Toby (not his real name) is not short on confidence. When we met for coffee with a mutual friend, he told me everything about how to sell a business, even though he has never sold a business. Toby is the CEO of a successful manufacturing company. Though not a shareholder in the company, the owner has given Toby full control. To his credit, Toby acts and thinks like the owner. “The founder hired me in 2015 because he knew he had taken the company as far as he could,” Toby said with confidence. “But what the founder didn’t know was how his tight control over the company was killing it. The company wasn’t exactly on life support when I arrived, but it sure needed intensive care.” Toby went into detail describing the messes he had discovered, seldom stopping to take a breath. Finally, he paused for a sip of coffee, then forged right back into telling me everything he had done to turn it around. Toby was the guy wearing the cape in his own story (insert eye roll here). But beyond his annoying sense of self, I had to give Toby credit for making a series of difficult decisions. “Do you know what is more difficult than a difficult decision?” he asked me. He could sense I had no answer to his riddle, so he went on to explain,        “a difficult decision that is difficult to execute.” At that moment, I thought it was just a play on words, but as he went on to explain the decisions he had to make, his comment began to make sense to me. When he was hired, the company manufactured over 30 products with gross margins from 15% to 50%. You’d think anybody could see the logic of eliminating the low-margin products. But as Toby described it, the low-margin products were designed by the founder, and the process to manufacture them employed over 50 people. In other words, to do the obvious, dump those low-margin products, would create a lot of emotional pain for the company. But Toby explained that after making those difficult decisions, company profitability exploded, and they are poised for a 9-figure exit within five years. Though self-serving, Toby’s story makes a valid, though often under-appreciated point. Most difficult decisions are difficult to execute. Making a hard decision is one thing, then working out a plan to see that decision through has its own set of potholes and pitfalls. I’ve seen too many situations where a business owner agonizes over a difficult decision, and once he makes it, he has no energy to manage how the decision gets implemented. Many times, making a difficult managerial decision is only the starting point for a whole new set of problems. JIM CUMBEE is President of Tennessee Valley Group, Inc. a retainer-based business brokerage and transition mediation firm in Franklin, TN. Cumbee is an attorney and has an MBA from HarvardBusiness School. Jim is the author of Home Run, A Pro’s Guide to Selling a Business. https://www.amazon.com/Home-Pros-Guide-Selling-Business/dp/1599329239 .  He has a wide range of corporate and entrepreneurial experiences that make him one of the most sought-after business transition advisors in the state of Tennessee. The principles above are true, but the names and fact patterns are changed to preserve the parties’ identities.