Think Outside the Boss

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

Think Outside the Boss is a business podcast hosted by Unknown Host, with 0 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Think Outside the Boss, a business show with 0 episodes published.

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  Episode #26

  026: Her Acupuncturist Told Her to Stop or Die | Jackie Bondanza

  Aug 19, 202637 min

  How to scale a business without burning out starts with knowing the difference between grit that builds a company and grit that destroys the person building it. If you are the founder who cannot do anything in moderation, who runs until you almost break, this episode names exactly what that costs and what it takes to catch it before your body forces you to stop. Katie Armentrout, founder of Peoplefluence and host of Think Outside the Boss, talks with Jackie Bondanza, founder of Hounds Town USA, who took the pet care franchise from one location to 103 across the country and now works with founders on the systems that let them step back. Jackie explains why she implemented EOS, the Entrepreneurial Operating System, in 2021, what it took to move from the visionary seat to the integrator seat and back again, and the moment her acupuncturist told her point blank that her body was going to shut down if she did not stop. She also shares the advice from a former boss that changed how she owns her mistakes, and the failure during COVID that taught her more than any MBA could. If you have built something you cannot imagine walking away from, this conversation will show you how to keep building it without losing yourself. In this episode, you’ll discover: Why Jackie Bondanza says she cannot do anything in moderation, and how that same intensity that built Hounds Town USA almost broke her. What it actually took to grow a doggie daycare franchise from one location to 103 across the country in thirteen years, without a business background. How implementing EOS, the Entrepreneurial Operating System, in 2021 changed the way Hounds Town runs, and why it took hiring an outside implementer to make it stick. The moment Jackie's acupuncturist told her point blank that her body was going to shut down if she did not stop, and what she did next. Why moving from the visionary seat to the integrator seat and back again taught Jackie more about herself than any MBA program could. The advice from a former boss about owning your mistakes that Jackie still uses to lead through hard conversations today. Why Jackie now does hands-on consulting and fractional integrator work for founders trying to scale from 10 or 20 units toward 100. We talk about: 00:00 Meet Jackie Bondanza and her path from book editing to Hounds Town 01:17 When did Jackie first realize she was a leader 03:07 What her young employees needed that no training manual could teach 09:00 The train ride where she first envisioned 100 stores 12:26 The hardest phase of growth from 12 stores to 18 during COVID 15:12 Why she brought in EOS and what it took to implement it 17:23 Moving from integrator to visionary and what that shift taught her 29:40 The consulting work she started after stepping into the owner's box 30:09 Does an old dog really change, and what that taught her about leadership 36:14 What advice she gives founders chasing their own 100 unit milestone 38:44 Lightning round: DiSC, a favorite book, and best advice ever given 40:00 A failure she cherishes and the walk on song that hypes her up Resources: A Tree Grows in Brooklyn https://amzn.to/4bqgKew Connect with Jackie: LinkedIn: https://www.linkedin.com/in/jackie-bondanza-36ba783/ Instagram: https://www.instagram.com/houndstownusa/ YouTube: https://www.youtube.com/@houndstownusa424 Website: https://linktr.ee/houndstown Connect with me Instagram: https://www.instagram.com/katie_armentrout YouTube: https://www.youtube.com/@katiearmentrout LinkedIn: https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletter Website: http://www.peoplefluence.com #franchiseowner #foundermindset #founderburnout #entrepreneurialoperatingsystem #EOStraction #visionaryintegrator #scalingabusiness #franchisegrowth #smallbusinessowner #petcarefranchise #leadershipdevelopment #selfawareness #businessconsulting #womeninbusiness #executivecoaching #businessowners #thinkoutsidetheboss

