The Do’s and Don’ts of Tough Conversations

UPDATED: September 20, 2017
PUBLISHED: September 20, 2017

Imagine for a moment that you’re about to sit down with an employee to discuss exciting new changes to your company. Perhaps you’re bubbling with enthusiasm, sure that she’ll feel the same as you. Then you break the news and you’re met with a blank stare, a passive sigh or even an angry rebuttal.

No matter how prepared you might think you are, some conversations just won’t go the way you think they will. But that doesn’t mean you should give up and leave all tough conversations to work themselves out. After all, in an online survey of 1,000 employees, 91 percent said that communication issues drag executives down. The data revealed that most leaders were missing critical opportunities to engage that could position them as more trustworthy to their employees.

Related: 13 Communication Mistakes Leaders Make

As someone who’s been managing others for more than 25 years, I’ve seen the value of honest, open communication between an employee and employer, but I’ve certainly stumbled along the way. Although these communication mishaps aren’t my proudest moments, they’ve taught me valuable lessons as a manager, including how to repair relationships and have more constructive conversations. I’ve picked up on a few important do’s and don’ts on my journey, such as:

1. Do throw the script away.

Preparing for a tough conversation is imperative to its success. There’s a big difference between jotting down notes and drafting a script, though. The latter won’t do you any good.

A difficult conversation tends to go best when you think about it as just a normal conversation,” says Holly Weeks, author of Failure to Communicate. Because your counterpart doesn’t know his or her lines, the conversation can become awkward and artificial. For a more natural, productive conversation, opt for a few bullet points to address, and be flexible about the ensuing conversation.

2. Don’t dance around the issue.

It is important for you, as a manager, to be as explicit as possible during difficult conversations. Begin by declaring what you hope to achieve during this meeting and asking the employee to do the same. Then tackle the topic at hand, as well as the thought process behind it.

3. Do put yourself in the other person’s shoes.

As humans, we all possess preconceived notions, but holding onto those assumptions during tough conversations is a mistake. For example, a few years ago, I led a team that we needed to restructure. We needed to go much deeper in areas where we were the best and for which we were known as the experts, but this also meant letting go of some things that weren’t as important. So I had to have several conversations with employees on how their roles would shift. One conversation was a huge learning experience for me.

I was so confident in the direction of our group that I failed to explain fully one employee’s role and how it was changing. I assumed she would understand the importance of the shift because she was a senior leader, but I failed to articulate how she fit into the bigger picture specifically. Because of this, she didn’t understand her importance to the company and the value she added.

Related: 7 Communication Mistakes You’re Making at Work

It takes two people to have a conversation, so consider your counterpart’s perspective. Think through the issue at hand from your point of view. Then reflect on what your employee thinks the issue is. If you can’t answer the second question, ask him or her directly. When you work to empathize with your employee, she’ll be more open to having a productive conversation.

After speaking with my employee about the structural changes, I picked up on her social cues and asked her to tell me about how she was feeling. That’s when I realized I needed to put myself in her shoes. So I explained how shifting some of her workload would actually allow her to dive deeper into her area of expertise. After I did so, she became one of the biggest champions in the department for these changes.

4. Don’t get defensive.

It might be tempting to act defensively or even make yourself the victim during a difficult discussion, but you should avoid both of these tactics at all costs. Deflecting blame or making statements such as, “This is really difficult for me!” or “I feel terrible about this!” during a difficult conversation only makes you appear dismissive of your employee’s needs. Instead, acknowledge your role in the discussion and how you’ll work through the issue in collaboration with your employee.

5. Do show a little compassion.

Difficult conversations might not be pleasant, but compassion helps you deliver difficult news in an honest, fair manner. Ultimately, my restructuring conversation was successful because I responded to the employee’s needs with compassion. Once I understood why she was concerned, I was able to sympathize and respond accordingly. Keep in mind that it’s important to not only respond to employees’ concerns as they crop up, but also to stay ahead of them to reassure your employees that they’re valuable teammates.

Having a tough conversation with your employee is never easy or fun—especially when that employee reacts differently than you’d anticipated. But it’s still important to reflect on these experiences. After a draining conversation, take some time to consider what went well and what did not, as well as what you can do differently in the future. In conjunction with transparency, active listening and the right attitude, self-reflection will help you tackle difficult conversations head-on.

Related: 6 Communication Skills That Will Make You a Better Leader

Sarah Clark

Sarah Clark is the president of Mitchell, an award-winning public relations firm that creates real conversations between people, businesses and brands through strategic insights, customized conversations and consumer engagement. The agency is headquartered in Fayetteville, Arkansas, with additional offices in New York City and a strategic presence in markets across the country. Mitchell is part of Dentsu Aegis Network, which is made up of nine global network brands and supported by its specialist/multimarket brands. Dentsu Aegis Network is Innovating the Way Brands Are Built for its clients through its best-in-class expertise and capabilities in media, digital and creative communications services. Offering a distinctive and innovative range of products and services, Dentsu Aegis Network is headquartered in London and operates in 145 countries worldwide with more than 30,000 dedicated specialists.

Clark is one of the top strategic communications professionals in the country, with more than 25 years of experience in corporate communications and an exceptional track record in protecting corporate reputations and redefining perceptions in key areas of business.