Latina Cubicle Confidential™–Tough Questions to Ask Your New Boss

By Dr. Maria G. Hernandez
Latina Cubicle Confidential™

If you have just started a new job or you have learned that your old boss is being replaced, you will have a small window of opportunity to get to know your new boss and to learn how to work effectively with him or her.

During that “honeymoon” phase, you can try new things and test different ways of interacting but the grace period on that relationship only lasts so long. In order to shorten the learning curve of what your boss expects and what you need to do to manage expectations, it is better to ask some tough questions out front. Here are three key questions to ask of your boss early in your relationship:

What pet peeves do you have that I should avoid? There are always a few things that irritate each of us and it is to your advantage to check out what those might be for your boss. You may be surprised to hear these and yet better to find out early than later.

In my role as a coach, I can honestly say nothing surprises me anymore about what different executives may find irritating. “Don’t send e-mail after hours.” “Don’t be late to a meeting.” “Don’t come to me with a problem unless you’ve already thought of a solution, too”. “Don’t stop by my office without calling or e-mailing first.” It is always best to find out what pet peeve your boss may have when you can discuss this in general and not in response to a specific event.

How should we disagree with each other? Admittedly we all hope to avoid disagreements with our boss and yet these are bound to happen. When they do occur, you may find it awkward that some managers emphasize keeping a united front above solving the problem. For others, open disagreements or team dissention and healthy debates about different options are highly welcomed.

Isn’t this important to know ahead of time? Absolutely! If you ask your boss how should we disagree, you may discover that there are clear and effective ways to handle differences that actually strengthen your relationship with your boss. It also may lead to some important dialogue around anticipating areas of conflict.

The last question to ask your new boss is about your own needs:

What’s the best way for me to come to you if I need support? Many workplace environments today are asking employees to do more with less. While you may be the most resourceful contributor in your organization, there will be times when you will need more support in order to fulfill what’s expected of you.

Unfortunately, asking for help or more resources is often a source of anxiety for employees as it can be misunderstood as lacking the skills to do it all. Does your boss expect you to solve this issue on your own or within your team? Does he or she want you to determine what can be done with the resources available?

If you happen to be your boss’ “go-to” person and you keep getting all the difficult assignments, it can be a vote of confidence in your skills and it can be totally overwhelming, too. Here’s a useful question when you have been given yet another assignment: “This is a great opportunity that I want to give it my best effort — so which of my other existing projects can I drop in order to fulfill your expectations?”

It can be a great way for your boss to appreciate just how much of a workload you have and what’s reasonable to expect on your deliverables.

Tell me what you learned from your new boss at Latina Cubicle Confidential™ or join me live at the next LatinaVIDA™

Dr. Maria G. Hernandez has 20 years experience consulting in both the United States and Mexico to senior executives in Fortune 50 companies and facilitated change initiatives for elected officials and their staff. She has worked in academia, business, nonprofits, technology startups, and public agencies. For more information, visit Latina Cubicle Confidential™.

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