The Learn-It-All Podcast

Damon Lembi
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Jun 5, 2025 • 56min

176: Unfair Advantages: How to Turn “Different” Into Dominant | Juan Silvera

What if your background, your accent, or your “nontraditional” path was actually your biggest asset? In this episode, Damon sits down with Juan Silvera, global marketing executive and author of Improbably Successful, to unpack how underdogs win in today’s hypercompetitive marketplace. From surviving the streets of Medellín to leading global teams, Juan shares his powerful story and teaches you how to stand out—no matter where you start. Whether you're navigating career change, trying to build your brand, or wondering if you belong, this episode will challenge and inspire you.  In this episode, you’ll learn: What it means to be “improbably successful” How to reframe adversity as your leadership advantage Why discomfort and risk often lead to exponential growth A real-life framework for deciding if a big leap is worth it How to take a skill inventory that opens new doors The #1 career skill that wins in any role (hint: it’s not technical) How bilingualism and cultural identity can create opportunity Why personal branding isn’t vanity—it’s strategy What leaders get wrong about humor and communication How to project gravitas—even before you feel “ready”  Timestamps: 00:00 – What it means to be “improbably successful”  01:30 – Growing up in Medellín and the instincts it shaped  03:45 – Why street smarts aren’t enough in today’s workplace  06:00 – The move to Austria: risk, family, and transformation 08:40 – Advice for leaving a “comfortable” job  10:20 – Creating a personal framework for smart risk  12:30 – Planning during forced change: layoffs, pivots, uncertainty  15:00 – The skills audit exercise (supply vs. demand)  17:00 – Why transferable skills matter more than job titles  18:30 – Communication: the most valuable skill in any career  20:15 – How to assess (and improve) your communication  21:30 – Writing, listening, humor: Juan’s communication playbook  24:30 – Humor as a leadership advantage (with one big caveat)  29:45 – Finding and using your unique strengths  33:00 – Women in leadership: why EQ is a hidden superpower  36:30 – How second languages open unexpected doors  39:50 – Juan’s turning point: from last-ranked analyst to global leader  42:10 – Building and protecting your personal brand  45:15 – What people notice (and judge) before you say a word  47:00 – How Juan hired someone based on their online presence  50:00 – Why you need to treat yourself like a brand  52:00 – What Juan would add to the next edition of his book  53:00 – A reminder: never forget the fundamentals About Juan Silvera: Juan Silvera is a global marketing executive, storyteller, and the author of Improbably Successful: How to Win in a World That Wasn’t Built for You. Born and raised in Medellín, Colombia, Juan has led marketing and business initiatives across four continents and is known for his ability to bridge cultural divides and unlock hidden potential. His mission: help professionals from all backgrounds realize that what makes them different is exactly what makes them powerful. Resources & Mentions: Juan’s book: Improbably Successful on Amazon Juan’s website: juansilvera.com Juan on LinkedIn: linkedin.com/in/juansilvera Juan on X (formerly Twitter): @juansilvera  Connect With Us: Uplevel yourself and your team at Learnit.com Email us: podcast@learnit.com Follow Damon on LinkedIn Follow Damon on Instagram 
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Jun 4, 2025 • 18min

175: 5 Books That Made Me a Better Leader—and How I Actually Applied Them | Damon Lembi

