4 CEOs share their biggest mistakes (so you don't have to make them)

Written by Lauryn Schroeder
Published on Nov. 13, 2014

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You have this big idea, something that’s going to change the tech market for the better. You build a team, you raise some money, and before you know it, you’re running your own company. It’s an exciting time for young, first-time CEOs, but it’s also the most common time for mistakes to happen. Four Chicago-based CEOs have all been there, and thankfully they’re willing to share some inside advice to help prevent you from making the same mistakes.
 
1. Adjust when things don’t go as planned.
 
No matter how much you’ve prepared, surprises are inevitable. Your business model could be the epitome of perfection during the first operation year, but when things go wrong, you have to be willing to recognize an issue, determine how to fix it, and execute the strategy effectively. In a nutshell: “Resilience is the most underrated attribute of an entrepreneur,” said Amanda Lannert, CEO of Jellyvision.
 
When the Chicago-based multimedia production company Jellyvision launched in 2001, Lannert said the company had issues with pricing its products and services. Jellyvision set a lot of variable prices in its early stage, and Lannert quickly realized she needed to make adjustments in how Jellyvision entered the multimedia production market. “We weren’t paying attention to how the market was buying in the beginning,” she said. “Once we made some changes and adapted appropriately, we really started to get traction.”
 
It’s easy to get discouraged in the early stages of company operations, when speed bumps are more frequent, Lannert said, but “those who get up the fastest will win.”
 
2. Set goals you can either hit or miss
 
It doesn’t matter if you’re managing 100 people or running an empire of one in your garage, setting and working toward specific goals is crucial to the success of every business. 
 
Ravi Bhatt, CEO of software company Branchfire, wishes he had followed this golden rule when Branchfire launched in 2011. Bhatt said instead of setting goals that challenged the team in a specific way like, “We need to get 100,000 users by X date,” his team was settling for what he calls, “sort of” goals. 
 
“We basically had it in our minds that if we were doing okay, then we “sort of” met our goals,” he said. “We were settling on being mediocre.”
 
Quantitative goals are not only the best way to accurately track progress, they’re essential for keeping a company on track to succeed. Bhatt said Branchfire didn’t start modifying the company’s goals until a couple of years in, and he’s glad the lack of numerical focus didn’t hurt the team’s success. 
 
“The only reason we survived despite of that bad habit, was because of sheer luck,” Bhatt said. “And that’s not something you want to bank on in the real world.” 
 
3. Board members are resources, not people to fear
 
Most, if not all, CEOs have worked underneath someone at one point. They’re used to having a boss, or someone they’re required to report to. According to Glenn Trout, this mindset stayed with him when he became CEO of 
VelocityEHS is headquartered in Chicago, but with out remote-first program "Work For All" we have employees fully distributed throughout the US, Canada, UK and Australia.
 
 
“I used to believe that every board meeting had to be perfect and I had to have everything figured out internally beforehand,” Trout said. “A lot of small companies live in fear of their board and it really shouldn’t be that way.”
 
Through experience, Trout said he now knows that board members are often a valuable resource to a company, providing strategic investment ideas and guidance.
 
Desiree Wrigley, CEO of GiveFoward, agreed that a lot of first-time founders tend to focus their board meetings around the financials, when they should be using that time to engage their experienced advisors.
 
“A lot of first-time founders, we get our first check, and we’re so eager to prove them right and get them their money back,” Wrigley said. “But the focus should be on getting more useful interactions between you and your board.”
 
Wrigley said communicating financial information is important, but should be done between meetings. CEOs should focus on maximizing their face-to-face time with board members during meetings by asking specific questions and having productive conversations about the future of the company. 
 
“The meeting should be used to try and get value out of the relationships,” she said. “If engagement gets stronger in the meetings, the relationship will too, and they’re going to be more likely to help out when you really need it.”
 
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