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Why Your Most Caring Leaders Struggle to Scale Their Empathy

Micah Kessel on May 23, 2025

Most organizations, in the face of two managers with similar competencies, will naturally promote their most empathetic—those who excel at building trust, not only understanding individual needs but also embracing different perspectives and creating psychological safety within small teams. But when teams expand, the very skills that made them successful with 10-15 people often fail them when they’re suddenly responsible for 50, 80, or hundreds of employees. According to HBR, in 2023, 70% of newly promoted managers struggle with the transition from managing individuals to managing systems. Whether organizations realize it or not, this reveals a gap in operationalizing empathy, and with never-ending restructuring for strategic and financial considerations, those who do not receive direct care from their manager often fall to the wayside, losing their sense of purpose, engagement, and ultimately performing less well.

Better companies teach managers to be better listeners and emphasize the importance of psychological safety and taking different perspectives into consideration when helping a team move forward, but they don’t show them how to build that at scale. This is why many individual contributors lose a sense of their considerations being taken seriously and therewith, lose a sense of meaning. That’s sad considering there are effective ways to show you care about a group of people without a lot of personal time and it’s exactly that that helps ever-changing teams move forward together.

As you may know by now, at Empathable, we believe leaders learn better when we go beyond teaching them concepts – but rather, through real stories from real professionals. So instead of presenting a traditional analysis and set of approaches, I’ll take you through a real story from someone who I’m calling Akira Johns to respect their privacy.  This story  illustrates how one can scale individual empathetic talents to larger teams where you don’t necessarily have direct impact.

When Everything Changes

Imagine Akira Johns, a burgeoning manager at a Fortune 1000 who thought she liked her job, staring at her computer screen this morning, processing the announcement that: ‘due to company restructuring post acquisition, her team of 15 direct reports was about to become 80 people across three departments.’

Akira had built her reputation on being a thoughtful leader—knowing each team member personally, remembering their challenges, and ensuring everyone felt heard in meetings. But 80 people? How could she make the time to maintain those meaningful connections? She’d need three of herself. How would she know when someone was struggling? How could she gather diverse perspectives when she couldn’t possibly meet with everyone regularly? How would she keep everyone engaged?

Somewhat hopefully, she saw the next message in her inbox, which was from Akira’s beloved learning and development director who pinged her to let her know that with these big changes, she’d been selected to be part of a cohort of 100 burgeoning managers would be working with Empathable, an organization that specializes in scaling the weaving of empathy into essential leadership skills—starting with a facilitated kickoff, then a light-touch deep immersion learning experience. Once every two weeks for the next six months, Akira would join cohorts with four other managers to walk in the shoes of other seasoned managers coupled with best in class expert perspectives. People who had already considered deeply how to take into account all aspects of scaling empathy, taking no more than one hour of their time per month.

But this hour wasn’t filled with random perspective and opinion sharing, but rather the sharing of personal stories that help enrich each other, much like people have learned from one another for generations through the power of storytelling.

Akira was aware in advance that she’d learn the following:

  • Perspective-gathering protocols that her direct reports could implement with their teams
  • Communication templates that maintained her values while allowing for personalization
  • Structures for different types of feedback loops that ensured diverse voices reached decision-makers
  • Recognition systems that reinforced empathetic behaviors across all levels
  • How to leverage AI to condense longer-form shares in ways that still allow everyone to feel represented and give summaries for leaders to make informed decisions
Office Connections in Nature

Why Stories Change Everything

But here’s the thing: learning those conceptually doesn’t make the impact that we want it to. Empathable was offering the opportunity to learn that through stories.

Abstract concepts about “scaling empathy” don’t stick. But experiencing the challenge through someone else’s real story? That creates the kind of visceral understanding that drives behavioral change. Through immersive scenarios, Akira didn’t just learn about perspective-gathering systems—she experienced what it felt like to be a manager who had to make decisions affecting hundreds of people without adequate input.

This is the difference between intellectual knowledge and embodied wisdom. Data and facts don’t generally change people’s viewpoints, as stories do. Being able to leverage storytelling at scale is a fundamental starting point for how to bridge the empathy gap.

The First Test: From Theory to Practice

When her first major challenge came—rolling out a strategic initiative across her newly expanded team—Akira applied what she’d learned. Instead of attempting impossible one-on-ones with 80 people, she created structured listening sessions and designed feedback systems that ensured every voice could be heard.

Most importantly, she understood how to help those she did have direct access to impart empathy to their own teams. Making managers capable of building and maintaining empathetic cultures happens through an almost train-the-trainer methodology of allowing them to get better at practicing the deeper meaning of empathy that Empathable believes in—which is the ability to acknowledge the meaningfulness of one another’s stories to be as valuable as our own and get better at being curious about each other’s experiences.

