How to Keep Up with the Pace of AI: Build a Teaching Muscle

Faced with a challenging transformation curve, Vipin Gupta’s organization found that instituting a culture of teaching – where workers become peer educators – catalyzes an enterprise’s agility to adapt and improves collective engagement. In this article, the president, CTO, and chief product officer at FliptRx, a Former CIO at Toyota Financial Services describes how to treat education as a core business strategy.

How could strategies from pre-AI, pre-Covid times hold value today, as the businesses are changing even more quickly? In fact, a key lesson we discovered at Toyota Financial Services (TFS) in 2018 is even more relevant now –not in spite of AI, but because of AI.

The lesson is this: people can absorb change faster, learn more new skills, and modernize operations more effectively when they become teachers.

Not just learners of the new, but teachers of the knowledge they have already mastered.

This simple idea is the key to a durable culture of transformation and growth across the whole organization. At TFS, this teaching-first culture added a critical piece to our transformation puzzle as we strove to expand our fundamental business model: In less than a year, we were able to launch the industry’s first multi-tenant auto finance platform, expanding the legacy and strength of Toyota’s financial services to support a private-label captive finance business for other automakers like Mazda. 

As a result, we achieved remarkable growth in assets and operating income in subsequent years. And notably, we created this company-wide, teaching-first culture without adding a single dollar to the budget.

For leaders working to capitalize on the power of AI, or any modern technological leap, it has to be activated through education at the grassroots level. CIOs are well-positioned to activate it, though the responsibility to harness technology can no longer just be with the CIO or IT team alone. Everyone has to be a part of it.

Continuous education, when treated as a core element of business strategy, can become the operating system for scale, speed, and culture change. Here is a look at how we did it at TFS, and how a similar approach can help your workforce to drive change to realize the potential of AI today.

Education is a critical missing link in a business strategy

When I started at TFS in mid-2018, the company was unsatisfied with the results of its ongoing digital modernization efforts. While that was true at many (perhaps most) companies around that time, it seemed surprising to me as a new team member at TFS.

The workforce consistently scored in the 90-95% range in engagement surveys. Everyone cared. Everyone wanted to do the right thing. Why would an organization with such a highly invested, engaged workforce lag in its transformation efforts?

Seeking to understand, in my early days I spoke and listened to many people across the organization. My team and I asked a lot of questions. Ultimately we realized that the engagement scores measure individual engagement, not group engagement. Employees were pursuing excellence within the scope of their own silos. Broad business transformation efforts require a cross-functional engagement. 

However, this is easier to observe than to change. What we needed was a rewiring of human behaviors beyond one department. And classic corporate skills training wouldn’t be enough for the business changes we were embarking on, because rather than adding a static set of technical skills and information, we needed to create a workforce across the enterprise, not just IT, ready with new skills, competencies and practices for continual change.

The ability to change continuously is the most significant competitive edge for any business, but an organization can only move as fast as its people can! Why, then, is educating people to build an AI-savvy workforce often missing from business strategies, HR strategies, and even technology strategies? Most strategies that do exist focus on talent acquisition, but not every new trend can be addressed by talent acquisition. A large percentage of the workforce will always be legacy, and without lifting them, companies will feel the drag.

Learning new skills has to be a foundational habit. Leaders need to rewire the environment to shape new skills and behaviors required for digital and AI, and then for whatever is next. 
This realization gave birth to the idea of a Digital Academy at Toyota Financial Services, with the twist I described above: The focus was not on providing traditional training courses, but on turning our own skilled employees into teachers.  To unlock a more durable learning culture, we needed to activate an army of teachers.

Teaching, not training, makes learning stick

We realized that to be a truly digital company, we needed to shape new behaviors and skills at enterprise scale and with speed. To achieve that, we needed to activate habits of learning first. A habit that shapes other habits.

Learning had to be a way of working, not a tool for change management or a one-time investment. It wasn’t delegated to HR. It wasn’t limited to IT. It would include every function, every employee, and every consultant.

Instead of traditional approaches to talent development — outsourcing, certifications, repetitive training — we embedded teaching into the flow of work, the fabric of leadership, and the management expectations. What emerged was a digital academy. The academy became an engine of alignment, mastery development, and behavioral change — run entirely on internal energy and delivered at zero incremental cost. It became a self-growing movement. It was not set up as a program. It was a new way of working.

