Ask Me Anything: How to Talk to Your CEO

Ask Me Anything: How to Talk to Your CEO

By Roxane Hudon

Oh, the key to success! Where might it be? Or so you ask yourself, while twiddling away at your desk, refreshing your Twitter feed to check if your clever hashtag is trending. Before you make another endless ‘goals list,’ perhaps you should seek inspiration from up above…

Have a chat with your CEO; find out what drives her. That’s right, “her,” because, 2016. Too intimidated? We’ve compiled a cheat sheet of questions to help you break the ice and get to know her. Next stop: brunch dates & BFF necklaces! (Or, you know, maybe just the occasional friendly hello in the elevator.)

1) What did you do this weekend?

Wait, wait, don’t run away yet! We know this seems very basic, but it’s a gateway to a lot of other questions, and also a much more natural method of asking, “Sooo, what do you do for fun?” as if you’re on some weird, terrible date. It’s the quickest way to find out if she’s into binge-watching and eating pizza, extreme sports and tequila or quiet mornings of yoga and scribbling down ideas for the next big thing. We’re hoping for the former, but we’re guessing it’ll lean more towards the latter. In fact, she’ll probably laugh off “weekends” as a concept invented by lazy people. After all, you don’t become CEO by putting your feet up and pretending to do a crossword for your quirky weekend Instagram pic.

2) Your top 5 travel destination bucket list – what are they?

The Trans-Siberian Express or the winding streets of San Francisco? Hiking Kilimanjaro or lounging on a Colombian beach? Pick your journey, pick your hero and bond over travel tips and dreams. Who knows, maybe she’ll invite you to cruise the Pacific on her yacht (all CEOs have yachts, right?).

3) What’s the worst job you’ve ever had?

Sure, you could just ask her about career highs, but we’re going to venture a guess that they possibly include being a CEO. We’d much prefer to hear about her worst job. After all, we’re all human and sometimes we just need to hear about someone else’s failures to remind us that it’s not always been money, suits and power.

4) Biggest inspirations – now & then?

Who inspired her in her youth and who inspires her now? Perhaps she’s stayed true to her roots and still thinks Kurt Cobain, or whomever a teenage version of a CEO idolized, is the bee’s knees. Conversely, that would be a good segue question: “what kind of teenager were you?” Then, find out which movers and shakers are on her radar now and why. Maybe she sources inspiration from a particular podcast or book instead of the latest tech whiz, or maybe she just gets it from a morning moment of zen. Alternately, if you want to keep it light, just ask what she had for breakfast.

5) How do you become a CEO?

We saved the best for last! No, but seriously, how? We’d like to know. Supposedly, you can’t just send your CV to your favourite company and hope for the best. Every rise to the top is different, but perhaps her version will help point you in the right direction if you also aspire to an office with a view.

Bonus Question: What album would she want if stranded on a desert island?

A true classic.

Well, at least you can rent an office with a view.

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