AI and Distributed Work Push Leaders to Rebuild Culture Around Shared Learning
Key Points
As AI takes over transactional work, leadership is shifting toward more human-centered strategies for managing complex, distributed workforces.
Kelly Monahan, Ph.D., Co-Founder of Beyond the Desk, explains that modern leadership puts people first and centers on purpose, genuine collaboration, and relentless curiosity.
She prescribes aligning teams to a clear mission, designing shared projects, building everyday peer learning, rewarding how people make others better, focusing on 3–5 priorities, and protecting time to learn.
Modern leadership is about navigating profound complexity while putting people first. Profits follow when humanity leads the way.
Kelly Monahan
Co-Founder
Beyond the Desk
Economic pressure is pushing organizations to double down on cost control and operational efficiency, often reducing employees to line items on a spreadsheet. At the same time, AI is rapidly taking over the very work those efficiency efforts target, from routine tasks to performance tracking and process optimization. That overlap is forcing a shift in what leadership actually requires. As more of the operational load becomes automated, the challenge moves toward navigating complexity and leading people in more human-centered ways.
Kelly Monahan, Ph.D., a future of work expert and bestselling author, is one of the leaders evangelizing this management method. As Co-Founder of the advisory firm Beyond the Desk, she now helps leaders navigate the very challenges she tackles as an HR leader. Previously the Managing Director at Upwork and having held senior talent and research roles at Meta, Deloitte, and Accenture, Monahan has built a career on the front lines of workforce transformation, giving her a unique perspective on what it takes to lead today. She believes that amid financial panic, some leaders are losing sight of the long-term value of honoring employees’ needs.
“Modern leadership is about navigating profound complexity while putting people first. Profits follow when humanity leads the way,” Monahan says. One of those challenges stems from a distributed workforce. Measuring team performance proves more complicated for management in a world where hybrid, remote, and contract-based teams are the norm.
Presence isn’t productivity: “Historically, in-person management was driven by a ‘butts-in-seats,’ 9-to-5 mentality where you were only seen as working if you could be seen. That no longer holds true in a virtual environment where we’re all showing up as equals on a Zoom box,” Monahan notes. Distributed work is reshaping what leadership requires. Blended teams of full-time employees, contractors, and freelancers bring different expectations and motivations, making oversight less effective. Success now hinges on a leader’s ability to understand and engage people more intentionally. “Managing a distributed team is much harder than managing a team in person,” Monahan says. “Leaders need more support and cognitive capacity to do this well and engage people in a different way.”
To build more harmony within teams, Monahan suggests a complete rebuild centered on three foundational pillars: a core purpose, genuine collaboration, and relentless curiosity. This kind of human-centered leadership is a powerful way to foster the trust and belonging needed to navigate uncertainty.
The purpose gap: “According to Gallup, 42% of American workers today do not know why their company exists or is different than their competitors,” Monahan notes. Aligning people to a mission, she says, is the low-hanging fruit that unites a disparate workforce.
Forged in the trenches: Another piece of the puzzle is creating opportunities for meaningful collaboration between team members. “Oftentimes, managers think of work as a puzzle where we isolate people to go work on different pieces. I was really intentional about designing projects that required everyone, all hands on deck,” Monahan shares, adding that what brings people together isn’t “forced Zoom happy hours,” but engaging in the real work together.
Curiosity as a skill: Monahan says curiosity is the number one skill set of the future leader. “You have to get curious about what motivates different parts of your workforce, why they are showing up, and what they are trying to get out of the arrangement.” This emphasis on curiosity reflects a broader shift, as leadership increasingly requires learning how to lead a more diverse workforce.
The challenge for leaders is building a culture where knowledge sharing is consistently recognized and reinforced. Still, Monahan cautions that a purely transactional approach can backfire. Drawing on behavioral economics research, she notes that when people were paid to wear seatbelts, compliance dropped as soon as the incentive disappeared. The same dynamic applies in the workplace. Incentives may drive short-term behavior, but they rarely sustain the deeper mindset shifts required for lasting change.
Beyond cash for compliance: “Where I get concerned when we bring incentives into the workforce is that the bar then always needs to be there for that behavior. We start doing things for the incentive, not for our own well-being,” Monahan warns. She points instead to a more durable approach built around a simple question: how did you make others around you better? The shift places mentoring and learning at the center of performance. “When everyone is asked to consider how they are making others better, it creates a learning culture by default and fundamentally changes the focus of how you show up to work every day,” she says.
Choosing what matters most: The model works when learning and connection are built into the work itself, not added as another obligation. That requires discipline in what actually gets prioritized. “Many leaders today find themselves running after 12 to 15 priorities each quarter, but the human brain can’t compute that many asks. That’s not a priority list, it’s a to-do list,” Monahan says, arguing that narrowing focus to a few meaningful priorities creates the space for learning to happen in a way that feels integrated, not imposed.
Ultimately, Monahan argues that leadership systems should create the conditions for people to grow, not just perform. That starts with protecting time for development, even in small ways, to ensure learning does not get pushed aside as pressures mount. “I do worry that many individual workers will be left behind as AI continues to progress and leaders cut costs. Those that are not prioritizing learning today may be left behind,” she says.
But the case goes beyond performance. “We are human beings. When we come to work, I don’t care what your work arrangement is, you want to be treated with dignity. You want meaningful work. You want to be able to engage in the best of your talents.” In that environment, the leader’s role is clear: design systems that make growth, connection, and contribution part of how work happens every day.
