Self-Assessment Quiz – True or False:

  • There are instances when I need to place my needs ahead of others.
  • I know how to follow up on a closed-ended response.
  • I am not afraid to gently challenge authority.

A part of being self-aware on the job is not being afraid to ask for what you want, setting boundaries, and teaching people how to treat you. This includes bosses. If you answered TRUE to the questions in this week’s self-assessment quiz, you probably don’t have a problem in this area, but your cousins might need a little bit of help. So do me a favor, and forward this week’s post on to them.

If you aren’t asking for what you want on a regular basis, especially at work, what’s stopping you? Is it fear? And what specifically are you afraid of? Is it the word ‘No’?

If you ask your boss for a day off so that you can go to your daughter’s chess match, what’s the worst thing your boss can say?

A. You suck! You’re the worst team player EVAH! I hate you, and I wish I had never hired you.

B. The timing isn’t the best, but you’ve asked in advance, so let me think about it.

C. No.

Some might think the worst response is A. But my goodness, think of all the money you’d earn with that lawsuit! (I’ve had friends who are bosses and have been sued for far less.)

Some (like me) might opt to select B as the worse answer because it’s a non-answer. A passive aggressive non-answer at that. On the one hand, you were offered praise and acknowledgment because you planned ahead with your ask. This shows a certain level of respect. On the other hand, this answer sucks rocks because if the boss doesn’t get back to you after “thinking about it,” you have to circle back and ask her again. [Sigh] Why can’t people just make up their minds?

But those of you who selected C as the worst answer, well, you’re just flat out WRONG! At least with a “No” you have something to work with. Where some might see the response as one and done, I see it as an open-ended response. A chance to negotiate! Oh, goody!

When it comes to negotiating, I’ve been taught to softly repeat the response, with a question mark at the end. Then stop talking.


Wait, silently. Usually the boss won’t give you the same one-word response again. More than likely, she might take the time to explain her answer a bit more. If she does say a curt “No” again, prompt her (gently) for a more specific reason.

“May I ask why?” Again, using your softest Valley Girl “Becky-voice.”

Is your boss overworked? Has she been chewed out for being too soft and handing out too many days off? Does your boss resent that she can’t take time off to spend with her own daughter?

The point is you gently press until you have an answer. This strategy is usually a win-win for those of you who aren’t used to asking for what you want because it forces you to be a tad bit dogged IRT about getting a final answer. You’ve demonstrated to your boss (and hopefully to yourself) that you deserve a fully thought-out response. After one or more encounters like this with you, your boss will recognize that you’re nice, but you’re not a pushover.  And she hasn’t strung you out on some dubiously defined future timeline after she’s “thought about it” like she did in response B.

By the way, if you are truly afraid of getting a response like that in answer A, you obviously work in the television industry or in politics! (And yes, I’m straight up throwing shade at these industries because I’ve worked in them and know what I’m talking about). But for the rest of the working world, it’s a response so far removed from reality that you need to just get over yourself, open your mouth, and ask for what you want!

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