How To Talk To Your Boss About A Problem

Addressing problems with your boss can often feel daunting, stirring up hesitations and uncertainties–not to mention horrific anxiety (for some of us). Effective communication in these moments can be a serious life saver, fostering a productive work environment and driving positive outcomes. It just takes practice. Whether it’s during a performance review or in the midst of a regular day, framing the problem consciously and remembering to focus on solutions can pave the way for constructive dialogue and meaningful resolutions.

I recall a pivotal moment in my career when I found myself navigating a similar challenge. At a previous job, I encountered a pressing issue within a longstanding project. Rather than approaching my boss with apprehension or frustration, I applied a structured approach that prioritized collaboration and solution-oriented thinking. I remember planning my approach and sharing,

“I understand we’ve been doing this project for years, and at the same time I see these 3 challenges. Here are possible solutions to the challenges; what are your thoughts?”

By framing the problem as an opportunity for improvement and presenting concrete solutions, I shifted the focus towards the process rather than personal differences.

It taught me the transformative power of effective communication and conscious problem-solving in the workplace.

From my personal career and my work as a business and career coach for women of color, I have plenty of actionable strategies and insights that can empower you to navigate these conversations with confidence and clarity. And remember, effective communication is not just about voicing concerns—it’s about fostering understanding, driving progress, and cultivating a culture of growth and collaboration that in turn rewards you in your career advancement.

 

Practicing Conscious Communication Strategies

When thinking of how to talk to your boss about a problem, get started on the right foot. There are subtle yet powerful ways you can improve your communication and it starts with nonverbal cues that convey understanding and attentiveness.

Here’s how you can do it:

Keep Eye Contact and Open Body Language

Maintaining eye contact and open body language shows your boss that you’re started off engaged and ready to problem solve. Pay attention and make sure you aren’t giving signals of being closed off or upset (think crossed arms, angling away, rolling your eyes, etc).

Practice Active Listening Techniques

Ever heard the saying “listen to understand, not just to respond”? It’s all about using active listening techniques like paraphrasing and asking clarifying questions. It lets your boss know that you’re really tuning in and trying to get where they’re coming from.

Be Clear and Specific

When you’re sharing your thoughts or concerns, keep it clear and to the point. Don’t ramble or beat around the bush. Use examples to paint a picture and suggest actionable steps. It helps everyone stay on the same page and on track.

By adding these simple tweaks to your communication style when communicating with your boss, you’ll create an atmosphere of respect and understanding with your boss that goes a long way toward getting the problem solved.

 

Navigating Concerns During a Performance Review

A natural place to discuss longer-term problems or reflections about work in general is during your performance review. While I’m a firm advocate of addressing issues regularly (we’ll get to that soon), there are some scenarios in which you might want to bring up a problem during your review. And sometimes, your boss will unfortunately use this time to bring up concerns as well.

Tips for Bringing Up A Problem in a Performance Review

1. Choose the right moment. It’s a good idea to bring up the concern you have within the context of the discussion, if at all possible. What I mean is that it should naturally fit into the conversation depending on what is being discussed at the moment. If you don’t get that chance–don’t worry! You can bring it up to your boss toward the end of your review by saying something like, “It’s been so great to reflect on my year in review, and I was wondering if now would be a good time to bring up a concern I have.”
2. When you’re ready to bring it up, frame the problem in a constructive manner–like I shared in the intro to this blog. Use specific examples to illustrate the impact it’s having on your work or professional development. Stress that you are seeking a solution, and if you have a few in mind, be sure to show you’ve done the processing by mentioning them.
3. Show your boss you’re a team player by expressing your willingness to work together to find a resolution and improve the problem. It’s all about that collaborative spirit!

Tips for Responding to an Issue Brought Up by Your Boss:

1. Focus on remaining present rather than immediately planning your response. Listen attentively to your boss’s feedback without jumping in or getting defensive. Just like knowing when to bring up a problem, knowing when to respond (and how to respond calmly) is crucial.
2. Take notes during the review to make sure you’re catching everything your boss is saying. It shows you’re serious about understanding and improving, and it helps with the anxiety that might come with worrying you’ll forget what to say or respond to.
3. Don’t be afraid to ask for clarification. Use phrases like, “I’m hearing you say [abc], and that you need [xyz]. Is that correct?” It shows you’re engaged, not jumping to conclusions, and ready to take action.
4. Ask when you can check back in on the concern and give a progress update. It’s easy to want to avoid future conversations about something when we feel uncomfortable, but setting a check in date will make sure you don’t fall into avoidance.

 

Initiating Conversations Outside of Performance Reviews

Performance reviews may be a good time to tackle some overarching themes that have come up during the work year but, in reality, we often have issues that need resolving and discussing before those annual check-ins with our boss. Believe me, it’s not good to let concerns fester; it allows small problems to blow up into huge problems.

Here’s how you can confidently talk to your boss about a problem:

1. It’s all about consent. Before diving into the problem impulsively, ask your boss if it’s a good time to give feedback or discuss a concern. You can say: “Hey, I’ve been trying to work through an issue I’m having and would love to run it by you. Do you have time now or later this week?” If now isn’t ideal, suggest planning a time that works for both of you. It shows respect for their schedule, as well as their current mindset, and sets the stage for a productive conversation.
2. Timing and location matter. Be sure to choose a time and place that’s private and free from distractions. You want your boss’s undivided attention for this chat, and no body wants to overhear a conversation about a problem that might involve other team members.
3. As I’ve mentioned multiple times: frame the conversation in a constructive manner. This shouldn’t just be a vent session or a place for blame. Focus on specific issues and potential solutions rather than dwelling on the problem. This approach keeps things moving forward and refocuses the conversation on understanding and progress, rather than the bits that could be taken personally.
4. Last but not least, show some gratitude. Express appreciation for your boss’s time and willingness to address the concern. It goes a long way in fostering a positive and collaborative atmosphere.

 

Leveraging Weekly Meetings for Ongoing Communication

Weekly check-ins can be hugely beneficial when it comes to raising and preventing concerns in the workplace. These regular check-ins serve as invaluable opportunities to keep each other informed and address any challenges before they escalate.

During these meetings, make it a priority to provide updates on your progress and openly discuss any obstacles you’re encountering. By addressing issues early on, you demonstrate your proactive approach to problem-solving and your commitment to achieving success in your role long term. You also save yourself the hurt of finding out your boss had concerns during your annual review (note: a good leader should not put you through that, but it happens).

Don’t hesitate to raise concerns or seek clarification on tasks or expectations. Your boss will appreciate your proactive attitude and willingness to engage in open dialogue. That being said, the same rules as before apply; maintaining a positive and professional demeanor during these discussions is key. Even when discussing challenges, approach the conversation with optimism and a solution-oriented mindset.

By leveraging your weekly meetings in this way, you not only ensure that everyone is on the same page but also foster a collaborative and supportive work environment. It’s all about staying proactive, positive, and professional in your communication with your boss.

 

Conclusion:

Through consistent practice, you not only refine your leadership skills but also cultivate confidence in engaging in conscious conversations with your boss. Embracing feedback and nurturing a solution-oriented mindset contribute to your personal and professional growth, guiding your career journey in harmony with your core values.

If you would like further support in your career, business, or leadership, my team and I would love to support you in creating a sustainable life through our coaching services! You can schedule a 30-minute legacy business or career review call with me to see if it’s a good fit to work together, and you’ll receive 3 action-items from me.