Digital mentors are expanding the availability of coaching, while also clearing the path for deeper, more meaningful human connection.
Chris Ernst
Chief Learning Officer
Workday
Executive coaching used to be a corporate luxury good, reserved for the C-suite and the high-potential few. But as the pace of work accelerates, the need for guidance has trickled down to every manager navigating a difficult feedback session and every employee looking for guidance on their career.
We’re reaching a pivotal decision point: Do we insist on human interactions, or do we open the floodgates to AI input?
However, I’d argue there’s a third way: giving every employee a digital mentor that prepares them for higher-value human interaction. It democratizes the kind of expertise that used to be available for a select few while purposely clearing the path for deeper, more meaningful human connection. In addition to scaling a tool, we’re using technology to ensure that when our leaders do sit down together, they’re better prepared to lead with empathy and insight.
Report
The CLO as Moral ArchitectIntroducing digital mentors at a values-led company requires careful consideration. Leaders need to embrace a new role as moral architects, ensuring the right guardrails are in place. AI is now capable of human-like empathy and personalized logic; our job is to ensure this guidance remains rooted in our specific company values rather than generic algorithms.
This shift creates a low-stakes sandbox for development. Vulnerability is the engine of growth, but in a traditional setting, vulnerability with a manager can feel like a career risk—leading many to hide their skill gaps. However, when an employee uses an AI coach, the fear of judgment disappears. They can ask so-called “dumb” questions, admit to struggling with basic tasks, or practice a difficult conversation 10 times until they get it right—all in a private, developmental space.
With AI providing that safe space, leaders can then show up to the human meeting with confidence, from a place of strength.
Success in this digital landscape requires a clear point of view on employee privacy. It’s about making both paths available: AI for that safe space of honest self-reflection, and leaders for essential human relationships. We have to teach people how to navigate both, because while AI expertise is incredibly useful for providing content—the "what" to say—human wisdom provides the context. And context is decisive. It’s the difference between a generic feedback script and a conversation that resonates because you truly understand the person across from you.
While AI expertise is incredibly useful for providing content—the "what" to say—human wisdom provides the context.
We had an opportunity to test this out in our Asia, Pacific, Japan region, where we faced a classic scaling challenge: a rapidly growing, geographically dispersed population of people leaders. Traditionally, these managers might not have quick access to a busy HR business partner to get coaching on a management conversation, such as a quarterly career check-in, or sharing difficult feedback.
Through our pilot with an AI behavioral coach, we moved into true mentorship. Priyanka Das, Workday’s director of people consulting and employee relations based in Singapore, led the pilot. She explains to leaders that the tool is much more than a question-answer bot. It takes on the role of a coach, helping managers think through or give feedback in the moment.
The level of engagement metrics speak for themselves:
Adoption: Over 650 sessions completed within the first 6 months.
Reach: 70% of People Leaders in the region have engaged with the tool.
Stickiness: 55% of users returned for follow-up coaching sessions.
Frequency: Active managers used the tool an average of 5 times per month.
We reduced the volume of questions to our HR team, which was a key goal, but we also raised the leadership floor. By providing 24/7 support in multiple languages, we turned coaching expertise into a distributed utility.
A big caveat here is that AI isn’t a substitute for leadership; I view it as a capability multiplier. It closes the mentorship gap, ensuring that even our most remote leaders have a sounding board accessible to them at all times.
By providing 24/7 support in multiple languages, we turned coaching expertise into a distributed utility.
A valid concern remains: If AI provides the answers, we risk losing our ability to think through problems. I think of the AI coach as a safe rehearsal space. It allows a leader to trip over their words, test their empathy, and refine their message in private, so that when they finally sit down with their team, they show up with confidence and clarity.
While we currently see a distinction between structured AI advice and human wisdom, that boundary isn't static. As AI evolves, it may one day be capable of participating in those deeper, wisdom-based breakthroughs we currently reserve for human-to-human connection. But regardless of how the technology matures, our goal remains the same: using every tool at our disposal to make our workforce feel more supported, not less.
While the AI coach can handle the 2 a.m. "how do I phrase this" questions, at Workday we continue to invest in irreplaceable experiences, like our annual in-person People Leader Summit, and we value face-to-face moments like lunch with a trusted colleague, or a quick check-in with a teammate. These two forces—digital mentorship and human connection—mutually reinforce one another.
The hallmark of an AI-ready culture isn't a workforce that talks to machines; it’s a workforce that feels more supported and connected. By closing the mentorship gap with a hybrid solution, we ensure no leader has to navigate a key employee moment alone.
Report
The rapid advancement of AI has raised huge questions about its impact on jobs. Despite that, 83% of workers agree that AI will enhance human creativity rather than limit it. Learn more about the AI skills revolution in this new global Workday study.