Women@Forbes: What You Should Really Ask The People You Hire

By Cindy Gustafson, Chief Strategy Officer

If you’re reading this, there’s a 99.9% chance that you’ve already read a listicle titled something like “The only five interview questions you’ll ever need” or “Three surefire interview questions to ask.” So why bother with this one too?

For three reasons. One, I’m not in human resources. Two, I interview over 100 people a year. In all my years, I’ve only wound up with two people who were the wrong hire—and one doesn’t count, because he went on to work in the Obama administration. He was a brilliant guy, just not great at advertising.

And three, because let’s face it: the typical job interview is like a weird role-playing game. The conversation feels engineered. The candidate is anxious to impress. And you’re probably a little distracted by the other things you’ve put on hold to do this.

Sometimes interviewers try to loosen things up through “creative” questions. Someone once asked me: “If you were a shoe, what kind would you be?” Seriously?  You really think I’ll answer that truthfully? I’m a Manolo Blahnik stiletto (impractical at times, but worth the investment) – but that’s not what I said. It’s too easy for someone to make up the answer they think you want versus giving you the truth.

Here’s what you should really ask the people you hire. These questions may seem pedestrian, but the things they uncover are anything but.

Are you in the office today? Did you have to sneak away a bit?

As mundane as it seems, this is the best way to start a real conversation, because it gets to the deeper psyche of what’s at play here. If someone has endless time to chat that means they’ve either told their boss that they’re interviewing (“My CEO and I are close, and she knows I’m looking for new opportunities”) or they’re serious enough to take the afternoon off (“I have as much time as you need”).

But if it’s clear that this interview is on the down-low and they’re running back to the office, that’s a tell-tale sign that they’re not too serious about leaving. They may be considering what’s out there, but likely their heart still belongs to their current job and boss. Even if they’re qualified and initially say yes, expect to deal with heightened salary demands and counteroffers.

The middle ground is someone who’s really interested, but can’t take off too much time for valid reasons. You can see the difference between someone who says, “I have an hour and then need to get back” (and that’s it) versus someone who actually explains, “I want to make sure I don’t leave clients hanging on a deadline” or “Frankly, I don’t have as much autonomy as I’d like in my current role.”

What’s something you never want to do again?

This one takes everyone off guard a bit. Sometimes the responses are playful, sometimes they’re serious – but what’s crucial is that they’re always sincere.

One time someone answered: “Well, I just came back from vacationing with my in-laws. That’s never happening again.” It led to a great, transparent conversation about what you shouldn’t put up with.  Some of the most personal answers to this question have led to the best insights about someone’s character and what they’re like as a colleague.

When it comes to the work-specific answers, those uncover how a person thinks about not just their role, but a company and its leadership as a whole. It’ll tell you where they’ll likely to excel. Someone who complains about politics-ridden holding companies or company-wide assignments will have different needs from someone who bemoans the lack of resources on a project they led. Pay close attention – what someone despises doing is just as important as what they love.

Read the full article on Women@Forbes.