Reading books doesn’t make you a better leader—applying them does. In this solo episode, Learnit CEO and bestselling author Damon Lembi shares five books that have fundamentally shaped how he leads, makes decisions, and builds high-performing teams. But this isn’t a generic reading list. Damon reveals exactly what he took from each book—and how he’s put those lessons to work. If you're looking to lead with more intention, clarity, and impact, start here.In this episode, you’ll learn: The 3 big leadership lessons Damon took from Lincoln Why introverts often make the best leaders A decision-making framework every exec should master How to shift your org from hierarchy to teamship Why you can’t afford to ignore AI (and how to start) How to get real ROI from your reading habit What “learning without doing is treason” really means Why biographies beat business books (most of the time)  Timestamps: 00:00 – The most powerful leadership tool: reading (with intention)  01:10 – Book #1: Team of Rivals by Doris Kearns Goodwin  01:40 – Embracing diverse viewpoints and emotional control  03:00 – Lincoln’s “hot letter” method: emotional intelligence in action  04:00 – From criticized novice to strategic mastermind: Lincoln’s growth  05:00 – Book #2: Quiet by Susan Cain  05:45 – Why introverts lead best by listening, not commanding  06:45 – Advice for introverts—or leaders who manage them  07:30 – Book #3: Decisive by Chip & Dan Heath  08:15 – The WRAP framework: smarter decisions, less regret  09:00 – How Damon used it to rethink a CFO hire  10:00 – The 10/10/10 rule for cooling emotional decisions  10:45 – The trap of confirmation bias—and how to escape it  11:15 – Bonus: Damon’s book Good Decisions = Success  11:45 – Book #4: Never Lead Alone by Keith Ferrazzi  12:30 – Teamship vs. traditional leadership  13:10 – Why open candor beats conflict avoidance  13:45 – A roadmap for building trust, feedback, and collaboration  14:30 – Book #5: AI-Driven Leader by Jeff Woods  15:15 – Why AI is a mindset shift—not just a tool  15:45 – Damon’s example: building a comp plan using AI  16:30 – The 4-part prompt framework for high-impact AI results  17:00 – Bonus Book: The Learn-It-All Leader by Damon Lembi  17:30 – Being vs. Doing: Two halves of the leadership equation  18:00 – Final thought: Apply what you read—or it doesn’t count Resources & Mentions: Team of Rivals by Doris Kearns Goodwin: Amazon Quiet by Susan Cain: Amazon Decisive by Chip & Dan Heath: Amazon Never Lead Alone by Keith Ferrazzi: AmazonAI-Driven Leader by Goeff Woods: AmazonGood Decisions = Success by Damon Lembi & Kandis Porter: AmazonThe Learn-It-All Leader by Damon Lembi: AmazonLearn-It-All Podcast interview with Geeff Woods: Listen on SpotifyConnect With Us: Uplevel yourself and your team at Learnit.com Email us: podcast@learnit.com Follow Damon on LinkedIn Follow Damon on Instagram 
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Jun 3, 2025 • 54min

174: How to Build Self-Aware Leaders: The Framework That Scales Culture | Erin Lewellen

You can’t solve 21st-century problems with 20th-century mindsets—and today’s guest is on a mission to change that. In this episode, Damon sits down with Erin Lewellen, CEO of Tilting Futures, to unpack how immersive, global learning experiences are transforming the next generation of leaders. From building self-awareness to teaching systems thinking and reducing bias, Erin shares how her team is reshaping leadership education—and what every company can learn from their model. Whether you lead a team, a classroom, or a company, this conversation will challenge how you think about growth, feedback, and the power of perspective. In this episode, you’ll learn: Why self-awareness isn’t innate—it’s a muscle The “look in the mirror” rule every leader should follow How Tilting Futures develops young leaders from 100+ countries Why discomfort and difference drive transformational growth The #1 interview strategy to find self-reflective employees How to build a feedback culture rooted in trust, not fear The hidden cost of “meetings after the meeting” What most orgs get wrong about defining values How leaders can model curiosity and restraint in meetings Why you need to stop saying “they” and start saying “we”  Timestamps: 00:00 – Can you teach self-awareness—or is it innate?  01:45 – “Look in the mirror”: Erin’s foundational leadership habit  03:30 – What Tilting Futures is and how it works  05:35 – Why ages 17–22 are the sweet spot for impact  07:10 – Teaching empathy through global immersion and collaboration  08:50 – Travel as a tool for leadership and adaptability  11:30 – Erin’s Cape Town story: Context, humility, and lifelong change  14:45 – Leading meetings with curiosity and silence  15:55 – What changes in student mindset after 4 months  18:00 – The research: Reduced bias, more agency, stronger leadership  20:40 – How global cohorts shift perspective and prejudice  22:45 – Systems thinking and asset-based problem solving  25:30 – Behind the scenes: Building Tilting Futures’ internal culture  28:00 – “There is no ‘they’, only ‘we’”: One of their core principles  30:30 – How Erin interviews for curiosity and growth mindset  34:15 – Why soft skills are the hardest—and most critical—to teach  35:45 – Encouraging disagreement to find the best idea  38:00 – Practicing emotional honesty in meetings  40:30 – Ditching “the meeting after the meeting”  42:00 – Aligning staff and student values: One unified culture  44:25 – Keeping values alive in every meeting  46:45 – How this generation of students is different  49:30 – The Zimbabwean biomedical engineer who redefined her mission  52:00 – Erin’s why: Helping young leaders unlock their impact  54:00 – Scholarships, access, and how to get involved  About Erin Lewellen: Erin Lewellen is the CEO of Tilting Futures, a nonprofit redefining global education through immersive leadership experiences. With operations in Cape Town and Malaysia, Tilting Futures equips young adults from over 100 countries with the skills, networks, and self-awareness needed to solve complex global challenges. A former high school basketball coach and champion of inclusive leadership, Erin brings a systems-level perspective to everything from education reform to organizational culture. She’s also a Forbes contributor and advocate for integrating “soft” (human) skills into every stage of leadership.  Resources & Mentions: Tilting Futures website Erin Lewellen on LinkedIn Forbes article: The Soft Skills That Can’t Be Replaced By AI Apply to Take Action Lab Connect With Us: Uplevel yourself and your team at Learnit.com Email us: podcast@learnit.com Follow Damon on LinkedIn Follow Damon on Instagram 
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May 29, 2025 • 53min

