The H2 Leadership Podcast

Retire Often Why the Best Leaders Take Halftime Seriously: with Jillian Johnsrud

Jillian Johnsrud has taken thirteen mini retirements (sabbaticals) over the last twenty years. She's raised five kids (three adopted), built and renovated rental properties that changed her family's financial trajectory, and coached hundreds of leaders through their own sabbaticals. Her new book Retire Often might be the most practical and philosophically rich thing written on the subject. She joins Alan Briggs for a conversation about something most leaders get wrong: the assumption that caring about your work means never stepping away from it. Who this episode is for If you're a leader who runs hard and assumes the operation falls apart without you. If you've watched peers burn out and quietly wondered when it's coming for you. If you're caught between a 60-year-old generation that grinds and a 25-year-old generation that won't, and you're trying to figure out a third way. If your identity is so wrapped up in what you do that you're not sure what's underneath it. This one is for you. What you'll take away The halftime analogy that reframes extended rest as competitive strategy, not indulgence, and why the leaders running sprints through their break aren't the ones winning long term A clear three-part definition of a mini retirement (one month or longer, away from your primary profession, focused on something meaningful) and how that differs from a vacation How to address the four objections that stop almost every leader from doing this: money, work obligations, "what would I even do," and "what if it goes badly" Why "my whole identity is my work" isn't a badge of honor, it's a problem to solve before it solves itself The "spring cleaning" effect on your business or team when you step away, and why most leaders come back to a tidier, more efficient operation than the one they left Why your sabbatical plan is a hypothesis and your sabbatical reality is an experiment, and how that one reframe eliminates the emotional suffering most leaders inflict on themselves What Jillian thinks AI is about to change about leadership, and why the companies that figure rest out are going to dominate the next twenty years Quotes worth sitting with "The only options are you figure it out or you die at your desk." "Machines are getting better at being machines. Humans need to get a lot better at being human." "No one looks at the basketball players running sprints during halftime and goes, oh, they're the ones who really care. No, they don't. They're being stupid." "You're always more tired than you think." "You don't include yourself in the people first." Reflection questions If your identity is entirely defined by your work, what would it take to start building meaning and purpose outside of it before life forces the issue? What season are you actually leading from right now (spring, summer, fall, winter), and is your current pace honest about that? What would have to be true for you to take a real break with purpose? And what's actually stopping you from making that true? Resources Retire Often by Jillian Johnsrud, available wherever you buy books. The Sabbatical Journey field guide by Alan Briggs, available from Amazon & Barnes & Noble This episode is also featured on The Sabbatical Journey Podcast from our sister organization, Sabbatical Coaching Group, which helps leaders prepare for, experience, and return well from a life-changing sabbatical. Learn more at sabbaticalcoachinggroup.com. For coaching, frameworks, and tools to help you lead healthy and with higher impact, head to h2leadership.com.

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Another Meeting That Could Have Been an Email: Redesigning How We Work Together with Rebecca Hinds

3w ago00:32:51Tap to summarize

Rebecca Hinds, researcher, organizational designer, and author of Your Best Meeting Ever joins the Alan Briggs for a conversation that is long overdue in most, if not all organizations. Alan has threatened to write a book about meetings for years. He no longer has to. Why? Rebecca wrote it. After 15 years studying how humans communicate and coordinate at work, Rebecca brings both the research and the practical frameworks to help leaders stop letting meetings kill their culture — and start designing them as the powerful, expensive tool they actually are. If you've ever sat in a meeting wondering why you're there, or felt the creeping guilt of a calendar so packed with meetings that the real work gets squeezed into the margins, this one is for you. What You'll Learn in This Episode: Why we keep having bad meetings even when we know they're not working — and the visibility bias that drives the cycle What "calendar carnage" is and why it's not just a scheduling problem — it's a fundamental communication problem Meeting Doomsday — the 48-hour calendar cleanse that forces every recurring meeting to earn its spot back Why AI is making meetings worse, not better — and the specific behaviors Rebecca is watching with alarm The danger of sending your AI bot to a meeting instead of showing up yourself — and what it signals to your team Why brainstorming is one of the most overrated meeting types — and what the research says actually produces better ideas The four dimensions of meeting minimalism: length, cadence, attendees, and agenda items Parkinson's Law and why your 30-minute meeting will always take 30 minutes — and how the rule of halves fixes it How to convert every agenda item into a verb and noun combination — and why it changes everything The one meeting most organizations are cutting that they absolutely should not be: the manager one-on-one The question great leaders are asking about AI right now — and why it's not "what can I automate?" What Rebecca hopes meetings look like five years from now — and the mindset shift that gets us there Reflection Questions: If every recurring meeting on your calendar had to earn its spot back tomorrow, which ones would survive? Are you designing your meetings for yourself as the organizer — or for the people in the room? What would you do with your time if your meetings were cut in half — and is that answer worth fighting for? Resources Mentioned: Your Best Meeting Ever — Rebecca Hinds (available wherever books are sold) Working Genius Assessment — Patrick Lencioni and The Table Group (referenced by Alan) Marco Polo — async video tool used by the H2 team H2 Leadership Coaching — h2leadership.com Want more? Visit h2leadership.com for coaching, resources, and tools to help you lead well.

