In the world of startups and tech, no company or individual is immune from mistakes — even those at the very top. In fact, what defines many business executives is not that they've never made mistakes but rather that they've used them as opportunities for profound professional and personal growth.
Here’s what three tech leaders have to say about the big mistakes they made — and what they learned in the process.
Harry Hollines, Envysion’s Chief Administrative Officer, has only been with the company for two years, but he has years of experience leading business development for tech and software companies. He’s proof that you don’t work your way to the C-suite without making your share of mistakes — both personally and professionally.
The Mistake
“One big mistake I have made, and unfortunately I have made it a couple times in my career, is not making it clear what types of work, projects and initiatives that I want to work on that make me happy and excited to come to work. Often I did not make it clear what I wanted to do for fear that I would come across as selfish. It resulted in producing less than my best work and I was not fully engaged. It took me a while to realize that I was not actually being selfish but I was actually pursuing self-satisfaction, and I was losing sight of my goals and aspirations, which is actually detrimental to the company.”
The Lesson
“An important reality is that the company benefits from the latter because you are excited, focused and invested in driving value and producing results for the company. I recommend that every employee pursuing self-satisfaction understands that the outcome benefits the company as well as your yourself. That is a win/win.”
Connect First’s CEO Geoffrey Mina co-founded the company in 2005 after establishing a career as a software developer in New York. He’s the primary architect for the Connect First platform and has taken the product through five iterations in pursuit of an industry-leading, cloud-based contact center. Having been with the company from its conception, he’s seen his share of mistakes, but he’s also seen the valuable lessons that were learned and the growth that followed.
The Mistake
“At one point Connect First was being led by a CEO who chose to release an article titled ‘No New Innovations from Connect First This Year.’ Not surprisingly, it was a disaster and a giant mistake. Looking back now, I can see that his logic was sound, but the execution was terrible. It sounded like we were sitting around not doing anything, when in reality we’ve spent the last 18 months hunkered down innovating — rewriting the entire platform to make it more stable, reliable and robust.”
The Lesson
“The most meaningful lesson I learned from that was to ensure every employee who works for Connect First is properly aligned with our ethos. After that fiasco, we restructured the company and devoted time and effort to connecting with our employees in a way that’s brought about a fresh new outlook, positivity, cooperation and like-mindedness.”
Caitlyn Fagan joined the Zenman team at the end of 2011 as their Director of Project Management and quickly rose through the ranks to CEO. But despite the outstanding success she’s achieved as a young CEO, her professional journey hasn’t been without mistakes.
The Mistake
“My biggest career mistake was hiring on gut feeling only. Although certainly valuable to have in the hiring mix, using it solely can lead to turnover and will ultimately risk your business, especially when hiring for leadership positions. For me, it led to sales tanking and culture going out the window.”
The Lesson
“Now, I utilize a hiring process that includes a competency test catered to the position, a personality assessment, as well as several members of our team being a part of the interview process. It's great to like someone, but you'll end up liking them way more when they can exceed expectations for their position."
Photos via featured companies. Responses have been edited for clarity.
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