Difficult Conversations

by Barb, last solo post from Key West and feeling a little sad about it

Jane Darrowfield, the sleuth in my new Jane Darrowfield, Professional Busybody series specializes in solving problems that while vexing aren’t appropriate for the police or other authorities. For the most part her caseload is pretty trivial. Helping a woman leave her hairdresser and move to the one at the next chair. Or asking someone to stop feeding their neighbor’s cat, in a case of alienation of feline affection.

“In Jane’s opinion, many people sadly lacked the skill to have difficult conversations with acquaintances and neighbors. Given a noisy house party or a car parked blocking a driveway, people stewed in silence–or worse called the police–when a simple knock on the door and a polite request would have done the job. It was into this breach Jane had leapt again and again.”

Of course, it turns out not everyone needs Jane’s services. When she names her hefty fee, some potential clients decide they’ll tackle the problem on their own. And that is Jane’s intent–to get people to find their own solutions whenever possible.

Jane Darrowfield is my Jane Marple. But she’s American, she lives in the indefinite now, she’s divorced, not single, and she charges for her services. She learned a lot of what she knows about human nature not just by observing her neighbors (though there is plenty of that) but by toiling in corporate America.

In some ways Jane’s skill at having difficult conversations is wish fulfillment on my part, because I hate confrontation. In situations where I had to, particularly when I worked in a day job, I could put on my big girl panties and have the dreaded conversations. I’ve fired or laid off countless people. I’ve confronted people about the kinds of behavior that often signal substance abuse. I’ve even had the dreaded BO conversation. More than once.

But the closer conversations hew to the bone, the more freighted they are with emotional truth–the interventions, the declarations of love or hate, the boundary-settings, the expressions of deep and close grief–the more difficult they are for me. I’ve gone into plenty of situations white-knuckled, hoping things will go better this time, when I should have overcome my cowardice and said something.

Not that Jane’s life is perfect. She is deeply estranged from her son and only child and has been for more that a decade, at his initiation. All three of her bridge playing friends have pointed out, not unkindly, the irony of her running around solving other people’s problems while this cavernous hole remains in her own life–and maybe she should do something about it. So she has trouble tackling the big stuff, too.

My ramblings here are about being on the initiating side of difficult conversations. Being on the receiving side is never pleasant, because the receiver hasn’t had time to work up the courage and rehearse the interaction.

But sometimes these conversations have to be had. Recently I was in a business situation where someone, or more than one someone, lacked the courage to tell me something difficult. Or they just didn’t care and figured that meant I wouldn’t care either, if they considered my perspective at all. Not hearing about it and finding out on my own made the situation much worse. I’m not sure what the plan was here. Did they think I wouldn’t notice? In our interconnected world that was never a possibility.

Lately I seem to be reading so many stories of business and personal situations where a direct conversation might have made a situation better, or would have stopped it from spiraling out of control with horrible financial, public relations, and emotional results.

Readers: What do you think? Have we lost the skill of having difficult conversations? Did we ever have it? Or are they going on all around us and only the failures attract all the attention?

Feel free to give examples of conversations that have gone well and created healthier situations and conversations that have gone awry. And also feel free to blur the edges to protect both the innocent and the guilty. In fact, we encourage it!

25 Thoughts

  1. I seem to be having repeated difficult conversations with my son – the “no, you really do have to finish your senior year of high school” kind. Are they successful? Ask me in May when he’s supposed to graduate.

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  2. Oh, Barb, I am so with you on that! Confrontation curdles me, and like you, I’ve developed the ability to put on my big-girl panties when needed. Thank you for that phrase. I think the only chance of having such a conversation go well comes from genuine good will on the part of the initiator. And even then, it’s a 50-50 chance at best.

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  3. I think there’s a link between the short attention span culture and the avoidance of big conversations. They take planning, setting aside time and place,getting agreement from the other person to be there, and to not depend on an electronic device for comments. (Like this?)

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  4. I’m from the Midwest — the epicenter of being passive-aggressive. We’d rather hint and what we want instead of saying what we want. But over the years I’ve found it a tad bit easier to be direct. Ask my husband — lol.