173: The 80% Rule: How Leaders Can Overcome Fear, Stress, and Self-Doubt | Derek Sloan

Why does stress feel so normal in the workplace? Why does our mind default to the worst case scenario? And what’s the cost of this being our normal day to day life? In this episode, Damon sits down with Derek Sloan, who’s a licensed therapist, executive coach, and founder of Abridge Leadership to explore why so many professionals silently battle negativity and self-doubt, and what leaders can do to break the cycle. Whether you're navigating organizational change, dealing with anxious thoughts, or trying to model vulnerability in a remote workplace, this episode offers practical tools backed by psychology and made for the real world. In this episode you’ll learn: What The 80% Rule is—and how it can transform how you lead The hidden cost of “normalized” workplace stress Why vulnerability is a leadership superpower (when done right) The difference between confidence and self-efficacy How to spot fear-based thinking on your team Practical ways leaders can create clarity, safety, and connection And so much more! Timestamps: 00:21 – Why our brains default to negativity (60,000 thoughts, 80% negative)  01:53 – The thought-emotion-behavior chain: how negativity spreads  03:42 – What happens when dysfunction is normalized at work  05:45 – Breaking down The 80% Rule (3 surprising stats)  09:00 – Addressing real pain vs. future-focused fear  10:25 – The traps leaders fall into under stress  12:23 – A case study: when a promotion becomes a source of burnout  16:05 – What leaders can do during times of uncertainty  18:45 – The power of focusing on controllables  19:24 – 3 controllables: showing up as your best, staying hopeful, being transparent  22:30 – Why vulnerability matters more than ever  25:15 – Healthy vs. unhealthy vulnerability: where leaders get it wrong  29:09 – Understanding fear: how our brains exaggerate the future  33:27 – Self-efficacy vs. confidence—and why both matter  36:05 – How to give better feedback (that actually develops talent)  39:14 – Recognizing negativity loops in your team  41:39 – Why listening—not fixing—is your leadership edge  44:00 – The post-COVID shift: employees expect to be cared for  45:32 – Can remote work ever match in-person connection?  48:21 – Why loneliness is a hidden workplace epidemic  50:15 – Final takeaway: Take inventory. Where are you now—and how long have you been there?  About the Guest: Derek Sloan is a Licensed Professional Clinical Counselor (LPCC), Certified Clinical Trauma Professional (CCTP), and National Certified Counselor (NCC), He has experience in providing mental health and behavioral health services to individuals, couples, and groups. He founded and continues to operate a private practice in Kentucky. Derek is also a Certified Executive Coach and has a passion for leadership development. This has been a lifelong pursuit through his graduate degree in organizational leadership, building businesses, and leadership coaching/consulting. He works with executive leaders in top-level and industry-leading organizations, helping them enhance their emotional intelligence, communication skills, and decision-making abilities. His mission is to help organizations achieve their goals by prioritizing both leadership and mental health. Resources & Mentions: Follow Derek on LinkedIn Visit Derek's Leadership company Abridge Leadership Man’s Search for Meaning by Viktor Frankl Derek’s Podcast: Mental Stillness Damon's appearance on Mental Stillness: https://podcasts.apple.com/us/podcast/38-special-guest-damon-lembi/id1717076433?i=1000703632140Connect with Us: Uplevel yourself and your team with our trainings: www.learnit.com Email us: podcast@learnit.com Follow Damon on LinkedIn and Instagram 
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May 28, 2025 • 8min