The Scaffolding Effect

The cohort-based learning that Akira received during her training is something that she learned how to scale out so that she could create sub-cohorts within the groups she was managing. Each sub-cohort gave each other the opportunity to share experiences and created structured ways that those cohorts could communicate with each other so that they wouldn’t get caught up in opinion sharing or disagreement but actually in the value of each other’s experiences.

The Transformation: When Systems Create Culture

The results surprised everyone. “I’ve never felt so heard by a senior leader I barely know,” one team member commented during an anonymous survey. When a national social justice issue later affected employees, Akira’s systematic approach created what felt like a supportive community despite the organization’s size.

Her team of 80 ended up having higher performance metrics than her original team of 15, and she maintained one of the highest retention rates she’d ever experienced over the next two years. As a testament to the authentic connections her systems fostered, she was recently asked to officiate the wedding of one of her team leads.

The Ripple Effect

What happened to Akira’s team illustrates a fundamental truth: beyond empathy being personalized, when it becomes systemized and operationalized, it scales exponentially. Instead of one leader trying to be empathetic to 80 people, Akira created conditions where 80 people could be empathetic to each other.

This is the difference between empathy as an individual skill and empathy as an organizational capability. The former breaks down under scale; the latter gets stronger with it.

Group of adults sitting around a table dressed in business attire with a background of bridges across a chasm

The Blueprint: How Organizations Can Bridge the Empathy Gap

Akira’s success wasn’t accidental—it followed a specific pattern that any organization can replicate:

  1. Start with Experience, Not Theory Effective empathy training begins with learning how to listen to and share experiences and value those experiences to be as meaningful as your own, then builds frameworks to be able to share one another’s stories in a way that is both respectful but scales out the knowledge that stories contain that concepts often do not.
  2. Focus on Systems, Not Just Skills Don’t just teach managers to be more empathetic; teach them to create empathetic systems. Current perspective-gathering protocols and feedback mechanisms often feel very mechanical and don’t get to the heart of questions that allow people to share in longer form what their actual thoughts and feelings are. Choosing from a scale of one to five can be fine for things like engagement but doesn’t really afford the opportunities that longer-form sharing provides. With AI, survey taking can now accept longer-form thoughts that allow for more informed decision-making.
  3. Create Scaffolding for Scale The goal isn’t to make every manager capable of personal empathy with hundreds of people—it’s to make every manager capable of building and maintaining empathetic cultures within their sphere of influence through structured storytelling and experience-sharing systems.
  4. Use Cohort Learning That Scales Akira’s bi-weekly sessions with other managers weren’t just about learning content; they were about processing the challenges of implementing empathetic leadership at scale. This cohort approach can be replicated within organizations, creating networks of support and accountability.

The Future of Empathetic Leadership

The challenge that once kept Akira awake at night became her greatest opportunity for growth—and a model for her organization. What she discovered is that empathy doesn’t diminish when scaled; it transforms from a personal attribute into an organizational superpower.

office workers with tree

As organizations continue to grow and become more distributed, the ability to create empathetic systems will become a core competitive advantage. The leaders who master this won’t just manage larger teams more effectively—they’ll create cultures where empathy becomes everyone’s responsibility, not just their own.

The empathy gap isn’t insurmountable. With the right approach, your most caring leaders can become your most effective culture architects. They just need to learn how to build bridges through stories and systems instead of having individual conversations across an ever-widening chasm.


At Empathable, we help organizations develop leaders who can operationalize empathy at scale through immersive, story-based learning experiences. If Akira’s journey resonates with challenges in your organization, we’d love to explore how experiential learning can help bridge your empathy gap. Feel free to schedule time to connect here.

Redefining Empathy 

Micah Kessel on February 28, 2025

(+ Learning to Train Empathy the Right Way.)

We’ve got empathy all wrong. For years, I’ve been designing research-based immersive experiences that help people see through others’ points of view, and I’ve shared these experiences with about 20,000 people. Through this work, and through my time as a design lead at an emotions research lab, I’ve discovered something profound about empathy that challenges everything we think we know about it.

When people talk about empathy, there’s this assumption that we all know what it means. But if you looked it up in the dictionary, you’d find a definition that’s scientifically impossible: “the ability to understand how another person feels.”

Most people think of empathy as something you activate in the moment of disagreement—a switch you flip when tensions rise. But real empathy doesn’t work that way. It’s more like a foundation you build slowly over time, like a bank account you need to fill before you can make a withdrawal. Think about your oldest friends—you can disagree fiercely but still want to talk the next day. That’s not because you’re naturally more empathetic with them. It’s because you’ve built up a reservoir of shared experiences that creates understanding beyond any single disagreement.

