It's All Going To Be Okay with Jeff Reid

The Voice Lied

I pulled my own podcast data and didn't love what I found. 52% of my listeners are women. Only 16% of women who apply to be guests actually show up. That number sent me down a research rabbit hole — imposter syndrome, the broken ladder, the sponsorship gap, the airtime inequality — and into a solo episode that's equal parts data and personal confession. This week on Big Boss Biscuits: why women aren't showing up even when the seat is theirs — and what leaders, allies, and women themselves can do about it. Grab your biscuits. This one hits close to home.

Rethinking Servant Leadership

In this episode, Kirsten sits down with executive coach and former tech leader Keith Corbin for a conversation that challenges one of the most celebrated ideas in modern leadership — servant leadership. Keith argues that while the intention behind servant leadership is good, it can actually do more harm than good by masking the very power dynamics leaders need to confront head-on. Using Ted Lasso as a lens, Keith and Kirsten unpack how kindness and care — without transparency about power and accountability — can leave teams feeling blindsided when the hard moments come. Layoffs. Performance improvement plans. Tough decisions made at the organization's request, not the team's benefit. These are the moments that expose what servant leadership often leaves unresolved. Keith shares how he coaches leaders to move beyond the "good vibes" approach and build what he calls a foundation of transparency and trust — one where employees understand the structure they're operating in, the constraints their leader carries, and what it actually means to be led well. If you've ever struggled with balancing genuine care for your people with the hard realities of organizational life, this conversation will give you a new framework — and a lot to think about.

From Reluctant To Intentional Leadership

This week on Big Boss Biscuits, I’m joined by Frank Smith—leadership coach, culture consultant, and former “accidental CEO” who went from sitting on a folding chair learning the business… to running it for 20 years. No roadmap. No role models. And definitely no desire to become that boss. Frank calls his early years “reluctant leadership." We talk about the messy middle: the years of just keeping the lights on and avoiding the responsibility of leadership. The twist: even in those imperfect years, something unexpected happened. By simply trusting people, treating them with respect, and not making them fill out a form to buy $10 worth of super glue (yes, really), the business started to grow. In this episode, we get into: * The shift from reluctant to intentional leadership * How curiosity beats frustration every single time * The fine line between caring for people and holding them accountable * And why your employees are 100% talking about you at dinner tonight Frank’s philosophy is simple, but not easy: if you want people to care about your business, you better start by caring about them. And if that sounds like common sense… well, you already know how rare that is.

Leading With Heart, Not Just Numbers

This episode flips the classic leadership script: what if hitting the numbers isn’t the starting point—but the byproduct? Marty Imes unpacks why so many new leaders default to results-at-all-cost thinking—and how that mindset quietly sabotages the very outcomes they’re chasing. Drawing from his own early missteps (including a humbling moment of upward feedback from a team member named Nicole), Marty shares the turning point that reshaped his leadership: realizing that numbers don’t drive performance—people do. Through a candid, Ted Lasso-inspired conversation with Kirsten Penaloza, Marty explores the tension between performance and people-first leadership, and why leaning too far in either direction misses the mark. The answer isn’t abandoning results—it’s redefining what “winning” actually means. You’ll hear how Marty evolved from reactive, metrics-obsessed management to intentional, human-centered leadership—grounded in clarity, trust, and shared vision. He introduces his practical “Five F” framework (Fit, Finances, Future, Freedom, Fun) as a way to connect business success with personal fulfillment, and explains how meaning—not just metrics—drives engagement and retention. The episode also dives into: * Why high performers often struggle as new leaders * The hidden cost of unclear expectations * How to turn mistakes into momentum instead of blame * The role of psychological safety and trust in high-performing teams * What it really takes to lead like Ted… without the fluff At its core, this conversation is a reminder that great leadership isn’t about choosing between people and performance—it’s about building the conditions where both thrive.

It's All Going To Be Okay with Jeff Reid

Leadership isn’t a playbook—it’s more like improv… but with real consequences. Jeff Reid learned that the hard way when he became a manager at 25 with zero roadmap and a team suddenly depending on him. Turns out, you don’t need all the answers—you just need the guts to bet on people, face uncomfortable truths, and figure it out as you go. In this episode, Jeff shares what leadership actually looks like behind the scenes: navigating the chaos of the dot-com boom, making tough calls (including firing people), and realizing—sometimes too late—when it’s time to step in. We talk about missed signals, course corrections, and why “hoping it works out” is not a strategy. We also get into what does work: balancing empathy with accountability, giving people not just space but fuel to grow, and having the conversations you’d really rather avoid. Because those? They’re usually the ones that matter most. Bottom line: leadership is messy, humbling, and occasionally painful—but also where the real growth happens. So if you’ve ever wondered whether you’re doing it “right”… you’re not alone. And more importantly, it’s going to be okay.