Questions You Must Ask Your Boss

It can and does happen even to top performers: You see the axe falling on others, but you know it couldn’t happen to you. You’ve consistently gotten good performance reviews, and you play a key role in your organization. Your job is important! Yet…you now realize there may be some subtle, almost unnoticeable warning signs that you are ignoring or dismissing.

If you work for an organization of any size, you should always keep close track of its financial and operating performance–you should never be surprised when a round of cost cutting or organizational changes are announced. You should also ask your boss questions that are designed to gently probe and uncover what’s really going on—without actually making you sound concerned or anxious. Even if things are going extremely well at your firm, you should be asking some of these questions.

Remember, when you ask these questions you must tune into the other person’s body language, tone of voice, and demeanor as much as you listen to the actual words they use. 

       1. “What do you think my priorities should be over the short, medium, and long term?”

How engaged is your boss when he answers this question? Does he tell you to just “keep up the good work” or does he enthusiastically talk about specific programs and initiatives that he is excited to have you focused on over the next 6 to 12 months? The more vague he is, the more you should be concerned.

2. “Longer term, where do you see me going in the organization?”

Look for enthusiasm and specificity in her reply. Does your boss sketch out for you several potential roadmaps and talk about your value to the company? Or does she discuss your career in very general terms and show a lack of thoughtfulness and engagement? If there’s no clear, concise answer forthcoming to this question, you should dig a little deeper—and possibly be concerned.

3. “It’s been a while since my last formal performance review. Could you give me some feedback about how you think I’ve done over the last three months?”

Listen carefully to what your boss says in reply to this question. It may be a warning sign if you suddenly get negative feedback despite a string of positive reviews in the past, or if your boss hems and haws, as if he’s afraid to commit and be forthright with you. If he is very positive and gives you specific praise, that doesn’t mean you’re immune to a layoff, but it’s a good sign. It does happen that people are fired the day after a positive performance review, but you can often detect some cognitive dissonance—a disconnect between your boss’s body language and verbal message—when this happens.

4. “As you look ahead at our business, what are you most excited about? What concerns you?”

Does your boss exude authentic enthusiasm and passion when she answers this question? If she’s not very excited, and cannot give a convincing answer, then maybe something is amiss. At best, it may be that she feels her own position is not secure.

5. “You’ve had a very successful career so far. Where do you see yourself going from here? What else would you like to accomplish?”

Does your boss communicate a commitment to your company, and see himself as an integral part of the organization’s future? Or does he talk about eventually wanting to “do other things…”? You have to discern, in his answer, how committed to the organization and how passionate about it he is.

6. And, if you know your boss pretty well—you might try asking, “Overall—candidly—do you think I’m a good fit with this organization? What kind of organization do you see me best thriving in?”

Your boss—even if she knows something—isn’t going to let the cat out of the bag. But if she likes you and values you, she may just hint, by the way she answers, that maybe you should be looking around for something better or different. Frankly, anything less than an enthusiastic and clear “Yes!” should be cause for concern.

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