This misunderstanding of empathy reflects a broader misconception about how emotions work. Dr. Lisa Feldman Barrett, neuroscientist and author of “How Emotions Are Made,” puts it this way: “Your brain is not reacting to the world. It’s helping to create the world you experience.” This means your emotions are not universal—they’re constructed by your unique brain based on your unique experiences.

Here’s the truth: we’ll never understand how anybody else feels. We barely understand how we feel ourselves half the time. If I say I’m feeling happy, it’s not the same as your happiness. If someone says they’re feeling grumpy, I might say, “I understand,” but I don’t—not really. I’ve had a completely different set of life experiences that make me think about grumpiness in a different way.

As psychologist Paul Bloom notes, “Empathy is biased; we are more prone to feel empathy for attractive people and for those who look like us or share our ethnic or national background.” This misunderstanding creates problems. We end up thinking we understand someone else’s feelings when we’re statistically more wrong than right.

So what is empathy, then? Here’s what I’ve found:

Empathy is a verb—something you actively do. It’s the ability to acknowledge that someone else’s experiences are just as real and meaningful as your own. Not their opinions or perspectives, which might be harmful or wrong, but the life experiences that brought them to those perspectives. You don’t have to validate someone’s conclusions to acknowledge the reality of their journey.

Let me share an example from a recent session in a small town in Texas. I facilitated an experience where participants “walked in someone else’s shoes” by watching a point-of-view video. In most settings, when people watch an experience like this, the default response is to share opinions and perspectives. “I think the manager should have said X.” “I don’t agree with how they talked about heritage months.” “That kind of initiative makes me uncomfortable.” The room quickly divides into camps—those who agree with each other versus those who don’t.

This pattern of opinion-sharing might feel productive, but it actually reinforces division. It helps us identify who already agrees with us, creating insular bubbles of shared perspective. It’s precisely this mechanism that has contributed to our increasingly polarized society. We’ve optimized for opinion alignment rather than human connection.

Sometimes I’m even concerned that, subconsciously, this hunger for shared narrative is why war can be such an attractive proposition for some. Historically, war gives people a common story, a collective experience that helps them feel like part of a greater whole. It creates the togetherness that humans deeply crave. But war is perhaps the worst possible way to achieve that sense of narrative connection. It’s destructive, traumatic, and leaves lasting scars across generations—all to fulfill a need that could be met through simply sharing our stories with one another in times of peace.

That’s exactly what we practiced in our session that day. After watching the brief interaction in the break room, I guided participants away from opinions and toward personal stories.

Sharing a meal

I shared first. I talked about how my partner loves these Trinidadian snacks called doubles—fried shells filled with chickpeas that cost just two dollars each. I described how visiting these shops brings something grounding to my day: the Trinidadian women working together, chatting over loud music, making food with their hands. For a brief moment, I get to be part of Trinidadian culture, and it enriches my life.

Then one participant shared her story. She had lived in Saudi Arabia during high school when her father worked there. She described being invited to a Saudi home for what they called a “goat grab”—a meal where everyone sits on the floor with a large tablecloth. The hostess would throw pieces of food perfectly onto each person’s spot. They ate with their hands—goat meat that tasted like lamb, rice with delicious spices. She explained that despite not speaking the same language as her hosts, they could still communicate, and it became one of her most treasured cultural experiences.

Another participant shared his story about a Jamaican meal during a cruise vacation. He described how his wife was picky about food, but they both approached the unfamiliar Jamaican cooking with an open mind, not wanting to offend their hosts. He talked about trying spicy foods and unusual fruits that were outside his comfort zone, recognizing that what seemed strange to him was everyday life for the Jamaicans. “They were trying to bring you into their world,” he reflected.

Empathy makes everything better, but in high-stakes moments—with your boss, your loved ones, someone you manage—it’s absolutely game-changing. Those moments of tension or conflict aren’t when you build empathy; they’re when you need it most. If you’ve been practicing empathy, if you’ve built up that foundation of human connection through sharing and acknowledging stories, you’ll have the resources to navigate those challenging moments not just without catastrophe, but as opportunities for growth.

Think about it like this: empathy broadly improves your world and mission, but there’s also an acute value in those moments that really matter—the ones where people often just blow it. Having practiced empathy and built relationships with empathy at their core is what makes those moments less catastrophic and potentially transformative.

This understanding of empathy as an active practice—something we build through sharing and acknowledging stories—is why at Empathable, we create programs that help people walk in others’ shoes through point-of-view experiences and real-time dialogue. These programs give participants the opportunity to practice being empathetic in a supportive environment, strengthening that crucial muscle before they need it most.

