In Episode 19 of Do Diligence, I sit down with Kelly Conway and Rob Elliott to explore the intricate dynamics of a small business deal from both the buyer’s and seller’s perspectives. This episode marks a unique occasion as we bring together the insights of a buyer and seller simultaneously. Kelly, a seasoned executive, acquired Rob’s company, Pondera, which specializes in leadership consulting. We delve into their experiences throughout the transaction, discussing the emotional and operational challenges they faced, the importance of communication, and the strategies they employed to foster trust. Both share valuable lessons learned during the process, including the critical role of aligning expectations and the necessity of involving key team members early on. Whether you’re considering acquiring or selling a business, their insights will provide you with essential guidance for navigating these complex transactions.