172: Why A-Players Crash as Managers (The 5 Truths New Leaders Must Learn) | Damon Lembi

The 5 Truths Every New Leader Needs to Hear Becoming a leader isn’t just a promotion—it’s a complete identity shift. You’re no longer just executing the work. You’re coaching others to do it well. And that requires a new mindset, a new skillset, and a new set of daily habits. In this solo episode, Learnit CEO Damon Lembi breaks down the 5 truths he wishes every first-time leader knew. Whether you’re fresh in the role or mentoring someone who is, this episode is your tactical, no-fluff guide to making the leap from top performer to people-first leader. In this episode, you’ll learn: - Why leadership is about coaching, not doing - The #1 mindset shift you must make in week one - How to build trust by giving others autonomy (and space to fail) - Why the best leaders are great listeners—first - How to model the habits you want your team to follow - The key conversation to have with your boss (today) - What to do when your company won’t invest in your development - Why mistakes are inevitable—and what to do when you make one - How to lead without pretending to have it all figured out Timestamps: 00:00 – The biggest professional shift: from player to coach 01:00 – Truth #1: You win through your people, not by doing it all 01:45 – Why delegation is really about building trust 02:00 – The mindset shift: you're building a team of heroes, not being the hero 02:30 – Truth #2: Don’t rush in—start by listening and learning 03:20 – Why curiosity builds credibility and connection 03:50 – Truth #3: Model the behavior you want from your team 04:30 – Leadership is a constant stage—how are you showing up? 04:45 – Truth #4: Own your success—don’t wait for others to invest in you 05:15 – How Damon recommends new leaders start growing (even on their own) 06:00 – The $14 tool that every new leader should use 06:30 – Truth #5: You will make mistakes—so learn fast and lead through it 07:10 – The hard lesson Damon learned about avoiding tough conversations 08:00 – The recap: 5 truths every new leader needs to thrive 08:30 – Final thought: Great leaders aren’t born or made—they’re always in the making Resources & Mentions: Damon’s book: https://www.learnit.com/learn-it-all-leader-book-by-damon-lembi Learnit’s Delegation Greenlights E-Book: https://www.learnit.com/resources/delegation-greenlights-guide Learnit’s Delegate to Scale Your Impact Course: https://www.learnit.com/courses/delegate-to-scale-your-impact Learnit Article on New Manager Training Skills: https://www.learnit.com/blog/new-manager-training-skills The Learn-It-All Podcast with Chris Dyer: https://www.youtube.com/watch?v=hBUHOPtR6Yk Learnit Live Event: https://www.youtube.com/watch?v=vjLFoCepWOw Connect With Us: Uplevel yourself and your team at Learnit.com Email us: podcast@learnit.com Follow Damon on LinkedIn Follow Damon on Instagram
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May 27, 2025 • 42min