The results have been remarkable. Our initial studies have shown not just that clients enjoy and benefit from Empathable, but that we’re seeing an 85% completion rate (compared to the industry average of 20%), a 42% increase in empathy scores (which correlates directly with patient satisfaction), and a 28% increase in feelings of belonging (a key indicator for retention).

But numbers only tell part of the story. The real impact happens in those everyday moments when someone chooses curiosity over judgment, story-sharing over opinion-sharing, connection over division.

So here’s my challenge: practice once this week. Share a story with someone—a friend, spouse, or colleague—and ask them, “What story in your life brought you to that viewpoint?” Be present as they share. Good work should make you feel good, and I believe this will.

Because in the end, we are all collections of millions of memories that make us who we are. And those stories deserve to have time.

If you found this article valuable, I regularly speak on this topic for organizations and would be happy to discuss how we can support your people. Feel free to schedule time to connect here.

A case study for Empathable.

Micah Kessel on February 14, 2025

Teams lacking empathy are repeatedly shown to be less effective in performance, retention, and building a culture of trust, belonging and connection. Conversely, “empathetic leadership is positively related to job performance” (ccl.org). After four months of participating in Empathable’s learning platform, teams saw double-digit increases across various key measures that correlate directly to improved performance: 42% increase in feelings of empathy, 26% increase in likelihood of addressing problematic situations in the workplace, and 10% increase in emotional connection to peers.

The Future of Work: Balancing AI Innovation with Humanity

Micah Kessel on January 14, 2025

As artificial intelligence (AI) continues to reshape the professional landscape, we find ourselves grappling with a pressing question: How can humanity preserve its essence and empathy in a world increasingly dominated by machine intelligence?

At the recent ‘Work in Progress’ conference, we came together as a diverse group of investors, organizational leaders, futurists, and corporate coaches to explore this challenge. Spanning a 20-year age range and representing experiences across three continents, we shared a collective familiarity with the U.S. professional environment, which grounded our discussion in a shared context.

Our task in this working group was to redefine the roles of leaders, managers, and individual contributors in workplaces increasingly influenced by AI. As our conversations deepened, an additional goal emerged: to imagine what these roles might look like in a more distant, AI-integrated future.

To anchor this exploration, we first established several foundational truths:

  1. Acknowledging Humanity’s Current Role
    To imagine humanity’s place in an AI-driven world, we first needed to reflect on its presence—or absence—in the workplace over the past three decades and today.
  2. Recognizing Literacy as a Double-Edged Sword
    We noted that 100 years ago, the global population was 2 billion, with a literacy rate of just 15%. Today, with nearly 7 billion people, literacy has risen to 85%. While education is a gateway to freedom, its potential to foster a more humane workplace depends on its ability to equip individuals with usable skills and nurture cultural flourishing.
  3. Balancing AI’s Promises and Threats
    AI presents both opportunities and risks. It can amplify educational access and workplace productivity, but it also challenges humanity’s role in fostering empathy, creativity, and cultural connectivity.
  4. Examining the Human Condition at Work
    With significant investments in learning and development (L&D), talent development, and diversity, equity, and inclusion (DEI), we considered key elements that enhance or hinder individuals’ ability to learn and thrive in the workplace. These elements were categorized into seven dimensions:
    • Time: The availability or scarcity of it.
    • Agency: Individuals’ ability to influence outcomes.
    • Fulfillment: A sense of purpose and satisfaction.
    • Safety: Specifically, psychological safety.
    • Equality of Wellness: Access to resources that ensure well-being.
    • Visibility: The ability to be seen and heard authentically.
    • Elimination of Threats: Reducing barriers and hostilities.

Each participant rated humanity’s progress across these dimensions in three periods: before the internet, in 2024, and in a speculative future. This data, informed by the insights of ten diverse workplace experts, provides a nuanced view of how workplace experiences might evolve across three pivotal eras: “Before the Internet,” “The Recent Now,” and “An AI-Integrated Future.” Rather than offering definitive conclusions, these findings illuminate potential trajectories and areas of focus as we navigate an increasingly technology-driven landscape.

Balancing AI with Humanity Graph

Empowerment and Fulfillment

For these workplace experts, the perception of agency appears to have risen dramatically, moving from 43 in “Before the Internet” to 84 in “The Recent Now.” This rise suggests an increasing focus on individual autonomy and purpose in the workplace. However, the slight decline projected in the AI-integrated future (77) hints at lingering uncertainty around balancing human autonomy with technological intervention.

