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Oct 21, 2015
by James

Hiring for Culture Fit with Gary Vaynerchuk

Posted in Great Interview Questions

Hiring for culture fit

I’ve been a fan of Gary Vaynerchuk since the early days when he was pioneering the use of video content to grow his family wine business via WineLibrary TV.   I’ve read all of his books on the power of social media and, most recently, I’ve enjoyed his high energy rants on the #AskGaryVee Show.

Whenever I consume content these days, I listen for clues of how high growth companies – like Gary’s “Vayner Media” business – are conducting interviews and selecting talent.  I do this because innovative companies typically have an unorthodox approach to hiring.   Even if I don’t agree with what they’re doing, it still makes me stop and question all the conventional wisdom that drives my beliefs about talent acquisition today.   And if I’m not questioning the norms, I might as well just leave the profession.

On some recent episodes of the #AskGaryVee Show, I’ve noticed that Gary has been talking a lot about interviewing and HR in general.  He’s been consistent in how he describes his approach to interviewing so I thought I’d take a few moments and unpack his strategy because it goes against what I typically preach.  And even though it runs contrary to my own beliefs,  it makes total sense for his role in the organization and I think there is a ton of value to his process.


On Episode 152, Mark Cuban submitted the following question:

“Hey Gary…I’d like to know what your    “go-to” interview questions are.  The questions you have to ask every candidate that you interview, every time.”

While Gary doesn’t answer Mark’s question directly, he made some interesting points that I thought were worth sharing and learning from.   The following are excerpts of his rant along with my best interpretation of his interviewing strategy:

Point 1:  “With interviews, I really try to reverse engineer what the person wants.” 

This was one of the areas that Gary was most passionate about.  What he really likes to do with candidates is find out what their “end game” is.  What do they ultimately want to do?  If they want to start a competing Agency, he’s fine with that.  He just wants to know the truth so he can help them achieve their goals faster.

While I would typically advise clients to look for people who ultimately want to grow at their company, this is a refreshing approach to hiring that I see more often in startups who value talent over tenure.   When you know someone’s motive, then you hold the key to motivating them.   It’s a genius way to amplify employee engagement.   I think larger companies could learn a lot from this philosophy.

Point 2:  I try to break down a person in an interview within the first few minutes of meeting them — to get them to fully trust and believe in me.”

I don’t think Gary was insinuating that he does a “hard sell” on his candidates in the first few minutes.  What he’s getting at is something that’s really important to him from an engagement standpoint — “buy in”.  Does the candidate buy into Gary Vee and does he or she trust that Gary is going to make decisions that are in the best interest for THEM.

Ultimately, TRUST is a huge factor in engagement and it sounds like Gary knows this in his core.   He didn’t discuss “how” he breaks down the applicant, but I would guess that he has an enthusiastic, off-the-cuff, elevator pitch that lets the candidate know exactly what they’re getting into when they join one of his companies.

Point 3:  “When I interview, there’s times when I’m in complete Charlie Brown mode.  I don’t hear a word you’re saying…I’m just going by the feel.”

For those of you who don’t know what “Charlie Brown Mode” is, check out this link.  Basically, what Gary is eluding to is that sometimes interviewing is less about the questions and answers and more about the feeling you get in the presence of another human being.

It’s the hardest thing to quantify from an interviewing perspective but human intuition is a sixth sense that all great interviewers develop at some point.   Be careful though…it’s just one data point that you should evaluate across your entire interview process.  It shouldn’t receive a disproportionate amount of value.

Point 4:  “I ask almost everybody about siblings.”

Gary didn’t have a really strong belief around this statement – nor did he go into much detail – but I think I understood what he was trying to say.   In the hiring process, it’s really common for people who grow up a certain way (or who go to a certain school) to have a belief system about what makes someone capable of being successful.   HR practitioners call this a “bias”.

In Gary’s case, from what I could gather, he has a belief that there is a connection between people who have siblings and people who play nice together at work (aka Collaboration).  Presumably because of how he grew up.

Now, most HR folks would steer you away from using bias in the interview process — and rightfully so in most cases — but it’s important to note that biases can often be like clichés — there’s some truth to them or they wouldn’t exist.

For the record, I think there are better ways to assess someone’s ability to be collaborative so I don’t support asking about siblings, but if it works for Gary – and he’s okay with the risk – he should use this question as a part of his selection strategy.   My guess is, you probably can’t convince him otherwise!


From what I could tell, there are no competency-based “Tell me about a time when…” behavioral interview questions from Gary.   No case studies.  No trick questions.   Nothing that sounds remotely like a traditional interview.

No sir…

That’s because Gary’s role in the interview process is what I like to call the “Culture and Motivation Auditor”.   And for a CEO, who is probably the final interviewer, that’s exactly what he should be doing.

A Culture and Motivation audit is simply a relationship-oriented interview in which you and your candidate sit down and have a normal conversation between two adults.   You absolutely have some pre-planned “go-to questions”, but it shouldn’t feel like an interview.  It feels more like a counseling session where you’re really trying to get at the core of why someone wants to work for you, what they ultimately want to do with their career and how they fit into the organization and the job.   You want to make sure that they will be engaged in the vision.

There’s a time and place for structured, behavioral and achievement-oriented questions, but it’s not when you’re meeting with a top executive after several rounds of interviews.  Especially when that executive has an EQ as off-the-charts as Gary Vee’s.

In Summary

While Gary’s approach to interviewing has some unconventional parts to it, overall I think there is some learning to be had in how he spends his time focused on hiring for culture fit and motivation.    For him to have the freedom to focus solely on this, as opposed to technical skills, is a testament to how his HR team screens candidates before they get to him.

As for Mark Cuban, hopefully he extracted the same learnings that I did, even though Gary didn’t divulge his specific “go to” questions.    It would be interesting to hear the question asked in reverse as I’m sure that Mark has some interesting interview practices to learn from as well!

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