Gaining the Technology Leadership Edge

Explore the strategies behind Daniel Friker's impressive growth of a $300 million portfolio with nearly 50% profit increase. Mike and Daniel delve into the three fundamental tenets of business success: planning, executive sponsorship, and execution. Learn how utilizing data visualization tools like Power BI can drive incremental changes and improve operations. The discussion also touches on AI's role in productivity and the importance of a living business plan. Discover how top-tier clients like ExxonMobil are secured and retained through strategic relationships and shared goals. Perfect for anyone looking to elevate business acumen.

Sharissa Sebastian Depen joins Mike to unpack a leadership problem that hides in plain sight: why high achievers can have the title, salary, and influence—and still feel stressed, stuck, or unfulfilled. Drawing from her coaching work and her own career turning point, Sharissa argues that workplace happiness starts with alignment: knowing who you are, what you value, and why the next step actually matters.

A key reality frames the conversation: we spend over 90,000 hours of our lives at work, so misalignment becomes chronic stress, not a passing inconvenience. They talk through how to pressure-test your calendar with an 80/20 lens, why “achievement” can become a trap (“it will get better when…”), and how culture influences happiness—especially what’s in your control vs. what isn’t. Mike shares a concrete management example from Agile sprints: finishing early earned his team time off, and he kept the same team for five years.

What you’ll learn:

How to define success in a way that includes happiness

How to spot values misalignment before burnout

Why support systems, beliefs, and gratitude change how you lead day to day

What separates great individual performers from great leaders? In this episode of Gaining the Technology Leadership Edge, Mike sits down with David Kitchen (Coach Kitch) to break down the mindset shift leaders must make when moving from doing the work themselves to winning through others.

Drawing from his experience coaching elite athletes and executives, Coach Kitch explains why leaders are “beholden to how other people perform” and why delegation—not control—is the real superpower of leadership. He challenges common myths like “if you want it done right, do it yourself” and the idea that leading by example alone is enough. Instead, he introduces practical principles such as letting A players be A players, the 80% delegation rule, and staying in your zone of genius.

The conversation also explores hiring for future growth, why clarity of vision and values matters more than raw performance, and the red flags that signal someone is not ready to lead. From athlete metaphors to real executive decisions, this episode reframes leadership as coaching, not micromanagement—and shows how great leaders create performance by getting out of the way at the right time.

What if the biggest barrier to your leadership success isn’t strategy, talent, or execution—but communication?

In this episode of Gaining the Technology Leadership Edge, Mike sits down with Tissa Richards, repeat software founder, CEO, award-winning author, and global leadership expert, to unpack why most leaders think they’re communicating clearly—and why they’re often wrong. Tissa explains how failing to provide context and “the why” behind decisions creates misalignment, wasted effort, and burnout across teams.

The conversation dives into practical techniques leaders can use immediately, including feedback loops, active listening, and what Tissa calls cognitive kindness—the discipline of packaging information so it’s actually digestible. They also explore resilience as a leadership requirement, not a personal bonus, and why burned-out teams cannot innovate, scale, or sustain productivity.

From aligning strategy to execution, to articulating value with confidence, to building cultures that reduce friction instead of amplifying it, this episode is a masterclass on how clarity, resilience, and communication determine whether leaders—and their organizations—thrive or stall.

AI is no longer a future concept in customer experience—it’s already reshaping how companies engage, sell, and support at scale.

In this episode of Gaining the Technology Leadership Edge, Mike sits down with Alex Levin, founder of Regal.io and former growth leader at Handy, to explore how AI-powered contact centers are transforming entire industries. Alex shares lessons from scaling businesses through major mergers, building products at the edge of what’s possible, and rethinking the role of customer interaction in a world rapidly moving toward automation.

The conversation challenges the long-held belief that self-service always improves efficiency. Alex explains why removing human interaction actually hurts growth in complex industries like home services, healthcare, insurance, and education—and how AI voice agents are now restoring personalization at scale. They also unpack how proactive outbound engagement, real-time customer intent signals, and AI-driven experimentation have helped Regal clients drive billions in revenue.

This episode offers a clear look at where AI replaces humans, where it amplifies them, and why the contact center is shifting from a cost center to a growth engine. For leaders navigating AI adoption, customer experience, and scale, this is a practical, grounded view of what’s coming next.

Every leader faces curveballs. The difference between those who break and those who build something stronger is how they respond.

