Of all the questions I get asked as a headhunter (other than… what does a headhunter do?), the most common one is “what is the best interview question I should ask?”

Well, it really depends on what you want the question to reveal. Do you want specific information? Do you want to probe something deeper? Or do you want to get the person to sell themselves to you?


In no particular order, here are my top six interview questions. I don’t use all of them in every interview, but each has their own place:

  • If your worst enemy was here right now, how would he describe you?
  • Having understood this opportunity/our culture/the job in detail, what two reasons are there that make you unsuitable for the position?
  • What challenge are you looking for in your next position?
  • If someone told you that the two people they most admired in history were Abraham Lincoln and Josef Stalin, how would you react?
  • What have you learned about this opportunity during this interview that you didn’t know before we started talking?
  • after most questions are answered, I follow up with a variation on: Really? Why is that?

These may not be the best questions in the world, but they have served me well. Feel free to comment on any of them – I have thick skin! – and please feel free to suggest your own. Every day is a school day!

In case you need more questions to shake things up, check out these creative interview questions we’ve listed!

About Simon Lader

Simon Lader

I am an almost twenty year veteran of the IT industry. I started recruiting for IT sales and presales people in 1997 and I’ve been doing it ever since. Originally living in Manchester, UK, I now live in Las Vegas and specialize in helping startup and high-growth software vendors find the best sales and presales people in North America, Asia Pacific and EMEA. My three kids and long suffering wife keep me sane (or as close to it as possible) - which, as a Manchester United supporter, isn’t always easy! I probably watch too much Netflix and drink too much Single Malt Whisky, but what’s life without a little misbehavior now and then.
Click here to schedule a free 15 minute consultation phone call with me; or click here to send me a message.
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