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What's Coming for the Church: Trends, Readiness, and the Leadership Shifts Nobody Is Talking About

Apr 3000:46:31Tap to summarize

In this episode, Alan Briggs sits down with Holly Tate, founder of The Ready Network and a consultant who has spent 15 years serving churches, ministries, and organizations at the intersection of leadership development and strategic clarity. Holly brings a rare vantage point: nearly a decade at Vanderbloemen doing executive search for churches, four years as Chief Marketing and Services Officer at a leadership software company serving over 600 ministries, and now running her own coaching and consulting practice helping leaders and teams scale. The conversation covers a lot of ground and moves fast. From the moment organizations outgrow their basketball team culture and have to become a football team, to the trends Holly is watching unfold in real time around shared leadership models, AI adoption, spiritual formation, and what it means to actually be ready for what's coming next. If you lead a church, serve on an elder board, work as an executive pastor, or simply want to understand the challenges facing ministry leaders right now, this one is for you. And if you lead a business or nonprofit, Holly estimates about 70% of this conversation will translate directly. What You'll Learn in This Episode: Holly's 15-year leadership pathway — from cold calling at a radio company to executive search at Vanderbloemen to chief marketing officer at a leadership software company — and what all of it taught her about organizational health The doer to developer jump — why top performers get promoted into management roles they were never equipped for, and the tension that creates between executives and managers The basketball team to football team analogy from Larry Osborne's Sticky Teams — what breaks down when organizations cross that threshold and what leaders have to change about themselves to navigate it The READY framework — Reality check, Evaluation, Action plan, Delegation, Yes barometer — and how Holly uses it as a 90-day strategic planning process for churches and organizations Why the Yes barometer is the hardest part of the framework to implement — and why psychological safety determines whether it works The emerging trend of shared and co-leadership models in churches — Holly's two hypotheses for why it's happening and what's making it work What's really driving fear around AI in church culture — and why Holly believes leaders should be the first to explore it, not the last The discipleship disruption — why churches are rethinking spiritual formation from the ground up and what that means for buildings, campuses, and Sunday morning models What men on leadership teams are accidentally doing that excludes female colleagues — and the simple habit shift that changes it What Holly is obsessed with right now: the concept of readiness and what it means to be a truly ready leader in a world changing faster than ever Reflection Questions: Is your organization still running basketball team systems inside a football team reality — and what would it cost you to acknowledge that honestly? Where does your team need a Yes barometer — a shared language for what you're saying no to when you say yes to something new? As a leader, are you approaching AI and rapid change with anticipation or dread — and what would it look like to move toward curiosity instead? Resources Mentioned: Sticky Teams — Larry Osborne The Ready Network — thereadynetwork.com Leading Smart Podcast — Tim Stevens and Holly Tate (find it wherever you listen to podcasts) McCrindle Research — multigenerational leadership data H2 Leadership Coaching — h2leadership.com Connect with Holly: Website: thereadynetwork.com Want more? Visit h2leadership.com for coaching, resources, and tools to help you lead well.

