What the AI Shift Means for Your Career with Kelly Monahan
Kelly Monahan, Managing Director of Upwork's Research Institute and co-author of Essential, reveals why 77% of employees feel AI makes work harder, not easier—and what leaders can do about it. In this eye-opening conversation with Paul Estes, Kelly breaks down the real forces behind today's labor market shifts, from inflation and capital costs to the pandemic's lasting impact on customer behavior.
From her research on the frontlines of the future of work, Kelly shares practical frameworks for moving beyond resilience to "anti-fragility"—the ability to adapt and evolve when systems face stress and shock. Whether you're a leader trying to implement AI effectively or a professional wondering how to stay relevant, this conversation offers actionable insights on navigating our rapidly changing work landscape while keeping human creativity and relationships central.
You'll Learn:
Why the AI productivity paradox is happening and how to overcome it
The difference between AI as a tool versus AI as a teammate, and what it means for your workflow
How to move from fragile to anti-fragile thinking when facing career disruption
Why skills are becoming more valuable than degrees and how to credential them effectively
The "configuration mindset" that separates AI power users from frustrated beginners
How to preserve cognitive capacity for creativity in an increasingly automated world
What successful organizational AI strategies look like beyond mere cost-cutting
References Mentioned:
Essential by Christie Smith and Kelly Monahan
Antifragile by Nassim Nicholas Taleb
The Black Swan by Nassim Nicholas Taleb
Thinking, Fast and Slow by Daniel Kahneman
Subscribe to Expert Intelligence so you don't miss future conversations with industry leaders at the forefront of technological transformation. Each episode brings you practical insights to navigate our rapidly evolving digital landscape.
Producer: David Grabowski
Theme Music: Aleksey Chistilin
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30:36
Building Resilience in Uncertain Times with Samia Kornweibel
Generation X professionals are navigating an unprecedented perfect storm: young children at home, peak career responsibilities, and a business landscape in constant flux. Executive coach Samia Kornweibel joins Paul Estes to explore why so many mid-career leaders are experiencing what she calls "career meltdowns"—and how they can build resilience in an era where roles keep shifting.
Fresh from completing her AI coaching certification, Samia shares how she's helping leaders navigate the ethical integration of AI tools while maintaining the human connection that drives real transformation. Using Microsoft's suite of tools and her innovative CHAIR model (Clarity, Humanizing, Aligning, Integrating, Realizing), she demonstrates how coaches can responsibly leverage technology to enhance the coaching relationship.
You'll Learn:
Why Generation X is experiencing "career meltdowns" at the intersection of family, career peak, and rapid change
The "musical chairs" reality of modern corporate life and how to build resilience when stability isn't an option
How to create and maintain psychological safety as an intentional daily practice, not a one-time achievement
The CHAIR model for responsible AI integration in professional coaching and development
Why human accountability and connection remain irreplaceable in an AI-enhanced world
Practical strategies for using tools like Microsoft Viva Insights to enhance coaching conversations and time management
How to move from peripheral AI conversations to focused, ethical implementation
Subscribe to Expert Intelligence so you don't miss future conversations with industry leaders at the forefront of professional development and workplace transformation. Each episode brings you practical insights to navigate our rapidly evolving career landscape.
Producer: David Grabowski
Theme Music: Aleksey Chistilin
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30:09
AI's Role in Personalized Math Tutoring with Peter Relan
Peter Relan, founder of the YouWeb Incubator and initial Discord investor, joins Paul to discuss how AI transforms math education through his latest venture, MathGPT.ai. Growing up in poverty with parents who believed in education's transformative power, Peter is now paying it forward by creating around-the-clock math coaching for students facing critical academic hurdles.
In this eye-opening conversation, Peter reveals how his platform combines AI tutoring with human instructor oversight to address math numeracy challenges while maintaining academic integrity. From Peter's journey as a UCLA math tutor to his vision of personalized learning through AI coaches, discover how technology creates accessible, accurate, and cheat-proof math education that helps students overcome gateway barriers to their chosen careers.
