25 Toughest Interview Questions

It’s been a few months since I last interviewed salespeople. My resounding memory was of the low calibre of New York technology sellers. How they command such high pay remains a damning insight into many a tech firm today. Too many managers are so desperate to fill a cubicle they mistakenly take anything. Too many a rep stays in situ, never hitting quota, with each year a new excuse allowing them somehow to cling on to their seat.

During those sessions, one grey-haired chap went an entire interview without asking me a single question. He did manage to tell me how wonderful he was, mind. And he claimed to be on $100k basic. Incredible. Another candidate, at the opposite end of his career, handled every single ‘objection’ I gave with the same answer, “I’m telling you I can do it, just give me the chance to prove it”. Baffling.

Every now and then some bright PR spark manages to capture coverage uncovering ideal interview questions. The Telegraph just shared the latest such list, for these 25 toughest interview questions.

The one that seemed to garner the headlines, about how you fit a giraffe in a fridge, is pretty rubbish (and it’s supposed answer, even worse). I’m all in favour of abstract queries that get the answerer to unwittingly reveal exactly how they think, but this (and ones like who’d win and why in a fight between lion and tiger, and duck/horse poser) are all a bit too undergrad milkround for me.

I also remember the biggest hero one being vogue after an American Republican tv debate. The first four candidates gave heartfelt responses (one even said Churchill, bless him), the last one’s turn to answer was George Dubya Bush. He simply replied, ‘Jesus’. And look where that got us.

Yet there are a few of good steers in this list when it comes to selling assessment.

The first on their list I don’t like (what’d you do with a won million quid). But it did remind me of my days selling to business owners back in the 90s. We used to giggle at asking them what they spend their increased revenue (released by our wonderful wares naturally) on. Yet I can see a glimmer of relevance in the Sales interview. What would you spend your 110% of target commission on? It could reveal how much they can visualise, or are motivated by it. There are caveats of course, as my old thang about winners tend to be way more motivated by accomplishment over cash reminds me. Still, a useful chat could follow about previous commissions too.

The second, about which function is most useful in Excel, could easily be adapted to uncover true feelings towards sales reporting. Just ask around the crm brand they presently use.

The sixth, about overall divisional strategy, could also ably apply to any business section to understand the depth of strategic versus tactical blinkers or vision that exists.

And the final choice I also like a lot. Where a retailer may examine a quality perception between homeware and clothing, many a b2b outfit could demarcate along any two of their offerings. Whether they’re complementary or discrete. This’ll surely get to the nub of how much they really know (and care) about what they’re hoping to sell.

Of course, as with all these kinds of questions, some are also great to be asked by the interviewee to. Anything that creates a genuine conversation, especially one where the job-filler does most of the talking, is to be eagerly pursued.

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