How to Present a Problem to Your Boss

First, it was a need for coffee that caused you to walk by your boss’ door. Your next excuses included going to the copy machine, checking on a report’s status and once, you even made it into your boss’ office. Fortunately, a call came in, and you faded into the background.

You considered sending an email, but when you finally read all the drafts in your inbox, they looked too pitiful to send. What kind of subject line is “Important: Cause for Concern” anyway? Is this problem such a big deal after all? Will your boss think you’re helpless since you can’t handle this situation on your own?

When you feel at a loss, it’s okay to ask for help — especially from your boss. You won’t look like a bumbling idiot without an ounce of common sense. Everything you’ve read or learned says you’re the one who’s supposed to bring strategies and solutions to your boss, not the other way around.

If you’re nervous about confronting your boss about a problem, follow these five suggestions to present the issue with confidence.

1. Develop a Strategy for Approach

When it comes to approaching your boss, really think about how you will do it. Don’t pace outside your boss’ office or waste valuable working hours composing email drafts you won’t send. Instead, consider how your boss typically likes to be approached. For example, your boss may want face-to-face meetings, but they will expect you to be direct and results-focused.

For smaller matters, a simple email can quickly outline the basics of the situation. If you’re stressing out about having to write out all the details, keep the message concise and ask your boss for advice. In the subject line, mention the client or relevant file number. You can also request a meeting with this introductory email on the matter you want advice on.

For more significant matters, consider the weight of the issue. Are you pressed for time? Does the progression of the concern raise broader implications for the future of the company? Such weighty matters signal a need for an in-person conversation. Don’t interrupt an important meeting, but call or give a quick knock at your boss’ door.

2. Get Your Facts Straight

Don’t walk into your boss’ office or shoot off a quick email alerting your boss to a “fire” and expect them to put it out. You’re going to need details for the questions that will be undoubtedly brought up. What’s going on? How did this start, and what’s been done about it?

When your boss asks what’s been done so far, it doesn’t mean you’re being accused of not solving the issue yourself. Your boss wants to know what’s been attempted and what hasn’t worked so you can come up with a valid strategy quickly, and the answer to this question saves everyone time.

Forget bringing solutions to the table. Bring the relevant details and facts that arm your boss to understand what’s going on and decide the best course of action. Don’t forget to bring along any critical documentation to back up your statements.

3. Weigh the Potential Results

A situation can go from bad to worse when the pros and cons aren’t weighed. There is no single result to any given situation, and those many sides may seem overwhelming when you’ve stared the case in the face for hours. You need the outside perspective of your boss.

Before you present the situation, weigh the potential results again. Remove the stress and fear from your analysis, and look at the best and worst-case scenarios. What’s the likely fallout? What about the middle ground?

Consider what about the situation makes it necessary for your boss to take a look. Has the fallout already started? It’s best to go to your boss before this happens, but be prepared to clearly communicate the stakes, along with the cause and effects.

4. Focus on Strategy, Not Self-Deprecation

The guilt of not having a solution might weigh on your professional conscious, but it doesn’t mean you should spend valuable time in your boss’ office apologizing. Focus on strategy, not self-deprecation.

Depending on the severity of the issue, you might feel guilty, embarrassed, lost and fearful. That’s natural, but remember, it’s your boss’ job to step in with their experience and guide you. So, express gratitude over guilt.

When you talk to your boss, don’t apologize for wasting their time or bothering them — it will make you appear indecisive or helpless. Some matters are outside your control. Try saying, “I’d be grateful if you could help me develop a strategy to best address this client’s concern.”

5. Create a Cheat Sheet With Your Boss’ Tips

When talking to your boss, listen actively and take notes. Use body language to show you’re taking in your boss’ advice, and make eye contact to demonstrate an open mind ready to get to work. You don’t want to present your boss with the same concern over and over again. If you get caught in that pattern, you’ll establish a relationship with your boss where they think you expect them to “save” you.

Your boss will step in and advise you, but it’s your responsibility to apply that advice using your unique skill set and experience. It’s your responsibility to learn from the situation to benefit and grow your career. Create a cheat sheet with your boss’ tips by using a spreadsheet or document to track client concerns, areas where you felt at a loss, advice given and strategies applied with the results. When the issue comes up again, you can check your cheat sheet, feel reassured and proactively respond.

Bringing It All Together Before Your Meeting

It’s normal to feel unnerved when approaching your boss for advice, especially if you’ve been taught to bring solutions to the table instead of concerns. However, you can’t let the issue grow into a potential wildfire — take the matter to your boss now.

Think of your strategy for the approach. Gather the facts, relevant documents and outline the stakes. During the meeting, focus on strategy rather than apologizing or feeling guilty. Don’t waste your time or your boss’ time. Take notes while listening and use these in the future to feel more empowered about developing strategies for situations that have you feeling less than confident.

You’ve got this. Now, go talk to your boss.

Open lines of communication are essential between a boss and employee, and asking for help is an opportunity for learning and growth. Comment the results of your conversation below and subscribe to Punched Clocks for more helpful tips to grow your career.


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Sarah Landrum is the founder of Punched Clocks.

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