What happens when organizations say upskilling is a priority—yet fail to deliver beyond day one?

In this episode of The Future of Less Work, host Nirit Cohen sits down with Leslie Kelley, Chief Growth Officer at Absorb Software, to explore why traditional upskilling isn’t cutting it—and what smarter, business-aligned learning looks like. Drawing on findings from Absorb’s new State of Upskilling 2025 report, Leslie explains why only 44% of companies offer training at onboarding, fewer than 10% continue when business needs shift, and why ownership of learning remains so fragmented.

Together, Nirit and Leslie unpack how AI can eliminate the “boring parts” of jobs while personalizing skill pathways, why the half-life of skills is shrinking fast, and how Gen Z is redefining career growth around learning velocity—not promotions. They also highlight why mentorship, coaching, and people-based learning remain the human edge in a digital-first workplace.

If you’ve ever wondered how to close the gap between intent and action in L&D—and how to build learning cultures that actually drive performance—this conversation offers both a reality check and a roadmap for what’s next.

https://youtu.be/oEqT6EyER-4

Guest Information:

Leslie Kelley is the Chief Growth Officer at Absorb Software, where she spearheads innovative growth strategies across product, sales, marketing, customer success, and account management.
With a proven track record in driving revenue and customer satisfaction from Seed through Series E, Leslie excels in aligning complex platforms with customer value. Her expertise spans revenue generation, business strategy, and cross-functional team leadership.
Prior to joining Absorb, Leslie held pivotal roles at 360Learning, SmartRecruiters, and ThirdChannel, where she consistently delivered exceptional results in sales and customer success. Leslie is passionate about challenging the status quo and building bold strategies that deliver unparalleled value to customers.

Upskilling report: https://www.absorblms.com/white-papers/state-of-upskilling-report/

Chapters:

00:00 – Why Is Upskilling Failing Beyond Onboarding?
01:30 – How Can AI Personalize Learning and Skills?
03:40 – Why Doesn’t Upskilling Stick in Organizations?
05:07 – Who Really Owns Employee Upskilling?
06:40 – Why Don’t Leaders Prioritize Learning Time?
08:43 – How Can Upskilling Align with Business Outcomes?
10:24 – What Role Does Culture Play in Learning with AI?
12:27 – Why Is People-Based Learning Still Essential?
14:06 – How Can L&D Drive Business Strategy?
16:14 – What Makes Strategic Learning Collaboration Work?
18:03 – How Can Companies Balance Oversight and Agility in Training?
19:53 – What Does Always-On Upskilling Look Like?
20:56 – How Can Leaders Tie Learning Directly to Business Outcomes?
22:59 – Should Companies Train Customers and Partners Too?
24:16 – What Will Learning Look Like in the Next Few Years?
26:33 – Why Human Connection Matters in Future Learning
28:15 – What Question Should We Ask About the Future of Work?
29:56 – How Is Gen Z Changing Expectations Around Learning?

What if pressure—not power—is what derails managers? And what if the key to great leadership isn’t more tools or authority, but a willingness to change yourself before trying to change others?

In this episode of The Future of Less Work, host Nirit Cohen sits down with Sabina Nawaz, global executive coach and author of You're the Boss: Become the Manager You Want to Be (and Others Need), to explore the invisible forces that make or break managers.

Drawing on over 12,000 pages of 360° feedback from executives at Amazon, Microsoft, Google, and more, Sabina reveals why promotions are often the most dangerous moments in a manager’s career—and how the very traits that
got you the role can backfire if left unchecked. Together, they unpack the pressure-pitfalls and power-gaps that derail even the most well-meaning leaders, and the simple, evidence-based strategies that can help you avoid them.

You’ll learn about the Time Portfolio, the Yes List, the 10-Second Pause, and other practical tools to lead with clarity, trust, and intention. Sabina shares how to communicate your leadership “operating system,” how to delegate without disaster, and how to stop reacting and start reflecting—even if it’s just for 10 seconds a day.

