How to Talk to the Man

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There’s any number of reasons why you may be avoiding your bosses’ offices. You may be behind on a project and know if you appear, he or she will demand an update. You may have just screwed something up and are waiting for the dust to settle a bit before you make your presence known. Or you might thoroughly intimidated by the dragon in the head office, and want to avoid that person at all costs. Whatever your reason for refusing to darken this person’s door, unless it’s the first reason listed here, get over it.


Hopefully, you don’t have a mean supervisor or your boss isn’t crazy. This happens. I had a supervisor who micromanaged me and the rest of the people in our department into the ground. We gave new meaning to the phrase “disgruntled employees.” We were bitter, angry, and likely two or three spreadsheets away from a full-scale, mutinous revolt. This woman stressed me out so badly I broke out in hives and then, in front of everyone, she loudly asked me—of the almost-always-clear-zit-free-skin—“What’s wrong with your face?” It took everything I had not to scream, “You!!! You crazy bee-yotch!”


If you have a worse situation, you have my sympathies. If your reluctance to beard the lion in his den is more related to your own nervousness and apprehension, there are certain things you can do to ease yourself into the chair across from the big desk.



  1. Formally make an appointment to come in for a talk. That will set the tone for a discussion about your future prospects with the company, your desire to take on additional responsibilities in order to train for a leadership role, etc. Don’t just barge in and expect your boss to drop everything and make time for you. That’s not the way to grease the proverbial wheels of opportunity. Be considerate and patient. The decision to take a proactive role in your future is very important, but it may not be as important and urgent to someone else.
  2. Don’t assume that your supervisor’s reaction to your request is a forecast of their response to what you’d like to discuss. If he doesn’t respond immediately, it doesn’t mean he doesn’t care. If she wants to know what’s the deal before committing to a time and you tell her, don’t assume she’s already made up her mind. You know what they say about assuming: ass – you – me. However, if the boss isn’t taking you seriously, or is brushing you off, be persistent. Evaluate the situation and time when you made your request. If it’s a particularly busy time for the company, your request for face time may have to wait. If your boss is ignoring you, this offers its own hints about your place in the company and/or your future with the organization.
  3. If you think the situation can be saved, ask your supervisor if he or she would prefer that you address your concerns to someone else. “I would really like to sit down with you for – minutes to discuss –. When would be a good time for you?” Or if he or she is blowing you off, you might try, “The timing never seems quite right for our meeting. Would you prefer that I speak with (insert their boss’ name here) instead?” Be polite, but whatever you do, don’t give up. You have needs just as the organization has needs, and in an arm-wrestling match between the two, you should win.
  4. Come prepared. Bring notes. If you have something to reference while you’re running through your concerns or ideas, you’ll be less nervous and appear more professional. Come with action items. Meaning, come with questions that you want answered as well as a few ideas or activities that you’d like to manifest in the future: managing or taking the lead on a project, taking advantage of an educational opportunity for which you’d like the company to pay, etc. Clearly outline the benefits to the organization rather than emphasizing the pluses for you. Use numbers if you can. “If I learn this new technology or earn this certification productivity will improve by X percent. I will be able to help maintain this system and we can cut back on the consultants’ hours which will save money…” ROI and metrics are always excellent ways to convince a senior leader to come around to your way of thinking.
  5. It’s okay to be nervous, but remember your boss is a human being. He or she goes to the bathroom and blows their nose the same way you do. If this is someone you admire a great deal or perhaps wish to emulate, remember no matter how much of a dynamo they are in the office, your supervisor or boss is not perfect. No one is, so there’s no need to be afraid or intimidated. You too have value in the organization, and unless you take a chance and brave that big, bad head office, you won’t know how much or how little.
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