What We’ve Learned About Digital Wisdom, Seven Cohorts In
When we started the Digital Wisdom Collective, we weren’t entirely sure where the journey would lead. What we did know was this: most major initiatives fail not because of technology, but because of people.
Now, seven cohorts later, the patterns are clear.
We’ve worked with managers, directors, architects, and founders from all kinds of industries. They’ve come in carrying heavy loads, often the “go-to” people in their organizations who are relied upon to keep digital initiatives moving even when the odds were stacked against them. And they’ve left with something that sticks: more confidence, a bigger voice at the table, and a mindset shift that helps them bridge silos instead of being crushed by them.
The numbers back it up: 69% of our alumni were promoted within 12 months. Many report saving their organizations months of rework and consultant spend. But beyond the stats, what stands out is a sense of lightness — of leaders realizing they don’t have to run themselves ragged to be effective.
Across seven cohorts, some consistent themes have emerged.
Leadership Growth: Improved communication, listening skills, and role modeling
Confidence & Presence: Stronger voice and elimination of limiting beliefs
Professional Development: Promotions, project success, and organizational improvement
Intentional Approach: Greater awareness of actions and goals
Personal Growth: Self-reflection and excellence pursuit
Collaborative Spirit: Enhanced teamwork and communication
Still, the most common question we get is: “What is Digital Wisdom?”
Building collective intelligence into technology
Here’s what we’ve learned: Digital Wisdom isn’t a skill you can check off a list. It’s not a new app, tool, or certification.
Digital Wisdom means building collective intelligence into technology.
It’s the human operating system for the digital age — the missing layer that ensures technology doesn’t just get installed, but actually works in practice.
AI models evolve several times a year. But what about our collective intelligence models? If we don’t continuously upgrade how people think, learn, and collaborate, we’ll never keep pace with the technology we’re deploying — and we’ll miss the chance to create a new way of co-existing between human and machine skills.
Digital Wisdom makes sure human insight, alignment, and judgment are embedded into systems, so organizations don’t just scale technology, they scale wisdom.
Three types of infrastructure
To build Digital Wisdom into the core of their ecosystem, companies need to tend to and align three types of infrastructure:
Human Infrastructure: Developing confident, resilient leaders in the overlooked middle layer.
Wayfinding Infrastructure: Creating the shared models and frameworks that make complexity simple.
Technology Infrastructure: Building the systems and technical foundation that enables wisdom at scale.
Together, these three types of infrastructure form a stable foundation that keeps progress from stalling, and allows people to intelligently navigate your ecosystem.
Seven cohorts in, we know this much: Digital Wisdom isn’t optional. Without it, organizations repeat familiar patterns. They over-invest in tools and tech and under-invest in people. They stack new and better tech on top of a shaky foundation.
Where to start
The good news is that building Digital Wisdom doesn’t have to be hard — but it does take intentional investment.
The most underserved area in every organization is Human Infrastructure, which makes it an ideal place to begin.
Identify those primed for growth. Every team has those people who are eager to bring new ideas, drive change, and try to do things differently. They connect the dots and bring perspectives into alignment. More often than not, they feel lonely — they ‘tick’ in a new way, but are stuck working within the organization’s legacy silos and patterns.
Make an intentional investment. Give them a community, a sandbox and opportunity to test ideas and build leadership muscle.
Let them create ripples. They’ll influence their immediate work area first. Cross-functional collaboration weakens silos and expands impact from there.
Build a self-reinforcing cycle. Give these firestarters the chance to identify the next wave of leaders. One spark lights another.
Leverage momentum. Research shows that once just 5% of people in an organization adopt new skills and mindsets, it creates unstoppable momentum across the whole system.
Why wisdom now?
AI doesn’t wait. It’s advancing with every release and model upgrade. If we don’t invest in upgrading human and wayfinding infrastructure at the same pace, the gap between what technology can do and what organizations are ready for will only widen.
Wisdom doesn’t appear overnight — it is learned through experience and intentionally passed down as new generations rise. Digital Wisdom is no different — in the digital age, investing in Digital Wisdom should be considered a necessary operating expense for forward-thinking companies, not a one-time transformation initiative or a side project.
Because it touches technology, people and financial outcomes, this investment requires cross-functional alignment between the CIO, CPO and CFO. Heading into another IT budget round for 2026, this is the moment to make Digital Wisdom part of your strategy — not as an HR initiative but as a core IT and infrastructure expense — one that strengthens your entire ecosystem.
👉 Want to know where your organization stands today? Start with our Digital Wisdom Maturity Assessment — a quick way to see your baseline and what’s possible.