Think Outside the Boss

012: She Saved a Client $30K in 5 Minutes. Here's the Question She Asked | Kendra Ramirez

51 min · 13. maj 2026
episode 012: She Saved a Client $30K in 5 Minutes. Here's the Question She Asked | Kendra Ramirez cover

Beskrivelse

Most business leaders aren't behind on AI because they lack access. They're behind because no one told them they already have it and no one gave them permission to use it. In this episode of Think Outside the Boss, Katie Armentrout sits down with Kendra Ramirez, CEO of KR Digital, Claude Ambassador, and one of the most trusted AI voices in the B2B space, to cut through the noise, the overwhelm, and every excuse keeping leaders on the sidelines of the AI era. Kendra has been building AI since 2018. She's delivered hundreds of sessions, consulted organizations of every size, and once saved a client $30,000 in five minutes by asking five questions no one else thought to ask. This is not a conversation about AI being the future. It's a conversation about why it's already here and what to actually do about it today. From auditing your current tech stack, to why Claude outperforms ChatGPT for voice-driven content, to the data security questions your team is afraid to bring to leadership, Kendra makes AI feel less like a threat and more like the smartest colleague you've never properly introduced yourself to. If you lead a team, run a business, or have been quietly waiting for someone to tell you it's safe to move, this episode is that moment. In this episode, you’ll discover: * Why most businesses are already sitting on AI they've paid for and never activated * The five questions that saved one client $30,000 before they signed a single contract * Why Claude outperforms ChatGPT for human-sounding content and how to switch without starting over * What AI Skills are and why they permanently solve the "re-explaining yourself" problem * The non-negotiable data security rules every leader needs to understand before putting anything into AI * Why free AI tools are more expensive than you realize * How Kendra built a globally read AI newsletter that generates revenue without ever pushing it * The mindset shift from waiting for organizational permission to leading your team into the AI era * Why human-centered AI implementation outperforms technology-centered every single time * How to use your personality assessments inside AI for stronger leadership and team communication We talk about: * 00:00 The real reason your team is waiting on AI and why it starts with you * 04:00 Kendra's early leadership instincts and what it means to "manage up" the right way * 08:00 Why silencing the person who always asks "why" is a red flag, not a relief * 12:00 From technical recruiter to digital pioneer: building a business before anyone believed in it * 16:00 How to trust your gut when every coach in the room says you're wrong * 20:00 Limiting beliefs don't just live in you, they live in everyone giving you feedback * 24:00 Where to start with AI when you genuinely don't know what you don't know * 28:00 The $30K wake-up call: audit your tech stack before you buy anything new * 32:00 Claude vs. ChatGPT: what's actually different and whether you should switch * 36:00 What AI Skills are and how they eliminate the re-explaining problem for good * 40:00 AI data security: what's actually safe to put in, and what never should be * 44:00 How Kendra runs AI enablement from the C-suite to the front line * 48:00 Why human connection is the highest-leverage business strategy of 2026 * 52:00 Lightning round: personality assessments, faith, $10K lessons, and walking out to Alicia Keys Connect with Kendra * LinkedIn: https://www.linkedin.com/in/kendraramirez/ [https://www.linkedin.com/in/kendraramirez/] * Website: https://kendraramirez.com/ [https://kendraramirez.com/] * Newsletter: https://kendratech.substack.com/ [https://kendratech.substack.com/] * Get Out of Your Head by Jennie Allen https://amzn.to/4mWXp9j [https://amzn.to/4mWXp9j] Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #AIforBusiness #Leadership #Entrepreneurship

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Alle episoder

16 episoder

episode 015: The Workforce Blind Spot Costing Companies Billions | Teresa Tanner cover

