Better Coffee Chats: Don’t Just Ask Me Why

I get a lot of generic networking outreach requests from students. I remember doing that myself — I don’t think I was anywhere as organized, composed or focused, nor was I really clear what networking could realistically do for me, other than Career Services having made a strong impression from constant repetition that it was important.

So wherever you are in your career journey, if you’re reaching out to strangers to broaden your perspective and get advice — good for you! Kudos for each outreach message you hit send on, because it never stops being just a little nerve-wrecking.

With that said, it’s easier to get into the groove of networking sooner if you start getting value out of the conversations you’re having, and for that, you have to be asking the right questions. Bearing in mind that most people (especially in American culture!) will gear towards the positive, and that most people will not think very deeply about what might benefit you (that you haven’t asked), the onus is definitely on you to prepare thoughtful questions that can get you insightful answers. (Especially if you’re trying to suss out a workplace culture because you know for whatever reason you might need to give years of your youth to a company, and you don’t want to be stuck in a cesspool; particularly applicable for international job seekers!)

So if I get a message that tells me you’re “interested in learning more about what I do and my personal career journey” (yes, I’m looking at you, CUeLINKS auto-generated template message for students!) — I know you haven’t the slightest idea what you’re asking or why you’re even asking. (My career journey went from hospitality to domestic work to consulting. You really want the whole spiel? And you think it’ll fit in 20-30 minutes?)

What to ask instead? Here’s a thought: don’t ask me why I made a certain decision; ask me to reflect on it — what did I learn from it? What would I do differently, if anything? What advice would I give you if you were considering the same decision?

You want to get to the juicy nuggets of wisdom in the “if I knew then what I know now” sentiments. Every decision is a trade-off, so everyone who’s reflecting should have some variation of that.

Don’t ask me why I made a certain decision; ask me to reflect on it.

To illustrate: if you ask me why I went to graduate school, I would tell you that I had discovered that I didn't want to be in hospitality anymore, and after being an au pair in Spain, I needed to get back into the corporate world and get a benefits-paying job. I had figured my chances of getting hired by any big (recognizable) company were very slim coming out from hospitality and domestic work, so I needed a reset by going back to school. I also knew that there was no other way for me to get back into the US unless I did school again and had a chance at going on an OPT. So that's why I went to graduate school. In the US.

That's not very helpful for you, is it?

If you asked me why I went to business school, I would tell you that I had originally been considering a JD/MBA — actually, I originally had started by considering a JD/PhD, switched to thinking about a JD/MBA, and ultimately ditched the JD part. If you asked me why I didn't pursue the JD, I would tell you that I met someone who told me that I would have signaling issues as my goal was to get into consulting but I was interested in getting a legal education, but I didn't really want a JD to become a lawyer. This person convinced me that anyone from the legal field would always see me as not quite a lawyer, whereas anyone in the business field would always see me as a lawyer, and therefore I was gonna have signaling problems. A JD would have been a very expensive extra credential that wasn't going to help me in my quest to get into consulting.

If you had asked me why I chose WashU St. Louis for business school, I would've told you that because I was applying for JD/MBAs, this was the only place where my JD acceptances and MBA acceptances sort of lined up. (I basically had to apply to law schools and business schools separately, and indicate I was interested in doing a dual-degree but was considered for admission separately but each school.) WashU’s law school waitlisted me, and their business school accepted me.

If you asked me why I picked Cornell for undergrad, I would tell you that my high school only allowed us to apply to six universities — eight if you petitioned and got that approved — because our college counsellor at the time refused to send more transcripts, and being an international student, I picked 4 Ivies, Stanford and Emory (because a friend had gotten a full-ride scholarship there) to apply to, then accepted the offer from the highest ranking school I got accepted to. Plain and simple. I had never visited the campus, I barely believed in differences in “campus culture” and didn’t think it was possible to assess that via published brochures on homogeneously welcoming statements online.

None of these would be helpful—unless you also happen to have gone into hospitality or some other career in an area that wasn't particularly intellectual, and you looked up the chain of command one day and realized you didn’t want your boss’ boss’ boss’ job, so you needed out. Then you went rouge and took a delayed gap year (whether or not you decided to take all the fun out of it by also working as an au pair) or for whatever other reason you stepped out of the corporate world.

If you asked me about my career journey, so much of it would be irrelevant to you. If I were a good raconteur you could walk away with the sense that you heard a good story, but it’d help you not one iota with navigating your own future.

And you’d have wasted the 20-30 minutes you asked me for because it didn’t serve you on your journey.

Better Questions

Here’s what you should be asking instead (if you’re interested in doing an MBA at some point, for example):

• Was going to business school the right decision for you? Why or why not?

• What did you learn about thinking about graduate schools through your experience that I should be thinking about now?

• Having gone to business school, is there anything you would change about how you were thinking about MBA programs when you were applying?

Now we're getting interesting.