3 Difficult Conversations You Need To Have With Your Boss


There are certain conversations with your boss that are tempting to avoid, but these are often the ones that are most crucial to your career.  It’s difficult having to admit to a mistake or to ask for something that you just aren’t getting in your current work environment, but open communication on these matters ensures that everyone can do their job correctly and is happier in the long run.

Here are a few examples of conversations with your boss that are difficult to have and why they are so important.

1. Admitting You Made a Mistake

Why is this important?  Because if you try to hide from it, you will ultimately hurt the company by failing to bring it to anyone’s attention; and if you try to blame it on someone else, you will hurt others and, very likely, yourself.  The reality is, whenever you are working for or with others, and even when you are in charge, it’s imperative that you maintain open communication with all involved parties so that everyone can do their best possible job.  Trying to cover up your tracks impedes progress and creates the possibility of further oversights.  Admitting a mistake is never easy, and that’s why people respect you more when you’re able to do so.  It becomes an occasion where you can reevaluate where you’re at, and move forward in a positive way.  Moreover, the consequences will likely be far less severe when you come clean right away, rather than let others discover the blunder later on.

2. Lightening the Workload

People are often terrified of having this conversation with their boss, because they feel that asking for a lighter workload will make them appear weak or serve as grounds for their superior to find someone else to do the job.  These fears aren’t groundless, and before you go to your boss with your concerns, you should do your best to determine if you are being reasonable.

There is really nothing wrong with taking a step back and going over your priorities with your boss.  The last thing your boss wants is for you to give a subpar performance or to let projects slip through the cracks because you lacked the time or energy that your work required.  Sometimes it’s necessary to pause and go over deadlines and expectations.  You’ll be able to work out a plan with your boss that works for you both, and he or she may have some suggestions for you on how to more efficiently complete your work.

3. Asking for a Raise

Many employees hesitate asking for a raise, either because they feel they will appear unreasonable or because they worry that their boss might opt to hire someone else who will do the job for less money.  Before you have this conversation, make sure you put together a few talking points that will allow you to explain why you need and deserve a raise.  Remember that timing is key as well – you’re probably not going to get a bigger pay day after your first couple months at a company, but once you put in the hard work, your boss is more likely see it your way and feel that you deserve what you’re asking for.  Employers want to keep their workers happy, and they understand that this often means offering competitive salaries.

(Here’s some helpful advice on what NOT to do when asking for a raise.)

Don’t let tough conversations leave you with a pit in your stomach.  Just think through what you’re going to say, and be ready to accept what your boss has to offer in return.  Working together and maintaining open communication will take you far.

What are your experiences broaching these subjects with employers?

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