In this episode of Gaining the Technology Leadership Edge, Mike sits down with Joelle Kaufman, a 25-year B2B SaaS executive, go-to-market leadership coach, and generational cancer survivor, to unpack her Curveball Method for leading through adversity. Drawing from her experience helping build over $4B in market value—and navigating cancer personally—Joelle explains why challenges are constant, but panic is optional.

The conversation explores how leaders can slow down under pressure, separate reactions from reality, and make better decisions when the stakes are high. Joelle walks through the five core elements of her approach: clarifying what matters most, leaning into strengths, choosing a possibility mindset, deploying the right resources, and leading with clear communication. She also shares practical frameworks for building resilience, regulating emotions, setting boundaries, and turning even devastating events into long-term advantages.

This episode is a grounded, deeply human look at leadership under pressure—and how the way you “swing” determines what comes next.

What if one of the most painful moments in your life became the catalyst for your greatest professional breakthrough?

In this episode of Gaining the Technology Leadership Edge, Mike sits down with Brian Strong, CEO of 10Hats, to explore a leadership journey shaped by sales, startups, setbacks, and perspective. From selling railroad materials to telecom, founding and exiting a GovTech software company, and ultimately stepping into the CEO role at 10Hats, Brian shares how wearing many hats prepared him to lead with clarity and empathy.

Brian opens up about the unexpected injury that forced him to slow down—and ultimately rethink his career path—leading to entrepreneurship and a successful software exit. The conversation dives into why startups are the ultimate leadership classroom, how sales builds the foundation for any executive role, and why aligning technology with real client needs requires trust, perspective, and genuine partnership.

This episode is a powerful reminder that leadership isn’t about titles or ladders—it’s about understanding people, solving real problems, and becoming the kind of leader you’d want to work for.

Your competition is evolving—but are you?

In this episode of Gaining the Technology Leadership Edge, Mike welcomes Christopher Larsen, a technology executive, coach, and founder of KnowledgeGain, to explore a powerful intersection most leaders overlook: cutting-edge technology and ancient holistic practices. With a background in engineering, executive leadership, and mindfulness-based coaching, Christopher explains why technical excellence alone is no longer enough to lead effectively.

Christopher shares his journey from climbing the corporate ladder at IBM to realizing that success without fulfillment leads to burnout, disengaged teams, and poor decision-making. The conversation dives into why modern leadership demands emotional awareness, presence, and empathy—especially as AI, information overload, and constant change accelerate pressure on leaders.

Together, they unpack practical ways leaders can integrate mindfulness, breathing techniques, and self-awareness into their daily routines to improve clarity, decision-making, and team communication. From letting go of control to truly listening, this episode challenges traditional leadership models and offers a grounded path forward for leaders who want to evolve without losing their edge.

What if the leadership style you were taught is the very thing pushing your best people away?

In this episode of Gaining the Technology Leadership Edge, Mike sits down with Haley Anthony, combat veteran, leadership coach, and founder of Rise Executive Coaching, to unpack why fear-based leadership is not just outdated—but actively harmful to performance, culture, and retention. Drawing from her military background and years of transforming struggling teams, Haley explains how intimidation, avoidance, and control quietly erode trust and drive high performers out the door.

The conversation explores how empathy functions as a practical leadership skill, not a “soft” extra. Haley shares real examples of creating psychological safety, meeting employees where they are, and replacing punishment-driven motivation with intrinsic engagement. They also dive into common warning signs of toxic cultures, the hidden cost of turnover, and why leaders must be willing to hear hard feedback without becoming defensive.

This episode is a practical guide for leaders ready to move from fear and authority toward inspiration, accountability, and human connection—without sacrificing results.

What if the key to stronger teams isn’t fixing weaknesses—but fully understanding and leveraging what people naturally do best?

In this episode of Gaining the Technology Leadership Edge, Mike welcomes Jennifer Pasquale, a dual-certified Gallup CliftonStrengths coach, to explore how strengths-based development transforms individuals, teams, and entire organizations. Drawing from her work with corporate teams and military spouses, Jennifer explains how self-awareness becomes the foundation for engagement, connection, and performance.

Jennifer shares her personal journey of feeling professionally “off center” and how discovering her own strengths gave her language for who she is and how she adds value. The conversation dives into what happens when individuals finally feel seen and understood, why curiosity is essential to collaboration, and how strengths can both fuel success and become barriers when overused or misunderstood.

They also discuss common misconceptions about strengths-based coaching, why there is no “perfect” strengths profile, and how leaders can create environments where people contribute confidently and authentically. This episode is a powerful reminder that belonging, clarity, and performance all begin with understanding yourself—and being curious about others.