Skip to main content

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 CEO questions I think every employee should ask their company leader.

1. “What is your finish line?”

Aka, what does success look like to them? What does their finish line look like? When I tell my employees my end goal is to buy the New York Jets, it allows them to understand that my behavior is long term. It tells them I’m playing for a fifty-year narrative. That means I won’t cut corners. I don’t overvalue the quick dollar. I’m playing for long term keeps. And if the employee really gets that, they’ll see that that creates interesting long term stability.

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?”

Recent learnings. Knowing what a chief executive pays attention to is crucial. But it’s just as important to know how they plan to factor them in. It’s a very significant proxy to see where their focus is in the short term and their ability to improve on it.

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

The reason this CEO question is so important is that it’s an opportunity for your leader to bullshit and say “nothing.” And you know that can’t be true. But hey, then you know your CEO doesn’t have a problem giving you bullshit.

Or, these questions get 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 the strongest and weakest relationships in your family?”

Family dynamics play out in the business world a lot more than people realize. The way a chief executive, and anyone for that matter behaves with their family has an enormous impact on how they operate the company and how they treat their employees. The same is probably true for you; this question can give you a glimpse into how the business is managed and why.

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

The one thing I truly want all my employees to know about me is my intent. And my intent is this: to win at all costs, but only if it results in equal benefits for myself and my employees.

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

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. 🙂