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Dreading that difficult conversation with your boss?

Whether it’s asking for a raise, requesting a deadline extension or confronting your boss about a misunderstanding, most of us will have difficult conversations with our managers at some point in our career. But Alison Green is here to help you navigate the stormy seas of office politics! With ten years’ experience as a workplace advice columnist Alison knows exactly what to say, and in her book Ask a Manager she takes on the tough discussions you may need to have at work. In this extract Alison gives sage and practical advice on how to have tricky conversations with your boss.


Conversations with Your Boss

Conversations with your boss can be stressful even when they’re relatively routine. The uneven power dynamic can mess with your head and make you approach conversations far more delicately than you need to, or even convince you not to have the conversation at all.

But for the most part, you’ll get the best results if you approach your boss as if she’s a normal human, not royalty or a terrible ogre. That’s sometimes easier said than done, though, so here are some general operating instructions to follow:

  • Don’t overthink it. Overthinking will cause you a lot more stress and anxiety than is probably warranted and it’s likely to make you less effective, too. You’ll wind up dancing around the issue, or using formal wording that sounds odd and unclear. Just be direct and straightforward.
  • Keep your ego at bay. The more you can approach the conversation from an emotionally detached place, the more effective you’re likely to be. This doesn’t mean that you can’t have emotions; it just means that you can’t let them drive the conversation. For example, if your boss gives you some critical feedback and you get defensive or upset, you’re less likely to truly process the guidance she’s giving you. Instead, calmly ask for more information and talk through your options. That should lead you away from defensive responses like “No one told me not to do it that way!” and toward more constructive responses like “Would it be better to do X?” or “I think X is happening because of Y. Let me try Z and see if that solves it.”
  • Think like a consultant. Employees’ relationships with their managers sometimes resemble a parent/child dynamic more than a peer-to-peer relationship—and that’s not a good thing. To avoid that, try thinking of yourself as a consultant and your boss as your client. Consultants are able to sidestep that parent-child dynamic because they’re independently offering their services, and while they want to make their clients happy, if they ultimately can’t see eye to eye on something important, they can part ways without a ton of drama. And really, that’s true for employees, too—employees just tend to lose sight of it.
  • When you bring concerns to your boss, frame them from the perspective of “What makes the most sense for the organization and why?” rather than “I want X.” The former is the perspective that your boss will need to take, so it’s better for both of you if the conversation starts there. However . . .
  • If something really just comes down to “I want X,” it’s okay to be straightforward about that. If you’re in pretty good standing with your boss and you have some credibility built up (in part because you don’t approach her with “I want X”-type requests on a daily basis), then sometimes it’s okay to say, “I know that this doesn’t sound like a big deal, but it’s driving me crazy. Could we try doing X instead?” or “X is really important to me. Can we talk about whether there’s any way to make that happen?” Good bosses want to make good employees happy, so knowing what would make you happier is actually great information for them to have.
  • Make it clear that you understand that your boss may have different information or a different perspective than you. In many cases, your boss really will have more information than you do, and you should approach sensitive conversations with that in mind. For example, if you’re concerned about why your boss moved a high-profile project from you to your coworker, start by saying, “I realize that there might be reasons for this that I’m not privy to” as opposed to just launching into “I’m really upset about losing this project.” You’ll have more credibility, and you won’t put your boss on the defensive.
  • In some cases you’ll get better results by asking for a short-term experiment rather than a permanent change. If your boss is resistant to what you’re asking for, suggesting a short-term trial rather than a permanent change can be a good way to lower the stakes. For example, if you want to work from home on Thursdays and your boss isn’t convinced it makes sense, she might agree more easily if you don’t ask her to commit to it forever. Instead, say, “Could we try it for the next three Thursdays and see how it goes? If it causes problems, of course I wouldn’t continue. But it could be a good way to test it out.” This approach works for all kinds of requests, from asking for more autonomy in your work to suggesting a different format for staff meetings.