However, I learned a funny thing as I advanced in my career:
The relationship between a manager and her employee (at least a healthy
relationship) allows for transparency on both ends. While that doesn’t mean you
should ask your supervisor about her deepest insecurities, there are some
common questions that most people are afraid to ask, even though the answers
are really important to know.
For example, these:
1. How Are You Doing
Yes, you already might ask this one. But I’m not talking
about mumbling it aloud as you walk in at the beginning of the day, with your
headphones in, barely paying attention to the answer. But instead, really
This concept seemed ridiculous to me earlier in my career. I
just assumed that because my manager was my manager, things were pretty good
for her. She was making more money than I was, so that was a start. And I mean,
she was a boss, right? Things couldn’t be so bad.
But when I started asking her how she was doing and made it
clear I was really asking, I realized that as much as I valued the times when
she checked in on my overall state of mind, it was something she appreciated
even more when I reciprocated. So don’t be shy about checking in on your boss’
well-being. Maybe she’ll say “fine,” or maybe she’ll tell she’s really stressed
about an upcoming deadline (clueing you into why she might be a little short
with you later in the week). Either way, there’s no downside to asking.
2. Am I Doing a Good
There are few feelings worse than the uncertainty of how well
(or not) you’re doing at your job, so if you’re ever in doubt, don’t be afraid
to ask your boss for her thoughts.
Some companies are better than others about providing
constant feedback, even beyond yearly review periods. I’m fortunate to work
under someone who will tell me when I’m doing a particularly good job or if
something needs to improve. But if that’s not the case for you, there’s no harm
in asking for feedback about your overall performance.
Of course, your relationship determines if this is a casual
conversation, or a more formal discussion—but either way it’s one that’ll
benefit both of you. And unless your manager has a total vendetta against you
and wants to sabotage your career (as well as make her life more difficult in
the process), odds are that she will be willing to tell you how you’re doing
and what areas you can improve in.
3. What Do You Prefer
When it Comes to Communication?
When my work email became easy to access on my phone a few
years ago, my world changed. “I can work all the time now,” I thought, “I never
have to wonder if I’ve left anything undone!” As ridiculous as that sounds, I
just assumed my boss was also working around the clock because it was so easy
to do. Turns out that wasn’t the case at all and that she didn’t expect (or want!)
to receive my “completed assignment” and “non-urgent” questions on a Saturday
afternoon. From her response, I simultaneously learned how my work habits could
affect people in a negative way, as well as how to communicate better with my
Along those same lines, posing this question’s also a good
way to find out if your supervisor even expects you to check in after hours. I
recently responded to something on a Sunday and got an email back from my boss
that said, “This could’ve waited until Monday! Go to bed!”
While you should be prepared to hear an answer you’re not
thrilled with, you can ask what the expectations are when it comes to
back-and-forth email protocol (does he or she want you to respond to every
message or just those with a question?), sending long-term project updates (how
often does he or she want a progress report?), and meeting preparation
guidelines (should you be speaking up more, less?). The responses will only
improve your relationship.
4. How Did You Get to
Where You Are Today?
OK, so this might be the type of question you asked when you
were interviewing for your current job. If so, that’s great. But even if you’ve
scratched the surface, there’s a lot you can learn from your boss’ career
story, especially if you’d like to be in a similar position down the road.
And what you’ll learn will probably surprise you. I used to
think that anyone who managed people got that status because they never made a
career mistake. Ever. But the more I’ve asked people about their paths, the
more I’ve realized that all of them overcame a number of obstacles before
landing in their current role.
For some, that meant dealing with a longer-than-expected
period of unemployment. For others, that meant feeling overwhelmed by their
work. In any case, it’s a good way to see how you can advance your career,
while also taking solace in the fact that the people above you aren’t perfect,
either. And for that very reason, you can ask this question more than once, in
a variety of ways. The more you can learn from your manager’s story, the better
you’ll be able move forward on your own path.
I know it can be hard to speak up about something you’re
curious about, especially when it comes to your boss. And sometimes, you’re
going to get answers you’re not thrilled about. But whether it’s your overall
performance you’re wondering about or current project expectations that are
unclear, don’t be afraid to ask these questions. I mean, ever. If you sit idly
by and just wait for the answers to come to you, you’re not only keeping
yourself in the dark about your day-to-day, you’re also preventing yourself
from growing into an even more impressive professional.
Photo of co-workers
talking courtesy of Shutterstock.