The pre-Internet workplace was described with words like “transactional,” “command + control,” “punch the clock,” “dehumanizing,” and “a lack of individual purpose.” These words paint a picture of a rigid and authoritative environment where work was often seen as a means to an end, marked by linear, serial processes and a lack of personal fulfillment.

In contrast, fulfillment shows a steady rise over time, peaking at 79 in the AI future. This suggests the possibility of work increasingly aligning with individuals’ aspirations and values, aided by systems designed to enhance meaningful engagement. The AI-integrated future is imagined as a period of “empowered potential,” “creativity,” “personal agency,” and “a world beyond scarcity.” Experts envision workplaces where humans have the “time and tools to be their fuller creative selves” and find fulfillment in a “harmonized” and “adaptive” environment.

Equality and Visibility as Emerging Priorities

The data suggests a notable upward trend in Equality of Wellness and Visibility, with both metrics growing substantially from their pre-Internet baselines (33 and 34, respectively) to over 70 in the AI future. This may point to a growing recognition of fairness, inclusivity, and transparency as critical drivers of healthier and more equitable workplaces.

The pre-Internet era’s emphasis on “static knowledge written by homogenous experts” and “binary, authoritative systems” contrasts sharply with the “searching for creative alignment,” “greater autonomy,” and “remembering humanity” that characterize the recent now. Yet, challenges such as “unequal access,” “overload,” and “generational differences” remind us that progress remains uneven.

In the AI future, experts envision workplaces marked by “decentralized ownership,” “greater purpose beyond work,” and “humanized systems.” Such changes imply the potential for workplaces to transcend structural inequalities and focus on cultivating “flexibility, choice, and impactful contributions.”

Challenges in Psychological Safety and Threat Mitigation

While Psychological Safety has grown from “Before the Internet” (46) to “The Recent Now” (66), its projected stabilization at 65 in the AI future suggests potential barriers to further improvement. This may reflect the complexities of fostering emotional well-being in increasingly digitized and augmented environments.

The pre-Internet workplace, described as “authoritative and firm” with a “lack of individual purpose,” offered limited support for psychological safety. The recent now, while more “collaborative” and “flexible,” also carries challenges such as “frustration,” “burnout,” and “overwhelmed information flows.”

The AI-integrated future, imagined as “peaceful,” “constant learning opportunities,” and “adaptive,” offers the possibility of greater psychological support but also raises questions about the human-technology dynamic.

Meanwhile, the Elimination of Threats metric remains relatively unchanged across the three periods (46, 48, 47). This suggests enduring challenges in addressing perceived or systemic risks, even as workplaces evolve.

A Changing Relationship with Time

The perception of Time undergoes a profound shift, with the metric rising from 58 in “Before the Internet” to 77 in the AI-integrated future. This evolution reflects how technology might transform notions of productivity and work-life integration.

In the pre-Internet era, time was often “linear,” “serial,” and “analog,” reinforcing rigid and dehumanizing structures. By “The Recent Now,” the group describes a world that is “constantly connected,” “digitized,” and “global,” yet often leaves individuals feeling “overwhelmed” and “burned out.”

The AI future is imagined as a time when workplaces enable “more time and less work,” fostering “seamless experiences” and providing individuals the space to “harvest creativity” and pursue “greater purpose beyond work.”

A Vision for the AI-Integrated Workplace

These expert perspectives highlight possibilities for an AI-driven future. While advancements in agency, fulfillment, equality, and visibility suggest a promising trajectory, the plateauing of psychological safety and stagnation in threat elimination underscore areas requiring intentional focus.

Rather than presenting a utopian vision, these insights invite reflection on the nuanced interplay between technological progress and human well-being. As workplaces evolve, leaders are encouraged to design systems that enhance not only productivity and fairness but also intangible elements like trust, safety, and emotional resilience.

Tomorrow’s Roles: Preparing Leadership and Teams for an AI-Integrated Future

As workplaces evolve toward an AI-integrated future, the roles of leaders at every level must adapt to meet the demands of this new era. The insights from workplace experts suggest a future where decentralization, creativity, equity, and human empowerment become central pillars of success. For C-Suite executives, venture capitalists (VCs), and board members, this means redefining their responsibilities to align with emerging priorities like psychological safety, adaptability, and the seamless integration of human and AI capabilities.

The following outlines essential additions to their job descriptions, ensuring leadership not only navigates but thrives in this transformative future and that managers and teams can play their harmonious role herein. These changes reflect the need for a more human-centric approach, balancing technological innovation with purpose, inclusivity, and well-being.

