Five Questions Every Sales Manager Should Ask During One-on-Ones

Most sales managers know regular one-on-ones are important. But too often, those conversations turn into status updates, pipeline inspections, or rushed check-ins, leaving little room for meaningful development. In this episode, Matt Sunshine breaks down five simple questions that can transform one-on-ones into stronger coaching conversations. You’ll learn how to: Reinforce what is already working Uncover where salespeople are getting stuck Encourage reps to take ownership of their next steps Make skill development more focused and measurable Identify the support each salesperson needs to succeed The best one-on-ones do more than review performance. They create reflection, accountability, trust, and long-term growth. Because when managers ask better questions, salespeople give better answers, and better answers lead to better performance. Matt Sunshine The Center for Sales Strategy