171: The Founder Flywheel: Retention First, Revenue Second | Richard White

The modern workplace runs on meetings. But too often, those meetings become time sinks instead of value drivers. People scramble to take notes, miss critical insights, and leave unclear on what to do next. Meanwhile, leaders drown in back-to-back calls with no bandwidth to spot patterns or coach teams effectively. And yet... what if meetings weren’t the problem, but the raw material for your company’s next big leap? In today’s episode, Damon is joined by Richard White, CEO and founder of Fathom breaks down his best lessons as a 3x founder and how he’s building the future of work. In this episode, you’ll learn: Why retention—not revenue—should be your first startup focus How Richard built a viral product without a sales team for 12+ months The underestimated power of onboarding and customer support How to create a freemium product that actually drives word of mouth Why AI will soon give every employee a “highlight reel” of what matters most The truth about building in the AI era: it’s not about features—it’s about output quality  Timestamps: 00:00 – Richard’s early builder mindset and why he couldn’t be an employee  01:22 – Why articulating the “why” is a founder’s core job  02:07 – Finding his tribe in the first batch of Y Combinator  04:25 – How confidence and founder networks shaped his journey  05:44 – The trap of over-relying on advice vs. trusting your instincts  07:51 – Why Richard calls UserVoice his “founder finishing school”  08:38 – Lessons in cross-functional leadership and scrappy execution  11:05 – Advice for technical founders who undervalue sales  12:33 – The insight that sparked Fathom: meetings are broken  14:44 – How he hired a “sales team” with nothing to sell  15:05 – Why he delayed monetization and focused on retention first  17:57 – Building customer feedback loops into the product  19:32 – From 1,000 users to viral growth via the Zoom Marketplace  21:50 – The psychology behind freemium and referability  24:42 – Why onboarding was a 9-month engineering priority  26:47 – Balancing new features with polishing the UX  28:58 – The contrarian view: meetings aren’t bad—meeting waste is  29:22 – How Fathom reduces meeting bloat and improves async sharing  31:36 – Using Fathom to streamline the hiring process  33:39 – What’s next: AI that watches every meeting and summarizes insights  36:05 – Generating case studies and internal docs from conversation data  36:52 – Cross-org AI search and the power of complete data sets  37:59 – What separates great AI products: obsessive quality control  39:51 – The future belongs to teams that can turn conversations into knowledge  Resources Mentioned: Fathom Connect with Richard White on LinkedIn UserVoice  About the Guest: Richard White is the founder and CEO of Fathom, a free AI-powered meeting assistant that helps teams skip note-taking and unlock insights from every call. He’s a three-time founder, early YC alum, and product-obsessed builder who believes meetings are the new knowledge base—if we capture them right. Connect With Us: Level up your sales team at Learnit.com Email us: podcast@learnit.com Follow Damon on LinkedIn 
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May 22, 2025 • 52min

