Something profound is happening inside organizations. AI is no longer a shiny new tool that sits on the edges of workflow. It has moved into the center of how people learn, create, and make decisions. Yet the speed of this shift has created a tension that every leader can feel. We are entering a year in which technology, behavior, culture, risk, and productivity collide in ways leadership teams can no longer ignore.
Across a series of internal conversations with leaders at Data Society, from AI strategy to learning design to people operations, a single theme emerged. 2026 will divide organizations that treat AI as a quick efficiency play from those that build real capability, real judgment, and real readiness.
The Illusion of Readiness
By late 2025, most organizations believed they were ready for AI integration. Tools had been deployed. Workflows had been updated. Teams were experimenting, and executives were optimistic. Yet beneath that surface, confidence was a striking problem. Very few companies understood how their people were actually using these tools or whether they were using them well.
As Merav Yuravlivker, Data Society’s Chief Learning Officer and Co-Founder, put it, “There is a lot of shadow AI that exists where employees will type queries into tools that the organization does not approve. When people experiment, it usually happens in small pockets. It is not cohesive. It is not consistent.” She also noted that this leads to duplicate work and makes it almost impossible for breakthroughs to spread across the company.
This is the quiet risk inside most enterprises. Teams are moving fast with tools they do not fully understand. Leaders assume that adoption equals readiness. And AI is generating content and making decisions at a pace far exceeding human review. As Michael Harwick, Director of Learning Design, observed, “AI makes it very efficient to get to the wrong place.” That sentence is a perfect summary of where many teams are heading unless something changes.
Action to take now. Review how your teams are using AI in practice. Do not focus on the tools in place. Focus on the capabilities your people actually have. If they cannot recognize hallucinations or evaluate risk, your system is already drifting.
The Cultural Strain Beneath the Surface
AI advancement is not just a technical shift. It is creating a cultural rupture within teams that cannot be ignored. People are not simply adapting to new tools. They are evaluating their own value, identity, and future within their organizations. Many employees now worry that their work is being automated out from underneath them and, as Global VP of People Catie Maillard noted, “It’s completely valid to feel nervous about how AI is going to shake up your role. The truth is, we are all standing at a moment where we get to figure out and build what our future roles are going to look like – which can be energizing, though also extremely stressful and chaotic.”
This tension is showing up in morale, psychological safety, and a growing fatigue from expectations that seem to change faster than the support structures around them. Senior Vice President of Learning Meghan Cipperley emphasized the strain this creates on learning culture. “You cannot expect transformation when people are overwhelmed and unsure where they fit. If we want AI adoption to work, we have to create space for people to learn, to practice, and to rebuild confidence in their own skills.”
Yet while some organizations respond with layoffs tied to AI adoption, Merav was blunt about the shortsightedness of that choice. “It feels unimaginative just to fire people because you think AI can automate enough of what they do,” she said. She argued that the real strategic opportunity lies elsewhere. “The bigger swing is keeping your team intact and giving them more tools to see how you can capture a larger share of the market or create new revenue streams.”
The cultural divide is widening between organizations that see AI as a replacement for people and those that see AI as a multiplier for human creativity, judgment, and value creation. The following year will make that difference impossible to ignore.
Action to take now. Train your managers and teams not only in AI tools but in how to communicate through technological disruption. Psychological safety has become a core business capability, not a soft skill.
Learning Transformed. From Content to Judgment
AI has made content cheap, instant, and endless. It has not made judgment any easier. In fact, judgment is now the core capability gap separating teams that merely use AI from those who use it wisely. Learning leaders are discovering that the real challenge is no longer content creation. The hard part is helping people develop the reasoning skills required to apply AI responsibly, contextually, and with confidence.
Michael Harwick sees this shift emerging inside every learning environment. “AI will generate thirty ideas where before we only had three. The role of the instructional designer is shifting into a critical editorial function, advocating for what will be stickiest and make the most sense for learners.” Rapid content production is now effortless. What matters is the human ability to evaluate risk, synthesize meaning, and interrogate output with clarity. As he put it, “The burden of generating practice shifts to the AI, but humans must focus on critical evaluation and reflection.”
Meghan Cipperley, Senior VP of Learning, reinforces this distinction. “You cannot lift and shift content into a new format and call it transformation. Leaders must help people learn how to think, not just learn how to click.” Her point signals a structural change in learning itself. If organizations continue to treat AI as a content engine rather than a catalyst for better thinking, they will miss the strategic opportunity entirely.
This marks the beginning of a profound evolution. AI can accelerate tasks, but it cannot decide what matters. It cannot understand nuance or context. It cannot replicate the nonlinear journey of human mastery. As Michael explained, “LLMs simulate knowledge acquisition, but that is not how people learn. The process is dramatically different from narratives of cognitive growth that our SME can articulate. We can capture the stories, the aha moments. That is the part the machine cannot do.”
