Ten Questions To Ask In Your Next Employee One-On-One

BusinessTen Questions To Ask In Your Next Employee One-On-OneByChristopher Kaufman,Forbes Books Author.for Forbes BooksAUTHOR POSTExpertise and opinions of authors published by ForbesBooks. Imprint operated under license. | Paid ProgramJun 01, 2026, 12:25pm EDT--:-- / --:--This voice experience is generated by AI. Learn more.This voice experience is generated by AI. Learn more.Empathetic leadership creates better employee one-on-ones.gettyMost employee one-on-ones are little more than surface-level check-ins—something that comes up on the calendar that both employer and employee want to check off and get over with. However, treating one-on-ones in this way means a missed opportunity to create space for honest dialogue. Empathetic questions are the key to having a productive conversation that will encourage openness and build trust.The Value of Empathetic Questioning in Employee One-on-OnesEmpathetic leadership is essential to creating a psychologically safe workplace—and that has tangible benefits for individuals and businesses alike. Psychologically safe organizations see significantly 76% higher engagement, for example, and 50% greater productivity.One way to create a psychologically safe workplace is by creating frameworks for feedback—like employee one-on-ones. Of course, it’s not enough to just put those frameworks in place; you want to make the most of them. That means practicing active listening and actually acting on the feedback you receive.Ten Empathy Building QuestionsSimon Sinek has a well-known story about a conversation he had with a barista at a Las Vegas hotel—Noah—who seemed to be exceptionally happy at work. Upon questioning, Noah revealed that he really liked his job and one reason for that was the supportive management, who would often stop by his coffee station and ask, “Do you need anything to do your job better?” That was it. A simple question showed Noah that his managers were supportive, caring, and watching out for him (rather than watching...