170: The 5 Learning Styles That Build Real Leaders | Scott Allen

Leadership isn’t just about vision. Instead it’s about showing up in the everyday moments if you want to shape great teams, cultures, and results. There’s myth that some people are “born leaders” but in today’s episode, leadership expert Dr. Scott Allen shares why leadership is learned, practiced, and most importantly, deeply personal. In this episode you will learn: Why the idea of “natural-born leaders” is outdated The science behind charisma (and how to develop it) What leadership styles have in common with golf clubs The difference between authority and influence—and why influence wins Why “thinking partners” are essential for every leader How to combine knowledge, skill, mentorship, and experience for true growth Timestamps: 00:14 – Are leaders born or made?  01:49 – What science says about charisma and learnable leadership  03:48 – How problem-solving, negotiation, and communication can be developed  06:00 – Leadership styles and the “golf club” metaphor  08:42 – Making leadership training stick: from hacks to habits  09:43 – Why self-awareness is foundational to great leadership  12:08 – Character, curiosity, and the power of learning  13:02 – Can self-awareness be taught?  15:36 – Curiosity as a leadership superpower  17:02 – Coaches who deflect blame vs. leaders who take ownership  18:12 – Empathy, ego, and the limits of expertise in leadership  20:26 – Why catchers make great managers  21:43 – Influence: the real heart of leadership  24:07 – Trust as the currency of leadership  25:48 – Influence tactics: from logic to coalitions  28:18 – Timing and persuasion in leadership conversations  30:01 – Why knowledge alone isn’t enough—real-world learning is essential  33:22 – The five domains of leadership learning  35:27 – Creating learning organizations with psychological safety  37:54 – The role of thinking partners in leadership development  41:04 – How to find (and build) your bench of thinking partners  46:57 – Why one partner won’t solve everything—and that’s the point  49:01 – “Who you are is how you lead” – Scott’s favorite leadership quote  50:39 – Final thoughts on responsibility, reflection, and showing up for others  About the Guest: Dr. Scott J. Allen is an award-winning educator, keynote speaker, and leadership expert. With over 17 years as a professor and more than 60 peer-reviewed publications, Scott brings academic rigor, humor, and real-world insight to every engagement. He's co-authored several books on leadership and hosts Practical Wisdom for Leaders—a podcast ranked in the top 2.5% globally. He also publishes a weekly newsletter for busy practitioners, highlighting four leadership articles. Scott energizes audiences at marquee organizations such as Toyota Motor North America, Cleveland Clinic, NASA-Glenn, Nestlé, Progressive, Whiting Turner, Sam's Club, the Federal Reserve Bank of Cleveland, and Progressive through his dynamic keynotes, workshops, and retreats. Whether on stage or in the boardroom, Scott’s expertise in leader development, the future of work, and executive communication empowers leaders to drive meaningful, lasting change.  Resources & Mentions: Connect with Scott on LinkedIn: https://www.linkedin.com/in/scott-j-allen/  Visit Scott's Website: www.scottjallen.net Listen to his Podcast: https://www.scottjallen.net/podcast  HBR Article: Leadership That Gets Results by Daniel Goleman: https://hbr.org/2000/03/leadership-that-gets-results  Influence by Robert Cialdini: https://a.co/d/hl0KHmq  Pre-Suasion by Robert Cialdini: https://a.co/d/hl0KHmq  Gallup’s workplace engagement stats: https://www.gallup.com/workplace/654911/employee-engagement-sinks-year-low.aspx#:~:text=In%20the%20latest%20reading%2C%20from,than%202020's%20high%20of%2036%25 Tiny Habits by BJ Fogg: https://a.co/d/81197UZ  Atomic Habits by James Clear: https://a.co/d/81197UZ  Connect With Us: Learn more about our leadership and team development trainings: www.learnit.com Email us: podcast@learnit.com Follow Damon on LinkedIn and Instagram 
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May 21, 2025 • 7min

169: The Podcast Move That 10X’ed My Network and Confidence | Damon Lembi

Damon Lembi never set out to become a podcaster. But 2 years, 160+ episodes, and thousands of conversations later, he can say this with confidence: podcasting has been the single most transformative tool in his professional growth. In this solo episode, Damon breaks down the 8 ways podcasting has made him a better leader, communicator, and human being and why every professional should seriously consider stepping behind the mic. In this episode, you’ll learn: - Why podcasting is the ultimate communication gym - How storytelling on-air can make you more persuasive off-air - What podcasting does for your confidence and clarity - The hidden networking power that comes with each episode - Why podcasting forces you to become a better listener and improviser - How hosting a show accelerates your learning and thought leadership - The simple way to turn one podcast guest spot into 10 pieces of content - Why your personal brand matters (even if you don’t think it does) Timestamps: 00:00 – Damon’s confession: The one unexpected thing that changed his career 00:35 – #1: How podcasting sharpened his communication 01:10 – #2: Why repetition made him a better storyteller 01:50 – #3: Overcoming fear and building confidence through reps 02:30 – #4: 10x network growth—and the power of asking 03:00 – #5: How the mic made him a better listener at work and at home 03:45 – #6: Learning to improvise and build trust fast 04:20 – #7: The accelerated learning effect (and why it feels like free coaching) 05:15 – #8: How podcasting helped him build a real, visible personal brand 06:10 – Guesting vs. hosting: Where to start and what tools to use 06:50 – Why you don’t need followers—just courage 07:10 – A final reflection: Podcasting made me better. It can do the same for you. Resources & Mentions: Episode with Marques Ogden: https://youtu.be/dqsRJhGIeFI?si=98MKdtArx30guTBEEpisode with Stephen M.R. Covey: https://youtu.be/iP6cnAqNwIc?si=pl6lCTHKgM9v-sn5Episode with Doug Conant: https://youtu.be/418p49ClihY?si=YuLozGLm4VsFXM1BEpisode with Dr. Jessica Kriegel: https://youtu.be/TUJ-8zUolI4?si=UNYpf_LwQ5pzi2NiEpisode with Matt Dixon: https://youtu.be/0LpEfvxsOYs?si=mAEJwxIREFnmeg3gPodMatch: Tool to book guest spots: https://www.podmatch.com/Opus Clip to make podcast clips: https://www.opus.pro/Pat Flynn’s Guide: How to Start a Podcast in 2025: https://www.smartpassiveincome.com/Connect With Us: Level up your sales team at Learnit.comEmail us: podcast@learnit.com Follow Damon on LinkedIn Follow Damon on Instagram
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May 20, 2025 • 1h 7min

