How to Ask Tough Interview Questions

Interviewing is a skill. Some of us may bend over backwards trying to make our interviewees comfortable, that we forget to ask the tough questions. While it’s all well and good to try and establish a rapport with a prospect, you still need to make sure that you’re getting to the heart of whether a particular applicant will get the job done. Here are 4 tips to get you on track:

1. Bring in Someone Else: As a business owner, you’ve probably accepted (or at least acknowledged), your strengths and weaknesses. Decide where interviewing falls for you. If you know it’s not one of your areas of excellence (or interest!), bring someone else in to do some screening for you. Even if you work alone, ask someone you trust to jump on the phone or grab a quick coffee to add another layer of vetting to your process.
2. Seek out the Specifics: “I’m a self-starter.” “I’m detail oriented.” “I have experience running and managing large projects.” Sounds great! But every time you hear one of those too good to be true statements, ask for a specific example from the candidates work history. Another approach is to dig into the candidates resume and ask questions about that. “So, I see you were a manager at company x. Give me an example of what you did when you were there that shows that you’re the most organized person on the planet.”
3. Open Ended Questions: It’s amazing how much information you can learn just by asking some seemingly simple questions. “Tell me about yourself.” With that little phrase, valuable information tends to come pouring out. Did the applicant spot the opportunity to sell himself to you? Was she polished? Too polished? Babbling on and on? Talking about yourself can be difficult to do, so you can really learn a lot here just by listening. And remember, if someone can’t sell themselves, can they sell your product for you?
4. What Was Your Worst Job? For those who breeze right through the self-promotion, you want to probe at the other side of the coin-- failures or weaknesses. Just as we want people on our team who are rock stars at work, we also want people who can take direction, admit when they need help or when an idea was just plain bad. In asking about a worst job, you want to understand what it was about that experience that made the candidate unhappy. You also want to make sure that your organization isn’t strikingly similar to the one that the applicant hated. So, for example, if you hear things like, “I wasn’t happy because there weren’t enough people around for me to talk to,” you may conclude that this applicant won’t fare much better at your 8 person startup!