The Biggest Culture Mistakes These 6 Business Leaders Made and How They Bounced Back From hiring bad apples to failing to improve communications as you scale, there's no shortage of ways to cripple a company's culture. Fortunately, there are ample ways to rebound from them, too.

By Kim Lachance Shandrow

Opinions expressed by Entrepreneur contributors are their own.


The companies featured in this article are included in our Top Company Cultures list.

When it comes to company culture, one bad apple is all it takes to spoil the bunch. A single dreadful hire can wreak havoc on a company's culture, particularly when it comes to how well employees work together.

Kris Duggan agrees. The CEO and co-founder of BetterWorks, an enterprise software maker, says hiring someone who isn't the right cultural fit -- like a disc in the spine that's out of place -- undermines teamwork and cohesiveness all throughout a company, top to bottom. Picking the wrong individual for the job, she says, has "a negative ripple effect on the organization, as the new hire pulls in a different direction than the team." In other words, it's a pain.

Related: Creating and Keeping a Positive Company Culture

Onboarding a poor cultural match is far from the only company culture blunder employers make. We asked six business leaders, Duggan included, what their biggest culture-related mistakes were and what they learned from them. Here's what they said:

1. Hiring employees who don't have that certain 'sparkle.'

Company: BetterWorks
Headquarters: Palo Alto, Calif.
Founded: 2013

As most startups know, your first initial growth spurt can be challenging to company culture. There were a couple instances when we weighted the candidate's experience and background more heavily than their "sparkle." This can have a negative ripple effect on the organization as the new hire pulls in a different direction than the team. We learned quickly that employees with passion and drive for our mission will ultimately be a better long-term fit, even if they have slightly less experience. That being said, we've been fortunate to secure employees with both the experience and the sparkle and have grown our team very successfully with these priorities in mind.

Now we're preemptively working to prevent future mistakes that could be caused by our own growing pains. Our vision, alignment techniques and mission for becoming one percent better every day are the fundamental pieces to our company culture.

-- Kris Duggan, co-founder and CEO of BetterWorks, a company that provides enterprise software to carve out and manage goals.

Related: Why This International Church-Staffing Firm Puts All of Its Eggs in the Culture Basket

2. Not staying on top of employee engagement as you scale.

Company: FlexJobs
Headquarters: Boulder, Colo.
Founded: 2007

Probably the biggest thing we've learned is that not everything we try is going to work forever. For example, in a remote company, the way meetings are conducted has a big impact on how useful they are. We came to a point when our typical meeting format was no longer useful to our team. We'd grown and we needed to change the way we were conducting meetings to make them more collaborative and action-oriented, so that everyone's time was used wisely. We did research, asked for ideas from the team, tried out new meeting formats and found one that works much better for us…for now!

-- Sara Sutton Fell, founder and CEO of FlexJobs, an online job service that helps people find part-time, flexible and telecommuting jobs.

3. Failing to regularly remind your team about company values.

Company: Clockwork
Headquarters: Minneapolis
Founded: 2002

We learned that you have to remind people about company culture. It doesn't just happen -- or at least a positive, productive one doesn't. It takes constant attention and ongoing conversations. We also learned that saying there's an open door policy doesn't mean people will proactively take advantage of that. We now have multiple channels for people to give feedback and suggestions. Culture changes and building that reality into the culture itself makes change less traumatic for people.

-- Nancy Lyons, co-founder and CEO of Clockwork, an interactive agency specializing in digital strategy, content, design and technology.

Related: 5 Secrets to Maintaining a High-Performance Culture in a Growing Company

4. Not hiring 'nice' people.

Company: TeamSnap
Headquarters: Boulder, Colo.
Founded: 2009

There are three key attributes of people who thrive in our company culture: being nice, being self-directed and communicating well. If any of those three pieces are missing, a person won't succeed. We've been good about only hiring nice people, but we've occasionally missed on the second two components and those folks didn't last long. Communication, in particular, is absolutely crucial in a distributed company. If someone can't gracefully operate in chat, email and video, they'll frustrate their teammates and create a roadblock to success.

-- Andrew Berkowitz, co-founder and chief creative officer of TeamSnap, an online service and management software for sports teams.

5. Winging it without a process or structure.

Company: MailChimp
Headquarters: Atlanta, Ga.
Founded: 2001

Early on, when MailChimp was still in startup mode, we were nervous about imposing too much structure on our teams. We thought that process would crush our creativity and thought that our values were obvious to everyone in the company. But as the company began to get bigger and bigger, we realized that we really needed—and that our employees really wanted—to deliberately promote our values and organizational processes in order to grow. Resisting structure early on made it more challenging for us to put it in place when we really needed it.

-- Marti Wolf, chief culture officer of MailChimp, an email-marketing service.

6. Not investing in tools and resources.

Company: HubSpot
Headquarters: Cambridge, Mass.
Founded: 2006

We've made a lot of mistakes throughout the years. That's part of the adventure, and I think it's important to take some chances that don't work out; otherwise, you're likely playing it too safe. Some of the mistakes that we've made throughout the years include not investing enough in training and tools for middle management and not prioritizing the candidate experience aggressively enough early on. Navigating some of the challenges that come along with global scale and culture has also been trying, such as not investing enough in thinking through tools and programs to help employees connect across offices. We're always looking to improve, so mistakes are part of the fabric of our culture. The goal is to just keep addressing them every day and getting better.

-- Katie Burke, vice president of culture and experience at HubSpot, an inbound marketing and sales platform.

Related: What Cultivating a High-Performance Company Culture Means to These 8 Business Leaders

Interested in being part of our 2016 Top Company Cultures list? Sign up to receive updates about the upcoming list.

Kim Lachance Shandrow

Former West Coast Editor

Kim Lachance Shandrow is the former West Coast editor at Previously, she was a commerce columnist at Los Angeles CityBeat, a news producer at MSNBC and KNBC in Los Angeles and a frequent contributor to the Los Angeles Times. She has also written for Government Technology magazine, LA Yoga magazine, the Lowell Sun newspaper,, and the former U.S. Surgeon General, Dr. C. Everett Coop. Follow her on Twitter at @Lashandrow. You can also follow her on Facebook here

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