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Bridging the Gap: How We Building Leaders Create Trusted Teams with Laura Kriska

Apr 2300:36:07Tap to summarize

In this episode, Alan Briggs sits down with Laura Kriska — cross-cultural consultant, speaker, and author of The Business of We — for a conversation about one of the most underestimated challenges in leadership today: the invisible gaps that keep teams from reaching their full potential. Laura was born in Japan, raised in Ohio, and spent her early career as the first American woman working inside Honda's Tokyo headquarters. What started as a fascinating cross-cultural immersion became a three-decade career helping leaders and organizations bridge the us versus them gaps that quietly undermine collaboration — whether those gaps are cultural, generational, geographic, or simply the difference between how two departments approach a problem. If you lead a team of any kind, the frameworks Laura shares in this episode are immediately actionable and long overdue. What You'll Learn in This Episode: Laura's origin story — born in Japan to missionary parents, raised in Columbus, Ohio, and what that unique upbringing taught her about cultural differences hiding in plain sight What happened on her first day at Honda's Tokyo headquarters — and the split-second decision she made that shaped her entire philosophy of cross-cultural leadership The We Building framework — what it means to bridge an us versus them gap and why the best leaders do it even when they don't agree with or like the difference they're bridging The trust continuum: stranger → acquaintance → colleague → trusted colleague — and why most teams get stuck at colleague and never make it to trusted Why cultural differences are inevitable and predictable — and what changes when leaders start treating them that way The difference between visible and invisible cultural differences — and why the invisible ones cause the most damage The Team Machine — Laura's 90-minute interactive simulation that exposes the real collaboration behaviors teams bring to work every day Three categories of action for bridging any cultural gap: safe actions, challenging actions, and radical actions What males can specifically do — with humility — to better include female colleagues in their work cultures How hybrid work and the pandemic have made silos worse and what leaders can do about it right now Reflection Questions: Where in your organization is an us versus them gap quietly costing you collaboration and trust? When did you last take a safe, challenging, or radical action to bridge a cultural difference on your team? Are the people you lead stuck at colleague — and what would it take to move them to trusted colleague? Resources Mentioned: The Business of We — Laura Kriska (available wherever books are sold) The Accidental Office Lady — Laura Kriska (her first book chronicling her Honda experience) Harvard Business Review — co-authored piece on the Team Machine (coming May 2025) Connect with Laura on LinkedIn (her most active platform) H2 Leadership Coaching — h2leadership.com Want more? Visit h2leadership.com for coaching, resources, and tools to help you lead well.

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Dream Big. Think Boldly. Do Now: With Mitch Matthew’s

Apr 1600:50:05Tap to summarize

Making Time for Your Next Chapter — mitchmatthews.com/time (free with code H2LEADERSHIP) In this episode, Alan Briggs sits down with Mitch Matthews — coach, speaker, and host of the Dream Think Do podcast — for a conversation that feels less like an interview and more like two coaches getting honest with each other over coffee. Mitch is the CEO of a training organization focused on helping executives, entrepreneurs, and founders define what success actually means to them — and then build a plan to go after it. What unfolds is a wide-ranging, practical, and genuinely fun dialogue about dreams, the questions that unlock them, the questions that shut people down, and what it looks like to lead well in a moment of historic change. If you've ever locked up when someone asked you what your big dream is — or if you've watched someone else lock up when you asked them — this episode is going to reframe how you think about that conversation entirely. What You'll Learn in This Episode: Mitch's origin story — from a 12-year-old loitering at a bike shop in Iowa to discovering his life's calling at a Schwinn Selling School at 14 Why Mitch calls his work "success coaching" instead of life or executive coaching — and why that distinction matters The Dream Think Do framework — why dreaming has to come before thinking, and why most people start strategizing too early Why the question "what's your big dream?" actually shuts people down — and the better questions to ask instead The power of the word "might" — and how one small word change opens up possibilities that pressure closes off What semantic interference is and why it matters for every leader, coach, mentor, and manager in the room The story of the first Big Dream Gathering — how a product nightmare in 2006 became a movement now happening on college campuses and corporate retreats across the country Why dreams have seasons — and how to tell the difference between a dream that isn't right and a dream that just isn't right yet How the best leaders are navigating AI — standing in the tension of what's scary and what's possible at the same time Why AI is actually making people hunger for real human connection — and what that means for coaches and leaders Alan and Mitch coach each other live on the question "what do you want?" — and what makes a great clarifying question great Reflection Questions: What's something you want to experience more often — and what would it take to give yourself permission to pursue it? Are you dreaming before you think, or are you jumping straight to strategy before you've given yourself enough space to imagine? Where in your leadership are you standing in the tension between what's scary and what's possible? Free Resource from Mitch: Mitch put together a training called Making Time for Your Next Chapter — built specifically for high achievers who want to figure out what's next but feel like they don't have the time to even think about it. It's normally $97, but he's making it free for H2 Leadership listeners. Head to mitchmatthews.com/time and use the code H2LEADERSHIP at checkout. Connect with Mitch Matthews: Website: mitchmatthews.com Weekly "4 Things" email: mitchmatthews.com/4things Instagram: @mitch.matthews Facebook: @mitch.matthews.104 LinkedIn: linkedin.com/in/mitchmatthews Dream Think Do Podcast: mitchmatthews.com/blog/ Resources Mentioned: Making Time for Your Next Chapter — mitchmatthews.com/time (free with code H2LEADERSHIP) Gradually Then Suddenly — Mark Batterson The Second Mountain — David Brooks (referenced by Alan) Working Genius Assessment — Patrick Lencioni (referenced by Alan) H2 Leadership Coaching — h2leadership.com

