3 communication techniques for challenging conversations

Whether it’s restructuring or giving constructive criticism, here’s how leaders in the workplace can soften the blow of a hard discussion

communication techniques hero arrow hitting a bulls eye

Leaders in the workplace are more than likely to conduct tough conversations. Maybe it’s downsizing and letting workers go, a large-scale corporate restructuring, or providing constructive criticism to a junior employee—these situations require a certain level of empathy and finesse, as well as a variety of communication techniques to make sure your message is well received.

The conversations may not be fun, but they are fundamental to your role as a leader. Here are a few communication techniques you can use to make them easier for you and your employees.

1. Provide feedback that’s candid but respectful

According to Ben Horowitz, the co-founder of venture capital firm Andreessen Horowitz, difficult conversations aren’t just uncomfortable; they’re unnatural. After all, it’s normal to want to keep the peace and get along with other people.

“If your buddy tells you a funny story, it would feel quite weird to evaluate her performance,” he writes. “It would be totally unnatural to say: ‘Gee, I thought that story really sucked. It had potential, but you were underwhelming on the build up, then you totally flubbed the punch line. I suggest that you go back, rework it, and present it to me again tomorrow.’ ”

Yet that’s exactly what a CEO is supposed to do. Horowitz calls it “high-frequency feedback.” By providing critical perspectives on every facet of the business, leaders can create a culture of feedback where candidness is not only expected but respected.

Feedback should be straight to the point: You don’t want to coddle, but nor do you want to humiliate. Horowitz describes it as being direct without being mean. He also warns that “watered down feedback can be worse than no feedback at all because it’s deceptive and confusing to the recipient.”

Finally, be cognizant of your colleagues’ personalities and preferred communication styles. “Everybody is different,” writes Horowitz. “Some employees are extremely sensitive to feedback, while others have particularly thick skin… Stylistically, your tone should match the employee’s personality, not your mood.”

working on projects
Slack-Powered HR

Learn how Slack-powered HR departments accelerate change, save time, and strengthen relationships across their organizations.

Learn More

2. Use communication techniques that foster a dialogue

High-frequency feedback might help foster a positive work environment where difficult conversations are easier. But some situations are much more delicate, requiring patience, preparation and empathy. In an article for the Harvard Business Review, Joseph Grenny, the co-founder of leadership training company VitalSmarts, recounts his experience of getting ready to fire a longtime colleague.

“We’ve spent many thousands of hours observing how people manage these moments, and our recurring observation is that, unfortunately, when it matters most, we do our worst,” Grenny writes. “We cower or coerce, obfuscate or exaggerate, contend or defend. Our research shows the primary predictor of your success in a crucial conversation has less to do with how you use your mouth, and much more to do with what you do before you open it.”

If you’re anticipating a sensitive conversation, come to the table well informed. When you support your comments with hard evidence, it prevents heated opinions and emotions from taking over and lets cooler heads prevail.

“Share the facts and premises that led you to your conclusion,” writes Grenny. “Lay out your data. Explain the logic you used to arrive where you did. Gathering the facts is required homework for a healthy conversation.”

He says that leaders owe it to their colleagues to build their case in a “patient, honest, and vulnerable way” and to be open to being challenged. This last part is crucial: No matter how well prepared you are for a difficult discussion, be curious and willing to listen.

Horowitz expresses a similar sentiment when he says that feedback is a dialogue, not a monologue. “Your goal should be for your feedback to open up rather than close down discussion,” he writes. “Encourage people to challenge your judgment and argue the point to conclusion.”

3. Keep communication lines open to avoid unresolved tensions

After Grenny let his colleague go, he continued to support him as he looked for a new job, which shows great leadership and communication. Dealing with the aftermath of a difficult conversation can be just as touchy as the actual discussion, but you should never neglect it.

“We often want to ‘forget’ or purposely avoid recognizing that a hard conversation took place,” notes Dolores Bernardo, whose work in management and talent development spans companies such as Google, Accenture and Airbnb. “That’s a mistake, because it leaves you powerless, and leaves your colleague guessing at how to handle the situation, as well. My advice is to: a) proactively follow up, b) acknowledge that it was a tough situation, and c) focus on the positive.”

She describes working with a sales director who was discouraged after his new bosses harshly shot down his ideas. So what did Bernardo encourage him to do? She told him to write an email thanking them for their criticism. “In the email, he acknowledged that it was a challenging conversation and then focused on the positive—the fact that they had identified and discussed some big issues, which he was thankful to have out in the open.”

This is sound advice for both employees and managers. It shows a commitment to being open, driven and solutions-oriented. It turns the difficult conversation into an open door instead of an obstacle and helps all parties find a path forward.

As a leader, addressing tough topics is part of the job—whether it’s an underperforming colleague, a corporate shuffle, or trust issues on your team. But with the right communication techniques, you can guide these discussions productively from start to finish: Provide well-researched rationales for your decisions, be open to debate, create a culture of quick feedback, give thanks for input, and keep the conversation going.

collaboration in the workplace image of people working together in different spaces
Manage large, complex teams with Slack’s Enterprise Grid

Unlimited workspaces give every group a place to organize their work.

Get started

Slack is the collaboration hub, where the right people are always in the loop and key information is always at their fingertips. Teamwork in Slack happens in channels — searchable conversations that keep work organized and teams better connected.