Gary Vaynerchuk Talks About Building a Healthy Workplace Culture and Cultivating Kindness

Initiating and navigating difficult conversations is a common challenge for business leaders, including Gary Vaynerchuk, the CEO of VaynerMedia and chairman of its parent company, VaynerX. I spoke with him after reading his latest book, Twelve and a Half: Leveraging the Emotional Ingredients Necessary for Business Success. I wanted to learn more about his efforts to be a more effective communicator and stronger leader by combining kindness and candor. 

The similarities in our perspectives are striking, especially given our very different communication styles. Gary has a quick mind and bold, outgoing manner, whereas I am more deliberate and reserved. But we are both passionate about the power of self-awareness and kindness to help people lead more fulfilling lives at work and home. So I wanted to dive into this a bit more and see what we could learn from one another.

Gary was friendly and forthright. He spoke openly about his greatest challenges as a leader and the steps he is taking to address them. Over the course of our conversation, we identified a five-step process to improve communication by combining kindness and candor:  

  1. Acknowledge your default position. 

Gary often credits empathy and kindness for his business success. But given his public persona, I was surprised to learn that he tends to sacrifice candor for kindness in his relationships. 

His natural tendency is to lead with trust, which is a rather unusual way of relating to people in the workplace. "I have enough self-confidence that giving trust instead of having it earned is incredibly easy for me," says Gary. "I think that comes with giving people the benefit of the doubt. I go into every situation, even ones that are strikingly black and white, with the hope that there's some rationale or explanation for what seems to be a very obvious misstep or negative move."

His observation about the connection between building trust and giving others the benefit of the doubt is also validated by my proprietary communication model, which I teach in my program, The Communication Protocol. Giving and receiving the benefit of the doubt allows us to grow trust, connect, and move on from conflicts. 

But there is a crucial difference between giving people the benefit of the doubt and making excuses for their behavior. Gary knows that his "bleeding heart" tendencies sometimes lead him to shy away from being candid with people who take advantage of his kindness or underperform at work. 

  1. Understand the impact of your behavior. 

What happens when you sacrifice kindness or candor? You risk damaging your company culture. If you are too candid, you risk coming across as a mean-spirited bully. If you are too kind, you risk coming off as a push-over instead of a leader. 

"At some point, I had to talk to myself about my lack of candor," says Gary. He was using his desire to be kind as an excuse to avoid difficult conversations, and he and his team were paying the price. After failing to address an employee's poor performance, he realized that avoiding the issue sent the wrong message: "Some of those people even became entitled and delusional about their skillset."

  1. Explore your underlying beliefs. 

Your beliefs shape how your approach kindness and candor. "Unfortunately, people are so binary with these things," says Gary. "Like, if you want to build a big business, well, you better have sharp elbows, and you better step all over everybody -- I just never saw it that way."  

And that mindset made it easier for Gary to believe that everyone was doing their best and that no one would try to manipulate a situation to their advantage.

Kindness in the workplace creates a safer environment for everyone, and it should be a given. But it can't take the place of addressing performance problems or workplace conflict. As leaders, we need to be both kind and forthcoming about our expectations. 

  1. Take responsibility for your approach. 

By paying attention to how we communicate and how others respond to us, we learn what works well and what we might need to modify. When we take responsibility for our behavior, especially for a mistake or wrongdoing, we demonstrate that we are accountable to ourselves and our teams. It allows others to trust us again - provided that we take steps to change our behavior.

"The fact of the matter is, most people just don't want to be accountable," says Gary. "I don't think it's known or accepted in popular culture, but accountability is one of the quickest ways to get to happiness." 

That happiness comes from aligning your behavior with your values. Once Gary realized that his lack of candor was out of alignment with his values, he addressed it directly. 

  1. Find your balance. 

Finding the right balance between kindness and candor will take time. You have to be patient as you practice a new way of communicating.  It won't always be easy, and you won't always be perfect. But it's worth the effort. 

Kindness and candor don't have to be in an antagonistic relationship. You can combine the two and start practicing kind candor. "That's where you get the magic," says Gary. That subtle shift reframes the nature of candor and makes difficult conversations a lot easier. 

Initiating and navigating difficult conversations in the workplace is a skill that takes time to develop and there are practical tools that can help. That's my area of expertise. But you never have to sacrifice kindness or candor. You can take a page out of Gary Vee's book (literally!) and practice kind candor. 


©Copyright 2022 Debra Roberts, LCSW All rights reserved. No portion of this material may be reproduced without permission from the publisher.

A version of this article was initially published on as: Gary Vaynerchuk on the Power of Kind Candor