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Outside the Box: How to prepare for conversations you dread

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It’s easy to chat with people when the topic suits you. You’re happy to rave about a restaurant or lambaste your least favorite politician.

On the flip side, dreaded conversations keep you up at night: rejecting your adult child’s repeated requests for money, demanding a refund from your contractor for shoddy work, alerting colleagues that you resent their ageist comments.

Retirees may figure they’ve earned the right to be blunt. But diplomacy still matters, especially if you want to settle a score without lasting rancor.

In the lead-up to these difficult encounters, you might fret, sweat and turn into a nervous wreck. Or you can prepare sensibly by planning what to say and how to say it.

Let’s focus on the latter option.

You want to rise to the occasion, right? So use the acronym RISE as your road map:

Raise your concern. Begin by saying, “I’d like to discuss something with you.” Then pause, breathe evenly and, if you want to extend the courtesy, ask if this is a good time for them to talk.

“Getting their permission helps,” said Dave Anderson, president of Learn to Lead, a leadership training firm in Agoura Hills, Calif.

Once you’re ready to proceed, introduce the core issue clearly. Don’t dance around it, over-explain or justify why you’re bringing it up.

Succinctly summarize your concern, adding specificity if possible. Examples:

I’m concerned that you’ve asked me three times this month for more money.

I’m not pleased with the quality of your masonry work on my chimney.

I don’t appreciate your references to my age in our last two board meetings.

Strike a conversational tone, even if you’re fuming inside. There’s no need to come across as a scold.

“The biggest mistake is to make it a lecture that sounds condescending,” Anderson said. “Don’t trot out your accountability voice” where you act like a teacher telling a misbehaving student to get with the program.

Invite their input. If you’re like most people, you’ll want to keep talking so that you can elaborate on the problem, throw in a related (or unrelated) complaint or reveal how much you resent having to grapple with such a painful subject. Resist that urge.

Instead, establish a speak-listen rhythm. Stop and ask them to chime in, because soliciting their feedback sets the stage for a more fruitful give-and-take. Examples:

Do you see how this is a problem?

Can you see why this concerns me?

What do you think is a solution?

Listening to their reply might give you valuable information that can help you forge a reasonable compromise or mutually agreeable solution. And they’re more apt to buy in if you let them vent or at least explain themselves.

“Don’t assume they see your concern as a problem,” Anderson warned. “If they don’t see it as a problem, they won’t care about a solution to what they deem a non-issue.”

Suggest a solution. After you ask for their input and follow up with clarifying questions—dignifying their views along the way—you’ll reach a point where you understand their perspective and you sense that they understand yours.

That’s when you can propose a path forward. Examples:

Can we agree that, instead of asking me for money in the year ahead, you will follow through on the three commitments you just made?

So I’ll revise the contract—and we’ll both sign it by Friday—so that it reflects the new price and new time frame for you to finish the job.

To confirm, you will not make such comments again?

Watch your voice tone as you propose a solution. Remain polite but firm.

“A lot of times, you can start out well and then shift and get haughtier if others don’t respond well and argue,” Anderson said. “It’s when you start picking up a slightly higher, rattling voice tone” that you risk sabotaging yourself by failing to mask your simmering sense of grievance.

To calm down and reduce the odds of ratcheting up tensions, Anderson advises “going a little lower and a little slower.” Adopting a lower, more resonant vocal pitch while speaking more slowly makes you sound more composed.

Express gratitude. End with a one-sentence statement of thanks. Examples:

Thank you for making this promise to me.

Thank you for being fair and resolving this.

Thank you for your willingness to address this.

By thanking them for agreeing to address the issue, you’re bestowing advance praise for their forthcoming positive behavior. Better yet, you’re putting them in a bind if they relapse.

“Now if they screw up again, it’s not just the original issue but they’ve also gone back on their word to resolve that issue,” Anderson said.

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