5 Survival Tips for Difficult Conversations

I suspect everybody on the planet has a tough talk “To Do” list – the list of difficult conversations we really should have, but keep putting off.

Talking with your significant other about their parents, asking your best friend about the money they owe you, telling your co-worker to quit making loud personal calls. Oh, and explaining the birds and the bees to your…. now 10-year-old. Well, that one he may have figured out without you.

We put these difficult conversations off because we dread the reaction, we don’t want to start a fight, or don’t want to handle it badly or sound petty. Interestingly, the way we bring things up (or respond to their attacks) actually makes it more likely that we’ll do damage.

Here are 5 insights to help you sidestep typical traps, and have a real conversation:

1. Don’t Ease In or Be Indirect. Anxious about a confrontation, we instead come at the topic sideways, and this is bound to leave them feeling ambushed. Making indirect suggestions or using leading questions will only make it worse. You’re implicitly communicating: “what I want to say to you is SO BAD… I can’t even say it directly.”

Stating the issue more directly actually makes it less of a big deal: “Hey, do you think you could keep it down? I’ve just got to focus to get this out the door…..” or “By the way, if I remember right, you still owe me some money. Any idea when you might be able to pay it back?”

2. Stop Their “Hit & Run” with Humor. Sometimes you’re skipping along happily through your life, and someone else lobs a sarcastic remark in passing and “bam!” you are left feeling ambushed and abandoned. Perhaps you are at your parents’ house for Thanksgiving and your aunt, ever critical of your “insistence on working” rather than staying home with the kids full-time, watches your boys bop each other on the head and comments, “Yes, well, I’m sure they just don’t get enough attention.”

You can fume. Or you can speak up. I’d speak up, and with a bit of humor, “You know, if I thought that staying home would mean they wouldn’t fight… boy that might actually change my mind!”

But don’t leave it at that, because you risk simply returning sarcastic quip for hurtful quip. Actually say: “But I should ask, do you think they would behave differently if I were home? Because that’s interesting…”

3. Realize the Issue Isn’t the Real Issue. Whatever the argument is about – where you’ll spend the holidays, who forgot to call the plumber, what you’re having for dinner – chances are this isn’t the real issue driving the dispute. If the conversation becomes difficult, what you are really fighting about is how you’re each feeling treated by the other. Do you care about my feelings? Can I rely on you? Do you appreciate all I do for you?

Not every fight has to be about these larger issues, but humans are hard-wired to see patterns and to seek emotional safety, so whatever the themes are in your relationship, they will play out over and over under the cover of everyday squabbles.

4. The Real Issues Need to Be Managed….Not Resolved. Ready for this? Marriage researcher John Gottman of the University of Washington says that 64 percent of the fights married couples have are the SAME fights they are having five years later.

This is either really depressing, or really liberating. In other words, most of the things we fight about aren’t actually resolvable. It’s a process of managing differences in preferences, habits and personalities – differences that aren’t going to go away, so we might as well quit getting worked up about “how they are” and instead focus on working out ways to get around those issues.

5. Talk Backwards as Well as Forwards. Since so much of what we fight about are really surface reflections of deeper differences, put your energy into understanding those differences. If you argue about money, talk about where your attitudes, fears and habits around money came from. How did your parents handle money? What are your worst fears?

This is helpful even when the topic seems more mundane. For the first five years of our marriage, my husband and I could not pick out a Christmas tree without having an enormous fight. We fought about when to go. We fought about where to go. We fought about which tree. We fought about why he was being so difficult and ruining such a joyous expedition (which it decidedly was not).

This is actually one of the fights we’re not having anymore. It’s because we finally sat down to talk about our early family experiences and resulting emotional associations with getting and decorating the Christmas tree. Needless to say, we had opposite experiences and traditions, and I was replicating exactly the obligatory, pressured early experience he had always dreaded. Simply understanding what he was reacting to, and his understanding that this wasn’t my experience or intention, actually changed things. We decided to create our own tradition around the tree, which he is in charge of.

We’ll go get the tree any day now… right?

Sheila Heen is the co-author of “Difficult Conversations.” She also lent her expertise and communication know-how to Today is Have The Talk Day so visit the site to learn more about how you can be a better communicator.


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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