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Advice / Succeeding at Work / Work Relationships

Talk it Out: 3 Templates for Having Tricky Conversations With Your Boss

Hard conversations are pretty much what they sound like. But, sometimes having a difficult discussion’s the difference between being unhappy and getting what you want. So while initiating one in the workplace isn’t fun, you could stand to gain respect, a promotion, or extra income—all good things. Emerging from the conversation unscathed comes down to three smart moves.

First, never go into a difficult conversation unprepared. Think long and hard about what, exactly, you want to accomplish and how you want to use your energy. As my mother used to say, “Pick your battles.” Use your resources to address significant misunderstandings or problems professionally and thoroughly, letting the small stuff go.

Second, bring evidence. Does your boss think you messed up the department budget? Login to your budget system to show him where you stand as you talk through it, instead of just saying, “It’s fine! I did everything right.” Is your employee making the same design mistake over and over? Bring copies of the drafts and your notes from previous meetings.

Third, find your sense of calm, and keep your cool. This can be tough if you feel like you’ve been wronged or you’re really frustrated. But barging into someone’s office full of rage only exacerbates the problem. Consider the other person’s point of view. It’s unlikely she doesn’t have a single valid point. If you can find some common ground, you’re more likely to be taken seriously. Practice your talking points so you’re calm and collected when it’s time for the real conversation.

What does this look like? Read on for some templates you can use as a general guide in these tough talks.

1. You’ve Received Unfair Negative Feedback

Criticism always stings a bit, but unfair criticism flat out burns. Whether this happens during a formal evaluation or a less-formal chat with your supervisor, if it’s significant enough to impact your reputation or compensation, you’ve got to be your own best advocate. 

It’s best to start by acknowledging that at least some of the feedback is helpful; when you address it, you’re demonstrating that you understand how to work on the issue. Once you’ve done that, you can segue into the feedback that needs attention. Bring supporting documentation (if you have it) and avoid getting defensive. Wrap up with a suggestion for avoiding such a misunderstanding in the future. Here’s how this conversation looks:

I’ve thought really hard about the feedback you shared with me regarding [something accurate]. I see where you’re coming from. I wanted to let you know that I [insert what you’re doing to address the problem here].

I also want to talk about [the feedback that you believe was unfair]. I was caught a bit off guard when you expressed so much concern. But, it occurred to me that [this particular thing might have contributed to the misunderstanding]. Here is [evidence supporting your argument that you are, in fact, doing your job well].

I thought it might be helpful for us to communicate a bit more regularly so that you are more aware of my progress on various projects. [Make a suggestion of how you can avoid such a misunderstanding in the future. A regular email? A short, weekly meeting?]

2. Your Boss Is Impeding Your Progress

Whether he’s a micromanager, can’t make a decision, or has a tendency to change his mind halfway through a project, your boss’s mismanagement is a problem for you. This situation obviously needs to be handled with kid gloves; accusations and demands aren’t productive, but neither is simply wishing for his management style to change.

Set up a meeting, practice addressing the topic in a composed manner, and then go into the appointment with confidence, armed with evidence. Begin the conversation graciously and acknowledge your desire to do good work. Then, in a respectful way, be honest about the problem and how it’s affecting your performance. It might also be appropriate to ask if there’s something that you’re missing.

For example, with a micromanager, you might ask if there’s a particular concern driving the frequent check-ins. Here’s how it might go:

Mike, thanks for making time to sit down with me. You know how important the product launch is, and therefore, how important it is to me. I’m really struggling to move forward, though, and part of the problem is [insert the issue, in a professional and non-attacking way]. I’d really like us to find a way for me to be as productive as possible. I have a couple of ideas and would love to hear your thoughts too.

Could we talk about striking a balance that will keep you [whatever your boss needs to stay informed, to maintain some flexibility with clients, and so on], but be a bit easier for me to manage? [Insert your suggestion here and listen for your boss’ feedback. This will allow you to you wrap up with a concrete plan for improvement that addresses both of your needs.]

3. You’re Leaving Even Though Your Boss Is Awesome

Let’s be real, giving two weeks notice when you hate your job isn’t usually that difficult. But if genuinely like your boss and you have a good rapport, telling her that you’re moving on can actually be really tough. What if she takes it personally? What if it hurts your relationship? Of course, if your manager is so good that she set you up to move onward and upward, it’s unlikely she’s going to be shocked or upset when that happens. Still, it’s important that you break the news in a way that solidifies and doesn’t harm your relationship.

First, arrange to deliver the news in-person, before you tell another soul. This person poured time and energy into you. No matter how tempting it might be to avoid looking her in the eye when you tell her you’re leaving, she deserves to hear it from you in a gracious and professional way.

And timing matters. Break the news at a relatively calm time of day so you both have some time to process. It’s a nice touch if you can get away from the office for lunch or happy hour, but if time doesn’t permit or you’re truly concerned he won’t take the news well, then ask for a 20 or 30 minute meeting. And of course, explain that you plan to be as proactive as possible in making the transition a smooth one. 

Suzanne, thanks for carving out some time to meet with me on short notice. [Insert your feedback about how helpful your boss has been as a mentor, and how grateful you are here.]

You’ve been so incredible, in fact, that I've been recruited by another company. I accepted an offer as District Manger of Thetford's Unicorn Emporium yesterday. Your influence made this opportunity possible for me, and I'm grateful beyond measure.

I’ve already been thinking about my transition, and I obviously want to make it as painless as possible. [Insert your input about how you will wrap up projects and generally be helpful. Maybe you’ve written an updated job description, put a binder together for the next person, provided extended notice, and more. Ask your boss what he or she needs from you and develop a plan for your transition.]

The situations above don’t cover every possible difficult conversation, and they don’t take it into account the many different things the other party might respond with, but hopefully you noticed some common threads. Regardless of the specifics of your situation, it’s essential to plan ahead, have a calm and prepared approach, demonstrate a professional demeanor, and put forth a solution-focused mindset. Tough conversations will still be tough, but with the right navigation, they can also be productive.

Photo of employee talking to her boss courtesy of Westend61/Getty Images.