The H.I.T. Podcast

Is artificial intelligence changing the way companies hire, organize, and operate? And could the Chief of Staff become one of the most important roles in the modern workplace?On this episode of The H.I.T. Podcast, host Toby Kennedy welcomes Kristen Arnold, a strategic operator and consultant with more than 15 years of experience in organizational development and team execution, to explore the evolving relationship between leadership, artificial intelligence, and the future of work.As organizations embrace AI and rethink traditional workplace structures, Kristen explains why the Chief of Staff role is gaining momentum**—serving as a trusted second-in-command who helps executives streamline operations, manage priorities, and focus on the bigger picture.But what happens when AI enters the equation?Kristen discusses how companies are building leaner, more agile teams by combining human leadership with AI-powered tools. While automation can help manage workflows and improve efficiency, essential human skills like judgment, communication, adaptability, and problem-solving remain critical.The conversation also examines how HR professionals are navigating employee concerns about AI, changing expectations around job security, and the shift away from traditional organizational structures.IN THIS EPISODE:The Rise of the Chief of Staff – Why more founders and executives are turning to strategic operators to help lead their organizations.AI as a Partner, Not a Replacement – How artificial intelligence can amplify human capabilities and streamline everyday operations.Smaller Teams, Bigger Impact – Why startups are using AI tools and versatile employees to accomplish more without dramatically increasing headcount.The Human Advantage – Why emotional intelligence, problem-solving, and navigating complex relationships remain essential workplace skills.Rethinking the Org Chart – How traditional hierarchies may give way to flexible "constellation teams" supported by specialized AI agents.HR's Role in AI Adoption – Addressing employee concerns, establishing AI governance, and helping organizations manage workplace transformation.The Future of Job Descriptions – Why employers may increasingly focus on tasks, skills, and problem-solving rather than rigid job titles.Changing Employee Loyalty – Exploring the increasingly transactional relationship between employers and employees.THE BIG TAKEAWAY: The future of work isn't simply about replacing people with technology. It's about rethinking how people, leadership, and AI can work together to create more effective organizations.Whether you're an HR professional, business leader, entrepreneur, or executive navigating the rapid evolution of workplace technology, this conversation offers valuable insights into what's ahead.

Thinking about switching your company's HR or payroll system? Before you make the move, there's some important work to do!On this episode of The H.I.T. Podcast, host Toby Kennedy welcomes PJ Higgins, a payroll and HR technology expert, to discuss the challenges of selecting, evaluating, and implementing new HR systems—and how organizations can avoid costly mistakes along the way.Too often, companies jump into searching for new technology without first understanding what's actually broken. PJ explains why successful transitions begin with "doing the work before the work"—evaluating existing processes, identifying real business needs, and establishing clear expectations before engaging potential vendors.From navigating flashy sales presentations to managing implementation challenges, this conversation offers practical guidance for HR professionals and business leaders looking to make smarter technology decisions.In This Episode:Before You Switch: Determine whether your challenges are technology-related or could be solved by improving existing processes.Build Your Wish List: Assemble an internal team, identify non-negotiable requirements, and establish clear decision criteria.Evaluate Vendors Wisely: Leverage trusted industry relationships and ask the questions that matter most.Watch for Red Flags: Learn how to recognize sales presentations that focus more on awards and promises than actual solutions.Demand Better Demos: Make vendors demonstrate your most important workflows from beginning to end—not just their best features.Plan for Implementation: Understand the time, resources, and internal support needed for a successful transition.Test Against Your Goals: Make sure your new system delivers on the requirements that drove your decision in the first place.The Big Takeaway: The right HR technology isn't necessarily the system with the most features. It's the one that solves your organization's actual problems—and is implemented with the right preparation, people, and processes.Whether you're considering a new payroll provider, evaluating HR technology platforms, or preparing for a major system transition, this episode provides valuable insights to help you make a more informed decision.

We're bringing back a Halloween favorite from The H.I.T. Podcast! In this special episode, we explore creative ways to celebrate Halloween in the workplace while keeping festivities fun, professional, and inclusive.From office costume contests and team activities to seasonal treats and decorations, we share practical ideas for boosting employee morale and strengthening workplace culture. We also discuss best practices for ensuring everyone feels comfortable participating and how HR professionals can avoid potential workplace challenges during holiday celebrations.Whether your organization goes all out for Halloween or prefers a more low-key approach, this episode offers simple ways to encourage team spirit, build connections, and make the season memorable.The H.I.T. Podcast, powered by Montage Insurance Solutions, delivers timely insights and engaging conversations for HR professionals, business leaders, and company executives.

