“I don’t know, Jim, I think it’s time to sell. I just can’t seem to pull the trigger.” I met Jack (not his real name) a few months ago because our grandsons play on the same baseball team. We’ve never talked business, but recently Jack casually asked, “How's the market, Jim, are you staying busy?” That opened the door to talk about the current market for private businesses, at which point Jack opened up about his thinking. I assume Jack is in his mid-60s, and he looks a bit tired. He told me he’s been thinking about selling, but he hadn’t come to terms with the timing. “I like what I do,” Jack said, “but it seems the everyday things are beginning to wear on me.” Jack’s business is too small for a private equity buyer but too large for an individual buyer. Therefore, when it’s time to sell, Jack will likely be talking to strategic buyers. That’s why I suggested we spend an hour or two whiteboarding the names of companies that might have a strategic interest in his. I told Jack I had developed a template to facilitate this process. Once we have listed the names of potential buyers, we can then begin to think through strategies to discreetly gauge their interest in Jack’s company. I told Jack that just waiting for them to come to him might work, but if selling is on his near-term radar, a degree of proactivity will be productive. Selling to a strategic buyer requires artful outreach and thoughtful planning borne of having done it many times. My guess is this summer Jack and I will have more conversations as we watch our grandsons on the diamond. 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.