446- Why IT Leaders Should Not Lead With No w/Bret Henning

Bret Henning started college as a music major and entered technology through a trade school and a computer operator job. He handled backups, printers, support, and disk drives before moving into programming and application work. Building systems for accounting, payroll, inventory, and manufacturing gave him an education in how a business runs.Bret traces the shift from computers as an after-the-fact record to computers as the place where work happens. He recalls how Y2K made technology’s place in the business harder to ignore and describes an early web sales interface that turned month-end reports into current information people could act on during the month.The conversation then turns to shadow AI. Bret explains why an immediate no can drive employees around IT instead of changing their behavior. His approach starts with questions, listening, and a clear explanation of risk. IT still has to offer an option that meets the employee’s need. He also shares why he hires teachable people with customer service experience, how empathy affects vendor and employee relationships, and why trust starts before a difficult business conversation.