Additions to Job Descriptions for C-Suite Executives, VCs, and Board Members in an AI-Integrated Future

For the C-Suite

  1. CEO (Chief Executive Officer)
    • Champion decentralized decision-making and empower cross-functional collaboration between human and AI teams.
    • Foster a culture of continual learning, adaptability, and creativity within the organization.
    • Lead efforts to align corporate vision with broader societal goals, such as equity, sustainability, and well-being.
    • Ensure transparency in AI implementation and its alignment with ethical standards.
  2. CFO (Chief Financial Officer)
    • Integrate long-term, purpose-driven metrics into financial planning, focusing on sustainability, equity, and impact.
    • Leverage AI to optimize resource allocation while considering human energy and well-being.
    • Analyze the financial implications of transitioning to more flexible work structures, such as reduced hours or creative sabbaticals.
  3. COO (Chief Operating Officer)
    • Orchestrate adaptive workflows where human and robotic agents collaborate seamlessly.
    • Ensure operational strategies prioritize psychological safety, inclusion, and fulfillment.
    • Implement systems to measure and enhance team member alignment with organizational purpose.
  4. CHRO (Chief Human Resources Officer)
    • Prioritize emotional intelligence and psychological safety as key components of leadership development.
    • Develop programs to support human creativity, flexibility, and well-being, leveraging AI for personalized career pathways.
    • Address systemic inequities by implementing tools and policies that create a level playing field for all employees.
  5. CMO (Chief Marketing Officer)
    • Emphasize the integration of storytelling and humanized branding in AI-driven campaigns.
    • Advocate for transparency in AI usage to build trust with consumers and stakeholders.
    • Focus on aligning brand identity with societal values, emphasizing empowerment, purpose, and inclusivity.
  6. CIO/CTO (Chief Information/Technology Officer)
    • Lead ethical AI innovation, ensuring systems augment human potential rather than replace it.
    • Design technology systems to support decentralized ownership and adaptive collaboration.
    • Monitor AI systems for unintended biases and align their outputs with organizational values.

For Venture Capitalists (VCs)

  • Evaluate startups based on their ability to harmonize AI advancements with human empowerment and societal impact.
  • Advocate for funding models that prioritize creativity, well-being, and sustainability over pure scalability.
  • Mentor founders on the importance of psychological safety and equitable practices in building resilient organizations.

For Board Members

  • Ensure strategic oversight prioritizes long-term societal impact alongside shareholder returns.
  • Act as stewards of ethical AI deployment, holding organizations accountable for transparency and fairness.
  • Provide governance that supports flexibility and creativity in the workforce, aligning with evolving values of the AI era.
  • Promote alignment between organizational purpose and global challenges, encouraging a higher purpose beyond profit.

For Managers

  • Enable Purpose-Driven Work: Act as a guide to help individuals align their roles with their personal aspirations and the broader organizational mission.
  • Promote Collaborative Leadership: Shift from directive management to coaching and facilitation, empowering teams to co-create solutions in collaboration with AI systems.
  • Leverage AI for Personalized Support: Use AI to identify team members’ needs, skill gaps, and career development opportunities, offering tailored growth pathways.
  • Balance Workload and Well-Being: Advocate for flexible schedules, creative sabbaticals, and AI-enabled efficiencies to help reduce burnout and enhance fulfillment.

For Individual Contributors

  • Embrace Lifelong Learning: Commit to continual skill development, especially in areas where human creativity, emotional intelligence, and decision-making complement AI capabilities.
  • Cultivate Creativity and Innovation: Harness AI tools to unlock new ways of thinking, problem-solving, and generating impactful ideas.
  • Adapt to Hybrid Collaboration: Learn to work seamlessly with AI agents, understanding their capabilities and leveraging them to enhance productivity and outcomes.
  • Prioritize Purpose and Impact: Seek roles and projects that align with personal values, leveraging AI to achieve greater meaning and influence in your work.
  • Advocate for Equity and Inclusion: Actively contribute to creating an environment that is fair, inclusive, and supportive of diverse perspectives and talents.

Far Beyond Tomorrow: Futurist Roles for a Changing World

A recurring theme in the conversation was the evolution of leadership models. One participant proposed moving away from rigid hierarchies:

“What if leadership itself shifts from this hierarchical structure into this infinity model of leadership where things are done, and the person who’s leading does it based on whoever has the most expertise in that area?”

This vision of leadership emphasizes adaptability, with leaders transitioning fluidly between roles to support collective expertise. Such a system could foster collaboration and inclusivity while dismantling traditional power dynamics.

The rapid pace of technological change demands new professional roles to address emerging needs. Suggestions included:

  • Regeneration Specialists: Focused on reciprocity, ensuring organizations give back to the ecosystems and communities they impact.
  • Nervous System Regulators: Addressing the overwhelm caused by constant change and fostering holistic well-being in business.
  • Chief Potential Officers: Helping individuals and organizations embrace their full creative potential by moving past scarcity-driven mindsets.