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TL;DR
As AI takes over transactional work, leadership is shifting toward more human-centered strategies for managing complex, distributed workforces.
Kelly Monahan, Ph.D., Co-Founder of Beyond the Desk, explains that modern leadership puts people first and centers on purpose, genuine collaboration, and relentless curiosity.
She prescribes aligning teams to a clear mission, designing shared projects, building everyday peer learning, rewarding how people make others better, focusing on 3–5 priorities, and protecting time to learn.
Kelly Monahan
Beyond the Desk
Co-Founder
Co-Founder
Economic pressure is pushing organizations to double down on cost control and operational efficiency, often reducing employees to line items on a spreadsheet. At the same time, AI is rapidly taking over the very work those efficiency efforts target, from routine tasks to performance tracking and process optimization. That overlap is forcing a shift in what leadership actually requires. As more of the operational load becomes automated, the challenge moves toward navigating complexity and leading people in more human-centered ways.
Kelly Monahan, Ph.D., a future of work expert and bestselling author, is one of the leaders evangelizing this management method. As Co-Founder of the advisory firm Beyond the Desk, she now helps leaders navigate the very challenges she tackles as an HR leader. Previously the Managing Director at Upwork and having held senior talent and research roles at Meta, Deloitte, and Accenture, Monahan has built a career on the front lines of workforce transformation, giving her a unique perspective on what it takes to lead today. She believes that amid financial panic, some leaders are losing sight of the long-term value of honoring employees’ needs.
“Modern leadership is about navigating profound complexity while putting people first. Profits follow when humanity leads the way,” Monahan says. One of those challenges stems from a distributed workforce. Measuring team performance proves more complicated for management in a world where hybrid, remote, and contract-based teams are the norm.
Presence isn’t productivity: “Historically, in-person management was driven by a ‘butts-in-seats,’ 9-to-5 mentality where you were only seen as working if you could be seen. That no longer holds true in a virtual environment where we’re all showing up as equals on a Zoom box,” Monahan notes. Distributed work is reshaping what leadership requires. Blended teams of full-time employees, contractors, and freelancers bring different expectations and motivations, making oversight less effective. Success now hinges on a leader’s ability to understand and engage people more intentionally. “Managing a distributed team is much harder than managing a team in person,” Monahan says. “Leaders need more support and cognitive capacity to do this well and engage people in a different way.”
To build more harmony within teams, Monahan suggests a complete rebuild centered on three foundational pillars: a core purpose, genuine collaboration, and relentless curiosity. This kind of human-centered leadership is a powerful way to foster the trust and belonging needed to navigate uncertainty.
The purpose gap: “According to Gallup, 42% of American workers today do not know why their company exists or is different than their competitors,” Monahan notes. Aligning people to a mission, she says, is the low-hanging fruit that unites a disparate workforce.
Forged in the trenches: Another piece of the puzzle is creating opportunities for meaningful collaboration between team members. “Oftentimes, managers think of work as a puzzle where we isolate people to go work on different pieces. I was really intentional about designing projects that required everyone, all hands on deck,” Monahan shares, adding that what brings people together isn’t “forced Zoom happy hours,” but engaging in the real work together.
Curiosity as a skill: Monahan says curiosity is the number one skill set of the future leader. “You have to get curious about what motivates different parts of your workforce, why they are showing up, and what they are trying to get out of the arrangement.” This emphasis on curiosity reflects a broader shift, as leadership increasingly requires learning how to lead a more diverse workforce.
The challenge for leaders is building a culture where knowledge sharing is consistently recognized and reinforced. Still, Monahan cautions that a purely transactional approach can backfire. Drawing on behavioral economics research, she notes that when people were paid to wear seatbelts, compliance dropped as soon as the incentive disappeared. The same dynamic applies in the workplace. Incentives may drive short-term behavior, but they rarely sustain the deeper mindset shifts required for lasting change.
Beyond cash for compliance: “Where I get concerned when we bring incentives into the workforce is that the bar then always needs to be there for that behavior. We start doing things for the incentive, not for our own well-being,” Monahan warns. She points instead to a more durable approach built around a simple question: how did you make others around you better? The shift places mentoring and learning at the center of performance. “When everyone is asked to consider how they are making others better, it creates a learning culture by default and fundamentally changes the focus of how you show up to work every day,” she says.
Choosing what matters most: The model works when learning and connection are built into the work itself, not added as another obligation. That requires discipline in what actually gets prioritized. “Many leaders today find themselves running after 12 to 15 priorities each quarter, but the human brain can’t compute that many asks. That’s not a priority list, it’s a to-do list,” Monahan says, arguing that narrowing focus to a few meaningful priorities creates the space for learning to happen in a way that feels integrated, not imposed.
Ultimately, Monahan argues that leadership systems should create the conditions for people to grow, not just perform. That starts with protecting time for development, even in small ways, to ensure learning does not get pushed aside as pressures mount. “I do worry that many individual workers will be left behind as AI continues to progress and leaders cut costs. Those that are not prioritizing learning today may be left behind,” she says.
But the case goes beyond performance. “We are human beings. When we come to work, I don’t care what your work arrangement is, you want to be treated with dignity. You want meaningful work. You want to be able to engage in the best of your talents.” In that environment, the leader’s role is clear: design systems that make growth, connection, and contribution part of how work happens every day.