If you’ve ever felt overwhelmed by the demands of leadership, unsure how to manage in an AI-disrupted world, or worried that being helpful might make you a micromanager—this conversation is for you.

https://youtu.be/_Ab8DggaFUA

Guest Information:
Sabina Nawaz is the author of YOU’RE THE BOSS: Become the Manager You Want to Be (and Others Need) and an elite executive coach who advises C-level executives and teams at
Fortune 500 corporations, government agencies, nonprofits, and academic institutions around the world. During her fourteen-year tenure at Microsoft, she went from managing software development teams to leading the company’s
executive development and succession planning efforts for over 11,000 managers and nearly a thousand executives, advising Bill Gates and Steve Ballmer directly. She has written for and been featured in Harvard Business Review, The Wall Street Journal, Forbes, Inc., Fast Company, NBC, Nasdaq, and MarketWatch.

Chapters:
00:00 – Why managers fail under pressure
01:40 – The question that predicts leadership success
03:00 – Why promotions are the most dangerous moment
05:30 – When strengths turn into weaknesses
08:45 – How to stop being misunderstood as a leader
10:30 – Power isolates you from your impact
11:40 – Can AI make management harder?
13:10 – Why busyness is a trap, not a badge
13:55 – The Blank Space technique for overwhelmed managers
17:20 – Micro habits that actually work
18:45 – The “Yes List” and how to use it
19:55 – What is a Time Portfolio?
21:45 – Are you spending time on the right things?
22:45 – One habit that separates great managers
24:20 – 10 seconds that can change your day
25:00 – From positional leadership to co-creation
26:00 – The sole provider trap
27:00 – How to delegate without disaster
28:45 – A five-step delegation dial
29:30 – The question every manager should ask themselves

What happens when the tools we use to work stop being background apps—and start becoming the very space where work lives?

In this episode of The Future of Less Work, host Nirit Cohen sits down with Sanchan S. Saxena, Head of Product for Atlassian’s Teamwork Collection (including Jira, Confluence, and Loom), to explore how the digital workplace is evolving into the new office—and what that means for collaboration, leadership, and productivity.

Sanchan shares a vision where the browser becomes a central workspace, agents work alongside humans, and asynchronous communication replaces endless meetings. He explains why video has become his most powerful leadership tool, how Atlassian saved 5,000 hours of meeting time in two weeks, and how AI is moving from assistant to co-creator—freeing people up to do more meaningful work.

Together, they explore what it takes to build trust and transparency in distributed teams, how success is being redefined in the age of AI, and why the future of work won’t be fully human—or fully machine—but powered by both.

If you’ve ever wondered what a great workplace looks like when the “place” is entirely digital, this episode offers both a playbook and a glimpse of what’s next.

https://youtu.be/bLhfJ4HXZsY

Guest Information:

Sanchan Saxena is Head of Product for Atlassian's Teamwork Collection, which includes Jira, Confluence, and Loom. Prior to joining Atlassian, Sanchan led product strategy at Coinbase, Airbnb, Instagram, and Microsoft.

How Atlassian Teams Saved 5,000 Hours of Meeting Time in Two Weeks

https://www.atlassian.com/blog/loom/atlassian-meeting-research

Chapters:

00:00 — What Makes a Digital Workplace Truly Work?
01:26 — Can Remote Collaboration Be Just as Effective?
03:17 — Should We Be Replicating Physical Workspaces Online?
05:22 — What New Workflows Does Digital Enable?
07:31 — How AI Agents Are Replacing Meeting Attendance
09:24 — What Work Should AI Take Off Our Plate?
10:53 — Is AI Changing How Leaders Define Success?
13:01 — Can Humans and AI Work as Teammates?
15:01 — How to Stay Connected Across Time Zones
16:49 — How to Replace Meetings with Asynchronous Video
19:29 — What Happens When You Cancel 5,000 Meetings?
21:46 — How AI Links Conversations to Action
23:23 — What Distributed Leadership Looks Like in Practice
25:30 — How to Align Teams Without Physical Presence
27:24 — Can Video Build Trust Across Cultures?
29:27 — Why Video is Easier Than You Think
30:48 — How Gen Z is Reshaping Workplace Communication
32:30 — Will AI Agents Become Our Teammates?
34:43 — Closing Thoughts: Why Humans Still Matter Most