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How do YOU deliver bad news?

Way back when I was in Airman Leadership School and the NCO Academy, part of our training was in how to counsel people. They would give us made up, (often) wild scenarios to act out (though they had probably happened to someone, right?). Sometimes the fictionalized scenarios were crazy, other times they were just awkward. One time, I remember, we had to walk through the scenario of counseling an Airman on hygiene. Yes, that’s right.


The priority in those trainings was to learn how to deliver news so the person could understand the message without being demoralized or unnecessarily offended. There really is no great way to tell a person they smell less than pleasant, but the goal was to communicate the message so that the Airman would understand that others were complaining, it had a negative impact on morale and the team, and that hygiene was important, then leave the meeting resolved to make a positive change rather than just leaving upset or embarrassed (or both). To achieve this, they taught a tool I called the “compliment sandwich”: start with good news or praise, put the bad news in the middle, and finish with something good.


Although I rarely have to tell anyone that they stink these days, as an estate planning attorney, I am faced with lots of uncomfortable conversations. Delivering bad news is difficult, especially when it deals with family, or when it’s intensely personal. The “compliment sandwich” concept is something I still use today, because it helps me to gently deliver news my clients may not want to hear – like that this not a very good case, or that the way they’ve set things up isn’t good. Delivering bad news can be hard, especially when people die without an estate plan and the family members don’t understand that Florida law has a process for how things go in such cases but it’s rarely a process that people enjoy when they have a front-row seat and it’s their family member’s estate that’s being handled.


A while back, I was approached by a friend from out of state seeking my advice after a relative died. It’s worth mentioning here that I am quick to remind them that I cannot give legal advice outside of Florida since I am barred in Florida – but it got me thinking about how many people just want reassurance that what they’ve done is ‘ok’ or that everything will turn out juuuuuust fine even though they failed to seek legal guidance from a qualified professional. In situations like these, it’s almost impossible for me to give them that reassurance because it is highly likely they’ve made some missteps along the way that may be expensive to fix. And that means it’s going to be a difficult conversation for both of us. When someone comes in for a consultation like this, and they’ve already done things they shouldn’t with the paperwork, the property, etc., it can be difficult to reassure them that I can help. This is where I find myself employing that counseling sandwich: I can help you. Now here’s the bad news, here’s where things will be tricky or difficult, or where the wrong moves have already been made. But there’s hope that there can be a good outcome, and here’s what we can do to get there. It doesn’t change the hard truths about the person’s situation—just like using a “compliment sandwich” doesn’t keep an Airman from having to accept that he smells bad—but delivering bad news with kindness and encouragement and compassion sure does make those hard truths a bit easier to take.


Have you ever thought about how you would deliver bad news? What techniques or approaches do you use when you have to talk to someone about something difficult? Please comment below; I’d love to know!





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