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The Biggest Mistake I Made As A CEO

I didn’t plan on starting a company. I always wanted to go work for a large multi-national business and be a Fortune 500 CEO. When I was a student I looked at leaders like Meg Whitman & Ursula Burns as my role models. I started my career on Wall Street in the 80s and had a successful career in Corporate America at companies like Procter & Gamble and Coca-Cola and worked at 3 different startups as the head of marketing. I started the company right after 9/11 when the economy was in disarray and I put a stake in the ground targeting organizations that no longer had marketing departments but still needed help on a discreet basis but could no longer make a full-time commitment. The economy rebuilt, social media became pervasive, capital markets reopened but then during the Great Recession of 2008–2011, I realized the market had shifted again and clients needed to show more ROI and could no longer approve retainers so my work shifted to more project based relationships in smaller chunks even though they spent the same or more with us on an annual basis. We repositioned ourselves from an alternative agency to a strategic partner that adds bandwidth to your team and can solve problems quickly. We help our clients justify bringing us in to save time and money by focusing on quick wins that show a return so they can invest longer term in more strategic initiatives. We are problem solvers and business builders more than a vendor.

My biggest mistake was not realizing sooner that the people you start with are not always the ones who grow with you.

The hardest lesson I learned when I started my company is not getting rid of weak people earlier than I did in the first few years of my business. I spent more time managing them than finding new customers. I knew in my gut they were not up to snuff but out of loyalty to them I let them hang around much longer than they should have. It would have been better for everyone to let them go as soon as the signs were there. They became more insecure and threatened as we grew which was not productive for the team. As soon as I let them go the culture got stronger and the bar higher.

It is true that you should hire slowly and fire quickly.

I did not make that mistake again later on so learned it well the first time. I wish I had known it even earlier though but lesson learned for sure! In my experience if you are not making any mistakes you are not making any real progress either. To learn and grow you have to try new things, shake up your routine and get out of your comfort zone. It can be hard to laugh at mistakes but I remember one week when I had 3 or 4 talks lined up over a couple of day period so I went from one evening event to a breakfast the next morning to a lunch and evening talk the following day. I enjoy public speaking and get a lot of referrals and business that way. The morning after my final speech I showed up at a meeting with a prospective client along with a few of my colleagues and I realized I was completely out of business cards. I was so embarrassed and my team laughed at me since I always remind them it is important to be professional and prepared all the time. I ended up sending a hand written thank you note to the prospect with my card enclosed and we won the business so I turned my mistake into a good outcome plus I have never run out of business cards again!

My top 3 tips for turning a mistake into a business opportunity

  1. Do a post mortem when things go badly. You always learn more from failure than success so while it is still fresh on your mind take the time to look back at the key assumptions and decisions with hindsight and see what you missed so you don’t make those mistakes again.
  2. Ask for input from many perspectives to see where things broke down. Was it is communications disconnect, lack of clarity around the goal or a team morale issue? Be open to feedback so people are honest with you so again you do not make that error next time.
  3. Review the metrics and data. Sometimes it can be human nature to try to spin the story or you don’t hear the truth but the data and facts do not lie so follow the breadcrumbs and see where they lead you. Make sure you are measuring what matters most because you get what you measure. It is a shame to waste a good learning opportunity and leaders set the culture so make sure your organization embraces every mistake, learns from it and moves forward.




Business leadership advice, from real business leaders. The Helm is a carefully curated collection of insightful content from the business frontlines.

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Paige Arnof-Fenn

Paige Arnof-Fenn

Paige Arnof-Fenn is the Founder & CEO of global marketing and branding firm Mavens & Moguls based in Cambridge, MA.

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