Good Work Shouldn’t Be This Hard explores what happens when good people try to do important work inside a system that makes it harder than it should be. Host Jenn Gray talks with executives and operators navigating complexity, growth, and change in education, healthcare, legal, and anywhere else a broken system is getting in the way. Together, they unpack where existing systems create unnecessary friction, who pays the price, and what possibilities emerge when we rethink how the work is designed. To connect with Jenn, visit https://jenngray.com
Protecting Healthcare Access Through Physician Recruitment with Tammy Hager
What if the hardest-to-fill physician roles aren't recruitment problems at all?
In this episode, healthcare operations and physician recruitment leader Tammy Hager shares why recruitment and retention have to be thought about together and what it really costs when a specialty goes unfilled. She explains why she doesn't start with recruitment when she's recruiting and names the one metric healthcare leaders should check before they ever look at time to fill.
Connect with Tammy (https://www.linkedin.com/in/tammyhager2008/)
Connect with Jenn (https://jenngray.com/)
Hager Healthcare Consulting (https://app.notion.com/p/jenn-gray/URL)
24 Sept 2026
Business Model Barriers to Justice with Ryan Hurley
What if hiring a lawyer didn't mean handing over a blank check and hoping for the best?
In this episode, Ryan Hurley, founder of Litix Legal, pulls back the curtain on how the billable hour turned inefficiency into a business model, how Arizona's new Alternative Business Structure rule made his transparent, flat-fee pricing possible, and what's still making the legal system harder than it should be.
Connect with Jenn (https://jenngray.com/)
Connect with Ryan (https://www.litixlegal.com/)
17 Sept 2026
Perverse Incentives In Education and Healthcare with Aaron Bare
If a system keeps producing outcomes nobody actually wants, is it broken, or is it working exactly as designed?
In this episode, incentives strategist Aaron Bare joins Jenn to unpack the hidden and perverse incentives in the education and healthcare systems – and why chasing test scores and billing codes so often pulls us further from the outcomes we actually want.
Aaron shares what two decades of facilitating strategy inside hundreds of organizations taught him about incentives, why he believes AI will accelerate whatever is already broken inside a system, and what it actually takes to become a creator instead of a consumer in a world engineered for your attention.
Connect with Aaron (https://aaronbare.com)
Connect with Jenn (https://jenngray.com)
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Apple Podcasts (US)
5.0 / 5
18 ratings
Spotify
5.0 / 5
6 ratings
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