Should You Speak Up To Your Boss?

It can be a tough call. Here are seven things to keep in mind:

1) Power: Bosses intensely dislike hearing the word "no." They generally value "team players," "problem solvers," people who will jump right in and take the assignment even if they don't know what they're doing. As long as their heart is in the right place. Part of giving you an assignment you can't handle is to see what you do under pressure from them.

2) Organizational culture: Does the organization expect you to be a straight shooter or are you supposed to diplomatically say "yes" to everything and then figure it out later? Do they expect you to grow by taking "stretch" assignments and learning as you fall down? Then you may have had a mis-impression about your true job scope. I believe I once found the description for my current job in my files, and then I promptly lost it and forgot about it, because the scope is always changing. I like that. Not everybody does!

3) Your personality:  Are you like a vacuum in that you can can inhale a lot of toxic dust and then empty out the dustbin at home? Or will you carry it around like black smoke all day unless you express yourself right then and there? If your personality style is to be more direct and upfront then it is probably unhealthy for you to be something you are not - and that can hurt you later on.

4) Resources: Are you being asked to do something you absolutely cannot do, or that you can do with some training and support? Maybe the thing to do is to say, "If you give me XYZ training, staff, etc. I can do a great job with this."

5) Personal ethics: One can feel it is unjust to be hired for A then asked to do B. In my mind, for a full-time employee this is normal since nobody can predict what the financial needs of the organization will be and you sort of have to be flexible. Then again, if you've been truly misled and committed yourself to a full-time job on overtly false premises that's something else. (Note: this is not legal advice.)

6) Generational communication style: I will be very broad brush about this and share my impression that:
  • Gen Yers tend to be more focused on needing to know exactly what to do in order to succeed. (Gen Z, younger than Gen Y, is not like this - they care a lot less about the rules and tend to make them up as they go along.)  Gen Y also tends to feel more entitled to rewards, advancement, etc. 
  • Gen Xers tend to be more focused on getting things done - result matters more than process and they work more autonomously. 
  • Baby Boomers like to solicit input but in the end want to have the final say. 
  • Matures just expect you to listen. 
7) Boss's Psychological State: Is the person you're talking to rational, or nuts? I am really not kidding about this: If they are rational you can have an honest conversation. If they are irrational, neurotic, psychotic, deluded, paranoid, sadistic, narcissistic, etc. then they are carrying around a personality disorder all the time. So your presence in the room gives them a chance to let off steam in your direction - and they don't even see you. Fortunately I don't deal with people like this 99% of the time, but the other 1% of the time, my best advice is to run in the other direction!

Bottom line - 3 lessons:
  1. If you want to earn a living you sometimes have to go outside your comfort zone. 
  2. The one who has the pocketbook generally makes the rules. 
  3. No matter what, be true to yourself because otherwise you'll be miserable anyway.
If it's not a good fit between you and your employer, it's about more than a single conversation. There is always another job - or you can start your own company.