Action to take now. Redesign your learning ecosystem to focus on higher-order human skills. Teach people how to ask better questions, frame hypotheses, interpret context, validate AI output, and evaluate risk. These capabilities will define the workforce of 2026 and determine which organizations use AI responsibly and which fall behind.
The Technology Reckoning
AI systems are not static. They drift, evolve, and require continuous oversight. They also demand architectures that prioritize explainability, governance, and transparency. As Roy Hwang, Chief Technology Officer, has warned, there is a dangerous tendency to assume that once a model is deployed, the hard work is done. It is not. The real work begins after deployment.
Roy put it simply. “AI does not follow the rules of traditional software development. As AI changes and adapts, so too must your systems and operational model. A flexible architecture underpinned by clear rules and careful planning is paramount.” Without that rigor, the consequences accumulate quickly. Models begin to behave unpredictably. Data pipelines degrade. Interpretability suffers. Risk escalates. And confidence collapses.
Action to take now. Conduct a full review of where AI is operating in your organization without documented governance, oversight, or performance monitoring. Fix the gaps before your customers, regulators, or partners find them.
Revenue in a Noisy Market
Despite the hype around sales automation, executives closest to the revenue function are seeing a different reality. Rob Daniel, Chief Revenue Officer, expressed deep skepticism about AI replacing outbound teams. “I am not optimistic about AI as an SDR for outbound. Even if something works, the opportunity closes quickly. It is cat and mouse.”
Yet he is bullish about AI’s potential to improve inbound engagement and shape buyer enablement. Rob is also very clear about what will matter most in 2026. “Conferences will be more important than ever. They are the only venue without noise. It is just you and your prospects.”
This insight reflects a broader truth. AI can scale content, but it cannot scale trust. It can prepare teams, but it cannot build relationships. Companies that rely solely on automated engagement will face diminishing returns. Companies that blend AI with real human interaction will differentiate.
Action to take now. Reevaluate your buyer journey and identify the moments where human connection creates value. Use AI to support those moments, not replace them.
The Capabilities That Will Matter Most
Across all of these conversations, a remarkable consistency emerged around the human skills that will define high performers in 2026. Curiosity is becoming essential again. The ability to ask good questions is no longer optional. As Michael pointed out, “The ability to frame a business question and translate it into a grounded hypothesis has multiple points of failure, and it is a major gap we need to shore up.”
Merav echoed this sentiment, emphasizing the need for a “high level of understanding of what people are using AI for and validating the answers.” Employees must become detectives inside their own workflows, willing to interrogate the logic of the tools they use.
Even perspective-taking, a skill many people have not practiced intensely in years, is becoming a requirement. As Cadi noted during the discussion, “If I cannot say, now look at this as this persona with this context and make the changes so it fits that perspective, then a lot is lost.”
Action to take now. Update your competency model to reflect the skills required for an AI-integrated workforce. Focus on thinking skills rather than task skills.
The Strategic Divide of 2026
The coming year will not split the market between large and small companies, nor between tech-driven and traditional companies. The real divide will form between organizations that react and organizations that plan. Some will pursue efficiency by cutting staff and hoping that AI will fill the gap. Others will invest in capability building, responsible adoption, and workforce readiness.
Merav offered a sharp critique of the former. “It is unimaginative to fire people simply because you think AI can automate their work. The real opportunity is figuring out how your team can generate new revenue streams and capture a larger share of the market.” This perspective is the heart of the 2026 story. The most competitive organizations will treat AI as a strategic amplifier of human ability, not a replacement for it.
Action to take now. Choose your direction intentionally. If you want resilience, innovation, and sustainable capability, commit to AI literacy and upskilling now.
2026 Belongs to the Prepared
2026 is not a year to wait and see. It is a year to act with precision and foresight. AI literacy, AI upskilling, and advisory support have become inseparable from business strategy. Human judgment is now the differentiator. Learning is now a risk mitigation strategy. Culture is now a performance driver. And technology is only as strong as the people directing it.
Organizations that invest in readiness will shape the market. Organizations that do not will spend the next several years trying to catch up.
If you want your 2026 strategy to be grounded in the realities of how AI, learning, people, and performance intersect, we would be honored to partner with you.
Book time with our advisory team to help you shape your 2026 AI strategy.
FAQ: The 2026 AI Readiness Questions Leaders Are Asking
AI readiness goes beyond deploying tools. It refers to an organization’s ability to use AI responsibly, effectively, and consistently. This includes workforce skills, governance, data quality, cultural alignment, leadership understanding, and the ability to evaluate AI output critically. Many organizations appear ready on the surface but lack these underlying capabilities.