Workplace Culture Doesn’t Matter. Until It Does.



11 min read

Opinions expressed by Entrepreneur contributors are their own.


Every company has a culture from the very day the decision is made to start it. Whether your culture is intentional or accidental, it’s there. And it governs all the explicit and subtle, obvious and invisible ways that it’s OK to behave in your workplace. 

Behavior is the driving force. It’s not what you’ve written down, or what you hope it to be. It’s actually how the people behave, particularly in their interactions with one another. 

The healthiest cultures are ones where the people who founded the company and those that join have a mutual understanding of shared values and expectations. 

Recently, companies that thought everyone was on the same page found out they weren’t. Google, Coinbase and Basecamp have all faced major conflicts between the definition of culture defined by “leadership”and what the “team” experiences and cares about. Even though they all had their values written down, there is still plenty of room for interpretation.  

Related: Why Everything You Know About Employee Engagement Is Wrong

Up until these clashes, everyone “thought” they shared the same values and culture—so, how’d they get it so wrong?

The truth is company culture is serious, messy, human, interpersonal and complex. There is no formula, but there are principles we can use to be purposeful about the culture we build. Here are three that I believe are more important now than ever:

1. Trust

If you’ve read The 5 Dysfunctions of a Team, you know that trust is the first step in building a strong culture. Why? If colleagues don’t trust each other, they won’t be honest with each other. And if they’re not honest with each other, you’re doomed. There is no greater “tax” on any organization than mistrust. Trust is the currency of progress on a team. It’s a lubricant, like the oil in your car. Without oil, the parts of your engine grind away on each other and the engine fails. With oil, friction is reduced and the engine will take you anywhere you want to go. 

The fastest avenue to trust—and the most uncomfortable—is our willingness to be vulnerable. When teammates feel comfortable sharing themselves, they will work together more effectively—they will share feedback openly with each other for the company’s greater good—even if that means saying they disagree. Or, as we’ve seen during the pandemic, pointing out what we as leaders might be missing—like how our colleagues are coping with working from home, increasing hate crimes, social justice and even heated political discourse.

Conversely, if colleagues don’t trust each other, or fear being chastised for saying “I don’t know” or “I messed up,” the entire company could suffer as a result. At the individual level, lack of trust and vulnerability between teammates creates anxiety and tension, which reduces productivity. At the company level, this type of negative culture harms employee retention and stifles innovation.

Related: 4 Lessons from Steve Jobs That Are Still Relevant 10 Years After His Death

How do we create a culture of high trust? As leaders, we set the tone by being vulnerable with our teams and encourage them to share openly how they feel, too. Most importantly, do not punish people for being honest, as long as they are respectful and coming from a place that’s aligned with the culture’s values. 

At the start of the pandemic, Upside went fully remote and established a ritual: every morning at 8:45 am ET we get on a 15-minute (often 10 minutes or less!) Zoom as a company for rapid-fire updates ranging from our progress against quarterly OKRs, to who’s the HeyTaco winner of the week. At one of our monthly Director’s meetings, someone brought up the fact that they “hated” the frequency of our all-team meetings. I took the feedback and spoke with other people across the company to hear their perspective—a few thought we could change the cadence, but the vast majority felt the daily 8:45 am kick-off enhanced the culture. We kept the cadence and timing, I closed the loop with the person who expressed themselves on why, and I shared how grateful I was they voiced their point of view.

That situation reinforced my belief that successful companies thrive on feedback, but it also reminded me how important multiple sources of feedback at all levels and types are to minimize the risk of missing critical insights. At Upside, we’ve opened up a variety of channels to get feedback from the team beyond employee surveys and one-on-ones; my favorite is our monthly “Ask Me Anything” forum where tough questions are encouraged and vulnerability is celebrated. Just like customer discovery, it’s critical to make space for your team to give feedback and it’s crucial to get enough signal to know what to do with it. 

2. Individuals 

Many organizations quickly jumped to work from home when the pandemic hit—either the entire company or large groups of knowledge workers. As a result, we’ve gotten to know each other at a much deeper level—we are literally beaming ourselves from our homes. “I have four children” is an abstraction to my teammates until my college student taking classes from home wanders through a video meeting to grab a printout. We’re all getting to know much more about each other’s personal lives than ever before. And I believe this is both a great thing and one that is challenging many business cultures.