“We’re going to need to help people shake off the way we’ve always worked and move into our full creative selves,” one contributor emphasized.

The Role of Research and Real-Time Analysis

In a rapidly shifting environment, research and analysis will play a pivotal role in interpreting trends and mitigating risks. As one participant noted:

“There’s going to be a lot of trial and error, and researchers need to make sense of what’s happening. Real-time analysis becomes something totally different.”

To remain effective, these roles must bridge the gap between idealistic visions and actionable insights, ensuring that data-driven decisions align with both ethical principles and practical business needs.

Ethical Guardrails and Global Collaboration

As AI becomes increasingly integrated into decision-making, the potential for dehumanization is a concern. One participant posed the critical question:

“Who is advocating for humans? Who’s going to stem the tide from an integration that destroys the human element?”

This led to discussions about roles like a “Protector of Humans,” tasked with safeguarding human dignity, ethical considerations, and societal balance. Another participant added, “Do we program AI to protect humans at all costs?”

The ethical challenges posed by AI development cannot be overstated. As one participant put it:

“Just because we can do something doesn’t mean we should. And even if we should, it doesn’t mean we should do it right now.”

Discussions highlighted the need for international standards and ethical governance to guide AI’s evolution responsibly. However, nationalism and competing interests may hinder such collaborative efforts.

Education and Creativity as Cornerstones

A shift toward a more human-centered future also requires rethinking education. A participant suggested:

“We need educators who can help bridge the gap between technological advancements and human understanding. Designers of education will be critical.”

This aligns with the call to nurture human creativity, distinguishing authentic human expression from synthetic creations.

Conclusion: A Protopian Vision

Amid the challenges, there’s a hopeful vision of a “protopian” future—a world where progress is incremental and grounded in reciprocity and shared humanity. As one participant concluded:

“For organizations to thrive, they must evolve to play a role in the kindness and regeneration of resources, shaping a society rooted in compassion.”

The future of work is not just about adapting to AI but about redefining what it means to be human in an interconnected, technologically advanced world. By fostering ethical leadership, embracing new roles, and prioritizing human creativity, we can navigate this transformation with purpose and resilience.

The Human Element: Reimagining Job Descriptions in the Age of AI

Micah Kessel on January 12, 2025

Written by Jennifer Brown and Micah Wonjoon Kessel (CEO of Empathable)

Read our summary published by Work in Progress here.

In the quiet corners of boardrooms and the bustling halls of tech startups, a revolution is brewing. As artificial intelligence reshapes our professional landscape, we face a profound question: Will this technological transformation enhance our humanity, or diminish it?

At the recent Work in Progress conference, a diverse coalition of minds—investors, organizational leaders, futurists, and corporate coaches—gathered to explore this critical intersection of human potential and machine capability. Their insights reveal a surprising truth: the future of work isn’t about artificial intelligence replacing human intelligence—it’s about redefining what it means to be human in an AI-integrated world.

The Paradox of Progress

The data suggests an intriguing story. A focused study by workplace experts at the conference, examining professional evolution across three eras—before the internet, today, and an AI-integrated future—revealed a fascinating paradox. The group’s assessment showed metrics for agency and fulfillment soaring (agency rising dramatically from 43 to 84 in recent years), while psychological safety remains stubbornly challenged, plateauing at 65 in their projected AI future.

Degree of Abundance Graph
Degree of Abundance

This isn’t just about numbers from a group poll—it’s about human experience. The pre-internet workplace, described by participants as “transactional” and “dehumanizing,” is giving way to something more nuanced. Today’s professionals report greater autonomy and purpose, yet struggle with what one participant called “overwhelmed information flows.” The message is clear: technological progress alone doesn’t guarantee human flourishing.

The Great Rebalancing

Perhaps the most telling insight emerged from our discussion of time. The perception of time—that most precious and finite resource—shows a remarkable transformation. In the AI-integrated future, our experts envision workplaces that enable “more time and less work,” fostering what they call “seamless experiences” and providing space to “harvest creativity.”

This isn’t about working less—it’s about working differently. The traditional model of time management is being replaced by what one participant termed an “infinity model” of leadership, where expertise, not hierarchy, determines who leads. This shift promises to fundamentally alter how we perceive productivity and purpose in our professional lives.

The Human Advantage

As artificial intelligence masters routine tasks, the working group’s insights revealed an unexpected truth: the most “human” elements of work—creativity, emotional intelligence, ethical judgment—become increasingly valuable. The future workplace demands what we might call “full-spectrum humans”—professionals who can seamlessly integrate technological proficiency with deeply human capabilities.

