Yes, I've had this situation a few times, when renting far away, or being "checked out" to do a test flight on someone else's aircraft. I pay close attention to the apparent ease of the "instructor" in the right seat, if they are looking around the cockpit like a lost puppy, I'll exercise more caution about them! There has been more than one occasion where late during, or after a flight, the instructor has asked me "how I did that" for something I'd flown during the check flight.
And. I'e been on the "instructor" side of this a few times too, having to train or check a pilot out in a type not familiar to me. Three things: Read and understand the flight manual, solo rehearsal in the cockpit before flying, and a solo flight, including stalls, and a few circuits before the dual. With those cautions, I've never had a problem. There have been occasions where right up front, I have declared that I am unfamiliar with certain advance avionics in the plane, just so we both knew. In that respect, I have found some newer pilots to be more up on the avionics than I. Preflight briefing, and all was well!