Think Outside the Boss

Katie Armentrout
  • 5.0 (16)
  • Entrepreneurship

Leadership would be easy if it weren’t for the people. Think Outside the Boss is a leadership podcast for business owners, founders, and people leaders who are tired of managing team drama and ready to lead differently, more human, more effective, and with a lot less exhaustion. Hosted by Katie Armentrout, a recovering corporate leader turned entrepreneur, this show challenges traditional leadership development and replaces it with something far more useful. Clear thinking. Better conversations. And one practical action you can try right away. Through honest solo episodes and real conversations with experienced leaders, Think Outside the Boss explores proven leadership frameworks, innovative ideas, and people-first tools you can actually use. No theory for theory’s sake. No performative leadership nonsense. You’ll learn how to: - Strengthen trust and accountability without micromanaging - Navigate team conflict and communication breakdowns - Build a culture where employees feel valued and customers stay loyal - Lead people with clarity instead of control There’s no silver bullet when it comes to people. But there are better ways to think, choose, and lead. No corporate lingo bingo. No meeting after the meeting. If leadership has started to feel heavier than it should, this podcast is your invitation to Think Outside the Boss. 🎧 New episodes weekly: https://www.peoplefluence.com/podcast

  1. 4d ago

    034: A 35 Year Marriage, Tested by Cancer | Monique & Dr. Eddie Cheeks

    Breast cancer early detection saved Monique Cheeks' life. She was diagnosed with an aggressive form of triple negative breast cancer last November, caught at stage one because she never let vigilance slip after watching her mother and aunt go through the same disease. Her husband, Dr. Eddie Cheeks, has faced this disease before too, decades earlier, with someone else he loved. If you have ever needed a reason to schedule the mammogram you keep putting off, this is it. Katie Armentrout, founder of Peoplefluence and host of Think Outside the Boss, continues her Leading Through Cancer series with Monique Cheeks, CEO of the Cheeks Agency, and her husband of 35 years, Dr. Eddie Cheeks, a practicing OBGYN who is legally blind and recovering from a stroke. You will hear how Monique turned sixteen rounds of chemotherapy and twenty rounds of radiation into a ring the bell celebration with thirty guests, and how leadership in this marriage has moved in both directions long before her diagnosis. Get your mammogram scheduled, then go find out who is leading you through your next hard season. In this episode, you’ll discover: Why early detection made the difference for Monique, and how family history of breast cancer kept her vigilant about mammogramsHow triple negative breast cancer, one of the most aggressive forms, was caught at stage one before it reached her lymph nodesWhy Monique refused to skip makeup or outfits for a single chemotherapy or radiation appointment, and how that choice became a mindset strategyHow Dr. Eddie Cheeks, legally blind and recovering from a stroke, became Monique's co-pilot for every treatment, after she had rehabbed him back to driving in five monthsWhat Monique's ring the bell celebration looked like, with thirty guests and the biggest ceremony her cancer center had ever seenWhy Dr. Cheeks believes there may be more prevention breakthroughs ahead for breast cancer, drawing a comparison to the cervical cancer vaccine (his own view, not a medical claim)Why Monique's advice, that you cannot want something for someone more than they want it for themselves, applies to leading a spouse, a client, or a team through any hard season We talk about: 00:00 Why Dr. Eddie Cheeks became Monique's co-pilot through cancer 05:46 Monique's triple negative breast cancer diagnosis 08:00 Why she got dressed up for every chemotherapy appointment 12:09 What facing this disease before taught Dr. Cheeks 17:15 Her diagnosis to surgery timeline in four weeks 21:28 How Monique rehabbed her husband back to driving after his stroke 25:00 Inside her ring the bell celebration with 30 guests 31:33 What breast cancer statistics have changed over the years 33:38 Why cervical cancer gives hope for a future breast cancer vaccine 39:28 What is the best advice Monique has ever received 44:00 Their walk-on and ring the bell songs Ready to lead through cancer, or any crisis, together? Get your mammogram scheduled, and follow along next week for part three of Leading Through Cancer with Katie's surgeon, Dr. Kathleen Raque. Connect with Katie at https://www.peoplefluence.com/newsletter-landing-pageipsahnqm. Resources: Eat Right for Your Blood Type https://link.amazon/B0bEMOMuj Connect with me Instagram:https://www.instagram.com/katie_armentroutYouTube: https://www.youtube.com/@katiearmentroutLinkedIn:https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletterWebsite: http://www.peoplefluence.com #ThinkOutsideTheBoss #LeadingThroughCancer #BreastCancerAwareness #EarlyDetectionSavesLives #TripleNegativeBreastCancer #CancerSurvivor #RingTheBell #CaregiverHusband #MarriageAndCancer #BreastCancerAwarenessMonth #WomenInLeadership #Peoplefluence #PodcastForLeaders #CancerJourney #HealthAdvocacy #MammogramMatters #KnowYourBody #StrongerTogether #LeadershipPodcast #HopeAndHealing

