We’ve all been there: We know we must confront a coworker, client, friend or significant other about some type of sticky situation. We assume the encounter will be uncomfortable, so we often put it off in hopes the problem will: (a) go away or (b) somehow take care of itself. Or, we repeatedly mull it over until we can no longer delay the inevitable and then finally stumble through the confrontation. Maybe we feel we deserve a raise or promotion at work but can’t bring ourselves to ask for it. Maybe we have to reprimand an employee we’re fond of or need to confront a coworker who took credit for our idea. Or, maybe we’re struggling to find a way to motivate our significant other to change an annoying behavior.

How to have tough conversations with anyone—and with less stress and more success? And what’s the best way to handle conflict, which is inevitable in any relationship? Keep reading…

“I Don’t Know How To Say This…”
Does anyone really look forward to having tough conversations? I know I don’t. For some, the task is almost unbearable. Stress levels rise, blood pressure goes up and the thought of what might go wrong or how badly feelings will be hurt is almost too much to handle. If all of this sounds familiar, you’re far from alone. According to a survey conducted by experts at Development Dimensions International, 20.4 percent of employees surveyed said they loathed having difficult conversations with their bosses more than:

(a) receiving a speeding ticket
(b) catching a cold
(c) paying taxes
(d) doing housework
(e) getting a credit card bill.

Initiating a tough conversation is never a fun thing to do, but it is often a necessary evil. The key to handling it successfully involves understanding the issue, then taking action to help solve the problem. Oh, and keep in mind that procrastinating doesn’t pay. In fact, if you can bite the bullet and force yourself to speak up before things get out of hand, you’ll definitely minimize the intensity of the talk.

Whether the tough conversation you need to have is with a boss, employee, coworker, friend, family member or significant other, follow these tips to keep your discussion productive and positive, regardless of your topic:

Give a heads up.Avoid blindsiding someone you need to have a tough conversation with. Surprise is a tactic better left for war than building a team or strengthening a relationship with a coworker or loved one. And instead of saying, “We need to talk,” which tends to send most folks into panic mode, try less intimidating phrases like, “I’d like to get your opinion on…,” “I’d like to talk to you about…,” “I’d like to get your perspective regarding…” or “It’s really important to me if we could take a few minutes to talk about…” Finally, confront the person you need to have a tough conversation with privately instead of in front of others (coworkers, fellow team members, kids, in-laws, etc.). Otherwise, they’re certain to become defensive, and your conversation will have no chance at being constructive.

Important: If the tough conversation you need to have is with a colleague or coworker with whom you have a contentious relationship, you might not be the top choice to offer advice or feedback regarding their performance or job effectiveness. In cases like this, consider “delegating” the task to someone with whom the person has a more amicable relationship. That way, he/she will be much more receptive.

Set the stage.You’ve heard the old adage that there’s a time and place for everything, and this is particularly true when discussing sensitive topics. Have your sit-down in a place that’s private, quiet and free of distractions—and if the conversation is happening at work, don’t initiate a dialogue when phones are ringing off the hook or important deadlines are looming. Make sure the person with whom you’re speaking isn’t tired, hungry or in a bad mood when you talk to him/her. As a rule of thumb, I’ve found the best time to have tough conversations is mid-morning. Delaying discussions until close to quitting time or sitting down to have a heart-to-heart talk with your significant other within minutes after you both get home from work probably isn’t a good idea.

Watch where you sit. For one-on-one conversations—especially those with emotional potential—sitting in opposite-facing positions creates a feeling of confrontation. Sitting across a table or desk adds even more of a barrier to the conversation and can increase tension, plus make the person you’re talking to feel insecure and defensive. If possible, try to sit at a diagonal angle of about 45 degrees, as this sets a more friendly, equitable tone. Be mindful not to place chairs so close together that personal space feels invaded, but don’t sit too far apart, either. The goal is to build feelings of cooperation and trust.

Try to start and end with a quick compliment. This is a great way to frame your talk and lets the other person know this isn’t an inquisition and that you’re not just focused on discussing negative behavior or performance. Find something positive to say about them from the get go, as this will make them more receptive to hearing what you have to say. Try to end your conversation on a positive note, too, so the person won’t walk away feeling like a failure.

