AI is transforming onboarding by turning scattered knowledge into instant context, helping employees ramp faster and contribute sooner.
Emma Coppin
Multimedia Content Lead, Thought Leadership and Customer Stories
Workday
Audio also available on Apple Podcasts and Spotify.
Onboarding is among the most stubborn challenges faced by HR departments far and wide. How can teams bring a new employee up to speed, quickly and effectively, on all of the important institutional knowledge and critical context that will enable them to thrive in their new role?
Checking both those boxes—speed and efficacy—feels like an impossible ask. Or it did, anyway.
With its ability to rapidly gather and synthesize massive amounts of information, and even tailor the details to specific roles and functions, AI has the potential to reinvent employee onboarding, alleviating the pains that have historically slowed down organizations and tripped up their newly added talent.
Chris DiBona, vice president in the office of the chief technology officer (CTO) at Microsoft, touched on this idea of rapid context-building during a recent conversation on the Future of Work podcast with Workday’s Kathy Pham.
While DiBona’s perspective focused primarily on grappling with the technicalities of open source and ramping up knowledge around codebases and systems, it’s an approach that can be embraced and applied much more broadly.
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Traditional onboarding has always been designed around information transfer: documents, training modules, walkthroughs. These are necessary, but often not sufficient on their own.
The reason is that context doesn’t live in a single place.
It’s spread across systems, embedded in workflows, and often carried informally by people who have learned through experience. New employees are expected to piece it together over time — through trial, error, and a steady stream of “quick questions.”
This creates friction that’s easy to underestimate but hard to overcome. That friction materializes in several ways:
Making matters worse: organizational complexity is only magnifying. Roles are becoming more versatile, AI is being integrated across workflows, and skill visibility for leadership is limited.
It all results in a familiar pattern: highly capable people taking longer than they should to gain full confidence and make a meaningful impact. Here’s where AI can lend a major assist.
Employees come to your company with established skills, and new solutions are continually making it easier to build and adapt them in real time. The struggle for a new hire is quickly grasping how to apply their skills and where to focus their development in order to succeed. In practice, the same nominal role can look totally different from one company or team to the next.
AI is the answer machine. When properly trained and prompted, it can cut through the uncertainty and deliver the pertinent details for any situation, in moments. Beyond just helping people complete tasks, AI helps them understand the environment in which those tasks exist.
Drawing from his early days at Microsoft, DiBona highlights how AI helped him quickly orient within a vast, unfamiliar organization.
“Having the ability just to say, okay, 50 years, 250,000 employees, countless efforts over the decades, coming up to speed in any new company. It's like, this is just gold, man,” says DiBona.
AI is evolving into a dynamic layer of institutional memory—one that can be queried, explored, and actioned in real time. That’s incredibly powerful for boosting the flow of information and the speed of time-to-productivity.
As DiBona notes, “They can get to the starting point so much faster now.”
Having the ability just to say, okay, 50 years, 250,000 employees, countless efforts over the decades, coming up to speed in any new company. It's like, this is just gold, man. - Chris DiBona, VP, Office of the CTO, Microsoft
Moving faster: it’s the directive being pressed upon leaders everywhere, with an expectation that quality and experiences won’t be sacrificed. AI makes this possible, but it’s hardly automatic. Getting this right takes thoughtful strategy and purpose-built platforms.
During his conversation, DiBona shared examples specific to the engineering realm that are relevant on a much wider scale. In any line of work, teams can benefit from thinking less about speed in completing isolated tasks, and more on reaching meaningful contribution overall.
With AI at hand, someone can get their legs under them far faster—and more autonomously—than in the not-too-distant past. “Spinning up new people on a project is so much better now than it was even a year ago,” DiBona shares.
Think about how this acceleration can take shape across various functions. In finance, AI can surface how reporting processes are structured, and why certain controls exist. In HR, it can connect policies, systems, and employee journeys into a cohesive picture. And in operations, it can map workflows across multiple systems and stakeholders.
The simple goal in every case is to reduce the time it takes new hires to understand how work gets done, moving them quickly from observation to action and from first contact to active contribution.
Research from Workday found that 93% of active AI users say it allows them to focus more on higher-level responsibilities, such as strategy and problem-solving. That’s because it cuts down the intermediate steps on the path to meaningful work. Accelerated, AI-powered onboarding exemplifies this perfectly.
Spinning up new people on a project is so much better now than it was even a year ago. - Chris DiBona, VP, Office of the CTO, Microsoft
No one should be looking at AI as a substitute for the interpersonal factors involved with growing comfortable at a new job. Getting to know colleagues, learning from their experiences, connecting with the purpose behind the work—these are all vital onboarding elements.
With AI systems as a resource for documented institutional knowledge, new employees can devote more time and energy to enmeshing themselves within the culture and team vibes. AI features can also lead to a more personalized, relevant employee experience right off the bat.
“Imagine AI systems that adapt to each employee's preferences, providing customized communication, benefits, and development opportunities,” wrote Workday’s Michael Brenner in forecasting the future of work. “This could mean anything from tailoring onboarding programs to suggesting relevant internal resources or even offering flexible work arrangements based on individual needs.”
The best part? You don’t have to imagine it. It’s already here, and here to stay.
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