, is what leadership actually looks like in a hard moment.
The Bottom Line
Delivering hard news well comes down to giving your manager three things: a clear picture of what is happening, a path forward, and enough time to react. Flag the risk early and in plain language, then bring a recommendation with the tradeoff named, even when you still need their call. Do that consistently, and bringing bad news becomes one of the moments that builds your manager's trust in you rather than denting it.
Jeanelle Teves is the Chief Commercial Officer at Bugaboo and founder of Work Lunch. She teaches communication, presence, and strategic leadership for ambitious professionals.
