ADVICE: Should I Tell My Former Boss?

womanadviceDear Alphanista,

I have a great job and work with some amazing people- so I am definitely happy where I am, but it’s still necessary to look to the future and think strategically.

Shauna (my former boss) and I both still work at the same company and under the same supervisor. I was promoted from being her assistant. Shauna was very instrumental in helping me to get to where I am today and, has consistently given me excellent work and career advice. However, it’s now my turn to fight for myself.

I am tempted to go to Shauna for advice because she was once in my shoes and she knows our boss and how to relate to him. It’s one thing to read advice columns in business trades and on career oriented blogs but, those people don’t necessarily work in your industry nor do they know your boss.

My concern is that I’m no longer her assistant but a colleague, which means we’re competing for dollars from the same pool but, I don’t consider myself a direct threat to Shauna as she’s still one or two titles ahead of me. My other concern is that alpha’s don’t always make their intentions known, asking her for advice would do that.

I do recognize that now may be a good time to focus on a side hustle but, until the side business takes off, you’ve still got to keep your day job. Should I ask my former boss for advice about how to position myself for my next promotion?




Dear Kayla:

You have to move strategically with this one.

Do not get too comfortable with anyone at work.  They are your colleagues, first and foremost, not necessarily friends.  With that said, keep your relationship with Shauna cordial, but focused.  Would you tell all your office colleagues your plan for promotion?  Probably not.  People talk and sabotage.  If not directly, then indirectly by putting doubt and resistance in your mind. Unless Shauna has a part in the decision making of your promotion, she really doesn’t need to know.  Your email also suggests that you may believe this, too.

You and Shauna are not that far about in titles.  It’s one thing advising a new college graduate at the same company, and another advising a young, bright professional who is on the fast track to success.   You are transitioning from that assistant to a professional.  You will not always be behind her at work, things can change.  How would that change your relationship?  People think about these things and may not disclose it.

However, I do believe you can get something out of Shauna.  Get her to talk about herself.  When she does, you’ll be able to derive your own answers about your boss.  You have to be savvy though.  Try something like this: “Hey, Shauna, there’s been lots of changes around here, how do you feel about it?”

The questions are general, but would get her talking about the climate and possibilities.  She may be negative and that is a red flag to NEVER tell her your intention, but if not, listen carefully, and ask more questions.  You’ll find out about your boss.  The other alternative is simply deal with your boss, whether it’s him or another in the future, you have to approach these situations one on one.  Prepare a list of reasons why you should be promoted and set up a meeting.  You can also wait for your review, go over it with him, and bring it up then.

In the meantime, play it cool.

With love,


One comment

  1. goldie says:

    GREAT ADVICE. I’m using to my job(s) to transfer to NY and follow my dreams but I’m feeling out the situation. esp because I feel they may or may not transfer me. In which case, I might just save my money and bounce. BUT I really love this company so it’s scheming and plotting time,

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