How AI coaches can help managers prepare for the tougher parts of their jobs

Being a manager is tough these days.

The supervisory ranks feel less capable to have the conversations needed to perform their jobs successfully. In fact, few have actually received guidance on leading their teams. Around 44% of managers say they’ve received management training, according to recently-published Gallup research.

Can role-playing with AI coaches help with that? Some companies hope so. HR Brew spoke with leaders from three companies about how their AI coaching products can help managers navigate the trickier parts of their jobs, like giving a critical performance review or discussing pay raise requests.

On LinkedIn. LinkedIn Learning first unveiled its AI-powered coach in October 2023. The platform has rolled out new capabilities since, including live-chat role-play initially released to customers in late 2024.

A menu of role-play practice simulations is available, including some context around the scenario, the level of difficulty, and estimated time each conversation should take. Some options first rolled out were among the most requested by customers, and included scenarios like “set improvement goals for an underperformer,” “approve vacation request,” and “addressing burnout.”

The AI and role-player will “converse” either via spoken word or text. The AI is adaptive, meaning the conversation will get more difficult if it’s going well, or easier if the user struggles.

After the session ends, users will receive an evaluation rubric listing their strengths and areas for improvement based on the conversation, a detailed transcript pinpointing feedback to specific parts of the conversation.

“When you’re trying to navigate a difficult conversation or something in the workplace, tips from a seminar, conversation with a mentor, a course, can only go so far,” said Jill Raines, senior director of product management at LinkedIn. “To do that as a manager, you have to do it. And probably you have to fail, and then you have to realize what you did poorly, and you have to do it again and again and again.”

On May 7, LinkedIn unveiled further updates to its AI coaching tool. Now, premium members can create and customize any scenario by describing the specific situation they want to role-play, as well as customizing the AI’s personality.

Meet CAISY. Skillsoft launched CAISY, its AI-powered conversation simulator, for general availability in September 2023.

More than 100 out-of-the-box role-play scenarios are currently available with CAISY. Skillsoft customers can build their own scenarios, allowing them to fine-tune the simulation to their business’s needs.

First-time people manager scenarios are a “massive use case” for CAISY, said Apratim Purakayastha, Skillsoft’s general manager of talent development solutions. Some pre-built scenarios applicable to managers include:

• overcoming hybrid team challenges;
• handling difficult conversations with grace; and
• handling requests for a pay raise.

“It’s very difficult being a first-time manager these days, handling pay equity conversations, handling diversity conversations, handling sensitive topics,” Purakayastha said. “When we saw generative AI, we saw a huge potential to create these scenarios.”

Users can practice as a manager, or as an employee. They select from four main behavior types: accepting, dismissive, defensive, or random (though Purakayastha notes Skillsoft is expanding the different personality types available). The AI’s safety features will stop the role-players if they say anything not suitable for work, like bringing up unrelated topics or sharing sensitive information.

Once the conversation is over, users receive a detailed report including a rating like “needs improvement,” “acceptable,” or “outstanding,” with a list of the skills they demonstrated well, and ones they should improve.

Looking ahead, Purakayastha said Skillsoft is looking into incorporating more capabilities customers want. Some requests include creating more out-of-the-box scenarios and more customization capabilities for CAISY, evaluations providing more specific scores than just “acceptable” or “outstanding,” and making the AI able to speak back and have a human-like avatar instead of a picture.

“At the end of the day, it’s still not human,” Purakayastha said. “But people want it to be more and more human-like, in multiple dimensions. And that is actually shaping our product direction.”

Meet AIMY. One newer entrant is digital coaching platform Coachhub, which launched its AI conversation simulator, AIMY, to select clients in February. It plans to make AIMY commercially available in June.

Coaching has historically only been made available to a company’s senior employees, but AI can help democratize that, said Laurel McKenzie, principal behavioral scientist at CoachHub.

“Your middle managers, I feel like they get lost in the sauce. They probably get a little bit of training when they become a manager, and they get a lot more options when they become directors and up,” she said.

AIMY has three modes available: goal-setting, discuss and reflect, and role-play. Only two role-play options were available during a recent demo, but CoachHub will add more.

After selecting a scenario, users choose the specific skill they want to develop, and whom AIMY should represent (a manager, direct report, or peer.) An optional field allows users to further describe the traits they want the AI to exhibit.

During the conversation, similar to LinkedIn’s product, AIMY will adapt to the user’s responses; If someone wants to improve emotional regulation, but becomes angry during the conversation, AIMY gets angry, too. Afterwards, users rate themselves on a scale of one to seven. They’re then given guidance on which skills to improve on, and a transcript of their conversation.

CoachHub aims to differentiate AIMY from generic generative AI tools telling users what to do instead of making them learn it themselves.

“It’s not just going to say: Here’s a five step guide on how to give proper feedback. It’s actually going to ask you coaching questions, to help you come to your own solutions, to solve the problem,” McKenzie said. “It’s not just giving you the fish. It’s going to teach you how to fish.”