You'll Learn:
How math courses often become gateway blockers that prevent students from entering their chosen careers
Why "innumeracy" is becoming a critical societal challenge comparable to illiteracy
The instructor-led approach that makes MathGPT.ai cheat-proof while still helping students learn
How AI can provide personalized learning experiences based on students' unique interests
Why the future of education lies in the partnership between human wisdom and artificial intelligence
The analytics dashboard that helps instructors identify struggling students in real-time
How AI can automate time-consuming workflows while preserving the irreplaceable human touch in education
Subscribe to the Expert Intelligence podcast so you don't miss future conversations with industry leaders.
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26:29
Mastering Career Chaos with Christopher Bishop
Christopher Bishop, a self-described "nonlinear multimodal careerist" who's navigated eight careers, joins Paul Estes to discuss his new book Improvising Careers: Succeed in Jobs That Don't Exist Yet (pre-order here). From touring rock musician opening for the Eagles to IBM executive to quantum technology expert, Christopher shares how to thrive in a world where the average person will have 8-10 jobs by age 38.
In this compelling conversation, Christopher reveals his "Future Career Toolkit" featuring practical tools for identifying your strengths and finding opportunities in emerging fields. Paul and Christopher explore how to leverage transferable skills, the importance of embracing technological chaos, and why you should apply for jobs even when you only have 60% of the listed requirements.
You'll Learn:
Why you should "chase the maelstrom" and seek out areas where business models are being transformed by new technologies
How Christopher transitioned from a professional musician to an IBM executive by recognizing transferable skills
The "Future Career Toolkit"
Why you should apply for jobs even if you don't have all the requirements, especially in bleeding-edge tech
How to develop a workplace "persona" that helps you succeed in new environments
Why the upcoming AI agent revolution represents opportunities rather than threats
Practical strategies for connecting with industry leaders to find career opportunities
Subscribe to the Expert Intelligence podcast so you don't miss future conversations.
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26:50
AI Literacy Starts with Play, Not Automation with Adam Hofmann
Adam Hofmann, leader of Elixirr's generative AI practice, joins Paul Estes to share insights on moving organizations from AI curiosity to implementation. Drawing from his journey from entrepreneur to AI strategy consultant, Adam reveals how shifting from technical experimentation to cultural engagement is key to successful AI adoption. Paul and Adam discuss the phenomenon of "present bias"—how our experiences with today's AI tools can limit our ability to envision their future potential.
From boardroom directives to CFO-led initiatives, this episode examines who's driving AI adoption and how companies can build momentum through targeted proof-of-concepts. Whether you're struggling with organizational alignment or looking for practical ways to start implementing AI, Adam's focus on playful experimentation offers a refreshing perspective on building AI literacy across your company.
You'll Learn:
How "present bias" limits our ability to see AI's exponential growth potential
Why CFOs and finance leaders are often surprising champions of AI adoption
The importance of identifying high-ROI use cases before diving into implementation
How to avoid the "internal cluster" problem when assigning AI ownership
Why making AI accessible and fun is crucial for organizational adoption
Simple ways to start building AI literacy by replacing everyday tasks
Creative approaches to AI experimentation, including Adam's music creation story
In This Episode:
Microsoft Copilot & Copilot Studio
Riffusion
ChatGPT
Claude
Azure AI Foundry
Service Now
Bolt.new
Cursor
Replit
The future is here, just not equally distributed.
Join best-selling author and seasoned business leader Paul Estes in ”Expert Intelligence,” a bi-weekly podcast that focuses on the human-centric, AI-enabled approach to work, shedding light on key trends like the freelance revolution, the rise of generative AI and the changing dynamics of the workplace.
With over 20 years of leadership experience at giants like Microsoft, Dell, Amazon, and numerous venture-based startups, Paul brings a wealth of knowledge and a unique perspective. Whether you’re a business leader seeking guidance in this new era or an employee looking for inspiration and insights to navigate complex changes, this podcast is your go-to resource. Paul and his guests offer practical advice and thoughtful analysis to help you understand and adapt to these shifts, ensuring a healthy and productive journey in your professional life.
Tune in to ”Expert Intelligence” every other week for engaging, conversational, and insightful discussions that will empower you to stay ahead in the ever-changing world of work.
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