10 Questions to Ask on Your Next Date/Job Interview

My father once gave me some fantastic dating advice:

On the first date, ask him what drugs he is taking, legal and illegal.

Subtlety isn’t my dad’s forte, and now you know I came by it honestly. But you can understand what pops was getting at. Before you get serious about someone, pop open the hood and poke around.

And so it goes with job hunting. So many of the things we really want to know, whether we’re seeking a personal or professional long-term relationship, often come from direct (and maybe mildly uncomfortable) questions that we tend to avoid.

With that in mind, let’s go over 10 of the most overlooked yet incredibly important questions you might want to ask on your next date and/or job interview.

1. How long was your last relationship and why didn’t it work out? Wouldn’t you want to know if the previous person lasted only six weeks? Or six years? And don’t you want to know why it failed? You may not get a completely straight answer, but you could get a nugget or two that prove helpful.

2. How long have your past relationships been and why did they fail? Finding out about the most recent relationship is good, but knowing about tenure trends is even more telling. Do most people stick around for five+ years? Or, has no one lasted longer than a year? Again, you may not get the full scoop, but I bet you’ll find something valuable. And, if the response was that it was always someone else’s fault, you’ve been warned!

3. How would you describe your reputation and it is accurate? Of course, you’re going to ask around about reputation anyway, but why not also ask the person sitting in front of you? Is that response in line with the other things you’ve heard on the street? Or is there a disconnect with reality?

4. Are your social media channels an accurate reflection of who you are? Social media profiles can be misleading in a Truman Show sort of way, so give them an opportunity to tell you what’s missing or what you should know that you can’t find online. Regardless of how accurate they claim their social media channels are, pay attention to what you see! Is the tone measured or it is one stop away from Crazytown? Does the organization have clear, consistent messaging? 

5. What should I know about your financial health? First, wouldn’t it be great if you could ask your date for tax returns and bank statements without seeming like you were a gold digger? Thankfully, the public has access to a nonprofit’s 990, and it’s a treasure trove of information about financial health (revenue, revenue sources, expenses, etc.). You should always inspect the 990 before you apply for a job with a nonprofit.
But why stop there when you can also ask the hiring manager for a bit more? And remember, if a hiring manager bristles at this kind of question, she may be hiding something. If the organization is thriving,  she will relish the opportunity to respond!

6. How would you describe your perfect mate? Give her the chance to tell you what she really wants. How close are you to what she outlines? If you can recognize that dream hire in the mirror, great! But if the description sounds more like your third cousin once removed you’ve never met who lives in Albuquerque, think twice. And perhaps most importantly, is she seeking the elusive unicorn?

7. How could your mate exceed expectations? Can the person clearly articulate what success looks like? And are those expectations realistic? If success is a riddle wrapped in a mystery, inside an enigma within a dream, it’s likely unattainable.

8. How would you describe your lifestyle, habits, and values? Or, in the job arena, how would you describe the office culture? This is another one of those low hanging fruit questions that people forget to ask. And it’s one of the biggest reasons things don’t work out, so why not ask? You may be a fit for the job, but if culture isn’t a fit, you won’t thrive there.

9. What are the benefits like? Does he cook? Will he walk your dog when you have to work late? Does he plan to court you with dinner at all the best chophouses? Or, what does the health insurance look like? Do you offer paid PTO? An HSA? 401(k)?

10. What’s the one thing I don’t already know about you that might be a deal-breaker? You might get a throw-away response here, but you might also learn that she doesn’t want children or that she’s an atheist or that she can’t stand college football. On the employer side, you might discover they don’t allow any virtual work or that there’s a business professional dress code in effect every single day. Can’t hurt to ask!

I hope these not-so-subtle inquiries will help you find the best match, whether on the dating scene or the job hunt.