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  Episode #25

  025: You Have to Disappoint People to Lead Them | Haider Ala Hamoudi

  Aug 12, 202635 min

  Difficult conversations as a leader are the ones nobody else can have for you. You can delegate almost everything, the budget, the calendar, even the hiring, but not the moment you have to tell someone their work is not working. If you find yourself softening bad news, avoiding accountability talks, or feeling guilty for disappointing your own team, you are not alone, and there is a real reason it feels this hard. Left unaddressed, that avoidance quietly costs teams trust, slows decisions, and turns small problems into resignations. Katie Armentrout, founder of Peoplefluence and host of Think Outside the Boss, sits down with Haider Ala Hamoudi, dean of the University of Cincinnati's Donald P. Klekamp College of Law and the first Muslim dean of a law school in the United States. Haider shares what the DISC assessment revealed about his own people pleasing pattern, why he still returns to Brene Brown's idea of daring greatly, and the specific line he uses instead of softening bad news to a direct report. He also opens up about growing his law school's applications by 50 percent, reaching some of the top bar passage rates in Ohio, and landing the largest naming gift in the school's history, all without losing his team's trust. If you lead people and hate disappointing them, this conversation will change how you think about that discomfort. In this episode, you’ll discover: Why the willingness to disappoint people, not avoiding conflict altogether, is the leadership skill Haider Ala Hamoudi says took him the longest to build. How the DISC personality assessment revealed a people pleasing pattern in Haider, and the specific script he now uses to say no without losing trust. What courageous leadership looks like in practice, drawing on Brene Brown's idea of daring greatly, and why vulnerability is part of that courage. How Haider grew University of Cincinnati College of Law applications by 50 percent and landed the largest naming gift in the school's history. Why being named America's first Muslim dean of a law school adds pressure that has nothing to do with the job itself. How Haider separates conflict as a transactional lawyer from conflict as a dean managing his own team day to day. Why loneliness at the top is real, and how Haider finds ways to communicate honestly without a peer to vent to daily. We talk about: 00:00 Meet Dean Haider Ala Hamoudi and his path to leadership 00:56 The two week Harvard program that first taught him about leadership 02:04 One leadership lesson that has stuck with him the most 04:30 How Haider leads differently through difficult conversations 06:58 Does conflict feel different for a lawyer than for a dean 11:23 Being named America's first Muslim law school dean 16:29 Why Haider chose law over medicine growing up 19:18 The move from civil rights law to Islamic finance 22:04 What surprised him about leaving law practice for academia 23:40 Why leadership can feel lonely even with a team around you 30:34 Turning around a law school's budget and reputation 35:41 Lightning round: DISC, books, and his walk on song Resources: Way of the Peaceful Warrior https://amzn.to/3RAhqHw Connect with Haider Ala Hamoudi: LinkedIn: https://www.linkedin.com/in/haider-ala-hamoudi-1b96311b/ Instagram: https://www.instagram.com/cincylawdean/ University of Cincinnati College of Law: https://www.law.uc.edu/faculty/directory/DeanHaiderAlaHamoudi.html Connect with me Instagram: https://www.instagram.com/katie_armentrout YouTube: https://www.youtube.com/@katiearmentrout LinkedIn: https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletter Website: http://www.peoplefluence.com #leadershipdevelopment #courageousleadership #difficultconversations #peoplepleasing #teamtrust #executiveleadership #leadershipskills #accountability #daringleadership #firstgenleader #lawschoolleadership #DISCassessment #leadershipcoaching #conflictresolution #civildiscourse #businessowners #thinkoutsidetheboss

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  Episode #22

  022: 70% of New Customers Quit Before Day 100 | Joey Coleman

  Jul 22, 202654 min

  The first 100 days methodology is the reason some businesses keep customers for years while others watch them disappear before the ink is dry. If you have ever wondered why a promising new hire quit within months, or why a happy sounding customer never came back, the first 100 days are where the answer lives. Research shows that 20 to 70% of new customers, and a strikingly similar share of new hires, never make it past this window, and most leaders have no idea it is happening. Katie Armentrout, founder of Peoplefluence and a leadership consultant for executive teams, sits down with Joey Coleman, the two time Wall Street Journal bestselling author of Never Lose a Customer Again and Never Lose an Employee Again. Joey walks through the real numbers behind customer and employee churn, from banking at 32% to auto mechanics at 68%, and explains what changes once a relationship survives day 100. You will walk away with a new lens for your own onboarding, whether you are welcoming a customer or a new hire. In this episode, you’ll discover: Why the first 100 days methodology matters: 20 to 70% of new customers quit before their 100 day anniversary, and the numbers on the employee side are nearly identical. Why 40% of new hires never make it to their one year anniversary, and why more than half of those departures happen inside the first 100 days. Why a net neutral customer experience is actually a negative experience, and what that means for how you design onboarding today. How Joey Coleman built his customer experience career through unlikely stops at the Secret Service, the White House, and the CIA. Joey's practical test for spotting broken customer experience: if your team ever says "it's our policy," you are telling customers not to come back. Why customers who reach day 101 feeling valued and appreciated typically stay for a minimum of five years. Why the persistence that makes a 13 year old exhausting to parent is the same trait that makes them successful at 30. We talk about: 00:00 Joey's advice for people who ask to pick his brain 01:15 Welcome and Joey Coleman's introduction 01:35 When did Joey first realize he was a leader, not a boss? 04:29 Growing up as the oldest of seven and learning persuasion 08:07 From the Secret Service and White House to customer experience 13:00 What draws someone to customer experience over sales 14:59 The professor who changed his career path 27:52 How Joey met his wife at a coworking space 34:57 Why do 20 to 70% of new customers quit before day 100? 39:00 The real cost of a bad onboarding experience for employees 43:35 Lightning round: books, love languages, and hype songs Resources: The Five Love Languages by Gary Chapman https://amzn.to/4vAR4Ty Pattern Recognition by William Gibson https://amzn.to/4f8Ns6o Never Lose a Customer Again by Joey Coleman https://amzn.to/45dSmcc Connect with Joey LinkedIn: https://www.linkedin.com/in/joeycoleman1/ Website: https://joeycoleman.com/ Connect with me Instagram: https://www.instagram.com/katie_armentrout YouTube: https://www.youtube.com/@katiearmentrout LinkedIn: https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletter Website: http://www.peoplefluence.com #First100Days #CustomerRetention #EmployeeRetention #CustomerExperience #EmployeeExperience #NeverLoseACustomerAgain #NeverLoseAnEmployeeAgain #LeadershipDevelopment #EmployeeOnboarding #CustomerOnboarding #JoeyColeman #ThinkOutsideTheBoss #KatieArmentrout #Peoplefluence #LeadershipPodcast #BusinessLeadership #EmployeeTurnover #CustomerChurn #ExecutiveLeadership #TeamCulture

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  Episode #21

  021: Are You Retiring 10 Years Too Early? | Derek Coburn

  Jul 15, 202647 min

  Retirement planning for entrepreneurs usually starts with the wrong question: how much do you need to save by 65? If you've been telling yourself you'll finally rest, travel, and enjoy life once you hit that number, this conversation is going to challenge your timeline. Katie Armentrout, founder of Peoplefluence, sits down with Derek Coburn, a financial advisor with 27 years in the industry and USA Today bestselling author of Let's Retire Retirement, to break down why the traditional retirement model is failing so many business owners. Derek walks through his Tale of Two Tonys math, showing how pushing retirement back five to ten years can cut your required monthly savings by up to 96 percent, then shares how he built a business and parenting rhythm around presence instead of postponement. If you're building something now and still waiting for someday to start living fully, this episode hands you the numbers and the mindset to start today. In this episode, you’ll discover: Why the traditional retirement math almost always overestimates how much you actually need, and how shifting your target retirement age by just five to ten years changes the entire equation. How Derek's Tale of Two Tonys breaks down the real dollar difference between retiring at 65 versus 70 or 75, using one client's actual numbers. Why financial advisors are financially incentivized to keep you saving and working longer, and the one question you should be asking about your own plan. How to build a business and a life around presence instead of postponement, including the exact schedule Derek uses to be done working by three o'clock. Why finding a job you don't hate can beat chasing a job you love, and what that reframe means if you're a burned out business owner right now. How Derek uses intentional car rides and a recurring family Q&A to build real connection with his teenage sons before they leave for college. Why the skills, relationships, and income you build in your 40s and 50s make it easier, not harder, to earn money later in life. We talk about: 00:00 Why the traditional retirement model is failing you 00:50 When Derek first realized he was a leader 04:00 The book passage that sparked this conversation 05:23 The Tale of Two Tonys retirement math explained 07:21 Why Derek cut his client base by 75 percent 09:00 What happens if every advisor adopted this approach 13:05 What do you say to someone who says they can't do this 18:41 The moment that changed Derek's relationship with time 19:32 How to teach your kids a healthy money mindset 26:32 What if you're already in your 60s with regret 34:37 How to prepare for a 30 minute car ride with your kid 41:59 Derek's favorite personality test and walkout song Resources: The 7 Habits of Highly Effective People https://amzn.to/4wvrOii Networking Is Not Working by Derek Coburn https://amzn.to/3R2iUK4 Connect with Derek LinkedIn: https://www.linkedin.com/in/derekcoburn/ CADRE: https://www.cadredc.com/ Website: https://www.derekcoburn.com/ Connect with me Instagram: https://www.instagram.com/katie_armentrout YouTube: https://www.youtube.com/@katiearmentrout LinkedIn: https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletter Website: http://www.peoplefluence.com #RetirementPlanning #FinancialFreedom #RetireLater #FinancialAdvisor #EntrepreneurLife #BusinessOwnerLife #WorkLifeBalance #IntentionalLiving #ParentingTips #MoneyMindset #WealthBuilding #Unretirement #DelayedRetirement #PresentOverPerfect #LeadershipPodcast #BusinessOwners #FinancialIndependence #ThinkOutsideTheBoss

