Hayes previously worked as a chaplain for the FBI’s critical response team for 15 years, dispatched to airline crashes and terrorist attacks to inform and counsel victims’ families. During that time, he developed a code for his ominous duties: Always deliver bad news in person. Always bring a partner (“95 percent of them defer to me to do the actual speaking of the words—nobody wants to experience sad”). Skip the euphemisms—they comfort no one except the person speaking them. Never abandon anyone until they have someone else to hold onto.

“You enter the arena of suffering with people,” he explained. To this day, some of the strangers he’s met while notifying them of the death of a child mail him Christmas cards.

Yet as seasoned as he is in ferrying tragic news, a few encounters still haunt him. “When you hear a mother howl—it’s a primal scream that you’ll never hear in the movies, you’ll never hear it anywhere else, except from a mother who lost her child,” he reflected. “Nothing can prepare you for that.”

To cope with life on the front lines of despair, Hayes said he initially “adjusted” with alcohol (he’s now 18 years sober). These days, he turns to daily swims and conversations with professionals. And if he had a chance to do it all over again, he says he’d choose the same career.

Still, he noted with a deep chuckle, “I don’t see people running to the door to do this full time.”

Indeed, sowing sad tidings has some folks running for the woods—literally, in the case of Aaron McManus. After years of assisting with mass layoffs as a Los Angeles-based HR consultant, he felt so crushed by cynicism that he quit in 2009 and fled for the Alaskan wilderness to work with troubled youth.*

McManus has since launched his own emotional intelligence consulting agency called e.i. growth, where he teaches clients the set of “ninja skills” and “calm detachment” he cultivated from years of scripting bad news. McManus, like everyone interviewed for this article, pointed to rehearsal as the most critical skill for emissaries of bad news.

As Christensen, the former “Grim Reaper” who now delivers straight talk to the C-suite as a communications director for high-tech startups, put it: “Once it’s done, I can sleep at night. It’s the nights before—when you’re trying to figure out how you’re going to broach the news—that keep me awake.”

Even world leaders need practice, said Daniel L. Shapiro, director of the Harvard International Negotiation Program, who uses role-reversal scenarios while coaching diplomats in the art of conveying bad news.

“It’s a very simple and very powerful exercise—how do you feel from the other side’s perspective when those words are coming at you?” he said. “Whether you’re conveying bad news to your employee or to [president Hassan] Rouhani in Iran or to the Israelis and the Palestinians, there are a lot of human emotional elements involved. And if you fail to do it well—watch out.”