How to Write a Compassionate Condolence Letter

When someone dies, courtesy dictates that we write our condolences. These letters can be some of the hardest thoughts we will put to paper, even for those of us who usually have a great facility for words. And sometimes, difficult circumstances surrounding a death can make this task even worse.

Consider what Simon Royston faced: Royston, founder of a recruitment agency in the U.K., had just placed a young man, who was in his early 20s, with a client. The morning he was to begin work, the employer received a voicemail from the new hire’s father saying that his son had died in a car crash on Friday evening.

The employer asked Royston to write a letter of condolence to the family. Royston had never met the candidate because a colleague had handled the recruitment process. Nevertheless, he wrote a letter about how terribly sad the news was.

“I will never know what reaction, if any, my letter received,” Royston recalled. “I feel, even today — nearly a decade after the event — that my letter would achieve nothing given their pain. But I also acknowledge that not communicating, not reaching out in some capacity, would have been the wrong thing to do.”

Royston’s gesture was exactly the right thing to do, according to Brooklyn, N.Y. funeral director Amy Cunningham, owner of Fitting Tribute Funerals.

Letters of condolence need not be literary masterpieces. They don’t have to be “good.” Even Ernest Hemingway ended a condolence by admitting, “This is not a good letter, Charlie. But I feel too sad to write a good one.”

But condolence letters must be written. They are greatly valued by those who receive them, and the most important thing is that you write and send them, even if you feel inept.

That said, there are good practices. Here are some tips on how to write a thoughtful condolence letter:

Proper condolence notes are handwritten and addressed, but the note can be typed and printed on ivory paper. Blank cards are also appropriate.

But, Cunningham urges, “Do not let searching for the right paper slow you down or interfere with your ability to get this done. If you know you’re not going to handwrite it, type it.” If you have reached the desperate point where an email might be all you can manage, be consoled that it is somewhat appropriate — and better than nothing.

Mail your condolence soon after the news is received, but it’s also fine if it arrives late. “There’s no such thing as a belated condolence letter,” Cunningham said. The recipient will be happy to receive it.

You might even consider sending more than one. The poet Emily Dickinson understood that grief comes in waves, so she didn’t write just a single note, but rather a sequence of notes. She knew that grief doesn’t have an expiration date and people can mourn months or even years later. Dickinson would often include fresh or pressed flowers with her notes.

Finally, be prepared: Cunningham has a special box with note paper, pens and stamps so she is ready to write a condolence whenever the need arises.

If you are stumped about what to say, Cunningham advises that you acknowledge the death and share a memory or anecdote. Write with sincerity and compassion. Tell a story about the person, but avoid delving into troubled or complex relationships.

“Saying anything about how the deceased has changed you or what effect they had on your life can be powerful,” she said. Sometimes, quoting appropriate poetry can help.

While you might want to make the bereaved feel better, providing comfort should not be your goal. “Maybe they can’t be comforted because the pain is so searing,” Cunningham explained. If you insist on comforting, you’re hanging yourself up again and it might make you give up.

Avoid these phrases:

• Don’t say: "I am sorry for your loss." This is a soft rule — so don’t be hard on yourself if you use the phrase — but Cunningham finds it clichéd. Say “I am here for you.” It’s a stronger statement. Or say: “I want to hear all the stories."
• Don't say: "passed away." Say “died.” This is another soft rule, according to Cunningham. “People say ‘passed away’ all the time. But saying someone died is more accurate, and people are moving toward greater honesty and accuracy,” she noted. “Why mince around?”
• Don’t say: “I know how you feel.” You can't assume to know how someone is grieving. A death from Alzheimer’s can be a relief, but even if the death is expected, you can’t assume the bereaved are relieved. Grief encompasses many emotions and people can experience a multitude of feelings in a single day.
• Don’t say “It’s God’s plan” or “He’s in a better place” to a secular person. You can say: “He’s at peace now” or “The suffering is over.”
• Don’t say, “Time will heal.” Similarly, don't dictate a timetable for their healing.
• Don’t say, “Tell me what I can do.” That throws everything into the bereaved person’s court at a time where he or she may be overwhelmed with grief and doesn't need another task. Instead, say what you will do, i.e., pick up groceries.
• Don’t mention your own losses. The focus should be on the bereaved, not you.
• Don’t go off topic. A condolence letter is not the time to bring up unrelated business, like vacation plans.
• Don’t make the condolence letter seem like a review of theperson. People commonly leave sympathies on Facebook and this can have unfortunate results. Cunningham recalled a woman who complained that people were posting condolences that sounded a lot like Yelp reviews, “Great woman, very loving. 5/5 stars.”

In addition to not knowing the person who died, there are other situations that can make condolence-writing even harder:

• The person died by suicide or succumbed to alcoholism or drug addiction
• You were not on good terms with the deceased or the family member you are addressing
• The death happened to a family member of a colleague you work with, but don’t know well

But even in sticky circumstances, there are ways of coping gracefully. If someone had a fraught relationship with his alcoholic mother who died, separate the sickness from the parent. You could say, “She gave birth to you and I’m so glad. How wonderful that you exist because of her.”

If someone had a bad relationship with her father, it’s best not to take the risk of saying, “I know you and your dad really had a bad relationship.” Or, “I know you and your dad really struggled with your relationship.”

Don’t even go that far, Cunningham cautioned. “Because in that moment — even though they hated their father — they don’t want anyone else to say that.” You can’t guarantee the comment will be well received, even if you two had dinner last week and she was complaining how horrible her relationship with the father was. “It might come off as minimizing their loss," Cunningham said.

When in doubt, stay neutral. Don’t worry if your condolence letters are boring; it's fine to say something like: “I remember you telling me about how your dad used to walk you to school."

If you are writing a condolence letter to a work colleague, you can say, “I’d like to hear your mother’s story at some point. Let’s go for tea,” Cunningham suggested.

Probably the most important thing about condolence writing is that you do it.

If you find yourself incapable of lifting your pen, remember: It doesn’t have to be perfect. You don’t have to be a wonderful writer.

What matters is that you take the time to extend your heartfelt sympathy to someone who is experiencing a loss.