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

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If you could see every obstacle your team trips over in a single day, how many times would they hit the floor?In this episode, nurse, healthcare finance leader, and executive coach Amy Yates unpacks why money and mission don’t have to compete, why the feedback loop between bedside and boardroom breaks down, and the simple, human questions that help leaders clear the path for their people.<a href="https://jenngray.com/" rel="nofollow">Connect with Jenn</a><a href="https://www.linkedin.com/in/amydianeyates/" rel="nofollow">Connect with Amy</a>

The Human Side of Healthcare Finance with Amy Yates

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What if the biggest bottleneck in your tech stack isn’t actually the tech?In this episode, former special ed teacher turned CTO Dan Fishman shares how his years in the classroom shaped the IEP software he helped build and ultimately sell. He also explains why tech people so often underestimate the cost of their work and what organizations need to understand before they ask what AI can do for them.<a href="https://jenngray.com/" rel="nofollow">Connect with Jenn</a><a href="https://www.linkedin.com/in/danfishman/" rel="nofollow">Connect with Dan</a>

From Classroom to Ed Tech & CTO with Dan Fishman

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What if the hardest-to-fill physician roles aren&#39;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&#39;t start with recruitment when she&#39;s recruiting and names the one metric healthcare leaders should check before they ever look at time to fill.<a href="https://www.linkedin.com/in/tammyhager2008/" rel="nofollow">Connect with Tammy</a><a href="https://jenngray.com/" rel="nofollow">Connect with Jenn</a><a href="https://app.notion.com/p/jenn-gray/URL" rel="nofollow">Hager Healthcare Solutions</a>

Protecting Healthcare Access Through Physician Recruitment with Tammy Hager

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What if hiring a lawyer didn&#39;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&#39;s new Alternative Business Structure rule made his transparent, flat-fee pricing possible, and what&#39;s still making the legal system harder than it should be.<a href="https://jenngray.com/" rel="nofollow">Connect with Jenn</a><a href="https://www.litixlegal.com/" rel="nofollow">Connect with Ryan</a>

Business Model Barriers to Justice with Ryan Hurley

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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.<a href="https://aaronbare.com" rel="nofollow">Connect with Aaron</a><a href="https://jenngray.com" rel="nofollow">Connect with Jenn</a>

Perverse Incentives In Education and Healthcare with Aaron Bare

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If you&#39;re bleeding margin every single day, what would it take to fix it before it&#39;s too late? In this episode, Jake &#34;The Ginger&#34; Anderson takes us inside the cannabis industry&#39;s biggest blind spot: businesses running on Excel spreadsheets and assumptions instead of real data — including the magnitude of losses operators take if they scale a broken system instead of fixing it first.<a href="https://jenngray.com/" rel="nofollow">Connect with Jenn</a><a href="https://www.linkedin.com/in/jaketheginger/" rel="nofollow">Connect with Jake the Ginger</a>

You Can't Fix the Margin You Can't See in Cannabis with Jake "The Ginger" Anderson

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If you could change one thing about education tomorrow — without contending with the bureaucracy, red tape, or &#34;how it&#39;s always been done&#34; — what would you fix first?In this episode, Dr. Renita Miller pulls back the curtain on what&#39;s really holding good educators back, who pays the price, and why change is so much harder than it should be.<a href="https://jenngray.com/" rel="nofollow">Connect with Jenn</a><a href="https://www.linkedin.com/in/renitamiller/" rel="nofollow">Connect with Renita</a>

Human Capital Investments in Education with Dr. Renita Miller

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