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Fight for Space Why Every Leader Needs Micro, Medium, and Macro Breaks

Apr 900:15:54Tap to summarize

In this episode, Alan Briggs brings two of his popular Taking Steps video emails to the H2 Leadership Podcast — short, practical teachings he sends to leaders every couple of weeks. Today's focus is space. Not the theoretical kind. The kind you actually have to fight for in a real schedule with real demands pulling on you from every direction. If you're constantly behind, constantly stressed, and never quite present in the moment — Alan has a reframe for you. Space is not a luxury. It is an occupational requirement of leadership. And if you don't fight for it, it is not going to show up on its own. Alan walks through three types of space every leader needs to build into their life, and then zooms in on one of the most powerful practices he's implemented in his own leadership — the quarterly think day. Eight hours, no meetings, no email, just deep thinking on the biggest decisions and opportunities in front of him. The results have been consistently transformative. What You'll Learn in This Episode: Why the way most leaders think about time is actively working against them The three types of space every leader must fight for: micro, medium, and macro What micro space looks like in a real day — and why even five minutes matters The Sabbath as a "get-to day" in a world full of have-tos — and why every leader Alan knows who takes it seriously wishes they had started sooner The quarterly think day — what it is, how Alan structures it, and why it costs about ten dollars and returns serious clarity Why leaders who only react are slowly losing their creativity and their purpose What it looks like to go from a full day of deep thinking to presenting clear objectives to your team How macro space — vacations and sabbaticals — isn't just good for you personally, it's essential for your team and your leadership The simple challenge: can you take two, four, or eight hours this quarter to actually think? Reflection Questions: When was the last time you had uninterrupted space to think about where you're actually going — not just what's in front of you right now? Which of the three types of space — micro, medium, or macro — are you most neglecting, and what would it take to fight for it this week? If you blocked a think day this quarter, what are the two or three big topics you'd bring with you? Resources Mentioned: Right Side Up Journal — available on Amazon H2 Leadership Coaching — h2leadership.com Taking Steps — Alan's monthly email and video series for leaders

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Expanding Your Network Without Being Weird About It

