Why Gen Z Struggles With Difficult Conversations At Work

Advancing in your career often requires navigating uncomfortable conversations, a skill that workplace expert Henna Pryor identifies as crucial. Successfully handling tense interactions, whether you're asserting an opinion or negotiating a raise, can significantly boost your professional trajectory. However, a growing number of employees find this kind of interpersonal discomfort challenging.

The Growing Discomfort with Workplace Conflict

According to Pryor, the founder of leadership coaching firm Pryority Group, many have become accustomed to solitude and quick technological solutions. "The reality is, many of us are very comfortable in our aloneness, and we've gotten pretty comfortable turning to ChatGPT for an answer, instead of asking our colleagues what they think," she says. This reliance on tech over interpersonal engagement means that managing high-stakes conversations requires a different, less-practiced skill set.

This challenge is particularly pronounced among Gen Z employees. Having started their careers during the peak of remote work, they've had fewer opportunities for face-to-face interactions where these skills are honed. Pryor's research indicates that younger people report feeling more uncomfortable at work and, as a result, tend to avoid conflict even in low-stakes situations.

Yet, the ability to communicate clearly during a conflict is highly valued. It demonstrates that you are capable of problem-solving, collaboration, and accepting feedback—all qualities that help build trust and strong relationships at work.

Pryor notes that while many people believe they are effective communicators, their skills often falter under pressure. To help, she offers three strategies to prepare for and remain calm during difficult workplace conversations.

1. Prepare with Positive Self-Talk and Research

If you anticipate a difficult conversation, such as a debrief on a failed project, preparation is key. Pryor recommends a simple out-loud pep talk to reassure yourself of your capabilities. "It's some version of, 'You've got this Henna. You're uncomfortable, but you can do this,'" she shares. Saying it aloud can make self-talk more effective.

As Harvard expert Alison Wood Brooks noted, even taking 30 seconds to plan what you will say can help you stay grounded. Pryor also suggests using technology to rehearse. She inputs the context of a conversation into an AI chatbot and asks for potential counterarguments. "It doesn't accurately predict what the other person is thinking or feeling, but it does expand my own perspective," she explains.

2. Have Go-To Phrases in Your Back Pocket

Memorizing a few key phrases can be a lifesaver mid-confrontation. Pryor often starts by acknowledging the awkwardness of the situation. "Whenever I enter a difficult conversation, it's almost an imperative for me to say, 'This is really hard for me to say, but I know it's important we talk about it,'" she says.

This approach helps frame the situation as "us versus the problem" rather than "you versus me," which can reduce defensiveness in the other person. Another of Pryor's favorite phrases is, "I am seeking clarity." She believes that reframing conflict as an effort to clarify an issue makes the conversation more productive and less adversarial.

3. Dont Shy Away from Small Opportunities

To build your confidence, practice navigating conflict when the stakes are low. Pryor suggests raising your hand in a meeting when you normally wouldn't or respectfully sharing a different point of view with a coworker. These small acts help build your "social fitness."

For remote workers, this could mean asking a colleague for a virtual coffee over a video call or sending a voice memo instead of a Slack message to deepen professional bonds. If you struggle with this, Pryor advises reframing how you view social risk. By confronting the choice you're making—prioritizing comfort over relationship-building—you may find the motivation to step outside your comfort zone.