Becker Business Podcast Summary

Episode: AI Leader of the Month: Sharon Easterling, Founder of Upskillz LLC
Date: October 16, 2025
Host: Scott Becker
Guest: Sharon Easterling, Founder of Upskillz LLC

Episode Overview

This special episode celebrates Sharon Easterling as Becker Business’s AI Leader of the Month. Sharon, founder of Upskillz LLC, shares her journey into healthcare technology, the mission behind Upskillz, and her perspective on preparing the workforce for AI-driven transformation. The discussion dives into the intersection of AI, continuous learning, human judgment, and how to foster resilience and adaptability through rapid change.

Key Discussion Points & Insights

1. Sharon Easterling’s Journey and the Mission Behind Upskillz

• Sharon's background is in healthcare revenue cycle, consulting in medical coding and clinical documentation improvement (CDI).
• She observed a persistent knowledge gap among health information professionals regarding emerging technologies.
• Upskillz was founded to "increase foundational knowledge of AI" in healthcare and leverage professionals’ workflow expertise for AI implementation.

“I wanted to create an avenue to help increase their foundational knowledge of AI, but also pull on what they needed...that’s what's needed in AI right now.”
— Sharon Easterling ([01:36])

2. Upskillz’s Offerings and Practical Solutions

• Custom AI products and micro-training to teach:
  • Foundational AI concepts
  • Prompting algorithms
  • Workflow optimization for healthcare professionals
• Tools that help integrate AI while safeguarding compliance, accuracy, and trust, especially outside of sensitive (HIPAA) environments.

“A big part of what we do is support systems that help people integrate AI without compromising your compliance or your accuracy or your trust.”
— Sharon Easterling ([02:59])

3. Balancing Human Judgment and Automation

• Focus on augmenting, not replacing human roles.
• AI streamlines repetitive tasks and surfaces patterns while allowing people to focus on decision-making and empathy.
• Examples: AI career coach GPTs that support daily workflow and personal professional development.

“It's not about replacing people...It's about protecting our brain for what it's best in, right? The decision making, the empathy, the analysis.”
— Sharon Easterling ([03:56])

4. Advice for Professionals Looking to Stay Relevant

• Start with small, consistent steps; you don't need to master everything at once.
• Learn enough to ask better questions—curiosity is key.
• Build learning communities and sandbox environments using de-identified data to experiment and develop low-risk AI skills.

“Learn enough to ask better questions...join a community so you can get some of that foundational knowledge.”
— Sharon Easterling ([05:15])

5. Surprising Lessons from Leadership and Teamwork

• Sharon is encouraged by the willingness of professionals to experiment and learn.
• Emphasizes that teamwork is essential for adopting and mitigating the impact of AI.

“I've found that with this new process, people are learning that they have to lean on others some more. This is a team process.”
— Sharon Easterling ([06:46])

6. Innovation and the Future of Work

• Sharon is excited about “Secura,” Upskillz’s automated software to mitigate denials and automate appeals for providers.
• Upcoming: A new website (upskillsadvisors.com) featuring online courses and a certification prompt program.
• The true potential is unlocked when people innovate with AI tools.

“Once people really realize what AI has the ability to do, innovation happens. And that is very exciting to me.”
— Sharon Easterling ([08:10])

7. Habits and Mindset for Resilience

• Make time for reflection (journaling, walking, white space in calendar).
• Focus on processing change, not just reacting to it.
• Reframe failure as a learning opportunity to stay grounded and curious.

“I also have learned to reframe failure...ask yourself, what did it teach me and how can I apply that going forward?...That shift...takes [judgment] to being more curious.”
— Sharon Easterling ([09:18])

8. Mentorship and Leadership Challenges

• Mentorship shaped Sharon’s career; both formal and informal mentors were crucial.
• Advocates for designing supportive, not performative learning environments.
• Stresses the importance of collaboration and providing safe spaces for honest feedback and questions.

“If we can design learning environments that are supportive and not performative, we can create more pathways for people to grow.”
— Sharon Easterling ([11:09])

Notable Quotes and Moments

• On the goal of Upskillz:
  “We needed a way to, to increase that knowledge with our professionals so they can step into AI and impact those workflows because they know the business and they know the work.”
  ([01:17])
• On learning AI:
  “Have a sandbox...where you can go in and just figure out how AI works and how you can use that in your day to day...build real skills in a low risk setting.”
  ([05:33])
• On the importance of community:
  “Don't isolate yourself. You know, bring in your team, have a learning partner, join a community...”
  ([05:19])
• On innovation:
  “Once people really realize what AI has the ability to do, innovation happens.”
  ([08:10])
• On resilience:
  “I try to use those things to process the change versus trying to react to the change...reframe failure...”
  ([09:03])

Important Timestamps

• 00:42 – Sharon describes her journey and inspiration for Upskillz
• 02:45 – Overview of Upskillz’s solutions for businesses
• 03:53 – Balancing people and AI in technology and training
• 05:05 – Advice for professionals to remain relevant and upskill
• 06:39 – Lessons learned from leadership and building a team
• 07:40 – Exciting current and future projects at Upskillz
• 08:59 – Habits and mindset for resilience and adaptability
• 10:25 – Mentorship, leadership challenges, and building supportive environments
• 11:44 – How to connect with Sharon and learn more about Upskillz

Connect with Sharon Easterling & Upskillz

• Follow Sharon Easterling on LinkedIn
• Websites: upskillsaccelerator.org, upskills.org, [upskillsadvisors.com](https://upskillsadvisors.com—coming soon)
• Email: info@upskills.org

Tone & Takeaways

Sharon’s approach is collaborative, empathetic, and focused on empowerment. Her optimism about AI’s impact in healthcare is grounded in the need for strong foundational knowledge, continual upskilling, and community-based learning. The episode is both inspirational and practical, equipping listeners with concrete advice on navigating technological change while emphasizing the enduring value of human judgment and resilience.