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Go ahead and cry at work. You’ll be a better leader for it

Wonolo’s CEO observes that even in this new era of work, there hasn’t been enough emphasis on prioritizing safe spaces and healthy expression of feelings in the work environment.

Go ahead and cry at work. You’ll be a better leader for it
[Photo: Engin Akyurt/Pexels]

I was standing next to my cofounder when he announced his departure from the company at our team’s all-hands meeting a few years ago. He gave a beautiful speech about his journey of building the company and shared several words of wisdom for the team to carry on. He then turned to me to see if I wanted to add anything. I looked at him and the audience. At first, I could not utter a single word. Instead, tears started rolling down my face.  

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About a decade ago, showing any sort of emotion at work was seen as unprofessional. However, this sentiment has shifted over the past ten years as workers, particularly millennials, began to prioritize a healthier work-life balance and move away from toxic work environments. 

When the pandemic hit two years ago, the line between work and life really began to blur, and it accelerated this prioritization. Leaders faced a moment of reckoning as work often had to take a back seat in order to navigate through a global health crisis. Many companies stepped up to the plate, providing unparalleled levels of flexibility and mental health support. As a result of these efforts and increased remote work, complaints about toxic work environments decreased while more CEOs integrated empathy into their leadership style. 

Even in this new era of work, however, there hasn’t been enough emphasis on prioritizing safe spaces and healthy expression of feelings in the work environment. Today, the workplace remains in a state of uncertainty as employees continue to quit at a record-breaking rate and millions of jobs go unfilled. While the pandemic certainly put things into perspective for many leaders, it’s not enough to offer psychological safety in the workplace only during unprecedented challenges. Employees always deserve to feel safe and supported.

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In order to attract and retain employees, especially happy employees, leaders need to prioritize psychological safety in the workplace and embrace the power of being vulnerable. 

Vulnerability is a strength, not a weakness 

We’re at a point where leaders are starting to show emotion in the workplace, but it’s important that we go even further to break down existing stigmas about expressing feelings at work. When leaders show authentic emotion, and encourage the rest of the team to do so, they help promote meaningful connections across the workplace. When leaders build up walls and only show themselves solely through a business persona, it limits employees from truly connecting with them. 

Research has found that workers need emotional communication from leaders. In my experience as a CEO, being vulnerable and expressing my true feelings, whether it’s crying over a sensitive issue or expressing concern over business outcomes, has enabled my employees to do the same. Being vulnerable serves as a reminder to the team that I’m human too, and leads to better, more open communication and a more positive work environment. While the idea of bringing your authentic self and vulnerability to the workplace is growing among leaders, we’re not completely there yet as only 44% of C-suite leaders believe it is okay to cry at work. 

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Creating psychological safety in the workplace 

In order to develop a workplace where employees feel comfortable being open about their feelings, CEOs (and all leaders) must establish an environment that feels safe. Psychological safety in the workplace means employees feel comfortable voicing their opinions or feelings without the fear of negative consequences. Since every employee is unique and every workplace is different, it can be difficult to create an approach to psychological safety that works for everyone, but the best approach is to start from the top. 

CEOs can lead by example by having open, empathetic, and transparent communication with their employees. For example, if there’s a day when I’m addressing the entire team and I’m supposed to spark motivation but for some reason I’m not feeling motivated myself, I’m open about my feelings. It can be as simple as saying “I know during this meeting, I should be lifting you all up to hit your monthly goals but to be honest, today I’m not feeling up to doing this,” and then explain your reasoning for why you’re feeling this way. Opening up and practicing what you preach encourages the rest of the team to do the same. When employees have a deeper understanding of their colleagues’ mindset, it allows them to approach conversations with more compassion, creating a more positive work culture. 

The rewards of vulnerability and authenticity 

Creating psychological safety in the workplace also means encouraging people to bring their authentic selves to work. We spend so much of our time at work. Why should we leave who we really are at the door? If employees feel overwhelmed with emotion about something that’s going on inside or outside of work and need to cry, that’s okay. If they’re feeling unmotivated at work and express this, that’s okay too.

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The point is: we are all human and should be treated as such at work. When CEOs and other leaders embrace this mentality, companies can experience direct and positive impacts. In fact, studies have found that when people believe their leaders are empathetic, they are more likely to be more innovative and productive at work, and turnover rates are much lower

No matter the size of the organization, employees should never be treated like a number. We’re all human, and we all experience our range of human emotions. Getting to a point where employees or leaders feel comfortable enough to cry at work typically means the company is doing something right. So, for all you leaders, I urge you to take a step back and ask yourself: “Would I feel comfortable crying at work?” If the answer is no, it’s time to get down to why. 


Yong Kim is the CEO of Wonolo.

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