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When You Need to Tell the Boss Something She Doesn’t Want to Hear


No one wants to be a yes man or woman, but after a couple of years of post-recession economic gloom and job instability, it’s hard to feel comfortable telling the boss bad news. Unfortunately, in order to do your job well, you’ll have to learn how to discuss tough topics with your manager. Here’s how to do it.


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“[Y]ou do have to be tactful,” warns Satinder Haer at Popforms. “No matter how big or little your input is, your boss is likely to be caught off guard. Even if your boss is open to hearing how they can help you be successful at your job, they aren’t used to getting critiqued; the last person they’ll be expecting unsolicited feedback from is someone they are in charge of managing.”

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There are a few things you can do to make sure that the conversation comes across as constructive, including:

1. Focus on the solution, not the problem.

The standard advice is never to bring your manager a problem that you don’t want him to solve (with the implied threat that you might not like the solution). The best plan is to never present your manager with a problem at all: come up with a solution, and then propose it at the same time as you bring the issue to your boss’s attention.

2. Let data make your argument for you.

No matter what your concern, facts and figures are more persuasive than undefined worry. If you want a raise, research salary ranges for your job title; if you want to prove that changing vendors would save money, put together a proposal comparing numbers.

3. Don’t get personal.

Even if you’re on friendly terms with your manager, remember that your life outside the office is not germane to the discussion. Don’t bring up your family’s financial situation when angling for a promotion, and don’t express concern about a business decision using the phrase “I feel.” Your boss might well have an emotional response to receiving what could be construed as criticism. Don’t exacerbate the situation by approaching the conversation emotionally.

Tell Us What You Think

What are your tips for communicating with the boss? We want to hear from you! Leave a comment or join the discussion on Twitter.

Jen Hubley Luckwaldt
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