    034: A 35 Year Marriage, Tested by Cancer | Monique & Dr. Eddie Cheeks

  2. Oct 7

    033: The Three Lies I Believed Through Cancer | Katie Armentrout

    Leading through cancer, or any crisis, starts with leading yourself first, and that is the hardest leadership job there is. Katie Armentrout was diagnosed with stage one breast cancer in May 2025, and as of this Breast Cancer Awareness Month she is sharing the year that followed, and the lies she told herself about how a leader is supposed to handle it. If you have ever tried to push through a crisis by pretending nothing changed, this episode will hit close to home. Katie Armentrout, founder of Peoplefluence and host of Think Outside the Boss, opens a three part series called Leading Through Cancer with her own story, a lumpectomy, twenty rounds of radiation, and the three lies she believed along the way, that she could push through it like everything else, that a leader cannot show weakness, and that hiding her suffering protected the people she loved. She leans on Dr. Kristin Neff's research on self-compassion, shares the ninety nine percent five year survival rate tied to early detection, and explains why the same vulnerability she teaches through Working Genius and EOS was the hardest thing to practice on herself. Get your mammogram scheduled, then go lead yourself through whatever crisis is next. In this episode, you’ll discover: Why Katie Armentrout believes leading yourself through crisis is the hardest leadership job there is, and how her own breast cancer diagnosis proved it.What Dr. Kristin Neff's research on self-compassion taught her about healing faster by being kinder to herself instead of pushing harder.Why the belief that leaders cannot show weakness is the opposite of what she teaches through Working Genius, Five Dysfunctions, and EOS, where vulnerability builds trust.Why hiding her diagnosis from her round table coaching clients backfired, and what happened when she finally told them the truth about crashing mid treatment.How early detection changed her outcome, including the statistic that catching breast cancer at a localized stage means a 99 percent five year survival rate.Why telling her three kids, then ages 13, 11, and 8, before her surgery became one of the clearest examples of leading her family through crisis.What her friend group, the Mapledale moms, taught her about receiving help, after thirty people showed up unannounced to mulch her yard. We talk about: 00:00 Why leading yourself is the hardest leadership job 01:28 Her breast cancer diagnosis and treatment timeline 06:30 Why she compares cancer to a plane crash she survived 08:41 The three lies she believed about handling crisis 10:26 Why one in eight women get breast cancer 13:33 What early detection means for five year survival rates 16:56 What Dr. Kristin Neff's work on self-compassion taught her 21:47 Why she told her coaching clients nothing would change 29:00 What made her stop hiding her diagnosis 36:30 How the Mapledale moms showed up to mulch her yard 39:00 How she told her three kids she had cancer 46:23 What she wants every leader to ask themselves next Ready to lead yourself through whatever crisis comes next? Get your mammogram scheduled today, and follow along next week for part two of Leading Through Cancer with Dr. Eddie Cheeks and his wife Monique. Connect with Katie at https://www.peoplefluence.com/newsletter-landing-pageipsahnqm. Resources: Self-Compassion by Dr. Kristin Neff https://link.amazon/B07tiUOv7 Connect with me Instagram:https://www.instagram.com/katie_armentroutYouTube: https://www.youtube.com/@katiearmentroutLinkedIn:https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletterWebsite: http://www.peoplefluence.com #LeadingThroughCancer #BreastCancerAwarenessMonth #SelfCompassion #VulnerableLeadership #LeadershipDevelopment #EntrepreneurLife #WorkingGenius #EOSModel #MentalHealthAtWork #WomenInLeadership #CancerSurvivor #EarlyDetectionSavesLives #LeadershipPodcast #SmallBusinessOwner #ExecutiveLeadership #CorporateCulture #CommunityOverCompetition #ThinkOutsideTheBoss #Peoplefluence

    033: The Three Lies I Believed Through Cancer | Katie Armentrout

  3. Sep 30

    032: Hundreds Waited Outside Her Office for Days | Detria Austin Everson

    Serving is a superpower, not a soft skill and not a nice to have you reach for once the real leadership work is done. Detria Austin Everson has spent more than two decades leading through crisis, from healthcare disparities to the 2008 housing collapse, and every time she found the same thing waiting at the center of it: service. If you have a heart for helping people but have only ever treated it as an extracurricular activity, this conversation will change how you see it. Katie Armentrout, EOS Implementer, founder of Peoplefluence and host of Think Outside the Boss, sits down with Detria Austin Everson, author of Serving Is a Superpower, to trace a career that runs through the Medical College of Georgia, the Neighborhood Assistance Corporation of America, historic Ebenezer Baptist Church, and the John Lewis Foundation. You will hear how her CLASS program brought culturally and linguistically appropriate care, backed by a 147 language phone line, into a hospital system, how the Home Safe Program helped tens of thousands of struggling homeowners during the mortgage crisis, and why staying behind for three extra weeks after one event taught her that proximity earns trust that a title never will. Stop leading from a distance. Get close enough to see the problem for yourself. In this episode, you’ll discover: Why Detria Austin Everson believes proximity, not title or org chart authority, is what actually earns a leader trust and loyalty that lasts.How the CLASS program she built inside a healthcare system used on site interpreters and a 147 language phone line to close cultural and linguistic gaps in patient care.What running the Home Safe Program during the 2008 housing crisis taught her, after meeting twenty five to fifty thousand struggling homeowners at nearly two hundred events.Why staying behind for three extra weeks after one Home Safe event, instead of moving straight to the next city, became the moment her team's trust in her changed for good.How her mother's decades as a career social worker shaped the idea behind Serving Is a Superpower, that everyone can be great because everyone can serve.Why she considers service a genuine competitive advantage for retention, culture, and loyalty, not just a value statement posted on a wall.What led her to walk away from a pre med track in college, and why she now calls that decision one of the failures she cherishes most. We talk about: 00:00 Why proximity is Detria's leadership superpower 01:12 When did she first know she was a leader 04:31 Running NACA's national housing crisis response 05:39 Leading the John Lewis Foundation 05:57 Becoming her mother, a career social worker 09:13 Why housing stability drives better health outcomes 11:00 The CLASS program and 147 languages of care 21:00 What makes leaders earn loyalty, not just authority 21:34 Why she stayed behind for three extra weeks 27:28 When service became a competitive advantage 33:40 The lightning round begins 36:57 Where to find Serving Is a Superpower Ready to lead with more proximity and less distance? Get Serving Is a Superpower and the companion workbook at https://servingisasuperpower.com/, and if you want help building a culture your team actually trusts, connect with Katie at https://www.peoplefluence.com/newsletter-landing-pageipsahnqm. Resources: Humility by Andrew Murray https://link.amazon/B0hFYN5iJ Connect with Detria Instagram: https://www.instagram.com/detriaaustineverson/Facebook: https://www.facebook.com/detria.everson/LinkedIn: https://www.linkedin.com/in/detriaaustineverson/TikTok: https://www.tiktok.com/@detriaaustineversonWebsite: www.servingisasuperpower.com Connect with me Instagram:https://www.instagram.com/katie_armentroutYouTube: https://www.youtube.com/@katiearmentroutLinkedIn:https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletterWebsite: http://www.peoplefluence.com #ServingIsASuperpower #ServantLeadership #ProximityLeadership #LeadershipDevelopment #WorkplaceCulture #TeamTrust #EmployeeRetention #NonprofitLeadership #HealthcareLeadership #HousingCrisis #CommunityLeadership #WomenInLeadership #ExecutiveLeadership #CorporateCulture #SmallBusinessOwner #LeadershipPodcast #CivilRightsLeadership #ServiceLeadership #ThinkOutsideTheBoss

  4. Sep 23

    031: She Hired Six Millennials. They All Quit in Eight Weeks. | Lee Caraher

    The Millennial Whisperer is the nickname PR veteran Lee Caraher earned the hard way, after six millennial hires quit her firm within eight weeks of each other and she decided the problem had to be her, not them. If you have ever been blindsided by a resignation you never saw coming, or found yourself assuming the worst about an employee who was late, distracted, or quiet in a meeting, this conversation will change how you read your team. Most leaders think they have communicated clearly. Most have not, and the gap between those two realities is where good people quietly walk out the door. Katie Armentrout, founder of Peoplefluence and host of Think Outside the Boss, sits down with Lee Caraher, founder and CEO of Double Forte and author of Millennials and Management and The Boomerang Principle, to unpack the four cultural forces reshaping how younger employees show up to work. You will hear how Lee's pass along able standard keeps deliverables from arriving half finished, why she borrows the Chief Reminding Officer idea from Patrick Lencioni's The Advantage to explain why leaders have to repeat themselves, and how her communication wheel model separates what actually happened from the assumptions that make leaders furious. Stop guessing why your team missed the memo. Start asking what you never actually said. In this episode, you’ll discover: Why six millennial hires quitting within eight weeks of each other taught Lee Caraher that blaming a generation is easier than examining her own leadership and communication gaps.What four generational forces, from helicopter parenting to grade inflation to Oprah Winfrey's message on self-respect, actually shape how younger employees interpret workplace expectations.How Lee's communication wheel model uncovers the real reason a leader is angry about someone being late, and why it is almost never about the clock.Why Double Forte's pass along able standard for deliverables eliminates the vague expectations that quietly wreck deadlines, client relationships, and team trust.What the Chief Reminding Officer concept from Patrick Lencioni's The Advantage means for leaders who assume they already said something clearly once.Why ambiguous words like end of day or late cause most workplace conflict, and the exact language Lee uses to replace them.How Double Forte's people first culture and industry leading investment in non billable time built an average client retention of 10.4 years. We talk about: 00:00 The bad day that earned Lee her nickname 01:30 Lee Caraher's forty year path into PR 06:41 Why her mother's illness led her to start Double Forte 09:46 What happened when six millennials quit in eight weeks 12:51 The chihuahua that started an office dog policy 18:00 Why every generation complains about the one after it 19:34 The four cultural forces shaping how millennials work 25:47 What Lee's communication wheel reveals about anger and assumptions 30:00 What pass along able means at Double Forte 35:50 Why leaders have to repeat their message more than once 39:19 What is the Chief Reminding Officer 40:04 Lee's favorite personality assessment and the advice she lives by Ready to stop guessing why your team missed the memo? Learn Lee's pass along able standard and the Chief Reminding Officer approach in Millennials and Management at https://leecaraher.com/, and if you want help building a team that communicates without the drama, connect with Katie at https://www.peoplefluence.com/newsletter-landing-pageipsahnqm. Resources: The Advantage by Patrick Lencioni https://link.amazon/B03ASjRy9 Traction by Gino Wickman https://link.amazon/B05is1aSk Connect with Lee: Website: https://leecaraher.com/Double Forte: https://double-forte.com/LinkedIn: https://www.linkedin.com/in/leecaraher/Books: https://leecaraher.com/books/ Connect with me Instagram:https://www.instagram.com/katie_armentroutYouTube: https://www.youtube.com/@katiearmentroutLinkedIn:https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletterWebsite: http://www.peoplefluence.com #MillennialWhisperer #ManagingMillennials #GenerationalLeadership #WorkplaceCommunication #LeadershipDevelopment #PRLeadership #CorporateCulture #EmployeeRetention #TeamCulture #LeadershipPodcast #SmallBusinessOwner #PeopleManagement #ExecutiveLeadership #ThinkOutsideTheBoss #DoubleForte #GenZAtWork #WorkplaceCulture #FounderLife #CommunicationSkills #HighPerformingTeams

  5. Sep 16

    030: We Grew 5X in 5 Years, Then Everything Broke | Rhiannon Hoeweler, CEO of MadTree Brewing

    Leading a founder-led business means stepping into someone else's vision, culture, and team, and finding a way to move all of it forward without breaking what made it work in the first place. If you have ever taken over a team, a department, or an entire company you did not build, you already know how delicate that balance is. Rhiannon Hoeweler knows it better than most. She became the first ever non-founder CEO of MadTree Brewing in Cincinnati, stepping in while the two original founders stayed on, and has since led the company from one location and 80 employees to four locations and more than 400. Katie Armentrout, founder of Peoplefluence and a Certified Working Genius Facilitator, talks with Rhiannon about what actually breaks when a company grows that fast, why three different service models across MadTree's locations turned into a payroll nightmare, and how MadTree became a B Corp and a 1% for the Planet member along the way, work recently recognized at Climate Week in New York City. Rhiannon also opens up about the workaholism her body keeps forcing her to confront, and the two career accomplishments, Zoo Access for All and MadTree's ReLeaf tree planting program, she is proudest of. If you are leading a team, a company, or a culture you did not build, this conversation will change how you think about trust. In this episode, you’ll discover: Why leading a founder-led business means earning trust from a team, and from the founders themselves, before you have built any of it yourself.What actually breaks inside a company when headcount jumps from eighty to over four hundred employees in just five years.Why three different service models across MadTree's four locations created hidden payroll and HR headaches nobody saw coming until the company had already scaled.How leaning on her two core strengths, relationship building and trust, lets Rhiannon lead well without knowing every detail of the business.Why MadTree became a B Corp and a 1% for the Planet member, and what that commitment looks like in daily operations.What Rhiannon is doing to break a workaholism pattern her body kept forcing her to confront, including a daily walk and gratitude writing.Why Zoo Access for All and MadTree ReLeaf are the two accomplishments Rhiannon is proudest of, and what they say about who gets invited to the table. We talk about: 00:00 What happens when a company gets the growth it dreamed of 01:00 When Rhiannon first realized she was a leader 03:00 Stepping into a founder-led business she did not build 05:00 What makes MadTree Brewing different in a saturated market 07:00 How MadTree grew from just beer into food and hospitality 09:00 When the founders' vision shifted beyond beer alone 11:00 Building toward zero waste and earning B Corp certification 13:00 What actually broke as MadTree scaled from 80 to 400 employees 15:00 The service model differences that complicated payroll behind the scenes 18:00 Why leaders should lean into their own strengths instead of everything 27:00 The career accomplishments Rhiannon is proudest of 34:00 Lightning round: DISC profile, favorite podcast, best advice, and walk-on song Resources: Acquired Podcast: https://www.acquired.fm/ Connect with Rhiannon: Website: https://madtree.com/ Facebook: https://www.facebook.com/MadTree/Instagram: https://www.instagram.com/madtreebrewing/ X: https://x.com/madtreebrewing LinkedIn: https://www.linkedin.com/in/rhiannon-hoeweler-4bb29a44/ Connect with me Instagram:https://www.instagram.com/katie_armentroutYouTube: https://www.youtube.com/@katiearmentroutLinkedIn:https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletterWebsite: http://www.peoplefluence.com #FounderLedBusiness #NonFounderCEO #LeadershipDevelopment #CompanyCulture #ScalingABusiness #SmallBusinessOwner #WomenInLeadership #CraftBreweryLife #BCorpBusiness #SustainableBusiness #WorkLifeBalance #BusinessGrowth #TeamCulture #TrustInLeadership #EntrepreneurMindset #ExecutiveLeadership #CincinnatiBusiness #MadTreeBrewing #ThinkOutsideTheBoss

  6. Sep 9

    029: What It's Really Like to Work With Your Spouse | Judson and Katie Armentrout

    Married entrepreneurs face a kind of pressure no corporate career ever prepares you for: building a company from nothing with the same person you raise kids with, split a mortgage with, and come home to every night. If you have ever dreamed about starting your own thing, or wondered what happens at home when both spouses walk away from steady paychecks at once, this conversation is for you. Katie Armentrout sits down with her husband, Judson Armentrout, for a rare look at what it is really like to be married co-founders, two people who each left stable corporate careers within two years of each other to build their own businesses from scratch, with three kids, a dog, and a mortgage riding on it. Katie Armentrout, founder of Peoplefluence and a Certified Working Genius Facilitator, and Judson Armentrout, founder of Building Block Solutions and co-founder of Barebones Solutions, talk through what changed when they traded a $1.5 billion Kroger supply chain and a Procter & Gamble career for entrepreneurship, and why Judson's risk tolerance runs higher than most. You will hear how the Working Genius framework shapes how they lead their teams and their kids, how Judson grew their sons' Cub Scout pack from 36 kids to more than 100, and what extreme ownership looked like the day he nearly got fired at Kroger. If you are weighing whether to bet on yourself, listen before you leap. In this episode, you’ll discover: Why the stress of building a company from scratch with your spouse is completely different than working together in an established family business.How Judson learned to lead through influence alone, with zero direct reports, during his first years at a beef processing plant.What it actually looks like day to day when two spouses each walk away from corporate paychecks within two years of one another.Why Judson's risk tolerance is higher than most people's, and how growing up watching his parents run their own businesses shaped that.How the Armentrouts use small family rituals, like a cake pop for every new client, to keep morale up during the hard seasons of entrepreneurship.What Judson learned about leadership, infrastructure, and asking for help while growing a Cub Scout pack from 36 kids to more than 100.Why Judson took full ownership of a quality failure at Kroger instead of letting his team take the blame, and what that taught him about extreme ownership. We talk about: 00:00 The real difference between family business stress and startup stress 00:35 Why this episode is for anyone who has ever wanted to start their own company 04:00 When did Judson first realize he was a leader 05:43 Learning to lead through influence with no direct reports at a beef plant 09:00 How Katie and Judson met in their MBA program at UNC Chapel Hill 14:14 Growing up in an entrepreneurial family and where his risk tolerance comes from 20:38 What is it really like to work with your spouse inside a startup 25:09 How the Armentrouts celebrate wins as a family with cake pops 29:04 What they hope their kids take away from a dual entrepreneurship household 35:40 How leading a Cub Scout pack of 100 kids made Judson a better leader 44:00 Judson's favorite personality assessment and why Working Genius fits him 47:12 The failure Judson cherishes most and what it taught him about extreme ownership Resources: Wisdom of the Bullfrog by Admiral William McRavenExtreme Ownership by Jocko Willink Connect with Judson: Website: https://buildingblock.solutions/ LinkedIn: https://www.linkedin.com/in/judsonarmentrout/ Connect with me Instagram:https://www.instagram.com/katie_armentroutYouTube: https://www.youtube.com/@katiearmentroutLinkedIn:https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletterWebsite: http://www.peoplefluence.com #MarriedEntrepreneurs #CouplesInBusiness #WorkingWithYourSpouse #CorporateToEntrepreneur #SmallBusinessOwner #FamilyBusiness #WorkingGenius #ExtremeOwnership #LeadershipDevelopment #EntrepreneurLife #BusinessPartners #RiskTolerance #SupplyChainLeadership #ParentingEntrepreneurs #StartupLife #WomenInLeadership #HusbandAndWifeBusiness #ThinkOutsideTheBoss

  7. Sep 2

    028: Why This Nonprofit Refuses to Give Anything Away | Joel Bokelman

    An upside-down org chart is a leadership model where power flows down to the front line instead of up to the top, and it is exactly what took Joel Bokelman thirteen years to build inside Changing Gears, a Cincinnati nonprofit that treats vehicle ownership as an anti-poverty tool. If you lead a mission-driven team, you already know the tension: you care about people and about profit, and no one ever taught you how to hold both at once. Servant leadership, distributed accountability, and an upside-down pyramid are not just nonprofit buzzwords here, they are the operating model behind 386 affordable cars sold, 76 trained technicians, and a growing affiliate network reaching new cities. Katie Armentrout, founder of Peoplefluence and a Certified Working Genius Facilitator, sits down with Joel Bokelman, co-founder of Changing Gears, to unpack how a Habitat for Humanity idea for cars turned into a scaling, mission-driven organization built alongside partner CityLink Center. You will hear exactly how Joel and his team used the Entrepreneurial Operating System, EOS, to fix an accountability gap a DISC assessment exposed, and why he still calls a single passive mistake one of his most important leadership lessons. If your team needs more trust and less top-down control, this conversation gives you a real, thirteen-year-tested place to start. In this episode, you’ll discover:An upside-down org chart puts your front-line team first, with leadership existing to remove barriers and support the people closest to the work, not the other way around.Joel Bokelman explains how a Habitat for Humanity idea for houses became Changing Gears, a nonprofit that has sold 386 affordable cars to families working out of poverty.A DISC assessment revealed a dangerous accountability gap on Joel's leadership team, and adopting EOS, the Entrepreneurial Operating System, is what finally closed it.Being mission-driven does not mean ignoring profit. Learn how Changing Gears funds most of its own programs through vehicle sales rather than relying on donations alone.Joel shares why a passive mistake did more long-term damage to his organization than any aggressive one, and what that taught him about decisive leadership.Hear how celebrating small wins, like handing a client the title to a paid-off car, keeps a mission-driven team from burning out on its own mission.Joel walks through how servant leadership, modeled by his father-in-law, became the upside-down pyramid that now shapes every hire and decision at Changing Gears. We talk about: 00:00 Why a car is an anti poverty tool 02:16 When Joel first realized he was a leader 04:14 How Marnie's rainy day moment started Changing Gears 07:49 What CityLink Center actually does for clients 11:23 Where Joel learned servant leadership from his father in law 12:37 What an upside down org chart really means 13:38 The DISC assessment that exposed a leadership blind spot 16:08 The vision to expand Changing Gears into new cities 27:45 A day in the life of a Changing Gears client 34:25 Building a culture people do not want to leave 37:35 Lightning round, books, advice, and a walk on song 42:51 How to donate a car or support Changing Gears Resources: CityLink Center: https://www.citylinkcenter.org/ Myth of a Christian Nation by Greg Boyd https://amzn.to/4glQvbY Connect with Joel: Website: https://changing-gears.org/ LinkedIn: https://www.linkedin.com/in/joel-bokelman-b165363a/ Instagram: https://www.instagram.com/changing_gears/Facebook: https://www.facebook.com/CG.org Company LinkedIn: https://www.linkedin.com/company/changinggears/ Connect with me Instagram:https://www.instagram.com/katie_armentroutYouTube: https://www.youtube.com/@katiearmentroutLinkedIn:https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletterWebsite: http://www.peoplefluence.com #ServantLeadership #NonprofitLeadership #MissionDrivenLeadership #UpsideDownOrgChart #TeamCulture #LeadershipDevelopment #SmallBusinessLeadership #EOS #EntrepreneurialOperatingSystem #NonprofitManagement #SocialEnterprise #TransportationEquity #CincinnatiNonprofit #WorkingGenius #BusinessOwnerLife #ExecutiveCoaching #FaithDrivenLeadership #ChangingGears #ThinkOutsideTheBoss