This transformation demands a fundamental reimagining of leadership roles across organizations. The workplace experts outlined how various positions must evolve to meet the challenges of an AI-integrated future:

C-Suite Evolution

Chief Executive Officer (CEO)

  • Champion decentralized decision-making between human and AI teams
  • Foster a culture of continual learning and adaptability
  • Lead efforts to align corporate vision with broader societal goals
  • Ensure transparent and ethical AI implementation

Chief Financial Officer (CFO)

  • Integrate purpose-driven metrics into financial planning
  • Leverage AI for optimizing resources while prioritizing human well-being
  • Analyze implications of flexible work structures and creative sabbaticals

Chief Operating Officer (COO)

  • Orchestrate seamless collaboration between human and AI systems
  • Ensure operations prioritize psychological safety and fulfillment
  • Implement systems to measure team alignment with organizational purpose

Chief Human Resources Officer (CHRO)

  • Prioritize emotional intelligence in leadership development
  • Develop AI-enhanced programs supporting human creativity
  • Address systemic inequities through innovative tools and policies

Chief Marketing Officer (CMO)

  • Integrate storytelling and human connection in AI-driven campaigns
  • Build trust through transparent AI usage
  • Align brand identity with societal values and purpose

Chief Information/Technology Officer (CIO/CTO)

  • Lead ethical AI innovation that augments rather than replaces human potential
  • Design systems supporting decentralized ownership
  • Monitor and address AI biases proactively

Beyond Traditional Roles

For Venture Capitalists

  • Evaluate startups based on human empowerment potential
  • Advocate for funding models prioritizing creativity and sustainability
  • Guide founders in building psychologically safe organizations

For Board Members

  • Ensure oversight balances societal impact with returns
  • Act as stewards of ethical AI deployment
  • Support workforce flexibility and creativity
  • Promote alignment between organizational and global challenges

For Managers

  • Guide individuals in aligning roles with personal purpose
  • Shift from directing to coaching and facilitation
  • Use AI to identify personalized development opportunities
  • Balance workload optimization with human well-being

For Individual Contributors

  • Commit to continuous learning in human-AI collaboration
  • Cultivate creativity and innovation using AI tools
  • Adapt to hybrid human-AI teamwork
  • Seek purpose-aligned opportunities
  • Champion workplace equity and inclusion

Beyond these evolving roles, experts envision novel positions emerging to meet future needs:

  • Regeneration Specialists who ensure organizations give back to their ecosystems
  • Nervous System Regulators who help manage the overwhelming pace of change
  • Chief Potential Officers who guide individuals and organizations beyond scarcity mindsets

The Ethics Imperative

Yet amidst this optimistic vision, the discussion surfaced a critical concern. As one participant pointedly asked, “Who is advocating for humans?” The data shows the “Elimination of Threats” metric remaining stubbornly flat across time periods (46, 48, 47), suggesting that technological advancement alone doesn’t address fundamental human vulnerabilities.

This leads to perhaps our most important finding: the need for what we might call “ethical infrastructure” in the AI-integrated workplace. “Just because we can do something,” one participant noted, “doesn’t mean we should. And even if we should, it doesn’t mean we should do it right now.”

A Protopian Vision Forward

What emerges from this exploration isn’t a utopian fantasy, but rather what we might call a “protopian” vision—a future of incremental yet meaningful progress, grounded in reciprocity and shared humanity. This future demands new approaches to:

  • Leadership: Embracing fluid, expertise-based authority
  • Education: Bridging technological advancement with human understanding
  • Workplace Design: Creating environments that enhance rather than diminish human potential

The transformation of work in the AI era isn’t just about adapting to new technologies—it’s about consciously shaping these technologies to enhance our humanity. As one participant concluded, “For organizations to thrive, they must evolve to play a role in the kindness and regeneration of resources, shaping a society rooted in compassion.”

The Path Ahead

The future of work stands before us not as a fixed destination, but as a journey of continuous adaptation and growth. The insights from this gathering of workplace leaders suggest that success in this new era will belong to organizations that can balance technological advancement with human flourishing, creating environments where both machines and humans can achieve their highest potential.

As we navigate this transformation, one truth becomes clear: the future of work isn’t about artificial intelligence replacing human intelligence—it’s about artificial intelligence enhancing human wisdom, creativity, and purpose. In this light, the challenge before us isn’t just to adapt to new technologies, but to use them as tools for unlocking the full spectrum of human potential.

The question isn’t whether AI will transform work—it’s whether we’ll use this transformation to create a more human workplace. The answer lies not in our machines, but in ourselves.

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