015: The Workforce Blind Spot Costing Companies Billions | Teresa Tanner

What if the talent problem isn't hiring, it's what happens after great people walk out the door? In this episode of Think Outside the Boss, Katie sits down with Teresa Tanner, former Chief Administrative Officer at Fifth Third Bank and founder of Reserve Squad, a company helping organizations build alumni talent communities so former employees can return for project-based work. Teresa spent 18 years at McDonald's Corporation and rose through the C-suite before leaving to solve a workforce problem she kept seeing over and over: companies watching incredible talent walk out the door with no plan to bring them back. Less than 10% of women who pause their careers ever return to the company they left. Most organizations assume that's just how it goes. Teresa built an entirely new business model to prove it doesn't have to be. This conversation goes deep on what it actually costs to lose a star employee, why the all-or-nothing structure of most jobs doesn't serve today's workforce, and what leaders can do right now to stop the bleed. But it's also a deeply personal episode – about insecurity, big mistakes, mentorship, leading as a woman in a man's world, and what it means to find your voice. If you've ever lost someone great and wished there was a better way, or if you're the person who left and never went back, this episode is for you. IN THIS EPISODE, YOU’LL DISCOVER: * Why less than 10% of women who leave a company ever return to it * What companies get wrong about retirees and stay-at-home parents * How Reserve Squad's alumni talent model works and why it's changing workforce strategy * What exit interviews kept revealing about identity, purpose, and the all-or-nothing trap * Why being afraid to be fired makes you a worse leader * How one boss's response to a ~$250K mistake became a masterclass in accountability * What it's really like to be the only woman in the room at the C-suite level * Why Teresa keeps the quote "don't be afraid to be fired" taped to her monitor * The advice that changed everything: hold your why tightly, stay open-handed about the how * What Teresa would go back and tell her eighth-grade self We talk about: * 00:00 The moment Teresa first realized she was a leader and why she lied about it * 03:00 From McDonald's to the C-suite: 18 years and what she learned * 05:00 The workforce problem Teresa kept seeing on the way out the door * 06:00 The stat that started it all: less than 10% of women go back * 08:00 How Reserve Squad works and why they become the employer of record * 09:00 The assumptions companies make about retirees and parents (and why they're wrong) * 12:00 Exit interviews, identity, and the all-or-nothing trap * 13:00 "We have to draw new boxes" and what the current talent structure is missing * 14:00 The inflection point: when Teresa started believing in her own potential * 16:00 The ~$250K mistake, the resignation letter, and the boss who refused to accept it * 19:00 What accountability without shame actually looks like in leadership * 21:00 Why she kept "don't be afraid to be fired" taped to her monitor * 22:00 What it was like to be the only woman in the room * 25:00 Finding your voice as a woman leader and passing that along * 26:00 Navigating motherhood and a C-suite career at the same time * 28:00 Lightning round: Enneagram, Egonomics, and Alicia Keys * 33:00 Where to find Teresa and Reserve Squad Resources: * Egonomics by David Marcum and Steven Smith https://amzn.to/43gYuj4 [https://amzn.to/43gYuj4] * Working Genius Assessment: http://www.workinggenius.comwww.workinggenius.com [http://www.workinggenius.com] * The Six Types of Working Genius: https://amzn.to/4fsKIkI [https://amzn.to/4fsKIkI] Connect with Teresa * LinkedIn: https://www.linkedin.com/in/teresa-tanner/ [https://www.linkedin.com/in/teresa-tanner/] * Website: https://reservesquad.com/ [https://reservesquad.com/] Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #AlumniTalent #LeadershipDevelopment #WomenInLeadership

3. juni 202634 min
episode 014: Why Smart Teams Still Fail (And the Tool That Fixes It) | Katie Armentrout cover

