Dear Sylvia: How can I step up and voice my concerns without jeopardizing my job?

It’s time to reveal our next “Dear Sylvia” question and answer. Be sure to check the bottom of this post for further instructions on submitting your “Dear Sylvia” questions.

Dear Sylvia,

There is a huge disconnect and generational gap in our office and I can feel the walls crumbling in around our business! Our principal is at retirement age and the majority of our staff is, on average, about30 years old. In the last couple of years our business has expanded to include different market sectors, but we have no business or transition plan in place, which makes employees nervous and leaves them unmotivated. With recent staffing changes, there has been no explanation of how responsibilities and goals will be met. Our staff is unhappy and our management team is going in different directions. I am a leader by nature, so in my “middle-management” position, how can I step up and voice my concerns without overstepping and jeopardizing my job? I am afraid we will lose some of our key employees if the atmosphere at the office does not improve. Please, help us!

Signed: At the End of My Rope

Dear “At the End of My Rope:”

The KEY to dealing with your difficult, frustrating, and scary question lies in the ART OF QUESTIONING.

I don’t know how much practice you’ve had in asking the right question at the right time for the right reason.

I suggest that you begin to ask a series of meaningful open-ended questions of your principal during team/staff meetings (assuming you have them).

Here are a few examples:  “What does our future look like?  Where are we headed? How will we get there?”  You can follow those questions with statements such as “I’ve been noticing that our internal culture is shifting, and all of us know that there is a great deal of global instability.  Change is real and certain.  “How do you envision that we will deal with this over the next six months?  The next year?”

You can also express a need for receiving greater clarity about your own role in the business going forward.  When doing this, be sure to focus on YOUR needs rather than on the principal’s deficiencies and oversights.  Say something like:  “I want to make ongoing, meaningful contributions here, and to do that I could benefit from more clarity around X, Y, Z.”

Finally, I would recommend that your entire staff engage in a SWOTT Analysis, an intensive exercise that identifies your company’s strengths, weaknesses, opportunities, threats, and trends.  This is a great way to prepare for the future–and a responsible forerunner to a credible strategic/business plan.  You could suggest this to your principal by asking:  “Do you see any value in conducting a SWOTT Analysis over the next few months?  I’m thinking this could be really useful to all of us as we plan ahead.”

To sit back and say absolutely nothing puts you and your colleagues in a very vulnerable position!  But your questions and ideas must be delivered with finesse, diplomacy, and great care.


Do you have a business question? Send your questions via email at or by mail to 4902 Carlisle Pike, PMB 297, Mechanicsburg, PA 17050.  Limit one question per person, please!

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