How to tell if a CEO is worth working for

If you’re looking to leave your company to work for another, you’ll want to consider this.


A few months ago, someone asked me for advice about potentially leaving one company to go work for another. He was curious what factors he should consider before making the decision.

He’d already vetted the role, the company, and the offer itself — all important aspects to consider. But I told him, in my opinion, the most crucial thing to vet is the CEO.

If you’re about to join a new company, you must figure out:

“Do I believe in the CEO?”

No company is successful with a CEO who can’t communicate, who can’t get everyone on the same page, who can’t hire well, and who can’t chart out a vision.

Personally, I remember interviewing at one of my first job out of college, and I remember it being really hard to tell if a CEO is “good” or not.

Plenty of CEOs sound like they’d be a good CEO. They’re charismatic, they’re articulate — but does sounding like a good CEO really make it true?

After almost four years of researching and observing hundreds of CEOs, I’ve learned to ask these four questions to discern whether or not a CEO is a good CEO:

#1: “When have you had to sugar-coat the truth — or avoid telling the truth — to your team?”

How a CEO answers this question reveals her barometer for integrity. Your CEO might laugh and say, “Oh, all the time,” a little too flippantly — signaling that she intentionally misguides employees habitually. On the other hand, if a CEO is too hesitant to admit anything substantial, that’s a red flag as well. It’s likely she’s holding something back. Ideally you’re looking for a CEO to level with you and admit in a nuanced, considerate way when she’s chosen to not be transparent with the team, and why.

#2: “What do you think is your own greatest leadership blindspot?”

This is a take on the classic, “What do you think your greatest weakness is” question — but with a twist. The word “blindspot” implies that the CEO has a weakness she might often overlook. So her answer to this will reveal her self-awareness. Does she have a hard time giving you a straight answer? Or is it clear that this is something that she’s thought a lot about, self-reflected upon, and perhaps even talked about with peers or an executive coach. If it’s the latter, it signifies that this leader has the humility and self-perceptiveness you’re looking for.

#3: “What does ‘success’ for the company look like to you?”

This may seem like an unassuming question to ask — perhaps it’s one you’ve asked the CEO already. However, we often don’t listen closely enough to the answer. If all the CEO is focused on is “winning” and “making money” and “dominating the competition” in her answer, I can guarantee that’s 100% what the work environment is going to revolve around. On the contrary, if she also talks about creating a sustainable, healthy culture, and making sure people feel fulfilled, challenged and supported in their jobs — you can bet that the work environment is going to reflect that. The answer to this question makes is crystal clear what a CEO’s priorities are.

#4: “What would an employee who’s left the company say it’s like to work for you?”

This may feel like a tough question to ask you prospective CEO — especially if they haven’t hired you yet. But it potentially is the most important question. The answer to it demonstrates how cognizant the CEO is of how they’ve treated employees in the past, and how willing they are to admit if they’d haven’t been the ideal leader. Be wary of CEOs who say only positive things, as it shows their refusal to recognize their shortcomings, or failure to understand how their own leadership behavior may have driven the other person away.

If you’re worried that asking these questions — particularly the last one — might offend your prospective CEO, that in itself is a sign that the CEO might not be who you’d hope for. The best leaders welcome tough questions, and will be impressed by your desire to better understand how they lead.

If anything, asking these questions will make you look better in their eyes. And, it gives you all the information you need to decide if they’re a CEO worth working for.


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P.S.: If you enjoyed this piece, please feel free to share + give it 👏 so others can find it too. Thanks 😊(And you can always say hi at @clairejlew.)

This article was originally published for Inc.com where I write a column on leadership.


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