014: Why Smart Teams Still Fail (And the Tool That Fixes It) | Katie Armentrout

What if you're not burned out because you have too much to do, but because you're doing too much of the wrong work? In this solo episode of Think Outside the Boss, Katie Armentrout shares the personal story behind why she left corporate America and the two books by Pat Lencioni that finally gave her the language to understand it. What she couldn't name in that meeting with her VP, a personality assessment helped her explain years later. This episode is a deep dive into the Working Genius assessment, a productivity tool and personality framework that helps individuals and teams understand what types of work energize them, what drains them, and how to have better conversations because of it. Katie breaks down all six types of working genius, what it looks like when a team is missing one, and how a single team map helped one of her clients go from launching 22 products in a year to 8, with 10x revenue growth. Self-awareness is the most important quality in any leader. Not communication. Not strategy. Not confidence. Self-awareness. And this episode gives you a practical tool to start building it today. If you've ever walked into your manager's office and said "I'm burned out, I'm frustrated, I'm unhappy" without knowing what to do next, this episode gives you the language you were missing. In this episode, you’ll discover: * Why burnout is usually about the type of work you're doing, not the amount * The six types of working genius and what each one means for your team * Why having smart, good people does not automatically create a healthy culture * How one team went from chaos to 10x revenue growth by finding their gap * Why self-awareness is the number one leadership quality (and how to practice it) * The difference between a personality assessment and a working genius team map * How to turn emotional conversations into solvable problems * What happens when a team skips the discernment phase (and how to fix it) * Why 80 to 85 percent of the benefit comes from taking assessments as a team, not solo * How to use a common language framework to reduce team drama and conflict We talk about: * 00:00 The moment that started it all: burnout, frustration, and not having the words * 03:00 Leaving corporate America and why Katie had no grand plan * 06:00 The conference that changed everything and Pat Lencioni's Five Dysfunctions of a Team * 08:00 How good people can still create a toxic culture (and what leaders miss) * 10:00 Introducing the Working Genius: the six phases of all work * 12:00 Why tenacity was draining Katie and what that reveals about burnout * 14:00 The conversation you could have had if your team knew working genius * 16:00 Real client case study: 22 products, missing discernment, and the team map that fixed it * 19:00 From launching 22 products to 8, and 10x revenue growth in one year * 21:00 Why 50% of your work should be in your genius zone (and what happens if it isn't) * 22:00 Self-awareness as the number one leadership quality and why most leaders miss it * 23:00 Why your team already knows your weaknesses even if you don't admit them * 24:00 How to claim your free Working Genius debrief with Katie Resources: * The Five Dysfunctions of a Team by Pat Lencioni: https://amzn.to/497rs8y [https://amzn.to/497rs8y] * The Six Types of Working Genius by Pat Lencioni: https://amzn.to/4dI8QOZ [https://amzn.to/4dI8QOZ] * Working Genius Assessment: http://www.workinggenius.comwww.workinggenius.com [http://www.workinggenius.com] * Reach out to Katie directly to receive your assessment code and a free debrief session. Email katie@peoplefluence.com and mention the podcast. Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #WorkingGenius #LeadershipDevelopment #TeamCulture

27. maj 202624 min
episode 013: You’re Growing Your Business… But Losing Control of Your Money | Jim Rasmussen cover

013: You’re Growing Your Business… But Losing Control of Your Money | Jim Rasmussen

