Tips to having those hard conversations

Hard conversations riddle life, and yet too many of us avoid them.

When serving as the managing editor of the then-daily Clarksdale Press Register, we had a few rules. A couple pertained to the handling of obituaries, which the publisher considered news stories. The death of anyone over 100 was front-page news, as was the death of any child in our small community.

I took on, one day, the task of writing the obituary for a four-year-old boy who drowned. Tough story. Almost impossible interview.

hard conversations
Hard conversations are a part of life. Be prepared and the way might be easier.

The mother and her friend came to my office. Even though the mother sat in front of me, she wouldn’t talk to me. Instead, she told her friend what to tell me.

“Tell him he liked Batman,” she said. “Make sure he knows spaghetti was his favorite food.”

The grief the mother bore made it a gut-wrenching interview.

The approach to hard conversations

It was the accidental drowning death of a child. Front page news in our little community of 20,000 people.

I obtained the police report and ambulance report. I took the funeral home’s standard obituary they submitted, and I made a list of questions, designed mostly to capture the personality of this little boy who loved Batman and spaghetti. A boy who enjoyed swimming and playing catch with his older brother. He was well-behaved at pre-k and was usually ready to go to Sunday School before any of the rest of the family was dressed.

It’s been 22 years, but it was a story that stuck with me.

The correlation

You are going to fire somebody, be ready. Have your script. Stay on task.

You are going to fire a client, same thing applies. Be prepared.

I remember as editor of the Daily News Journal, I had to retool the newsroom. Our problem is we had more editors than reporters and I wanted to restructure. The editorial layoffs, which involved six people, took less than an hour.

That’s how it should be. To the point.

Shift to public relations.

Not long ago, I was talking with a self-published author about his efforts to promote his work and increase sales. I wasn’t doing the work, just giving him a little advice to help him along the way.

He lamented the lack of sales on his first self-published book and I sat there listening for a minute.

Finally, I leaned in.

“Look, if I’m going to help, I have to assume three things. First, you have written a good story. Second, it is cleanly and carefully edited. Finally, you have a good blurb.”

He sat there a second.

“I don’t know science fiction very well, so I can’t judge the story, but you lack good editing, a professionally designed cover, and a good blurb. You published before you were ready, and you need to fix those before you start marketing.”

He just stared at me for a moment.

“But I’ve already spent $500 on Amazon ads,” he said. “They should’ve worked. That’s a lot of money.”

“The product is not ready.” At this point for me, the conversation was over.

He hemmed and hawed for a bit. I told him I’m not comfortable spending his money to promote a product that is not ready for promotion.

I once had a boss who said it is hard when some calls your baby (referring to her business) ugly. I was careful to not disparage his baby, a 600-page novel. But I had to be very honest about its preparation for publication.

I certainly wasn’t calling his baby ugly, but when I found errors on page 1, it was clear he wasn’t ready to promote what was essentially an unfinished product. And in that way, he was also not ready to be my client.

I know, but I couldn’t resist throwing this image in.

How to do it

When I have had to have hard conversations – telling a client I don’t want to work with them, firing an employee, interviewing a parent whose child died, as a teacher telling a parent their child is failing, or even talking to my daughters – I take several steps to prep for hard conversations.

  1. Think about the goal of the conversation. What do I want to accomplish with this hard conversation? What’s the end game here?
  2. Be ready to listen. This depends on what kind of hard conversation you are having. But sometimes, as an old boss used to say, people just need a “good listenin’ to.” And let them know you are listening. Be engaged, nod your head, and repeat back key pieces of information.
  3. Be specific. Once I was let go from a job and the reason I was given was, “I’m just tired of it.” When I asked what, I was told, “everything.” I’ll be honest, while I have some suspicions about what was going on, I honestly do not know what “it” and “everything” entailed in the senior leadership’s mind.
  4. Prepare a script. This is very important when you have to either deal with a situation that is going to get really emotional (for you or the other party), or there are potential legal pitfalls. I may or may not read the script (depends on legal, frankly), but having the points keeps me on track.
  5. Be direct but polite. Be concise. Avoid pleasantries and superfluous topics. Just take care of business. This doesn’t mean you can’t answer a relevant question, and it doesn’t mean you can’t be thorough, but tear the bandage off quickly.
  6. Consider a witness. I’ve had one for every firing I’ve conducted. Sometimes, it is just good practice and a little self-preservation. Even when having a hard conversation with a client, I like to either have someone listening, or if on Zoom, I record the conversation. I’ve never had such a conversation come back to bite me, but you never know when it could.
  7. Take some time afterward. A few years ago, I fired a construction client. He was the very definition of scope creep but my goodness, he paid well. And fast. So it was a tough decision. When I fired him, though, he got very aggressive during the conversation. Afterward, I had to decompress as I was furious. So, I went and took a walk – a pretty long one. I wasn’t going to be able to focus on work anyway, so I instead got my head and my emotions back in check.

They aren’t called hard conversations for no reason. Take a deep breath, be prepared, and do the best you can.

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