Time for a Difficult Workplace Conversation? Four Steps to Make It Easier
Copyright 2014 by Virgo Publishing.
Posted on: 11/07/2010


By Jean Kelley

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

So what makes these conversations so difficult? Often, they’re emotionally charged, and because of this, people have a tendency to react rather than respond. Or maybe someone feels verbally attacked and his fight or flight response kicks in, which escalates the conversation and immediately makes it complex. Examples of difficult work conversations include:

  • Talking to a co-worker about a problem he has that’s impacting your work
  • Giving the boss feedback when he’s doing something you don’t like or that’s de-motivating you
  • Critiquing a colleague
  • Talking to a team member who’s not keeping up his 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 discussion 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 the situation will improve or the other person will change his 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, escalating the situation to a standoff.

A better option is to learn the skills needed to have these difficult conversations and facilitate the dialogue with grace and tact. Realize that having these discussions 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 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.

Chances are that a difficult conversation is looming in your future. To make the most of it and 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 the other person. You initiate it so you can lighten your own load and ease your mind or frustrations. Yes, you know the other person might get defensive, but that’s OK. 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; 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 their heart. To avoid this, start with your motives. Why are you really having this conversation? If you’re not beginning with the right intention, it won’t go well.

Remember the only person you can truly prod is you. 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, state it 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. That’s called an ambush. Rather, ask for him to meet you for lunch or coffee. If the person is in another location and scheduling a face-to-face meeting is impossible, schedule a phone call. Face-to-face or voice-to-voice are the only options. This is not a conversation you can have in an e-mail exchange, instant-message thread or 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, it’s also conducive to a more intimate conversation where you can read each other’s intentions, energy and motives. When conversing 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, you can tell the person your take on the situation. Ask what he thinks happened so you can get his 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 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 said so you acknowledge the story and validate it. Often you’ll find the other person did not intend to be hurtful and didn’t know his 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, keep in mind you can’t change the other person. The only thing you can do is talk about how you feel about the situation and how his behavior has impacted you. The other person has to decide whether he wants to change. You can simply offer the opportunity for him to do so.

A Better Future

These difficult conversations are intimate and transparent. They put you and your feelings out there in a way that allows you to be seen (and judged) for who you really are. That’s why they feel so scary. But the more prepared you are, the better they 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.

Jean Kelley, an industrial sociologist and the founder of Jean Kelley Leadership Consulting, has personally interviewed more than 20,000 people.  She’s the author of Get a Job; Keep a Job and Dear Jean: What They Don’t Teach You at the Water Cooler. For more information, visit www.jeankelley.com.