What to Say in 16 Ticklish Situations

Tips on difficult conversations.

Posted May 18, 2019

Pixabay, Public Domain
Source: Pixabay, Public Domain

In ticklish situations, we often get nervous if not downright tongue-tied.

Of course, the right thing to say varies with the situation and the protagonists but perhaps these examples can be instructive.

CAREER

Asking for good pay

In interviewing for a job or in your compensation review, win-win negotiation is often possible when negotiating non-cash items. But when it comes to pay rate, negotiation tends to be a zero-sum game: Every dollar you extract from the employer is a dollar less the employer has. So you might use one of these openers:

Early in the interview or salary review, right after the boss praises you or nods in agreement, ask, "So what is the range you're anticipating paying me?” That avoids your low-balling yourself or pricing yourself out.

Or

In light of what I’ve done in the past (Show a bullet list of accomplishments, especially those that yielded profit) and what I’m likely to do in the coming months (also list those), and in light of these comparable salaries (also list those), it seems that my pay should be X. (Make it on the high-side of fair so there’s room to negotiate but you’re not being unreasonable.)

Asking a networking contact for a job lead.  The standard approach is to start with a fair amount of small talk. But unless it’s a person you speak with regularly, “Hi. It’s been a long time. What’s doing in your life?” can be seen as a ploy. It’s often better to start with The Ask and then move to the social talk. For example,

We haven’t spoken in a long time, so you might wonder why I’m calling. As you may or may not recall, I’ve been a substance abuse counselor for the county and been good at it, but honestly, I’m ready for a change—My clients’ problems are so severe. So I’m thinking about making a move from the county to Kaiser or other fee-for-service organization where the clients' problems aren’t as deep-rooted, Might you know someone I should talk with about a possible job lead?

Then you can say, “Now that the business part of the call’s done, what’s doing in your life these days?”

Suggesting a need for improvement. For example, your supervisee thinks poorly and thus writes poorly. Of course, thinking skills are difficult to improve but your best shot at encouraging  improvement might be, for example,

As others have suggested, your memos to staff haven’t been as well-reasoned or concise as they could be. I’d like to be of help. Would you prefer that I review a memo and note suggested changes using Word’s Track Changes feature, or would you prefer that we review  a memo together, with me explaining the thinking behind the changes I'll suggest?

Giving two choices, both acceptable, allow the person to retain some agency and, in turn, self-esteem.

If the person’s memos continue to be unsatisfactory, you have a paper trail of your efforts to improve the person, which can be essential in a termination procedure.

Firing someone. This is among the most difficult things a boss has to do. It isn’t as tough if the employee is part of a large layoff—It’s less of an indictment of that person. But if you believe it’s wise to fire an individual, that’s tough...and a litigation minefield.

Rather than immediately jumping to Legal’s or HR's Progressive Discipline approach, it can be wise to first try to counsel-out the person. That can avoid the time, money, and inordinate stress of, for example, being accused of racism, sexism, hostile environment, etc. Here’s an example of what you might try. Take the person out for coffee or lunch and, after a reasonable amount of bonding small talk, say something like:

I really appreciate much of the work you’ve done for us. You’ve fostered esprit de corps, enabled the team to avoid getting overwhelmed amid the stress, and even made the break room more attractive. Unfortunately, the job requires excellence in other crucial areas, for example, effectively problem-solving internally and with external clients. And despite efforts to coach you on that, I believe this is the wrong job for you. I’d like to try to help you find a better-suited position by writing a strong letter of recommendation that vividly portrays your strengths. What do you think?”

If that doesn’t work, you can always initiate the progressive discipline procedure.

RELATIONSHIPS

Paying the bill on a date

Mitigate the awkwardness by pulling out your wallet without saying a word. If the other person says nothing, it’s a sign of selfishness. If s/he offers to pay, think cosmically: Does this person have more money than you do? Is he offering to pay because of an atavistic social convention? Then decide whether to say, for example, “Thank you,” “Let’s split it” "I'll pay. You paid last time." or “It’s my pleasure to pay.”

When you don’t want to see a date again

After a date, one person often says "I’ll call" (or email or text,) knowing s/he probably won’t. Often, that's because of cowardice or not knowing how to let the other person down gently.

If you’re the person who’d like to not date a person again, try something like, “I really like X about you but I sense we’re not a good match because of Y. I, of course, wish you all the best.” Then stick your hand out, shake hands, and you’re outta there without having lied or creating false expectations. Plus you’ve given the person the gift of tactful but honest feedback, something that most reasonable people want.

“Why didn’t you call?” If you didn’t have the courage to say something like what was suggested in the previous paragraph and the person contacts you to ask why you didn’t call, you might try, “I didn’t have the courage. My bad. I really like X about you but because of Y, I don’t think we’re a good match.”

Asking about birth control and STDs. You’re about to have sex with someone for the first time. In many cases, you’re concerned about pregnancy and/or sexually transmitted diseases. Yet especially if you’re in the hot-and-heavy phase, it’s tough to stop for a discussion. So earlier, perhaps at dinner or even when kissing, if you can muster the restraint, pull back and, in a supportive voice, say something like, “It seems like we’re headed toward being more intimate so I feel I should ask you about birth control and about STDs. I’d really appreciate your being honest.”

That's brief, assertive without being too tough, and gets the issues raised. If you're not completely reassured by the answer, it may be time for a question such as, “Should we hold off until we get tested?" Or, "Should we use a condom? What do you think?”

Asking to have a monogamous relationship, move in, or marry. This, of course, is a biggie, one particularly in need of individualization. But you could do worse than this:

We are wonderful. (Insert three ways you’re compatible.) Would you marry (or move in or be monogamous) with me?