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  5. As an English Professor, I’m quite often on the initiating end of difficult conversations. No one wants to hear that their work is so deficient that they cannot pass a course they have paid quite a bit of money to take. Often these are students for whom English is their second (or third or fourth) language, and they are really trying, but they just can’t grasp the material. They are extremely frustrated, but it’s my job to make sure every student writes to a particular standard. What makes it even harder is that I teach online, so these conversations are written. Body language, tone, and inflection is missing, so things can be easily misunderstood. Also, we cover so much information that there is no time to dance around an issue. I have to be direct in a social atmosphere that no longer appreciates that trait.

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    1. My daughter also teaches English online, and when my granddaughter was born I filled in for her for a month. What hard work! And you’re right, the conversations with struggling students are so difficult.

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  6. Generally, I’m pretty good at putting on my big girl’s panties, but it sure isn’t easy. I do tend to hint around first to see if that works. I try to be kind and put myself in the other person’s place, but sometimes things just have to be said outright. I’ve had people curse me, cry, and walk away but I’ve also had people thank me for pointing out something they were unaware of. I think because I’m generally considered a nice person, most people assume I’m not confronting them just to be mean.

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    1. When I can, I do let people know if something’s not working. I call this “putting the cat on the roof,” from the old joke. It’s better if people aren’t blind-sided. I’ve also had people hug me after difficult conversations. As Heidi says, goodwill and respect go a long way. And caring, too.

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  7. I hate difficult conversations. I’m really bad at them and avoid them at all costs. There are a few I still wish I’d had over the years.

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  8. I hate them, but it’s interesting that in my coaching practice this is one of the issues that comes up the most. Difficult conversations, being kind (not necessarily nice), and giving yourself the space you need to move on. I think that these days one of the issues is that we are living in a binary, thumbs up/thumbs down world. And difficult conversations are rarely that clear.

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    1. Good point, Julie. Difficult conversations must be conversations, which means definitionally they won’t all be one way or the other. Even when you begin them with an immutable goal and have to stick to your guns, you have to take in and process what the other person is saying.

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  9. What a wonderful post and ensuing discussion, Barb. I’ve had some difficult conversations in my faith community over the years, especially when I was the person nominally “in charge.” I hate them all but ya gotta do it – and Friends are supposed to be good at conflict resolution. More recently I’ve had a few difficult conversations with a family member. By dint of both of us keeping ourselves open and listening, I think I’ve come to peace with his situation. Which is a huge blessing.

    I only had to manage people once in a day job and that was only one person. Did. Not. Enjoy.

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  10. Coming to peace with what we cannot change, because competent adults have agency and can make their own decisions, is often an important part of the outcome of difficult conversations.

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  11. Wonderful, thoughtful post, Barb. 🙂
    It seems that the last six months has been all about difficult conversations for me, medically, personally, and home renovation. On the renovation side, manufacturers don’t know there is a defect unless you tell them, so somebody has to be part of the conversation with me. I’ve learned that for the most part, the more quickly I speak up, the better result I get. I dread conflict and worry about it beforehand, so I make a list of my arguments and rehearse saying them. I keep notes, and follow up. Medically and personally? The sagas continue, but I hear that Mercury Retrograde is coming to an end soon. I’m hoping that time will help.

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    1. I have heard that about Mercury, too! Let’s hope. I think that you are right that sooner is better, but it’s also important to make sure you have all your facts at hand and aren’t just totally reactive. Seems like you have a good balance.

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      1. I have been burned when I lacked all the facts, so now I try to look at all sides of the issues while I make my lists. You’re quite wise not to be totally reactive.

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  12. When I got stuck being acting supervisor, I had to tell people things. I hated it! Often I put it off until I exploded which didn’t go well. Other times, the other employees bugged me “Tell her to stop humming or stop staring at me”. I prefer that people just figure out what I want done and do it. LOL

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    1. I’m laughing, but that was often the thing that gave me the courage to have these conversations–that it was profoundly unfair to the people who were working hard when someone wasn’t holding up their end–because the extra work got redistributed. It’s hard to take pride in your work and feel appreciated if people around you are not able to perform for whatever reason and the organization isn’t addressing it.

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  13. It’s funny. As I grew up I realized my parents were masters at avoiding the hard conversations- if you ignore it, it will go away. That left me vey frustrated, and I think that’s why I go the totally opposite way. I tend to confront things, even though it has gotten me in trouble once or twice.

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