How to Get (More) Comfortable Having Honest Conversations With Your Boss
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Having an open and honest dialogue with your manager can be intimidating, especially if you don’t have an especially warm relationship. (Think: the manager who only responds with “it was fine” when you ask about their weekend.)
But, getting into the habit of seeking out feedback and sharing your opinions on a regular basis (even if they conflict with what you know your boss wants to hear) can improve your relationship and enhance your performance. Demonstrating a commitment to growth and candor will help you to stand out as a lifelong learner who’s open to feedback (and score major points on your next performance review). You’ll also gain a more solid understanding of your manager’s expectations and hone in on your areas for improvement.
So, as awkward as these little chats might be, they’re well worth the effort.
Here’s how to get started:
If you don’t have a particularly comfortable relationship with your boss (and many of us don’t, sadly), you’ll want to begin laying the groundwork for open communication by initiating small but meaningful conversations.
Asking straightforward but probing questions like, “How do you think that presentation went?” or “Would you mind looking over these slides? I’d love another set of eyes” is a simple, safe way to get feedback-based communication flowing and build your comfort level over time so you can eventually talk about the bigger stuff.
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By initiating the dialogue first, you’ll make your manager feel more comfortable sharing her honest thoughts, too.
Start off a conversation by saying, “I felt that the meeting went well, but I think I could have done a better job of addressing the client’s concerns about our pricing. What do you think?”
This can go both ways, too. If you’d like your manager to adjust her behavior, you can say, “I felt good about that presentation, but I wonder if I should take the lead on discussions about timelines and deliverables in the next one. What do you think?”
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Set Up a Regular Check-in Time
I’ve found that I’m much more comfortable giving and receiving feedback when I know it’s coming. Ask your manager if she’d be open to carving out 15 minutes every week to sync up. These meetings don’t have to be mini-performance reviews, but rather opportunities to check in with each other.
Sometimes you might use your time to update your boss on the progress of a long-term project or ask clarifying questions about a new task. At other times, you might seek out specific feedback about a report you just turned in or your overall performance. The idea here is to get comfortable talking to each other on a regular basis—and talking honestly.
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Always Try to Dig Deeper
If your manager tells you that she wishes you were progressing more quickly, don’t take that at face value. Be curious—her idea of “progressing in a role” might be completely different than yours.
So, get on the same page by asking follow-up questions (hint: No question is a stupid question) such as “What would that look like?” or “When you say you’d like me to be more efficient, can you be more specific?” The more detailed you can get your manager to be, the more likely they’ll be more talkative and open going forward.
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Use Non-Confrontational Language
We all get frustrated with our bosses—especially when we feel that they aren’t understanding or appreciating our efforts. Rather than express this (and turn our manager off from speaking freely with us), repeat their concerns and try to resolve them in a professional, non-confrontational way.
For example, if you feel like your boss unfairly criticized your execution of an email campaign, you can say “I’m getting the impression that you’re concerned about the way I handled the ABC campaign. I’d be interested to hear your thoughts, and I’d like to walk you through my strategy and thought process, too.”
If your boss has given you vague or incomplete instructions, you can say something like, “My understanding is that you’d like me to have this to the client by Wednesday, is that accurate?”
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For yourself and your manager, that is. Having open, honest discussions can be challenging, and you both likely have a lot on your respective plates.
If your boss isn’t able to articulate feedback helpfully, or if you take his criticism personally, that’s OK. Try to put yourself in your manager’s shoes—is his boss stressing him out? Does he have a lot going on in his personal life? Is he simply uncomfortable delivering feedback? The key is to humanize your manager as much as possible and to remind yourself that any passive aggression or perceived apathy on his part likely has nothing to do with you.
Most importantly, be kind to yourself. These conversations aren’t easy, and they won’t always go well. But you’re brave for opening up an honest dialogue and will surely grow from these experiences—good and bad.
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Initiating a candid dialogue with your boss can be an intimidating endeavor (I can think of at least 57 things I’d rather do!). Remember that these open lines of communication won’t develop overnight. But, if you commit to consistently checking in, asking for feedback, and sharing your opinions, you’ll be well on your way to having genuine, productive chats with your manager.