What if the reason you’re not feeling wealthy… has nothing to do with how much money you make? In this episode of Think Outside the Boss, Katie Armentrout sits down with Jim Rasmussen, co-founder of Pando Wealth and former Chick-fil-A financial consultant, to unpack the truth most high performers avoid: making more money doesn’t automatically create a better life. After two decades helping business operators increase profit, Jim noticed a pattern. The income was growing, but the clarity wasn’t. Leaders were building businesses without building a financial plan, chasing growth without defining what it was actually for. This conversation flips the script on wealth, legacy, and leadership. From the emotional roots of money habits to the dangerous trap of comparison-driven investing, Jim shares what it really takes to move from reactive earning to intentional living. Because wealth isn’t just something you build. It’s something you steward, shape, and ultimately pass on. If you’ve been focused on growing your income but haven’t stopped to ask what it’s all for, this episode will change how you think about money, leadership, and the life you’re actually creating. In this episode, you’ll discover: * Why making more money without a plan leads to long-term dissatisfaction * The difference between a business plan and a financial life plan (and why most people only have one) * How comparison culture quietly drives bad financial decisions * The real reason high earners still feel financially insecure * Why “keeping up with the Joneses” destroys long-term wealth * The moment that changed Jim’s entire perspective on money and legacy * How to shift from reactive spending to intentional wealth building * The identity trap that keeps entrepreneurs stuck in financial stress * Why generosity is a core part of sustainable wealth, not an afterthought * The mindset shift that moves you from chasing money to leading your life with purpose We talk about: * 00:00 Why building wealth without a plan sets the next generation up to fail * 03:00 Growing up between scarcity and investing, and how it shaped Jim’s money mindset * 07:00 What Chick-fil-A operators taught him about income growth and financial confusion * 11:00 The wake-up call that shifted his focus from business profit to personal planning * 15:00 Why most leaders overspend as their income increases * 18:00 The leadership principle that drives culture, loyalty, and long-term success * 22:00 How comparison and social pressure lead to poor financial decisions * 26:00 Why entrepreneurs tie their identity to their business (and how to break it) * 30:00 The process of defining your personal vision for money and life * 34:00 How Pando Wealth approaches financial planning differently * 38:00 The risks of fast money, investing mistakes, and chasing returns * 41:00 Why steady, intentional growth always outperforms short-term wins * 44:00 Final advice for leaders who feel behind, overwhelmed, or financially stuck Connect with Jim * LinkedIn: personal [https://www.linkedin.com/in/jim-rasmussen-cpa-pfs-cgma-cka%C2%AE-cfp%C2%AE-cap%C2%AE-37804a11/] / company [https://www.linkedin.com/company/pandowealth/] * Website: https://www.pandowealth.com/ [https://www.pandowealth.com/] * Bags of Money * Get Out of Your Head by Jennie Allen https://amzn.to/4mWXp9j [https://amzn.to/4mWXp9j] Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #FinancialPlanning #BusinessOwners #WealthBuilding

20. maj 202641 min
episode 012: She Saved a Client $30K in 5 Minutes. Here's the Question She Asked | Kendra Ramirez cover

012: She Saved a Client $30K in 5 Minutes. Here's the Question She Asked | Kendra Ramirez

Most business leaders aren't behind on AI because they lack access. They're behind because no one told them they already have it and no one gave them permission to use it. In this episode of Think Outside the Boss, Katie Armentrout sits down with Kendra Ramirez, CEO of KR Digital, Claude Ambassador, and one of the most trusted AI voices in the B2B space, to cut through the noise, the overwhelm, and every excuse keeping leaders on the sidelines of the AI era. Kendra has been building AI since 2018. She's delivered hundreds of sessions, consulted organizations of every size, and once saved a client $30,000 in five minutes by asking five questions no one else thought to ask. This is not a conversation about AI being the future. It's a conversation about why it's already here and what to actually do about it today. From auditing your current tech stack, to why Claude outperforms ChatGPT for voice-driven content, to the data security questions your team is afraid to bring to leadership, Kendra makes AI feel less like a threat and more like the smartest colleague you've never properly introduced yourself to. If you lead a team, run a business, or have been quietly waiting for someone to tell you it's safe to move, this episode is that moment. In this episode, you’ll discover: * Why most businesses are already sitting on AI they've paid for and never activated * The five questions that saved one client $30,000 before they signed a single contract * Why Claude outperforms ChatGPT for human-sounding content and how to switch without starting over * What AI Skills are and why they permanently solve the "re-explaining yourself" problem * The non-negotiable data security rules every leader needs to understand before putting anything into AI * Why free AI tools are more expensive than you realize * How Kendra built a globally read AI newsletter that generates revenue without ever pushing it * The mindset shift from waiting for organizational permission to leading your team into the AI era * Why human-centered AI implementation outperforms technology-centered every single time * How to use your personality assessments inside AI for stronger leadership and team communication We talk about: * 00:00 The real reason your team is waiting on AI and why it starts with you * 04:00 Kendra's early leadership instincts and what it means to "manage up" the right way * 08:00 Why silencing the person who always asks "why" is a red flag, not a relief * 12:00 From technical recruiter to digital pioneer: building a business before anyone believed in it * 16:00 How to trust your gut when every coach in the room says you're wrong * 20:00 Limiting beliefs don't just live in you, they live in everyone giving you feedback * 24:00 Where to start with AI when you genuinely don't know what you don't know * 28:00 The $30K wake-up call: audit your tech stack before you buy anything new * 32:00 Claude vs. ChatGPT: what's actually different and whether you should switch * 36:00 What AI Skills are and how they eliminate the re-explaining problem for good * 40:00 AI data security: what's actually safe to put in, and what never should be * 44:00 How Kendra runs AI enablement from the C-suite to the front line * 48:00 Why human connection is the highest-leverage business strategy of 2026 * 52:00 Lightning round: personality assessments, faith, $10K lessons, and walking out to Alicia Keys Connect with Kendra * LinkedIn: https://www.linkedin.com/in/kendraramirez/ [https://www.linkedin.com/in/kendraramirez/] * Website: https://kendraramirez.com/ [https://kendraramirez.com/] * Newsletter: https://kendratech.substack.com/ [https://kendratech.substack.com/] * Get Out of Your Head by Jennie Allen https://amzn.to/4mWXp9j [https://amzn.to/4mWXp9j] Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #AIforBusiness #Leadership #Entrepreneurship

