Can a Jewish Man and Woman Fly Alone Together on a Private Plane?

Question: Is an employer permitted to take a female employee on his private jet to attend a business meeting?

Answer: I actually had this shailoh asked to me in the past. A male employer was flying on his private plane to a business meeting in Florida, and wanted to take a female employee along with him. The only people on the plane would be the male employer, the employee, and a non-Jewish male pilot. 

 The halacha is that when two Jewish men are alone with one Jewish woman, there is no problem of yichud [provided they are not prutzim, morally unbound]. If two non-Jewish men are alone with one Jewish woman, there is a problem of yichud. If one Jewish man and one non-Jewish man are alone with one Jewish woman, it is a machlokes haposkim whether there is a problem of yichud and it is best to be stringent. In this case, there is even more reason to be machmir, as the pilot will mostly be confined to the cockpit and won’t be keeping an eye on his two passengers. 

To get around the problem, I suggested that the employer take along another frum male employee for the trip. It should be noted that this was only a valid suggestion because they were planning on flying during the daytime. At night, even two frum men cannot be alone with one woman because there is a concern that one of them may fall asleep.