Is your team performing at its full potential—or is something holding it back?In this episode of The H.I.T. Podcast, host Toby Kennedy continues his conversation with executive coaching experts and authors **Tom Reynolds and Bryan A. Powell** about their book, "The Efficient Frontier of Teaming," and the strategies leaders can use to build stronger, more effective teams.Tom and Bryan introduce the concept of the "teaming inefficiency gap"—the difference between where a team is performing today and what it could achieve with the right leadership, culture, and collaboration.They also explore the bullseye method, a practical approach to setting shared goals, encouraging experimentation, and helping teams make meaningful progress without fearing failure.The conversation goes beyond traditional leadership strategies to examine how hiring, psychological safety, vulnerability, and artificial intelligence can help organizations unlock their teams' potential.In this episode:Understanding the teaming inefficiency gap and how to close itUsing the bullseye method to set goals and build momentumHiring for diverse strengths, perspectives, and team dynamicsWhy leaders should stop providing all the answers and start coachingBuilding trust through vulnerability, authenticity, and difficult conversationsUsing AI as a thought partner to strengthen creativity and critical thinkingHow a Ted Lasso-inspired AI coaching agent can help leaders navigate workplace challengesInsights from The Efficient Frontier of Teaming and the research behind the bookThe big takeaway: High-performing teams don't happen by accident. They require intentional leadership, shared ownership, trust, and a willingness to continually learn and improve.The Efficient Frontier of Teaming is available through major booksellers, including Amazon, Barnes & Noble, Target, and Walmart.The H.I.T. Podcast with Toby Kennedy

What separates a team that simply gets results from one that consistently performs at its best?On this episode of The H.I.T. Podcast, host Toby Kennedy welcomes executive and team coaching experts Bryan A. Powell and Tom Reynolds for a conversation about what it really takes to build and sustain high-performing teams.While organizations often measure success through revenue, productivity, and performance metrics, Bryan and Tom explain why the less measurable elements—trust, psychological safety, authenticity, and shared accountability—are just as important.The conversation explores why so many organizations believe they have high-performing teams when they may actually be maintaining the status quo. From creating space for every voice to strengthening relationships and navigating challenges, the discussion highlights practical ways leaders and employees can build stronger, more resilient teams.In this episode:What truly defines a high-performing teamWhy trust and psychological safety drive better performanceBalancing measurable results with healthy team dynamicsThe importance of conversational turn-taking and giving everyone a voiceCreating shared ownership and accountability at every levelHow vulnerability and authenticity strengthen workplace cultureWhy high performance requires both leadership direction and employee engagementHow HR can move beyond check-the-box training to create meaningful development opportunitiesThe takeaway: High-performing teams aren't built through metrics alone. They're built through relationships, intentional conversations, and a culture where everyone has the opportunity—and responsibility—to contribute.???? The H.I.T. Podcast with Toby Kennedy

What separates leaders who simply manage people from those who inspire them? The ability to tell a story people want to be part of.In Part 2 of Toby Kennedy’s conversation with Jonathan Lewis, President of McKee Wallwork, they explore storytelling, identity, responsibility, and what today’s workforce is really searching for. Jonathan explains why leaders need to provide context for the work their teams are doing—not simply communicate goals and expectations. A compelling story can help people understand where they’re going, why it matters, and the role they play in getting there.The conversation also dives into Jonathan’s book, The Rebuilders, which challenges people to take responsibility for rebuilding the institutions, organizations, communities, and relationships around them rather than simply criticizing what’s broken.They also discuss generational changes in the workplace, the search for authenticity and purpose, the dangers of comparison, and why Jonathan believes meaning comes through responsibility and commitment—not simply looking inward for fulfillment.In this episode:- Why great leaders are great storytellers- Connecting everyday work to a bigger mission- How relationships shape our identity- The impact of social media and comparison- Why younger generations are searching for authenticity- Responsibility vs. resentment- The ideas behind The Rebuilders- Finding meaning through commitment and character- What leaders can do to help rebuild workplace culture

What if the biggest workforce challenge isn’t compensation, benefits, or flexibility—but the story employees are being asked to believe about work?Toby sits down with Jonathan Lewis, President of McKee Wallwork, to discuss what their national workforce research reveals about the changing relationship between employees and their organizations.After studying 3,000 participants across the country, Jonathan describes a workforce increasingly defined by TFS: Transactional, Futureless, and Suffering. The traditional promises surrounding work, career, loyalty, and retirement no longer resonate with everyone the way they once did.So how can leaders respond?Jonathan introduces RQM: Relational, Quest, and Meaning—a framework for rebuilding the story of work around human connection, a shared future, and a sense of meaning in the challenges people face.Toby and Jonathan also explore the growing “Who” problem inside organizations, why culture and brand are increasingly connected, and why leaders at every level need to become better storytellers.In this episode:• How the workforce changed after COVID-19• What TFS reveals about today’s employees• Moving from transactional relationships to relational ones• Why employees need a future worth working toward• Creating meaning instead of simply trying to eliminate struggle• The organizational shift from How → Why → Who• Why a clear internal story can strengthen workplace culture• How leaders can connect everyday work to a larger purpose

