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