Life & Work Skills

How Successful Women Approach Their Boss With a Problem


Maybe you’re trying to smooth things over with an unhappy client. Perhaps you’re in the middle of a conflict with a co-worker. Or maybe you’re feeling stuck on a certain part of a project.

Regardless of your circumstances, the point remains the same: You’re dealing with an issue, and you’re not sure when and how you should loop in your boss.

On the one hand, you’d rather make him or her aware of the issue right off the bat — so you don’t run the risk of things going unresolved for too long. But, on the other hand, you don’t want to look like you can’t take initiative and handle problems for yourself.

So, how can you know when it’s time to run to your boss? And, perhaps more importantly, how can you make that conversation as effective and professional as possible? Here’s what you need to know.


Knowing When to Tell Your Boss

When it comes to knowing whether or not it’s time to bring your boss in on your issue, there’s one important question you should start out with: Have you already tried to solve the problem yourself?

If not, you should plan to explore any potential solutions on your own first. In most cases, your boss’s role should be to provide confirmation on a way forward or advice for any improvements — rather than handle all of the intricate details of a problem. But you’ll have a tough time explaining the issue and offering any recommendations if you haven’t already tried to tackle the roadblock yourself.

Maybe you’ll be able to solve the problem on your own through your attempts, and maybe you won’t. However, at least the conversation with your boss will be much more productive after you’ve completely navigated the problem on your own.

If you do get things resolved? You’ll then want to move on to this question: Is this something that your boss should be aware of anyway?

For example, maybe you keep running into the same roadblock, meaning your manager might need to tweak some work processes. Or perhaps your boss should be updated on the conflict you faced with a client, so that he or she has a better understanding of the relationship moving forward.

Your supervisor doesn’t need to be brought into the circle on every little work-related issue. However, if you think this is something that he or she needs to hear — and it’s best coming from you — make sure you tell him or her about the problem, even if it’s already been addressed.


How to Bring a Problem to Your Boss

You’ve decided that you need to let your boss know about the issue you’re dealing with. But how do you do so in a way that’s effective and efficient — and doesn’t make you look like a tattletale? Follow these steps.


1. Gather All Necessary Information

In order to help you identify a way forward, your boss is going to need all of the necessary background information. So make sure you take some time to pull all of that together before you schedule a sit down with your manager.

Who’s involved in this problem? What sorts of exchanges or mistakes led you to this point? Put simply, what nuts and bolts information should your boss know in order to get a solid grasp on what’s happening?

The more background you can give your boss, the more he or she will be able to help you craft a relevant and helpful solution.


2. Come Up With a Potential Solution

If there’s one thing that’s sure to irritate your boss, it’s constantly approaching him or her with problems — without ever coming up with any prospective answers.

You’re in your role not just to handle your daily tasks and responsibilities, but also to problem solve as best as you can. That means that — before knocking on your boss’s office door — you should come up with a potential answer to the problem you’re currently facing.

That way, you can present your boss not only with all of the necessary information about your issue, but also with your proposed next steps. With that starting point in place, you and your manager can have a much more productive conversation about the best way to move forward.


3. Set a Meeting

Chances are, the issue you’re dealing with isn’t a small one — otherwise you wouldn’t even bother telling your boss. With that in mind, this isn’t a discussion you’ll want to have in passing. Instead, you’ll want to get some time on your manager’s calendar when the two of you can sit down with undivided attention and talk things through.

Send your boss a short and sweet email that looks something like this:

Hi [Boss’s Name],

I’m running into an issue with [problem] and was hoping we could set up a time to talk this through. Do you have any time this week when we could sit down for 20 minutes?

[Your Name]

That way, you and your boss can have a common understanding of what exactly needs to be talked about — before you ever actually start the conversation.


4. Do Better Next Time

Of course, you’ll want to implement whatever solution you and your boss land on. But, even more important than that, you’ll want to remember that answer moving forward.

If and when you find yourself in a similar situation, you’ll be able to handle things for yourself (while still providing any necessary updates!) without needing to rely on explicit direction from your boss.

Knowing if and when you should loop your boss in on a problem can be tricky. You don’t want to jump the gun. But at the same time, you don’t want to seem like you’re sweeping things under the rug. Follow these tips, and you’re far more likely to choose the best route.


How do you know when it’s time to tell your boss about a problem?