Apr 201:03:35Tap to summarize

In this episode, Alan Briggs sits down with Stu Davis, Executive Director of COS I Love You — a Colorado Springs organization that brokers connection between the church, nonprofits, business, and public sector for a candid, practical conversation about what it actually looks like to expand your network without it feeling slimy, transactional, or just plain weird. This one was recorded live in a room full of leaders, and the energy of that conversation comes through. Alan and Stu have both spent years learning, and sometimes failing at the craft of genuine connection, and in this episode they pull back the curtain on how they think about it, how they've had to mature in it, and what separates the connectors who build real trust from the ones who just work a room. If you've ever walked away from a networking event feeling like you needed a shower, this episode is for you. What You'll Learn in This Episode: Why networking feels slimy — and the one thing that makes the difference between transactional and transformational connection The "engagement funnel" framework: how relationships move from acquaintance to friend to partner to collaborator to team — and why skipping steps is where things go wrong Why you should always state your agenda upfront — and how doing so actually builds more trust, not less The abundance vs. scarcity mentality in practice — including a story about a colleague who said one thing and did another What the best connectors do that most people don't — and why being only a connector isn't enough Alan's five-part framework for moving from intuitive to intentional connecting: grid, filters, environments, processes, and multiplication The green-light introduction — what it is, when to give it, and why it's one of the highest forms of relational trust Why name-dropping usually backfires — and what to do instead when you need to establish credibility How one dinner unlocked over $110,000 in business for Alan — and the mindset shift that almost made him say no Why "needy is creepy" — and what it looks like to refer someone to a competitor and actually gain trust by doing it The one question to always ask at the end of a meeting: "Is there any way I can serve you?" Reflection Questions: Who in your network do two people you know need to meet — and what's stopping you from making that introduction? Are you operating from an abundance mentality or a scarcity mentality — and would the people around you agree with your answer? Have you moved from intuitive to intentional in how you connect people, or are you still running it all out of your head? Resources Mentioned: COS I Love You: https://cosiloveyou.com/about-us/ Who Not How — Dan Sullivan (referenced by Alan) Right Side Up Journal — available on Amazon H2 Leadership Coaching — h2leadership.com About Stu Davis: Stu Davis is the Executive Director of COS I Love You, an organization in Colorado Springs that sits at the intersection of church and city — brokering relationships and building collaborative opportunities between nonprofits, faith communities, businesses, and public sector leaders. Want more? Visit h2leadership.com for coaching, resources, and tools to help you lead well. Leadership is complex, but it doesn't have to be lonely. Let's get after it.

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Why I Was Wrong About Goals: Direction, Destination, and the Both/And of Healthy Leadership

Mar 2600:23:53Tap to summarize

In this episode, Alan Briggs does something he's never done before — he opens by admitting he was wrong. For years as a leadership coach, Alan over-emphasized habits and healthy rhythms while under-selling the power of big, audacious goals. He watched too many leaders get crushed by massive targets they never hit, and he overcorrected. Now he's setting the record straight. The truth is, direction and destination aren't in competition. They need each other. Habits without a destination drift into maintenance. Big goals without daily rhythms become wishful thinking. The mature leader holds the tension between both — and that tension is exactly what this episode is about. Alan shares the personal story behind his upcoming trip to Machu Picchu — a promise made at his grandfather's memorial — and how that destination is anchoring his daily training and health habits right now. He also walks through what thought leaders like James Clear, Jim Collins, Angela Duckworth, and Benjamin Hardy all say on both sides of this conversation, and why they're ultimately pointing toward the same conclusion. What You'll Learn in This Episode: Why Alan swung the pendulum too far toward habits early in his coaching career — and what changed The "both/and" framework: how direction (daily habits) and destination (big stretch goals) work together Alan's Machu Picchu story and why a promise at his grandfather's memorial is driving his health right now What James Clear, Jim Collins, Angela Duckworth, and Benjamin Hardy all agree on Jim Collins' bullets and cannonballs concept and how to apply it to your leadership The "We are going to _____ by _____ because _____" formula for naming your moonshot goal Why measuring lead indicators (not just outcomes) is the key to real progress How the Right Side Up Journal connects big goals to daily habits in one place The boat and oars analogy — and what it costs you when only one oar is in the water Reflection Questions: What big goal have you been avoiding naming because you're not sure you can hit it? Are your current daily habits actually moving you toward a destination — or just maintaining where you are? Where have you been choosing between healthy and high impact, when you could be pursuing both? Resources Mentioned: Atomic Habits — James Clear Grit — Angela Duckworth 10X Is Easier Than 2X — Dr. Benjamin Hardy & Dan Sullivan Good to Great — Jim Collins Right Side Up Journal — available on Amazon Want more? Visit h2leadership.com for coaching, resources, and tools to help you lead well.

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What coaching actually does for a leader who is ready to grow.

