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Give Thanks: Business Mistakes I’m Grateful For

Nobody likes to make mistakes, but sometimes they have such a big — and eventually positive — impact that we’re actually thankful for them, despite the immediate pain or problems they might have caused.

Here are the stories of three entrepreneurs, myself included, and the mistakes they’re most thankful for. Our errors provide cautionary tales that could benefit anyone who is running a business.

Consider the Why

Early in his career, serial entrepreneur Sheldon Harris worked for Costco. He shares a humbling story about assumptions and leadership.

At one point I held the position of Front End Manager. I’ll never forget an incident with a newly hired employee named Cody. Costco had a policy that three occurrences of tardiness within 30 days results in a written warning. Shortly after Cody was hired, I noticed that he clocked in late. I documented it, just like I had been trained. But, then I started watching for it. Sure enough, it didn’t take long before Cody received three strikes. I remember thinking, “I got him.” So, I wrote up a formal disciplinary notice and sat down with Cody to present it. Cody didn’t deny the tardiness. But, he did have one question, “Aren’t you going to ask why I clocked in late?” That’s a question I should have considered. But now I’m in a room with this guy and I’ve already built a relationship of conflict. “Why did you clock in late?” I asked. Cody explained that he had observed me picking up trash and cardboard in the parking lot every day when I was on my way into the building. “I assumed that if it was important enough for you to do, then I should do it too.” It was a big lesson.

Stay In Your Lane

Michael Maas had built Crave Entertainment Group to $175 million in revenue. Then Michael and his leadership team got into trouble when they expanded internationally in areas where they had little competence and nearly lead the company to bankruptcy. Realizing their mistake, they discontinued or sold off everything related to the international expansion, refocused their energy on their core domestic business, and experienced a dramatic turnaround. From this mistake, Michael learned to resist the urge to pursue the new shiny object and instead, stay focused on the core areas of your business where you are an expert.

Plan For The End In Mind

I had built a company that derived almost all of its revenue from a particular kind of loan instrument. When Wall Street dropped support for these loans, my company was left without anything to sell. We laid off 240 of our 275 employees keeping 35 people to help us reinvent ourselves. Unfortunately, we kept too many people with nothing to do. We hoped to figure out something new, but eventually we ran out of cash and came hours from filing bankruptcy. From this mistake, I learned the need to cut early and cut deep in catastrophic situations. As hard as it is to face, we didn’t cut deep enough.

About CEO Coaching International

CEO Coaching International works with CEOs and their leadership teams to achieve extraordinary results quarter after quarter, year after year. Known globally for its success in coaching growth-focused entrepreneurs to meaningful exits, CEO Coaching International has coached more than 1,000 CEOs and entrepreneurs in more than 60 countries and 45 industries. The coaches at CEO Coaching International are former CEOs, presidents, or executives who have made BIG happen. The firm’s coaches have led double-digit sales and profit growth in businesses ranging in size from startups to over $10 billion, and many are founders that have led their companies through successful eight, nine, and ten-figure exits. Companies working with CEO Coaching International for two years or more have experienced an average revenue CAGR of 31% (2.6X the U.S. average) and an average EBITDA CAGR of 52.3% (more than 5X the U.S. average).

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