Q. One of my customers, someone I’ve done business with for many years, just lost his brother. I know from numerous conversations that my customer didn’t get along with his brother and barely spoke to him recently. What should I write in a condolence note in these circumstances? Somehow, “This is a terrible loss” doesn’t fit.

A. Complicated family relationships are all around us, and it’s definitely awkward when the connection between the bereaved and the deceased was contentious. Yet it’s hard to know what the mourner is really feeling at this time. People can be filled with guilt that they didn’t make more of an effort to reconcile. They can feel tremendous remorse. Or they can idealize the person they never had a good thing to say about. Love can be buried under the hard feelings.

I know one woman who raged at her selfish, supercritical mother. But when the mother died of a heart attack, the daughter felt devastated. From then on, she spoke of her mother with reverence and extolled her positive qualities. That’s why it’s important not to project your own feelings or assume what’s going on. You may be wrong.

Because this is a business relationship rather than an intimate one, the wisest course to keep your note short and general. For example, it’s very risky to speak of “your beloved brother.” If the deceased hadn’t been sick, you can say something like, “I’m sorry to hear about your brother’s death. It must have been a shock.” Another option is, “I remember you mentioning your brother on several occasions. With sadness, I send my sincere condolences.” You might also try, “I’m thinking of you at this difficult time. With sympathy on your loss.” Such words won’t get you into trouble because they don’t describe the kind of relationship involved, but they do acknowledge what has happened and demonstrate your concern for the bereaved.

You can also use variations of the same language when you see the person face-to-face at your next meeting or talk on the phone. It’s appropriate to say, “I’m sorry about your brother. This must be rough.” A sibling’s death is upsetting, regardless of the relationship. Or try another path with “How are you taking this?” Pause and give the person a chance to answer. Whatever the response may be, you can simply follow his lead.

If you have a question for Florence, please email her at fisaacs@florenceisaacs.com.

Florence Isaacs is the author of several books on etiquette, including My Deepest Sympathies: Meaningful Sentiments for Condolence Notes a.... She writes two advice blogs for Legacy.com: Sincere Condolences and Widow in the World, a new blog for bereaved spouses and partners.  

Image via Flickr Creative Commons / Mel B.