• Urban Info

What to say and what not to Say to Your Boss


Your boss holds enormous power over you. A lot when it comes to your salary, your daily duties and your future prospects. All of which means you really need to manage that relationship. Every word you say has the potential to launch you into upper management or sink you to the depths of the unemployed.

So, no pressure, right? Now that you’re nice and relaxed, let’s go over what are the worst and best things to say to your immediate supervisor:


“You are an undermining character with no principles and I am convinced that you want me to get you coffee for the rest of my working life.”


“I have learned a lot from you, but I want to try to transfer to another department. I think it is the best choice for both of us.”

Sometimes moving on is the best option for both you and your overlord. You get to breathe again and they get to suck the youthful energy out of another unsuspecting, eager entry-level career guy. It may be tough to pull it off, but best for your sanity and, most of the time, for your career.


“I am woefully underpaid. I deal with way too much grief from my co-workers and we don’t have enough support from the office.”


“I think my performance warrants a raise. I helped to seal some deals, I work very well with our difficult relationship in accounting and I exceed my quotas every month.”

Accentuate your positive accomplishments at work, rather than harping on the negative circumstances that keep you down. Bosses don’t want to be constantly reminded of the obstacles that stand in your way. Most likely, they have figured out how to deal with those obstacles in productive ways. Proving that you can do the same will go a long way towards getting that pay bump.


“I can’t do that. Marketing won’t give me what I need.”


“That will be difficult, but here is how I plan to get us around those roadblocks.”

Figure it out. Or at least pretend that you will be able to figure it out. Neglecting your chances of success from the get-go will get you nowhere. Try to give the impression that you can make miracles happen.


“That is how we’ve always done it. Accounting will have a problem if we try to change the protocol.”


“I think we can change that too, but it will take some massaging of egos over in that department.”

Acknowledging the potential difficulties of performing a task, while also committing to said performance is better than complaining about the rigid status quo.

Complaining about unchangeable circumstances will do nothing to endear you to your betters. It will only enrage them.


“I am so hung over.”


“My kid was up all night.”

By the time you hit your 30s, no matter how friendly you are with your boss, you should never share the details of last night’s extended happy hour. You had a few too many beers on a random Wednesday night? Just say that baby’s teething is worse than ever, and the cries kept you up all night. The Perfect rational way to cover for bloodshot eyes and a haggard look.

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