Saying no to request to be monogamous, move in, or marry

As with the turn-down for future dating, the goal is usually clarity plus honest but tactful feedback. For example, “Of course, I’m enormously flattered that you would ask me. I'm tempted because of A and B but because of X, I need to say no.”

Again, that’s clear, crisp, and not leaving room for begging you to undo your considered decision. Plus, it lets the person down as easily as possible, pointing out positives and tactfully and briefly listing a negative or two.

Asking about excessive spending

Many couples fight about money. Perhaps you can avoid the conversation turning into a screaming match with something like,

I’ve looked at the credit card bill. Candidly it’s scary. I’m bringing in most of the money, our financial future is far from secure, and I’d hate to think we’d ruin our credit or even lose our home if I lost my job, got a demotion, or one of us or our parents had a big health issue that wasn’t fully covered. I don’t want to go over the bill line by line—That’s demeaning. But as you look at it, what do you think?

Asking about substance abuse

Whether it’s your romantic partner, child, parent, or friend, it’s tough to confront a person about substance abuse, even when you see it devastating their life. No few-sentence spiel can address the issue, but it could be a first baby step, for example:

You know I love you. And this is really hard for me to bring up because it’s such a touchy subject, and I suspect you think, like most substance abusers, that you don’t have a problem, that you can handle it. But there, I said it: “I’m very worried about the toll your substance abuse is taking on your career, your relationships, your kids, even strangers—Fatal car accidents are so prevalent among impaired drivers. How can I be of help?

Asking about sexual cheating, The two of you have agreed to be monogamous but now you have the strong sense that your partner has strayed. Here’s one way you might bring it up:

I’ve noticed another person's smell on your clothes and even once on your body. Of course, it’s difficult to admit, and maybe you think we're better off keeping the affair secret, but do you think it’s wise for us to talk about it?

PARENTING

Why?!

Let’s say you want your child to come to dinner. S/he says, “Come on! Why?! There are only 10 more minutes in the TV show!!”

Of course, your response will vary with the child’s age but here’s an approach that might work with a two-year-old:

Dinner will get cold and the family eats dinner together. Sit down now.

With an 8-year-old, you might say,

Family is important. That’s why, except when there’s an important reason, we have dinner together as a family. Watching the last 10 minutes of SpongeBob SquarePants isn’t exactly an important reason.

With a teenager, you might say,

I’m aware that many families don’t eat dinner together and if they do, everyone’s looking at their phone. But it’s ultimately comforting and helpful for us to eat dinner together as often as possible. Sit down and tell me what you’re thinking about today or looking forward to tomorrow?

What were you doing with the door closed, making all those noises?

With a younger child, you might say, “Sometimes mommy and daddy like to have fun privately. We’re okay, we just make noises of happiness.”

With a teenager, you might say, “I think you know what we were doing. We were enjoying each other. With the right person, it’s quite a pleasure.”

Why do I need to know all the crap in school: the causes of the Peloponnesian Wars, quadratic equations, stochastic processes, the intricacies of Shakespeare?

I find that question tough to answer honestly. You might try this:

You may or may not ever use most of those specifics but success in life does require discipline, organization, writing skills, thinking skills, and yes, the willingness to do stuff we’d rather not do. Your courses should improve you in those. Plus, good grades can be a door opener.

POLITICS

In today’s hyperpolarized and intolerant times, most people perhaps wisely choose to not talk politics except with ideological kindred spirits, people in your so-called bubble or echo chamber. But I worry that that could contribute to societal dissolution. So when if feels right, you might want to dialogue with the other side. Let’s take today's perhaps most polarizing issue: President Trump.

Let’s say I dislike Donald Trump and I’m talking with someone who likes him. I might try this:

I can see why you’d like Trump. The U.S. had been a paper tiger, drawing lines in the sand, and when the Syrians crossed it, the U.S. ignored it. Trump's unpredictability has the plus of making other countries more likely to compromise, fearing he might go to war. Domestically, uncontrolled illegal immigration is a problem. For example, I know a carpenter who used to make $30 an hour, enough to support his family, but with the influx of illegals of whom many are willing to work for $15 an hour under-the-table, so my carpenter friend can no longer provide for his family. That said, I do find Trump problematic: His shoot-from-the-hip style results in misstatements. It’s insulting to women to have a president with his sexual history. His hubristic style turns off citizens and leaders worldwide. His belief in tariffs is ridiculed by both the right and left. And his otherwise full faith is the free market ignores the many people who can’t make it in a purely capitalist society. But I’d like to hear what you think.

The takeaway

Again, situations are so different as to resist being reduced to a script. But I wrote them in the hope that nuggets reside. A few general principles are used across a number of them:

  • Be concise. Long lectures tend to get tuned out. Say the essence; that delivers your core message undiluted.
  • Give a reason.  People understandably hate arbitrariness.
  • Give choices. Where appropriate, give a person two or three choices rather than an order.
  • Give honest feedback, tactfully dispensed. Yes, very occasionally, you want to shake a person from their armor of complacency. But usually, it’s wise to couch your statements about a person in a way that enables him or her to save face.
  • End utterances with a question, such as “What do you think?” No one wants their agency wrested away. You can still stick to your guns but it’s worth hearing what the person says. Who knows? You may even change your mind.
  • Be crisp. Many people can’t bear to deliver bad news so they soften it with ambiguity. That can give false hope to the recipient of the news. Yes, usually be kind and face-saving but be unambiguous about the wise thing you're asking for.

I extemporize on these issues on YouTube.

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