13. maj 202651 min
episode 011: Why Great Ideas Die Inside Companies (And How to Finally Get Them Out) | Fiona Stevenson cover

011: Why Great Ideas Die Inside Companies (And How to Finally Get Them Out) | Fiona Stevenson

What if your ideas aren’t failing… you’re just not built to carry them through? In this episode of Think Outside the Boss, Katie Armentrout sits down with innovation strategist and CEO Fiona Stevenson to unpack the uncomfortable truth behind why great ideas stall, die, or never make it out of the room. Because it’s not strategy. It’s not creativity. And it’s definitely not a lack of ideas. It’s human nature. Fiona shares what really happens inside innovation, from fear and perfectionism to leadership blind spots and the emotional resistance that quietly kills momentum. Drawing from hundreds of innovation projects and her new book Built for Breakthrough [https://amzn.to/4203tnN], she reveals why even “foolproof” processes fail when humans are involved… and what actually gets ideas across the finish line. This conversation goes beyond innovation. It’s about leadership, identity, risk, and the courage to move forward when you can’t see the path. If you’ve ever felt stuck between having an idea and actually executing it… this will shift how you think about everything. IN THIS EPISODE, YOU’LL DISCOVER: * Why innovation fails even when the process is “foolproof” * The hidden role fear plays in killing great ideas * Why not seeing the path ahead is actually a good sign * The difference between having ideas and executing them * How perfectionism quietly destroys leadership and innovation * Why your team mirrors your energy, not your intentions * The real reason leaving a stable career feels terrifying * How to build momentum when everything feels uncertain * Why energy, not time, is your most valuable resource * The mindset shift that turns ideas into reality We talk about: * 00:00 Why innovation isn’t actually the problem * 04:00 Fiona’s early leadership instincts and entrepreneurial mindset * 08:00 From corporate comfort to taking the leap into the unknown * 12:00 Why not seeing the path is a sign you’re on the right one * 16:00 The emotional reality of leaving stability behind * 20:00 How Fiona built a million-dollar business in year one * 24:00 The “say yes, make friends, experiment” growth strategy * 28:00 Why energy, not time, determines your output * 32:00 The power of working in your zone of genius * 36:00 Perfectionism, leadership, and the cost of hiding failure * 40:00 Why vulnerability transforms team performance * 44:00 The real reason great ideas stall inside organizations Connect with Fiona * LinkedIn: https://www.linkedin.com/in/fiona-stevenson/ [https://www.linkedin.com/in/fiona-stevenson/] * Website: https://fionastevenson.com/ [https://fionastevenson.com/] * Kindness At Work: https://www.kindnessatwork.com/ [https://www.kindnessatwork.com/] * The War of Art by Steven Pressfield [https://www.amazon.ca/Steven-Pressfield/e/B000AQ8R8Q/ref=dp_byline_cont_book_1] https://amzn.to/3OxunjR [https://amzn.to/3OxunjR] * Built for Breakthrough: https://amzn.to/4203tnN [https://amzn.to/4203tnN] Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #Innovation #Leadership #Entrepreneurship

6. maj 202651 min