Warren Berger

The Questionologist

Ask These Questions and Your Boss Just Might Promote You

It’s hard to know what your supervisors need most from you unless you inquire.

Posted Dec 12, 2018

© Warren Berger
Source: © Warren Berger

People are often hesitant to ask questions of their bosses. That’s understandable: Business environments are traditionally hierarchical in structure and questions, by their nature, can be seen as a challenge to authority. This issue seems to come up at almost every company I visit, with employees wondering: How can I ask questions of my supervisors without overstepping bounds or putting them on the defensive?

Before we get into how to ask questions at work, consider why it’s important to do so. Quite simply, it enables you to be better at your job. Particularly in today’s fast-moving and rapidly-changing workplace, it’s critical to keep inquiring about the evolving nature of the work you do. In effect, today we must all continuously ask some version of the questions, How is my job changing? and How might I do it better?

People may worry that asking these types of fundamental questions about your job—especially if you’re experienced and have been doing that job for some time—could make it seem as if you’re naïve or incompetent. But there are ways to mitigate that risk and reasons to believe the benefits may outweigh the risks.

Questions can demonstrate you’re open to change and willing to learn

Having spoken with a number of top executives about this, I’ve found most of them are keenly aware of the need for change throughout all levels of their organizations—and one of their primary concerns today is that mid-level managers and frontline employees may not be willing or able to change. One way to demonstrate that you are open to change, and willing to learn and adapt, is by asking questions—about how your industry or about how your specific job may be evolving over time, about what is expected of you and how those expectations may also be changing. Most bosses who are trying to manage change are apt to appreciate and even reward that kind of questioning, not punish it.

One way to lessen the risk that your questions might be seen as naïve is to “smarten up” those inquiries by doing some advance research. Take stock of how your industry or job may be evolving and use that information to frame your question. As in, “I’ve been observing that certain changes are happening in our business. I’m curious, how do you think this affects the way we do things as a company—and my job in particular?”

How best to “question up”

When “questioning up”—meaning, asking questions of someone at a higher level—your questions should always be asked in a way that shows 1) respect and 2) genuine curiosity. Don’t use questions to challenge authority or to complain. If a subordinate asks a manager, Why do we have to do this particular task? or Why are we still using this old equipment? it can come across more as whining than as curious inquiry.

To avoid falling into that trap, first ask yourself the same questions you’d like to ask your manager—and try to consider the situation from the manager’s perspective. Why are certain procedures and practices in place? Why is that old equipment still in use? What might be the benefits and costs of making a change (to policies or equipment)—and how difficult would it be to do that?

Having thought about these issues, and gathered some relevant facts, you can then ask questions that are more informed, empathetic, and practical. The question you ask should be framed less as a gripe and more as a possibility you’ve thought about and would like to explore further. As in: “I’ve observed our competitors are using new software that enables them to move more quickly. I understand the costs of that software may be prohibitive, but I’m wondering about some of the various ways we might respond—and whether there’s anything specific that I can do differently in my role?”

When “questioning up,” one of the best ways to show respect—and to learn important information from managers—is to ask for advice. As the Wharton School professor Adam Grant points out, people are usually flattered when you ask them for advice, and managers are no exception. When you ask a manager for advice, you’re often making her job a little easier—because you’re providing a welcome opening for that manager to give you constructive criticism.

Soliciting advice from your manager

One of the most common ways to solicit advice is, What would you do in my position? And that question works in many situations. But there are some interesting variations on it that can be even more effective in helping a manager tell you how to do a better job. Wanda Wallace, a workplace coach and CEO of Leadership Forum, recommends asking your boss, What does your ideal employee look like? This question allows the manager to offer constructive criticism in an indirect way, which can be easier on all parties.

Another question shared by Wallace: What’s the one thing that, if I did it differently, would make a difference to you? Katherine Crowley of K Squared Enterprises puts an interesting tweak on this question: She thinks you should regularly ask your boss, What is most important on your list to accomplish today—and is there any way I can help?

Both of those questions focus on the manager’s key needs and priorities while making clear that you’re interested in more than just doing your own job and you’re an available resource. Crowley notes that “People above you are often juggling multiple tasks and their priorities keep shifting.” It’s hard to know what they might need most from you at any given time—unless you ask.

What questions have you found effective in the workplace?

References

As the Wharton School professor Adam Grant... From my interview with Adam Grant, Sept 2017.

“What does your ideal employee look like?” . . . Wanda Wallace, “Questions Employees Should Ask Their Managers,” Jan. 5, 2017, in a guest post on Leading With Questions, www.leadingwithquestions.com/personal-growth/questions-great-employees-should-ask-their-leaders.

“What is most important on your list to accomplish today” . . . From my Aug. 2017 interview with Katherine Crowley of K Squared Enterprises in New York.