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  Episode #20

  020: Are You Building Culture Or Just Enforcing Rules | Katie Armentrout

  Jul 8, 202624 min

  A hybrid work policy for leaders is not really about where your team sits, it's about the culture you are willing to build and defend. If you are stuck debating remote versus in-office, you are asking the wrong question. This episode reframes hybrid work, return to office, and remote work policy around one thing: intention. Katie Armentrout, founder of Peoplefluence, spent 20 years in corporate leadership before building her practice around helping executive teams cut through conflict and drama. In this episode, she breaks down how Dropbox, Microsoft, and Goldman Sachs each built radically different work policies that work, and why the difference wasn't remote versus in-office, it was clarity versus arbitrary rules. You will walk away with three leadership principles you can apply before you write another policy. In this episode, you’ll discover: Why forcing a hybrid work policy from the top down without a clear culture behind it creates arbitrary rules that erode trust and drive turnover. How Dropbox's Virtual First model produced a threefold increase in job applicants, 15 percent faster time to hire, and a 16 percent increase in diverse candidates. Why Microsoft stopped counting office days and started designing specific office moments for kickoffs, creative sessions, and complex problem solving instead. How Goldman Sachs justifies its five day in office mandate through an apprenticeship model, and what CEO David Solomon says is actually driving that decision. The three leadership principles to apply before setting any policy: people follow the culture you build, design for the experience not the expectation, and leaders are the policy. Why the hybrid versus remote debate really only applies to knowledge workers, and what that means if you lead a team in healthcare, retail, or manufacturing. The gut check questions to ask your own team about where your culture actually stands today versus where you want it to be. We talk about: 00:00 Why your hybrid work policy might be the wrong question 00:38 The viral Instagram clip that sparked this episode 03:05 Three leadership principles before you set a policy 07:19 Dropbox's Virtual First case study 13:26 Microsoft's office moments, not mandates 22:00 Goldman Sachs and the five day apprenticeship model 27:19 Is remote work really only a knowledge worker debate? 27:55 Gut check, where are you on the continuum? 30:21 The three principles recap for leaders 31:17 How to reframe the hybrid work conversation for good Resources: Dropbox Blog Post: https://blog.dropbox.com/topics/company/Virtual-First-2025-Designing-a-culture-that-drives-impact Connect with me Instagram: https://www.instagram.com/katie_armentrout YouTube: https://www.youtube.com/@katiearmentrout LinkedIn: https://www.linkedin.com/in/katiearmentrout Newsletter: http://www.peoplefluence.com/newsletter Website: http://www.peoplefluence.com #HybridWork #ReturnToOffice #WorkplaceCulture #Leadership #ExecutiveLeadership #PeopleManagement #CultureBuilding #RemoteWork #LeadershipDevelopment #EmployeeRetention #WorkplaceTrust #TeamCulture #CEOLife #HRLeadership #ModernLeadership #BusinessCulture #ThinkOutsideTheBoss

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