I answered 9 successful CEO’s favorite interview questions

by jeffhilimire on February 24, 2014

Business Insider had an interesting article recently entitled, “9 CEO’s Share Their Favorite Interview Questions”. I thought it might be fun to try to answer these as if I was interviewing at their company.

On a scale of one to 10, how weird are you? – Tony Hsieh, CEO of Zappos

3. Maybe 4. I’m not too weird. I’m a pretty straight and narrow guy. It might actually be a 1. Crap, I guess I’m super boring.

I’d probably not get the job at Zappos.

Tell me about the time you realized you had the power to do something meaningful. - Simon Anderson, CEO of DreamHost.

In late 2012 when I was midway through my year with Leadership Atlanta. I realized that I had the power to do something meaningful, yet I hadn’t yet exercised that power. I’m still working on that and its why I’m doing things like this.

How would you describe yourself in one word? - Richardson-Heron, CEO of women’s organization YWCA

“Driven”. No matter what I’ve been focused on in my life – my family, tennis, my businesses – I’ve always been laser-focused and driven to make those things as great as they can be.

What would you do in the event of a zombie apocalypse? - Ashely Morris, CEO of Capriotti’s

Yikes. I’d first see how bad it was in my neighborhood and see what I could hear on the radio. If my neighborhood was over-run, I’d probably figure out how to secure the house and  ride it out until it was less active. Then I would gather my family as quickly as I could and load up the car with as much canned goods and food that would last. I’d try to get up to the North Georgia mountains and secure a place for us to live.

There are a ton of steps in between that I’d be doing – like syphoning gas from the car we’d leave behind, fashioning weapons to stab those dudes in the brain with, etc. – but the most important thing I’d try to do is be calm, both to help make the right decisions but also for my family’s sake.

Tell me about the last person you fired. - Marc Barros, CEO of Contour

In late 2012 I took over the business development and marketing (i.e. “sales”) components of Engauge. At the time we had two sales people and I was told by the board that I needed to likely hire a few more. Instead of taking their advice, I let go of the one we had that was failing and restructured the department completely, giving more autonomy to the one that was doing a great job and focusing resources around him. From that point, with only one sales person, we won 27 of 35 pitches. Sometimes addition can be the result of subtraction.

Tell me about your failures. - Jenny Ming, CEO of Charlotte Russe

Ah, I have many. Here is a list of 10 mistakes I’ve made. The biggest mistake I have made in my 15+ year career was not trusting my gut early into my time at the company that acquired mine. I knew a big change needed to be made but was counseled to wait until I had more clout within the board to pull the trigger on what needed to happen. While that was probably true – early on I wouldn’t have had the leverage or influence to make the change I ultimately made – at least I would have tried. The company had many bad years because I waited too long to make that change.

What was the last costume you wore? - Dave Gilboa and Neil Blumenthal, CEOs of Warby Parker

I wore a Star Wars costume to my son’s themed birthday party at our house last year.

Tell me about your crowning achievement. - Lou Adler, CEO of The Adler Group

I’m going to take my family out of this, otherwise it would be my wife and kids. Convincing my wife to marry me ;), stuff like that. In business, it is most definitely selling my first company.  Having come from the dorm room as a 21 year old, to my mother’s basement, with more than $90k in personal credit card debt keeping the company going, to finally selling it after ten years for +$20 million…that was the crowning moment in my career, no question.

Tell me about your last project. Who was involved and what was the biggest challenge? - Jana Eggers, CEO of Spreadshirt

My last significant “project” was taking my previous company from a stagnant, non-winning agency and figuring out how to change that after almost five years of lethargy. The challenge was that we still weren’t sure what kind of agency we were, how we were going to talk to people and what kind of business we wanted to win.

I restructured the team, giving them as much autonomy as possible. I refocused the board and our leadership team on what kind of business we’d be going after (mostly digital) and the benefits of that approach. I created three core tenets for the business development and marketing team, helping give us structure and purpose. And then…I was patient and trusted the plan. I knew it would take some time and I wasn’t worried about being fired if we didn’t hit our first quarter goals. Business development takes time and I was willing to wait. Fortunately I didn’t have to wait too long as we started winning very quickly after I made those changes.

Send to Kindle

Previous post:

Next post: