I am working in a lawyer’s office. The lawyer is frum, but on the modern side. There is a client that came in and the lawyer shook hands with her. Afterwards, the lady extended her hand to me. My practice is never to shake hands with any lady under any circumstances, with no exceptions. What should I do, to avoid embarrassing my boss? It is obvious that we are both Yidden, so I cannot say that for religious reasons I don’t shake hands.
The fact that he is your boss doesn’t matter here, because in any case the woman may get embarrassed. Do whatever you would do in any other such situation to avoid causing embarrassment. You can make sure to hold something large in your right hand, so it will be awkward to move it to the other hand and shake. You can bow slightly, as a show of respect, and that will give her the hint. You can also say that your custom is not to shake hands with women.