Some folks have children crawling over their laps during internal meetings, or they have a dog barking in the background during a client presentation. At this point, I’ve had a hundred Zoom conversations interrupted by our dogs letting me know that the mail carrier has once again done their job. While these situations can be “disruptive” to work in the traditional sense, they only scratch the surface of the distractions our teams may be dealing with on a daily basis. 

Consider our BIPOC colleagues. How are our Black coworkers getting through days when the news broadcasts that yet another unarmed civilian was shot dead by police? What does that do to their ability to concentrate on the presentation they are on deadline for? 

What is daily life like for our Asian colleagues who are enduring hatred and violence from bigots who wrongfully blame Asian communities for inciting the pandemic itself? Could there be something outside of work affecting their uncharacteristic lack of performance last Friday?

Related: 4 Keys to Increasing Productivity and Working More Efficiently

Of course, we’re talking about pervasive issues of racism and discrimination here. And I fully admit that our company culture is not going to change the world overnight. But, at a minimum, we can certainly do our part to create a culture that helps our team persevere through it all by giving them space to experience whatever they may be going through. 

It’s the kind of example we set that defines what we really mean by diversity and inclusion. Showing real acknowledgment and empathy is important to the individuals experiencing stress or anxiety and it sets the tone for the rest of the team. 

After George Floyd was murdered we shared one of the most powerful experiences for our culture at Upside. This was a moment where there was no standing still as a leader. I felt compelled to address the team, not only because of the intrinsic importance but also because not acting would have been equally defining for our team. Instead of running through the day’s priorities, I planned to address our shared trauma. What I did not plan for was being overwhelmed with emotion in front of our entire team, but my limbic system had other ideas, including lots of crying. My hope is that it created space for others to feel comfortable being vulnerable themselves.

3. Support 

We need to recognize that we’re all dealing with an array of issues in our lives, and it’s important from a company culture standpoint to understand that those “personal” challenges are coming to work with us. Many of our full-time employees spend more time communicating with their work colleagues than they do their own families. Which means they rely on each other for support and our company culture should allow everyone on the team to feel part of an inclusive workplace environment.

As leaders, we can support our colleagues to be more successful by creating a culture that accepts everyone. That means empowering our teams to support one another and giving them the freedom to express themselves. 

For some people, that may mean giving them space (aka time off) to deal with issues affecting them outside of work. Others may want to talk about it as a group or one-on-one (see my first point above about creating a culture of trust). There is no instruction manual. You simply have to be empathetic and willing to listen. The worst thing we can do is ignore these gnarly societal issues and pretend that they will not affect our team’s performance during the “work” day. Because they most certainly will. 

If we encourage discourse and listen to feedback, we are able to make adjustments when appropriate and acknowledge that we may not be able to “fix” everything.  

I’ve been leading companies for decades, and I am nowhere near a perfect leader. I believe in being resilient, and I expect my team to tell me when I’ve messed up. I want to continue to learn and improve how I support the team. 

At Upside, we’ve been very intentional about seeking to build a culture of diverse individuals and perspectives. People care for each other and support one another naturally. The benefit of this is that it has created space for me as a leader to actually learn, engage, and open my eyes to some things that I was oblivious to. 

As a result, I have been able to have some uncomfortable conversations with a number of my colleagues who trusted me enough to talk to me about hard things. Even better, the environment we’ve built at Upside empowers the team to speak with and support one another, and that’s something to be proud of. 

Is it possible to change a company’s culture?

The first step to changing a company’s culture is to identify what the current culture actually is. The way to find that out is to survey the team and speak with a cross section 1:1 Is there high trust? Is vulnerability acceptable? Are individuals recognized for who they are? Do teammates support one another? What are the behaviors and values that are apparent and accepted among your colleagues? How do those values line up with the written values? How open are people to talking about topics of race, gender, or sexual orientation? Are you really ready, as a leader, to listen and make change?

We’re constantly monitoring these (and more) and even setting clear company-wide OKRs to address them. We start small, run experiments and adjust. It’s hard work, but most things worth doing are hard. If you are a leader that’s got an awesome culture, I’d love to hear from you. And if you are a leader struggling a bit, I’d be happy to support you.



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