Mar 1900:38:59Tap to summarize

Most leaders have heard that coaching is valuable. Fewer have seen what it actually looks like from the inside. In this episode Alan Briggs and Jonathan Collier pull back the curtain on a real coaching relationship, using clips from Alan's conversations with Daryl Smith, gathering pastor at The Journey Church in Newark Delaware, to show what Healthy AND High Impact leadership looks like when someone does the work. Daryl stepped into a bigger role with real weight and made a decision: he was not going to just survive it. What happened next is exactly what H2 Leadership is all about. In this episode: Why stepping into a new role is one of the most common entry points into coaching and what separates leaders who thrive in the transition from those who just endure it The counterintuitive move that changes everything: why slowing down is the most high impact thing a fast-moving leader can do The org chart story: how Daryl went from sitting on an idea for six months to presenting it to his lead team in seven days and why his lead pastor is still referencing it today A full walkthrough of the Start Stop Keep tool and the five questions that helped Daryl step into 2026 with momentum, confidence, and direction What Daryl said about how coaching changed his marriage, his relationship with his kids, and his presence at home The line that will stay with you: Coaching helped Daryl listen to God more clearly, lead people more wisely, and live more honestly. That is Healthy AND High Impact in a single sentence. This episode is for the leader who: Just stepped into a bigger role and is figuring it out as they go Is grinding toward high impact but knows their health is taking the hit Has been thinking about coaching but has not pulled the trigger yet Connect with H2 Leadership: Website: h2leadership.com Leave a review on Apple Podcasts and help other leaders find the show

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Demystifying the Sabbatical: What It Is, Why Leaders Fear It, and Why You Can't Afford to Skip It

Mar 1200:48:09Tap to summarize

Sabbatical gets misunderstood, feared, and misused — and most leaders either wait too long to take one or avoid it altogether. In this episode, Alan joins Andrew Estes on the Nexus Church Planting Podcast for a conversation that cuts through the baggage and gets honest about what a sabbatical actually is, why boards resist it, why church planters think they can't afford it, and why the leaders who take it well come back with more vision, more creativity, and more fire than they've had in years. If you've ever thought sabbatical is for someone else, someone further along, someone with a bigger team — this one is for you. What You'll Learn: The difference between micro, medium, and macro rest — and why you need all three to lead sustainably Why sabbatical is not discipline, not a vacation, and not an escape — and what it actually is The abundance vs. scarcity mindset that determines whether a leader can truly rest Why boards and congregations fear sabbaticals — and how to address every one of those fears honestly The surprising truth about sabbatical as a leadership development tool for your entire team Why church planters can't afford to wait — and what to start doing now even if you're only three years in The six R's framework Alan uses to help leaders prepare well and waste nothing "Don't resign, redesign" — what it looks like to come back from sabbatical ready for the next decade Key Insight: You are not as valuable as you think — and that's actually great news. Sabbatical forces the leadership development your team needs, creates the empowerment you've been meaning to build, and reminds you that God was never depending on you to hold it all together in the first place. Reflection Question: What's your honest excuse for not pursuing sabbatical right now — and is it rooted in scarcity thinking or genuine wisdom? This episode originally aired on the Nexus Church Planting Podcast. We're grateful to Andrew and the Nexus team for sharing it with the H2 community. Connect with Nexus: Full episode: https://www.nexus.us/episode/06-alan-briggs--demystifying-sabbaticals Website: https://www.nexus.us Apple Podcasts: https://podcasts.apple.com/us/podcast/nexus-church-planting-podcast/id1838803043 YouTube: https://www.youtube.com/channel/UCd5AMLFOOTjdiQ8wiwMW51Q I nstagram: https://www.instagram.com/nexus_church_planting/ Resources Mentioned: The Sabbatical Journey Field Guide — available on Amazon Sabbatical Coaching Group — sabbaticalcoachinggroup.com Lilly Foundation Clergy Renewal Grants — lillyfoundation.org

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All episodes

Retire Often Why the Best Leaders Take Halftime Seriously: with Jillian Johnsrud

Another Meeting That Could Have Been an Email: Redesigning How We Work Together with Rebecca Hinds

What's Coming for the Church: Trends, Readiness, and the Leadership Shifts Nobody Is Talking About

Bridging the Gap: How We Building Leaders Create Trusted Teams with Laura Kriska

Dream Big. Think Boldly. Do Now: With Mitch Matthew’s

Fight for Space Why Every Leader Needs Micro, Medium, and Macro Breaks

Expanding Your Network Without Being Weird About It

Why I Was Wrong About Goals: Direction, Destination, and the Both/And of Healthy Leadership

What coaching actually does for a leader who is ready to grow.

Demystifying the Sabbatical: What It Is, Why Leaders Fear It, and Why You Can't Afford to Skip It