5 Things Every Employee Should Ask Their CEO

Gary Vaynerchuk
Dec 1, 2015 · 3 min read

Recently, on my YouTube show, my editor in chief Steve Unwin asked me a question that I thought was very poignant and interesting. Even more so than that, it felt daring. He wasn’t nervous to ask it. And it got me thinking about all the questions I’ve been asked as CEO of my company VaynerMedia. Some have really provoked me to think. Some have been filled with fluff. But overall, I realized that knowing what to ask if you are ever presented with the opportunity is incredibly valuable. So I thought I would put together this list of five questions I think every employee should ask their CEO in their life.

1. “What is your finish line?”

Maybe, if you can get them to be really honest, their answer will be something small, like “We want to be AdAge’s agency of the year.” Or “We want to be the number one app in the app store for at least a day.” It’s an extremely important question, and if you’re good enough at understanding what the underlying message behind the answer is, it will give you insight into where the company is actually going.

2. “What have you learned in the last year that will inform this company in the next year?”

3. “What’s the biggest vulnerability of the company?”

Or, this questions gets you real insight.

My answer to that question is usually pretty intriguing. I reply with “My death.” That speaks to either overconfidence or complete control. You make the call. Either way, I’m being honest with my employees and we usually have a very real discussion about it.

4. “What are your strongest and weakest relationships in your family?”

5. “What do you want for the employees of this company?”

I truly mean that. I often wish there was a magic button I could press that would transfer how serious I am about my intent to all the employees of VaynerMedia. Of course, being the owner of the company, there are disproportionate benefits between me and my employees (I’m thinking financially, for example). But I want success for everyone, whatever success might mean at all levels.

I’ll leave you all with this: you know you’ve had a great conversation if you come away convinced of your CEO’s intentions and motivations.

Thanks so much for reading! However, I know a lot can be lost in writing; to really see how serious I am about my intent, would love for you to check out this video where I answered my employees question on my show.

And if you liked this article, hit that heart button below. If you do that, more people will see the article. :)

Gary Vaynerchuk

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Family first! But after that, businessman. CEO of @vaynermedia. Host of #DailyVee & The #AskGaryVee Show. A dude who loves The Hustle @Winelibrary & the @NYJets