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Time for a Difficult Business Conversation? Four Steps to Make it Easier

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No matter what position you have in your home furnishings company, at some point you’re going to have to initiate a “difficult conversation” with a boss, co-worker, or colleague. This conversation could be between you and one person, or it could be between you and an entire group of people. It’s a conversation where each party has an opinion and a perspective, and they’re all very different.

So what makes these conversations so difficult? Often, they are emotionally charged conversations, and as such, people have a tendency to get hooked by their emotions and to react rather than respond. Or it’s a conversation where someone feels verbally attacked and the person’s fight or flight response kicks in, which escalates the conversation and makes it difficult immediately.

Some examples of difficult conversations include:

  • Talking to a co-worker about a problem he or she has that is impacting your work.
  • Giving the boss feedback when the boss is doing something you don’t like or that’s de-motivating you.
  • Critiquing a colleague at work.
  • Talking to a team member who is not keeping up their end of the bargain.
  • Confronting a co-worker or colleague about blatantly “bad” behavior, such as stealing sales or discrimination.
  • Pointing out someone’s shortcomings that are affecting the project or team.

The list is virtually endless.

Regardless of the topic or circumstances, these conversations are hard to initiate, especially when the stakes are high or you’re confronting someone you genuinely like. But the conversation must take place if you want to achieve any sort of happiness and satisfaction at work.

Unfortunately, most people avoid these conversations completely. They tell themselves that the situation will improve or the other person will change his or her behaviors, but that simply doesn’t happen. Other times people face the prospect of a difficult conversation head on, but then approach it the wrong way, making the situation escalate to a standoff. A better option is to learn the skills needed to have these difficult conversations and then facilitate the dialogue with grace and tact.

Realize that having these conversations is indeed your job. It’s not your boss’s responsibility to intervene and solve all your problems. That’s called triangulation. If you constantly go to your boss to smooth over your problems and professional relationships, you’ll never be viewed as a leader in your company. Additionally, by your boss having the conversation for you, the situation will usually get worse. So go to your boss for help with the skills needed to have a difficult conversation, but then you have to engage in the conversation on your own. Always remember that if there’s something bugging you at work, it’s your problem…so take care of it.

Easing the Stress.

Chances are that a difficult conversation is looming in your future. To make the most of it and to ensure it goes as smoothly as possible, keep the following suggestions in mind.

Decide to do it.

Having the difficult conversation is for you, not for the other person. You initiate it so you can lighten your own load and ease your mind or frustrations. Yes, you know that the other person might get defensive, but that’s okay. You have something to say, so you must say it.

Unfortunately, when a situation arises, people tend to fall into one of two categories: silence or violence (verbal). Most people become silent. They understate the problem, avoid it, or make excuses for it so they don’t have to address it. Other people come from an angry place and become controlling, coercing, and blaming.

But to be successful in business and in life, you have to acknowledge that it’s time to have a difficult conversation with someone…and then commit to doing it. No backing out, no making excuses, and no yelling. So make the decision and stick with it.


This is no time to “wing it” or talk “off the cuff.” This is an important conversation, and as such, you need to prepare for it. Before you approach the person, pre-script what you want to say. When thinking about what to say, most people have a tendency to speak from their head rather than from their heart. To avoid this, start with your motives. Why are you really having this conversation? If you’re not beginning the conversation with the right motive, it won’t go well.

Remember that the only person you can truly prod is you. Therefore, you have to speak from the heart and know what you want from the conversation. Chances are you want a win-win solution that makes the situation better. So be clear about what that solution looks like. As you do this, don’t forget that if you play a part in the situation too, state your part in both the problem and the resolution.

Finally, if possible, bounce your conversation script off a trusted colleague. To keep anonymity, you don’t have to say the person’s name, or you can choose someone who doesn’t know the person. Either way, get this outsider’s feedback to make sure you’re not sounding defensive, accusatory, or unprofessional.

Make an appointment

Whatever you do, don’t approach the person “out of the blue” and begin the conversation. That’s called an ambush. Rather, talk with the person and ask for him or her to meet you for lunch or coffee. If the person is in another geographic location and scheduling a face-to-face meeting is impossible, then schedule a phone call with the person. Face-to-face or voice-to-voice are the only options. This is not a conversation you can have in an email exchange, an instant message thread, or a Facebook wall post.

When doing the conversation face-to-face, meet over lunch or coffee rather than in someone’s office. Not only is a public location neutral territory, but it’s also conducive to a more intimate conversation where you can read each other’s intentions, energy, and motives. When doing a voice-to-voice conversation via phone, try to schedule it as early in the morning as possible when both parties are fresh and haven’t been bombarded with the day’s stressors yet.

Speak from the heart.

If you’ve done all the prep work, the conversation itself should flow naturally. Speak from your heart and talk about what you know to be true (the facts), not what you think (your perception of events). After you state the facts, then you can tell the person your take on the situation. Ask the person what he or she thinks happened so you can get their side of the story.

As you speak, avoid the word “you” as much as possible. Instead, focus on “I.” For example, don’t say, “You’re always missing deadlines, and that means all your work falls on other people’s shoulders. This just proves how inconsiderate and lazy you really are.” Instead, say, “When you continually miss deadlines, I have to work late to compensate so I can make my deadline. When I have to work into the night, I feel very frustrated and taken advantage of.” The second version focuses on how a certain behavior makes you feel rather than being accusatory on the other person. Additionally, be sure that you don’t talk in a parental tone or use authoritarian language, as that will make a tense situation worse. 

When the other person talks and you want to ensure understanding, paraphrase what he or she said so you acknowledge the story and validate it. Often you’ll find that the other person did not intend to be hurtful and didn’t know that their actions were causing anyone stress.
Before concluding the conversation, ask for what you want. For example, you could say, “Can we agree that from now on that you’ll meet your deadlines or give me an early heads up?” As you do this final step, keep in mind that you can’t change the other person. The only thing you can do is talk about how you feel about the situation and how their behavior has impacted you. The other person has to decide whether he or she wants to change. You can simply offer the opportunity for change.

A Better Future

These difficult conversations are intimate and transparent. They put you and your feelings out there in a way where you can be seen for who you really are and judged. That’s why they feel so scary to have. But the more prepared you are for the conversation, the better it will go. So don’t harbor feelings of resentment or anger toward others anymore. Decide to engage in a difficult conversation, prepare thoughtfully for it, and then speak from your heart. In the end, you’ll feel better for taking the plunge, and your work life will improve substantially.

About the Author: Jean Kelley, Industrial Sociologist and founder of Jean Kelley Leadership Consulting, has personally interviewed over 20,000 people.  She is the author of “Get A Job; Keep A Job” and “Dear Jean: What They Don’t Teach You at the Water Cooler.” Jean has positioned herself as America’s workplace coach.  For more information, visit www.jeankelley.com.

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