A Tech CEO Shares 4 Lessons Learned the Hard Way

At the start of 2009, I was in my 10th year at Net Friends, and I had just become a minority owner in the business. We had recently spun off our sister company, enabling us to focus our 16-person team solely on IT support services. Over the next 4 years, we grew 40% year-over-year, quadrupling our revenue and tripling our headcount to 47 people total.  

Despite these positive growth numbers, I was overwhelmed and unhappy – working at an unrelenting and furious pace yet still falling behind. I made a series of decisions that, if I had to do it all over again, I would not repeat. I’m sharing these missteps and lessons here in the hopes that my hard-won knowledge can help you find a shorter path to success.

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#1 - Failing to Appreciate Organizational Structure

Although we initially celebrated our flat structure and didn’t give much thought to job titles, this does not scale well. By August 2012, I had 45 people reporting directly to me because I had not promoted or hired any managers. Failing to implement some managerial infrastructure when we got to 10-15 people created all sorts of problems, problems made even more difficult to correct as we scaled up year after year.  

Lesson Learned: People perform far better when they understand their role, how their role relates to other teammates, and when there is accountability and job performance guidance that is best handled by a dedicated manager. Backfilling organizational structure is incredibly hard and tricky, and it is much better to have a structure in place that you bring people into vs. imposing a new structure on your team.

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#2 - Wearing Too Many Hats for Longer Than Necessary

All businesses are sustained in the early days of their existence by the founder(s) and first employees performing a wide variety of tasks. For me personally, I failed to relinquish working directly with customers and performing billable work. Even when I had 45 people reporting directly to me in 2012, I was putting in 30 hours per week directly supporting customers. The story I told myself at the time was that it was more efficient for me to just keep doing those tasks because the transition costs of delegating them to someone else was too great. Typically this thinking is just rooted in anxiety or pride, and the result is you fail to free yourself to focus on new challenges or have the time to focus on other important matters that need your attention.

Lesson Learned: When you relinquish responsibilities to your team by delegating tasks to the appropriate handlers, you gain back cycles to focus on growing and optimizing the business. You also empower the people on your team to deepen and grow their expertise as they absorb more upskilling opportunities.

Go to Part 2

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‍If you would like to chat with me and unpack further any of the lessons above, please reach out to me directly via LinkedIn.