Dreading that difficult work talk? AI may help
Say you have to confront an employee about a missed deadline or deliver some tough feedback. Or you have to negotiate a contract with a contentious vendor, or talk to the boss about something sensitive.
Let’s face it — nobody looks forward to the difficult work conversation.
Maybe AI can help.
“Honesty seems like such a simple concept, but the truth is, people are terrified of being direct and honest,” said Michelle Abdow, founder and president of Market Mentors, a marketing and PR firm. In her more than two decades in business, Abdow has learned the art of “confronting without being confrontational” — and it’s something she believes anyone can do with the aid of generative AI.
While businesses integrate AI into all sorts of workflows, many may have not yet considered the tech’s potential for perfecting one-on-one dialogue. However, Abdow suggests that AI-assisted communication could empower employees at all levels to engage in conversations they might otherwise seek to avoid. (Meanwhile, it’s not unheard of for companies to use AI to automatically monitor and fire underperforming workers. No difficult conversation necessary.)
“The magic of AI for difficult conversations is simple: practice makes perfect,” said Andrew Reece, chief AI scientist at coaching platform BetterUp. “By roleplaying with AI before having that tough talk with your colleague or client, you build confidence through repetition without risking relationships.”
Reece explains that AI can mimic different personality types and response styles, preparing users for a range of reactions they might encounter. BetterUp recently introduced 24/7 access to an AI coach to help employees roleplay uncomfortable conversations, brainstorm challenges and stay accountable.
“Organizations see the best results when they leverage both AI and human coaching as complementary forces,” Reece said. “Think of AI coaching as your practice field and human coaching as your game-day strategy.”
When it comes to coaching, that combination of man and machine appears to line up with employee preferences. According to BetterUp’s research, about one-third of people prefer human coaches while 15% prefer AI, but a majority want access to both.
Micah White, vp of research and development at CGS Immersive, which supplies businesses with extended reality (XR) solutions, likens such skills training to fitness training: The more you do it, the greater the results.
What does AI paving the way for difficult conversations actually look like?
Abdow offers the example of utilizing AI to prepare for a discussion with an employee who consistently misses deadlines. By prompting AI to structure the conversation, the manager gets guidance on opening the conversation in a positive way, acknowledging the employee’s value, then explaining the problem at hand with concrete examples. The manager then ties the individual’s performance to its impact on the company, sets expectations and consequences, and offers support while reinforcing responsibility.
The result, according to Abdow, can be transformative. “When you turn an uncomfortable conversation into a constructive exchange, everyone comes out feeling relieved,” she said. “Other employees recognize their leadership is dealing with the problem and not avoiding it. The situation solidifies a culture of accountability.”
CGS Immersive has taken AI-assisted communication a step further with Cicero, an unscripted, lifelike roleplay platform that allows employees to immerse themselves in difficult scenarios. “By using well-crafted AI simulators, you can create a safe place to practice, get real-time coaching and feedback, and reduce bias and improve practice,” White said. The approach allows employees to hone their communication skills through repetition without real-world consequences.
Colleen Tully, senior program manager of learning technology innovation at medical device maker Medtronic, one of Cicero’s early adopters, believes such a solution stands to revolutionize areas like sales enablement, surgical education and other medical training, calling it “a significant leap forward.”
Despite its promise in helping frame a tough talk, AI isn’t without limitations here. “It’s not a silver bullet,” said Rocki Howard, chief people and equity officer of Textio, an AI-driven HR support platform. While it can “break the blank-page barrier,” she noted, AI-generated responses could also lack depth and nuance without careful input. Meanwhile, over-reliance on the technology could create a false sense that things are improving with an employee when they’re not.
For HR managers looking to implement AI tools for workplace communication, Howard recommends employing platforms designed with bias mitigation and high-quality training data as top priorities. But at the end of the day, AI should be a guide, not a replacement for human judgment, she adds.
Josh Millet, founder and CEO of Criteria, a testing and talent assessment platform for employers, agrees, noting that while AI has the power to facilitate difficult conversations, it shouldn’t replace learning to navigate confrontation without the aid of machines.
“Over-reliance on AI can cause people to risk development of critical interpersonal skills needed at work like emotional intelligence and adaptability,” he said. “It also cannot fully understand or process the nuances of human emotion and reactions, so it’s important to recognize the tool’s limitations when using it as a guide for discussions.”