A few weeks ago, I had a wonderful conversation with Alicia Butler Pierre, the engaging host of the podcast Business Infrastructure, about how to deliver difficult news at work, and in particular, some of the hardships that can arise in family- or friend-run businesses when changes are necessary. She was finishing a series about “the one thing” listeners needed to know on a variety of topics, so I had to distill the whole subject of delivering challenging communications into a single statement.

Trying to include as much information as I could, with as broad an outlook as possible, I said, “It’s never a one-step or one-way process.” Alicia agreed, and pointed out, “The best way to deliver unpleasant news depends on the person that you’re talking to, and also on the type of news you’re actually delivering.”

When It’s Time for a Challenging Conversation

Do you have demanding, potentially disruptive communications to convey? If so, here are four takeaways from the podcast that may be helpful, whether you’re in a family-run business or not.

  • Your calendar plays a crucial role in managing significant communications. It’s very hard to put in enough time for planning a difficult communication and its delivery, and all too easy to avoid the issue or wait until the last minute and then dump-and-run. It’s worth it to schedule the prep and delivery with yourself, the way you would the preparation for a meeting to deliver a pitch to funders or customers. You can set three kinds of timeframes: thinking and planning time, the discussion or meeting itself, and the recovery time and follow-up discussions.
  • For difficult discussions, the medium really is the message. Once you figure out what to say, choose carefully how to say it — based on them, not you. Every business has some people who do better in a face-to-face or video meeting, where they can ask questions, and other people who actually do better if they can read an announcement, figure out their questions in private, and come back to discuss their concerns. And still other people might really need to hear the message in person, and in an email, and in the little weekly memo you send to everybody — 12 ways, 47 times. You’ve got a really big range for what the delivery might need to be, and then of course there is the interaction or the language itself. Tailor everything to the audience.
  • Follow-up is vital. The fact that you share information doesn’t mean things will change at their end. You may have thought about the content and crafted the language, but receiving the message is only the start of their process. You’ll need to check in with them afterward to see if there’s been any confusion or damage, to help with recovery if they are upset in some way, or to explain it again if they don’t understand it completely.
  • Take action if your delivery or the interaction goes awry. In many challenging conversations, there’s significant potential for things not to go as intended. Insufficient preparation could be the cause, or the topic might be as distressing to the person delivering the message as it is to the person receiving it. In almost all cases, you can take steps to repair the breach, even if you didn’t behave as well as you would have hoped. But it does require courage, not to be tough, but to go back to the audience and say, “Look, I recognize that I didn’t handle this perfectly — I’m sorry.” And then describe what went wrong. For example: “When I said X, I meant Y.” “I did not give you a chance to speak.” “I didn’t listen carefully enough when you were explaining your perspective.” “I was wrong about the facts.” And then, in effect, ask for a do-over: “Here’s how I’d like to pick this up again.” Or: “Here’s what I’d like to do at this point.”

Learn by Doing

The only way to become skillful at discussing complicated, disruptive, or otherwise difficult issues is by doing it, and then thinking about how to do it better next time. By emphasizing the planning, delivery, immediate follow-up, and recovery in case something goes wrong, you’ll give yourself your best chance of doing an effective job.