Bob Calls: Roleplay in Training

trainees-employees-mentors-appraising May 10, 2026

I had a coaching conversation recently that reminded me of a practice I’ve used for years but don’t talk about nearly enough. We were discussing how to move someone from a behind-the-scenes role into a front-facing position, and it surfaced a common mistake business owners make: assuming that someone who excels in the back office will naturally do well on the phones. In my experience, that’s rarely true. Most people are wired to be great at one or the other, and finding someone who thrives in both roles is the exception, not the rule.

That’s where training becomes critical, especially when it comes to customer-facing work. One of the most effective tools I’ve ever used is something I call “Bob calls.” It’s simple roleplay, but done intentionally and transparently. I let my team know upfront that I’ll occasionally call the office pretending to be a client. I’m always Bob. Sometimes I’m calm and reasonable. Other times, I’m frustrated, confused, or downright unhappy. The goal isn’t to trick anyone or play “gotcha,” but to create a safe way to practice real-world scenarios before they happen.

After the call, we break it down together. We talk about what went well, what could have been handled differently, and how to improve next time. Sometimes we even record the call so we can review it objectively. This approach has been invaluable, especially when hiring new team members. It quickly reveals how someone handles pressure, uncertainty, and difficult conversations.

The reality is that tough calls will happen. Clients will be upset, emotional, or demanding. Practicing those moments ahead of time builds confidence and competence. Over the years, these roleplay calls have helped my team deliver better service and respond with professionalism when it matters most. Small practice, big payoff.



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