I once had to initiate a tough conversation with Jason, an employee I managed. He was one of my favorites, and his customer service work was exemplary, but his sales process needed to be fine-tuned. He was great at telling the company story to potential customers, but he had a tendency to delve so deeply into that part of his presentation, that it often took too long for him to get to the pitch—which frequently resulted in losing the sale. I initiated my conversation with Jason by complimenting him on his ability to connect with customers and provide top-notch customer service. That enabled him to relax, making it easier for me to address the issue of him needing to tighten up his sales presentation. Once he understood that taking those steps would ultimately result in increased sales—and more commission for him—he was eager to fine-tune his presentation. I wrapped our conversation up with another compliment—telling him that, given his product knowledge and his knack for connecting with clients, this challenge would be a relatively easy transition for him to make. He agreed.

But get to the point. To avoid making tough conversations even more tense, skip the small talk. Beating around the bush just doesn’t work when you’re attempting to alter behavior or change routines. So, be honest and direct by stating—then describing—what’s on your mind, what’s bugging you, or simply what you’d like to see changed. Then ask for what you want. Having a discussion is great, but at some point you need to communicate exactly what it is that you’re asking the person to do. Is it being more punctual? Is it spending more time with the kids? Is it being more attentive to you? Spell it out.

Check your delivery. In your eagerness to get the conversation out of the way, be careful about how you sound. Does your voice have an edge to it, or does it carry a demanding tone that could make your listener feel defensive? If need be, take a deep breath before delivering your message, then do it in a calm, non threatening manner.

Look the person in the eye. Granted, this can be challenging to pull off when you’re having a tough conversation with someone, but making eye contact not only communicates sincerity, it’s also critical to keeping you both focused on the conversation. Looking the other person in the eye will also enable you to read his/her body language, which can provide you with valuable clues about how the discussion is going.

Listen for feedback. This is where you take everything you learned in Chapter Four and put it to work for you. Pay attention to the nonverbal cues the other person is giving off and use what you’re “hearing” to determine how to proceed with the conversation. If they’re becoming agitated or consistently more vocal, it may be time to take a short break or schedule your discussion to continue at another time.

Don’t make it personal. Keep the conversation focused on behaviors or habits you want to change, not the individual’s character. This way, you’re more likely to get the person to buy into your suggestions—and you’re far more likely to see positive results. Remember, feedback is not about insulting someone; it’s about telling him or her how to improve and excel. For example, you would never say to an employee you supervise, “Hiring you was a big mistake.” Instead, you would say, “You’ve been making quite a few mistakes that we need to work on.” Don’t speak “at” or “down” to the person, as this signals a lack of respect. Besides, nobody enjoys being humiliated, feeling stupid or thinking that they’re being treated like a child.

Take a “we’re in this together” approach. Ask questions like, “What do you think we can do to solve this problem?” or “How can we work together to improve this situation?” It’s always beneficial to make the individual feel like you’re tackling a problem together. This will also help strengthen your bond and likely result in the person making the desired changes more quickly, since it will feel like they have someone supporting their efforts.

Use gentle humor when appropriate. Depending on the severity of the discussion, you may find a window of opportunity to interject some humor. If it feels right (and be cautious here) to toss in a little humor with your message, this can be a powerful tool that lightens the mood of the conversation. Studies show that when used appropriately, humor won’t diminish the seriousness of the feedback you’re giving. In fact, it can actually help the person on the receiving end open up and take in what you’re saying without feeling so defensive. It’s important to know the person fairly well before applying this technique, however, as the last thing you want is for them to think the situation is a joke to you.

Wrap things up with a question. Once you’ve delivered your message, expressed your concerns and discussed moving forward, ask the person you’re addressing if he/she has any questions or ideas on how to carry out the new goals you’ve set. So often people resist change because they just don’t think they’re being heard. This is where “listening” plays a huge role. Hearing the other person out gives him/her a chance to vent and release pent-up emotions and frustrations.