  8. Aug 26

    027: You Are Not As Connected As You Think | Chad Littlefield

    Connection before content is the philosophy Chad Littlefield uses to explain why so many meetings, trainings, and offsites fall flat before they even start. If you have ever watched a room cross its arms the second you started talking, connection before content is the reason. Teams that skip it end up with feedback that never gets delivered, meetings nobody wants to attend, and trust that never actually builds. Katie Armentrout, founder of Peoplefluence and host of Think Outside the Boss, sits down with Chad Littlefield, M.Ed., co-founder and Chief Experience Officer of We and Me and creator of the We! Connect Cards, to unpack what actually builds trust on a team. Chad shares his professional arms uncrosser approach, walks through the difference between performance-based trust and vulnerability-based trust, and explains why a former surgeon general compared disconnection at work to smoking a pack of cigarettes a day. Katie adds her own culture of feedback quadrant, mapping what happens when a team has empathy without accountability, or accountability without empathy. If you lead people, run meetings, or just want your team to actually talk to each other, this conversation hands you language and tools you can use this week. In this episode, you’ll discover: Connection before content explains why teams disengage the moment a meeting starts with information instead of people, and how leaders can reverse that pattern in under a minute. The professional arms uncrosser approach shows you how to open a room, a training, or a hard conversation so people stop defending themselves and start participating. Performance-based trust and vulnerability-based trust are the two types of trust every team needs, and Chad Littlefield breaks down what happens when a team only has one. Katie Armentrout's culture of feedback quadrant maps four team cultures, from a culture of comfort to a culture of isolation, based on how much empathy and accountability a leader brings. We! Connect Cards were built to spark meaningful conversations in under two minutes, and Chad explains the one question that works even with a room full of skeptics. What you tolerate is what you endorse is the leadership principle Chad uses to explain why ignoring a struggling team member is never actually a neutral choice. Chad Littlefield explains why expertise without empathy reads as rude to a room, and what to do instead before you ever open a slide deck. We talk about: 00:00 Chad's opening line on why connection matters 00:14 Katie introduces Chad Littlefield and We! Connect Cards 04:01 When did Chad first realize he was a leader 08:21 What made Chad obsessed with human connection 10:54 What is a professional arms uncrosser 12:48 Why connection has to come before content 21:57 Performance-based trust versus vulnerability-based trust explained 24:31 Katie's culture of feedback quadrant breakdown 30:25 Why what you tolerate is what you endorse 35:33 Lightning round 44:13 Where to find Chad and the Connectors Summit Resources: Made to Stick by Chip and Dan Heath: https://amzn.to/4qi1JkT The Best Advice So Far by Eric Tyler: https://amzn.to/3TSZY1G Hell Yeah or No by Derek Sivers: https://amzn.to/3RQvQ6x Connect with Chad: Website: https://weand.me/ We! Connect Cards: https://weand.me/store/ Free connection tools: https://weand.me/free/ YouTube: https://www.youtube.com/@chad.littlefieldLinkedIn: https://www.linkedin.com/in/chadlittlefield/ Connect with me Instagram:https://www.instagram.com/katie_armentroutYouTube: https://www.youtube.com/@katiearmentroutLinkedIn:https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletterWebsite: http://www.peoplefluence.com #ThinkOutsideTheBoss #ChadLittlefield #WeConnectCards #ConnectionBeforeContent #WorkplaceConnection #BuildingTrustAtWork #PsychologicalSafety #LeadershipPodcast #TeamCulture #TrustAtWork #EmployeeEngagement #FacilitationSkills #LeadershipDevelopment #CultureOfFeedback #ProfessionalArmsUncrosser #AskPowerfulQuestions #ConnectorsSummit #KatieArmentrout #ExecutiveLeadership #WorkplaceCulture

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16 Ratings

About

Leadership would be easy if it weren’t for the people. Think Outside the Boss is a leadership podcast for business owners, founders, and people leaders who are tired of managing team drama and ready to lead differently, more human, more effective, and with a lot less exhaustion. Hosted by Katie Armentrout, a recovering corporate leader turned entrepreneur, this show challenges traditional leadership development and replaces it with something far more useful. Clear thinking. Better conversations. And one practical action you can try right away. Through honest solo episodes and real conversations with experienced leaders, Think Outside the Boss explores proven leadership frameworks, innovative ideas, and people-first tools you can actually use. No theory for theory’s sake. No performative leadership nonsense. You’ll learn how to: - Strengthen trust and accountability without micromanaging - Navigate team conflict and communication breakdowns - Build a culture where employees feel valued and customers stay loyal - Lead people with clarity instead of control There’s no silver bullet when it comes to people. But there are better ways to think, choose, and lead. No corporate lingo bingo. No meeting after the meeting. If leadership has started to feel heavier than it should, this podcast is your invitation to Think Outside the Boss. 🎧 New episodes weekly: https://www.peoplefluence.com/podcast

Information

  • Creator
    Katie Armentrout
  • Years Active
    2026
  • Episodes
    35
  • Rating
    Clean
  • Copyright
    © 2026 Katie Armentrout
  • Show Website
    Think Outside the Boss

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