Up In Your Business

Jason Randall
  • 4.7 (9)
  • Management
  • Updated Semiweekly

Up In Your Business with Jason Randall is a podcast for business leaders navigating the real challenges of running and growing a company. Each episode dives into the issues that matter most to employers today—from HR and compliance to benefits, leadership, culture, and day-to-day operational decisions. The goal is simple: give you clear, practical insight you can actually use. Hosted by Jason Randall, the show brings straightforward conversations, real-world perspectives, and expert guidance to help you make smarter decisions for your business and your people. Whether you're scaling your team, managing change, or trying to stay ahead of what’s next, this podcast is built for you.

Episodes

  1. 2d ago

    What Should Business Leaders Actually Know About AI Right Now? (#5)

    In this episode of Up In Your Business, I sit down with Chris Whitney, our technology leader at Questco, to explore the transformative role of AI in the workplace. We discuss how AI can streamline operations, enhance productivity, and empower teams without the fluff often found in tech conversations. Chris shares a compelling real-world case study involving the development of an AI-driven chatbot named Beth, which drastically reduced response times for benefits inquiries, highlighting practical insights for business leaders. Tune in to gain clarity on how to implement AI effectively, manage change, and ensure your workforce is equipped to thrive in an AI-enhanced environment.

    29 min

  2. Jul 1

    The Real Signs It’s Time to Seek Outside HR Support (#4)

    In this episode of Up In Your Business, Jason Randall and Sierra Silverberg to explore a critical question for business leaders: When is it time to seek outside help for HR? They discuss the signs that indicate your current HR setup might not be sustainable, such as leadership distraction, high employee turnover, and inconsistent policies. Sierra shares insights on how to recognize the tipping point, the common mistakes leaders make in this decision, and the value that professional HR support can bring. Whether you're in a reactive state or proactively planning for growth, tune in to learn how to evaluate your HR needs and ensure your business is set up for success.

    28 min

  3. Jun 24

    What Happens If You Fire Someone the Wrong Way? (#3)

    In this episode of Up In Your Business, Jason and Santos delve into the complexities of terminating employees and the potential pitfalls of doing it the wrong way. Firing someone is one of the toughest tasks a leader faces, and mishandling it can lead to legal battles and business disruptions. Joined by Santos Alvarenga, a seasoned HR consultant, we explore the importance of proper documentation, consistent communication, and clear policies. We discuss how emotional decisions and lack of preparation can lead to significant consequences, and we offer insights on how to handle terminations effectively to protect both the business and its employees. Tune in to learn how to navigate these challenging situations with care and precision.

    27 min

  4. Jun 17

    Do You Really Need HR Support, or Are You Fine Without It? (#2)

    In this episode of Up In Your Business, I dive into a crucial question for growing companies: Do you really need HR support, or can you manage without it? As businesses expand, the complexities of HR can quickly become overwhelming. I discuss the tipping point when informal HR practices begin to falter and the risks that arise when organizations lack structured support. Joining me is Jason Millman, an expert who shares insights on recognizing when your business has outgrown its DIY HR approach and the importance of implementing clear policies and consistent practices. If you're feeling the strain of managing HR alone, this episode offers valuable guidance on how to transition towards effective support that fosters growth and compliance. Tune in and discover the steps to ensure your business thrives while effectively managing its human resources.

    28 min

  5. Jun 10

    What HR Mistakes Can Actually Get Your Company Sued? (#1)

    HR risk usually starts earlier than most business leaders think. In this episode of Up In Your Business, host Jason Randall sits down with Christy Arnold, General Counsel and SVP at Questco, to talk about the HR mistakes that can create real legal, financial, and operational risk for employers. The conversation covers misclassification, hiring technology, documentation, terminations, inconsistent policies, and manager training. But the larger theme is simpler: small people issues rarely stay small when they are ignored. A delayed conversation, an undocumented performance issue, a misclassified employee, or an inconsistently applied policy can turn into an EEOC charge, demand letter, lawsuit, or years of expensive distraction. Christy explains where these problems usually begin, why leaders often miss the early warning signs, and what companies can do to reduce risk without turning HR into unnecessary bureaucracy.

    33 min

  6. Jun 3

    Episode 1 Teaser: Coming Soon

    In this first episode of *Up In Your Business*, host Jason Randall, Chief Growth Officer at Questco, is joined by Christy Arnold, Questco’s General Counsel and SVP, to discuss the HR mistakes that often seem small in the moment but can create serious liability for businesses. Together, they explore how issues like employee misclassification, inconsistent people practices, missing documentation, and rushed terminations can quietly increase risk — and what leaders can do to protect their companies before problems escalate.

    2 min
  • 6 Episodes

Ratings & Reviews

4.7
out of 5
9 Ratings

About

Up In Your Business with Jason Randall is a podcast for business leaders navigating the real challenges of running and growing a company. Each episode dives into the issues that matter most to employers today—from HR and compliance to benefits, leadership, culture, and day-to-day operational decisions. The goal is simple: give you clear, practical insight you can actually use. Hosted by Jason Randall, the show brings straightforward conversations, real-world perspectives, and expert guidance to help you make smarter decisions for your business and your people. Whether you're scaling your team, managing change, or trying to stay ahead of what’s next, this podcast is built for you.

Information

  • Creator
    Jason Randall
  • Years Active
    2021 - 2026
  • Episodes
    6
  • Rating
    Clean