While Digital Academy became a tangible face of this concept, the focus on activating teaching made the difference. Many companies have individual employee training focused on skills development, but miss the opportunity to use it as a strategic engine for transforming behaviors needed for new ways of working in the world of digital technologies and AI.

The Digital Academy consisted of three things: a physical space (one full floor in a building close to headquarters); a SharePoint hub that supported scheduling, collaboration and knowledge sharing; and a seven-member team that supported teachers and helped them shape their content.

There were no hierarchy, compliance mandates, or certifications. The framework was simple. Sessions were open, informal, and focused on real-world context — slide decks were optional. The entire platform was by the people, for the people, resulting in zero new costs.

Three principles to support continual learning

Three principles we learned will help guide your organization through the AI revolution and beyond.

1.   To multiply at organizational scale, unlock individual mastery

Training is transactional. Teaching is transformational.

We routinely asked our team members, not in a formal survey but in conversations, “What is your mastery? What are you really good at?” followed by “Will you teach it?” This simple invitation took them by surprise, but almost always resulted in a “yes.” Then we asked for an informal commitment to teach one to two hours each week. We called it Teach 100. A simple aspirational goal of 100 hours per year of teaching by each leader.

This was all voluntary. We didn’t set formal performance expectations. There were no presentations, no formal certifications, just people sharing their functional expertise honestly. And because the content came from the real world, not a vendor’s playbook, it was immediately helpful. Once it started, it grew – because it felt purposeful, energizing, and authentic.

We were operating on a belief that internal expertise combined with teaching while doing creates a powerful learning cycle:

Learn → do → teach → do → learn

Teaching reinforced confidence, deepened skills, and inspired peer respect. The act of teaching didn’t just help others — it elevated the teacher’s own thinking.

It was not about perfection. Authenticity is more powerful than polish. And the act of teaching made leaders more approachable, collapsing layers between leaders, managers, and members in an environment well-known for hierarchical formality. 

2.   Anchor with fundamental, shared skills

Before stepping onto a Toyota production line, workers must pass “Fundamental Skills” training. I experienced this firsthand at a Kentucky plant, where I struggled to correctly tighten a bolt - something I thought I already knew how to do. Through repetition, failure, and coaching, I learned the Toyota way of tightening a bolt. Only then did I graduate to be on the assembly line to add a connector module to the cars moving on the assembly line.

No one joins the car production line without fundamental skills training. Why should the digital production line be any different? In most companies, however, we let new employees and consultants “tighten bolts” on mission-critical systems with near-zero orientation in how our company works. This results in significant waste due to variations in practices, time to learn, and incomplete understanding of capabilities beyond their silos.

To reduce this waste, every contributor from every function of the company, whether employee or consultant, had to learn our business, products, practices, policies, standards, and design principles.

Importantly, we rejected siloed, self-paced learning in favor of cohort-based education. Real change happens when teams that work together build shared language and mental models together. Teams were trained as cohorts comprising employees from sales, risk, finance, call center, and more, all side-by-side. 

3.   Make it inclusive, self-driven, scalable, and low cost

Again, we didn’t create a new department or ask for funding. The Digital Academy was by the people, for the people. We created a space and invited our own people to lead it, which they did – some even posted “I teach” badges on their Outlook profile picture as a badge of honor.

The result? Over 1 million learning hours in 3 years. Zero dollars added to the existing IT budget. The whole effort was managed by a small organizing team and a lot of internal energy. 

Seeing your results grow

What began as a tactical fix to an expertise gap became a cultural movement and an engine for continuous change. In less than a year, we introduced dozens of core systems to deploy a novel multi-tenant captive auto finance platform from the ground up to launch Toyota financial services’ first private label business for Mazda Financial Services, introduced a new methodology of building enterprise software with digital factories like we build cars. These significant business advances were possible only because we activated human development first – the most essential ingredient in delivering the full promise of any change and transformation to be a digital or AI company.

As manufacturing saying in Japan goes “Monozukuri wa hitozukuri” - “Making things is making people.”

To make things, make people first. In 2018, the focus of this effort was on digital transformation; the same is needed even more in 2025 and beyond as we all embark on transformation for AI.

Teaching muscle is key not just for humans, but also for systems and agents in the age of AI. 

Companies with the best army of teachers will win the future.