What if your company could significantly reduce prescription drug costs without changing its pharmacy benefit manager or taking medications away from employees?In Part 2 of The H.I.T. Podcast, host Toby Kennedy continues his conversation with Louis Gallucci, CEO of Limitless Consulting Group, about how employers can take greater control of prescription drug spending through smarter sourcing strategies.Louis explains why self-funded employers should look beyond traditional pharmacy benefit managers (PBMs) and explore alternative purchasing options that can benefit both their health plans and their employees.From analyzing pharmacy claims data to identifying high-cost medications and exploring alternative sourcing channels like GoodRx and Mark Cuban Cost Plus Drugs, this conversation provides practical insights for HR professionals, benefits managers, and business leaders looking to control healthcare costs.In this episode:Why employees should have more flexibility in how they access prescription medicationsHow identifying your five most expensive drugs can reveal potential savings opportunitiesUnderstanding the difference between clinical strategy and pharmacy procurementHow employers can explore lower-cost sourcing without necessarily changing their PBM or formularyWhy reducing out-of-pocket prescription costs can help employees access the medications they needHow to request and analyze pharmacy claims data to identify unnecessary spendingWhy transparency matters when managing self-funded health plans and fiduciary responsibilitiesLouis also shares a practical starting point for HR leaders: Request a report of your organization's 10 most expensive medications over the past 12 months. Then work with your broker or benefits advisor to explore alternative sourcing options.The goal isn't simply to spend less on prescription drugs. It's to help employees access the medications they need while making smarter purchasing decisions for the organization.

Prescription drug costs are climbing—but the medication itself may not be the biggest problem. It may be how and where you're buying it.On this episode of The H.I.T. Podcast, Toby Kennedy welcomes longtime friend Louis Gallucci, CEO of Limitless Consulting Group, for a deep dive into one of the biggest challenges facing employer-sponsored healthcare today: pharmacy costs.With 20 years of experience across group benefits, carriers, voluntary benefits, benefits technology, and consulting, Louis explains why employers need to rethink the way they purchase prescription drugs—and start looking at healthcare through the lens of procurement.Pharmacy now represents a significant portion of overall healthcare spending, and Louis shares how a surprisingly small number of medications can account for an enormous percentage of a health plan's total costs.In this episode:Why prescription drug spending has grown so dramaticallyHow just a handful of medications can drive a huge portion of plan spendingWhy the sourcing channel can matter as much as the medication itselfUnderstanding the enormous pricing differences that can exist for the same drugWhy rebates and traditional PBM strategies may no longer be enoughHow alternatives such as direct sourcing are changing the pharmacy landscapeWhy HR leaders should start thinking more like procurement directorsWhat self-funded employers need to understand about their fiduciary responsibilitiesWhy employers need to take ownership of their claims dataThe questions employers should be asking their PBMs and benefits partnersOne of Louis' biggest messages is simple: employers are the buyers.Your PBM may administer the claims, but employers need to understand what they're purchasing, where the money is going, and whether there is a more efficient way to source the same care.And there's a personal connection to this episode, too—Toby and Louis go back nearly 20 years, from working together early in their careers to attending each other's weddings. Now they're sitting down to unpack how dramatically the benefits and pharmacy landscape has changed.

Employee mental and physical health aren't separate issues—and both can have a major impact on the workplace.In Part 2 of The H.I.T. Podcast, Toby Kennedy continues his conversation with Andrea “Andy” Notch Mayzeles, Workforce Health Consultant at Kaiser Permanente, about the realities of employee well-being and what organizations can actually do to help.With research showing significant levels of burnout, depression, and anxiety among today's workforce, the consequences extend far beyond individual employees. Absenteeism, healthcare utilization, retention, productivity, and even customer service can all be affected.But mental health is only part of the equation.Andy explores the often-overlooked connection between musculoskeletal health and mental health, including how physical pain can contribute to depression—and how depression and inactivity can make physical pain worse.In this episode:The impact of burnout, depression, and anxiety in the workplaceWhy musculoskeletal health deserves more attentionThe connection between physical pain and mental well-beingWhy psychological safety helps employees speak up before problems escalateHow micro-movement breaks can support physical and mental healthWhy simply taking a lunch break mattersWhy communicating benefits once isn't enoughCreating a “surround sound” approach to employee wellness communicationHow leaders, wellness champions, HR, and safety teams can work togetherWhy employees need to understand that resources like EAPs are confidentialOne of the biggest challenges isn't always a lack of resources—it's making sure employees actually know those resources exist and feel comfortable using them.Missed Part 1? Check out the first half of Toby's conversation with Andy on building workplace wellness that actually works.