Express your heartfelt sympathies. Some example messages would be, please know I am thinking of you during this painful time.Writing a letter of sympathy and condolence can be a comfort to people who have recently lost a loved one. Here is my suggestion on what to write in a sympathy card or message to your boss: "Please accept my condolences on the death of your ____. Writing a condolence message is an emotional task. Here's tips and examples of how to sign a sympathy card for coworkers, friends, and more. Avoid using uncomfortable words that may indicate that the death was tragic or gruesome. When writing your letter, imagine yourself in the other person's place.