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Vol. 39, No. 6

Are you avoiding a difficult conversation? Expert advice on tackling tough topics

by Marilyn Cavicchia

What do you do when you need to have a difficult conversation?

If you’re like a lot of people, said Patricia Pippert, president and founder of consulting firm P2 Enterprises, you avoid it for as long as you can, and you hope the situation—and maybe the person or people who are part of it—will go away


As time goes on, Pippert told attendees at the 2015 ABA Bar Leadership Institute, the situation that you’re failing to address can escalate. And if it's a workplace matter that involves staff performance, then other staff people might copy the bad behavior or start bad behaviors of their own because they know you won’t call them on it.

Whether they welcome the chance to take this advantage or are more diligent, and thus, disappointed in you for not effectively addressing the problem, either way, Pippert said, you can be sure that your staff is watching you and how you handle this unpleasant situation.

And as you become aware of what’s happening because of your avoidance, Pippert noted, you might be even more likely to continue avoiding the talk—because it’s uncomfortable to “look in the mirror” and face the fact that you’ve let things slide for too long.

Avoidance can even have health consequences, such as high blood pressure from the resulting stress or, in medical settings, irrevocable harm caused by mistakes that went unchecked. For example, Pippert said, a hospital in Arizona recently performed a textbook-perfect leg amputation—on a patient who came in for a tonsillectomy.

In the course of the resulting lawsuit, she said, it came out that no fewer than seven people saw something that seemed amiss but chose to say nothing. None of them spoke up, Pippert explained, because they didn’t want to rock the boat by daring to question the surgeon.

But if avoidance isn’t the best strategy, what is? Pippert gave attendees several tools to help make those difficult conversations more effective.

What outcome do you want?

Pippert referenced the second of Stephen Covey’s seven habits of highly effective people: Begin with the end in mind.

How you handle a difficult conversation will vary depending on what you most want to get out of it, Pippert said, citing an example from her personal life. At a family event, Pippert and her brother got into a heated dispute over which Ibsen play a particular line was from. This was especially bothersome because Pippert, a former actress, once had a part in one of the plays in question—so she especially wanted to win the argument. But more than that, she recalled, she wanted to maintain a relationship with her brother; this led to a more amicable approach.

In any conflict, Pippert said, it helps to first clarify what outcome you really want, and what behaviors would move you closer to that result. This includes how you behave even when you’re not in the midst of a difficult conversation, she added.

Whether with staff, members, volunteers, or anyone else, the little things you do to be pleasant—such as inquiring about how their pets or family members are doing—add “deposits in the emotional bank account,” Pippert said. That way, when you do need to say something difficult, she explained, they’re better able to listen to you and to take something constructive from what you say.

Know yourself—and others

Having a productive conversation means watching yourself and the person you’re talking to for signs that one or both of you need to take a short pause first, Pippert believes. For example, she said, you might notice that your hands are shaking from the effects of adrenaline; actors often experience this before a performance and take a minute to literally shake the stress out.

Pippert tends to flush when she’s stressed; now, she can recognize this signal early and avoid saying something she regrets. You might also notice that your peripheral vision starts to narrow. Whatever your physical response to stress, she said, your goal should be to notice it and self-regulate, so you can “catch it before you blurt.”

Taking a few deep breaths is one tried-and-true recommendation. The reason it works, Pippert explained, is that it counteracts the stress response that sends blood to your leg muscles in case you need to run away, and it sends the blood back to your brain so you’re able to think more clearly again.

Another good way to calm down, she said, is to ask yourself a question; this is a way to “scratch your brain” like an itch, which helps get more blood flow there.

There’s no shame, Pippert said, in telling the other person that you want to make sure to give your best ideas and are unable to do that at the moment. One attendee asked if this was a sign of weakness, but Pippert said that as she gets older, she’s less afraid of that perception. “I actually think that it shows my humanity,” she said.

One situation that can make employees especially anxious, she noted, is performance evaluations. If someone panics or seems to feel threatened, she recommended, tell them they can come back later.

You may think you’re too busy to offer this kind of pause, Pippert acknowledged, but in her experience, if you go ahead with the evaluation when someone is not at their best, there’s a good chance you’ll have to do it all over again.

Focus on specifics

“Most feedback is ineffective,” Pippert believes, “because it starts with the word ‘you,’ and there’s an index finger attached to it.”

For example, she said, in a case where an employee has been showing up late for work, starting with “You’re always late” will put the employee on the defensive and will cause him or her to dispute the “always” part. Also, Pippert said, it means you’re “telling yourself a story based on the facts,” when it’s often more productive to get the employee’s side of the story.

Better, she believes, is to start off by calmly saying that you’ve noticed the employee has been coming in late recently, or on some specific days, and that you wonder if there’s a reason for this. If you frame it this way, Pippert explained, the employee is more likely to acknowledge the problem rather than defending him- or herself, and might give you “a piece of information you didn’t have before.”

Perhaps there’s a sick family member, a transportation issue, or some other obstacle; you may be able to help the employee think of a possible solution. In any case, Pippert said, you will have alerted him or her to the fact that you’re aware of this problem, and you will have done so without making the general assumption that the employee is just lazy or doesn’t care.

Likewise, Pippert said, it’s important to be specific with praise, too—that way, the person you’re praising knows exactly which behaviors to repeat. A more general compliment can also come across as “backhanded,” she added; for example, if you say, “You really handled yourself well in that meeting,” the person might think, “Don’t I always handle myself well?”

Work on your questioning skills

In any conversation, and especially the difficult ones, questions play an important role, Pippert said, “because you don’t have all the facts”—even if you think you do.

Questions require some careful phrasing, Pippert noted; for example, “Why?” can sound threatening. Consider instead using phrases like “Help me understand …” or “Walk me through your thought process …,” she suggested.

Have you heard that you should never ask closed-ended—yes-or-no—questions? Those used to be considered bad across the board, Pippert said, but they can be useful in narrowing things down as you seek information. Do be careful, though, not to ask a whole string of yes-or-no questions in a row.

With a little planning, Pippert said, you can even use questions to prompt the other person to state your message for you. There’s an axiom in sales, she noted, that says, “People believe more what they say than what you tell them”—and they’re more likely to think something is a good idea if they believe they came up with it themselves.

Why bother?

Being so purposeful and thoughtful about difficult conversations and how to get what you really want from them might seem like a lot of work, Pippert acknowledged. It may even feel uncomfortable, if you’re used to more of a top-down approach that doesn’t take the other person into account quite so much.

Pippert reiterated that if you assume you already know what’s going on with the other person, you’ll be working only from incomplete information and assumptions, which might turn a small problem into a much bigger one and prevent you from benefiting from what that person has to offer.

“Let’s not write people off,” she said, “without having the conversation.”