168: If Your Win Rate Is 20%, You’re Doing It Wrong | Dave Brock

Dave Brock, author of the Sales Manager Survival Guide and leader of Partners in EXCELLENCE, delves into the crisis in B2B sales, revealing why traditional selling methods are failing. He discusses the alarming decline in win rates and the burnout of sales teams, stressing the need for a cultural shift focusing on curiosity and understanding over rote pitches. Brock also explores innovative AI tools aimed at revitalizing sales coaching and enhancing customer insights, ultimately advocating for a more engaged and motivated workforce.
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May 15, 2025 • 48min

167: The Difference Between Coaching & Managing Your Team | Kerry Rockers

If you want to be a successful leader in today’s fast paced world, stop focusing on just hitting your targets in business. Instead, you need to focus on understanding your team, so that they can help you achieve more than you could on your own. But how do you do that? In today’s episode, Damon is joined by Kerry Rockers, an executive coach, HR veteran, and passionate advocate for helping leaders build more human-centered workplaces. In this episode, you’ll learn: Why great coaching isn’t about fixing people, but about helping them hear their inner voice again How to navigate career pivots with clarity and confidence The difference between leading and managing—and why it matters now more than ever Why HR is more strategic than it’s ever been Simple shifts to help your team find meaning in their work Timestamps:  00:20 – The true goal of coaching: helping people remember what they already know  02:14 – Coaching the ambitious vs. the stuck: what’s different?  03:34 – What makes someone “coachable”?  04:26 – Kerry’s journey from HR executive to full-time coach  06:47 – How HR has evolved in the past 20 years  07:50 – Making the leap to entrepreneurship (even if it’s unexpected)  09:26 – How to approach a career pivot with intention  12:19 – Why experimenting and networking is key to a successful transition  13:58 – Tools for gaining clarity on what you want next  15:44 – How to learn in a way that works for you  16:40 – Why more people are searching for meaning in work  18:07 – How Kerry helps clients discover their values  19:52 – The calendar and checkbook audit: aligning time and values  20:20 – How managers can help their team feel more connected to their work  22:21 – Listening for values in everyday conversations  23:52 – One simple way to become a better listener  24:52 – A powerful 1:1 question Kerry uses to surface meaning  26:36 – What to do if you’re not good at receiving feedback  28:03 – The trust cost of canceling 1:1s  30:02 – What a “stay interview” is and why every manager should use it  33:12 – How to keep top talent even when change isn’t possible  33:44 – One mindset shift middle managers need to build trust  35:50 – The story of the leader who helped Kerry make a pivotal leap  39:23 – Tools for increasing self-awareness (and why it matters)  42:08 – Can self-awareness be taught?  43:18 – How StrengthsFinder helped one client reframe chaos into purpose  45:46 – How to work better with different strengths on your team  47:07 – Final thoughts on intentionality, curiosity, and leadership About the Guest: Kerry Rockers is a certified executive coach and former global HR executive with over two decades of experience. Kerry has consulted and coached leaders across multiple business lines and functions (Technology, Digital Channels, Wholesale Banking, Corporate Support teams etc.) with significant experience working internationally.  Her business acumen and broad experience working with teams and leaders during times of change help her quickly understand her coaching client's challenges.   Resources Mentioned: Kerry Rockers' Website Connect with Kerry on LinkedIn CliftonStrengths Assessment Connect With Us: Uplevel yourself and your team with our trainings: www.learnit.com Email us: podcast@learnit.com Follow Damon on LinkedIn: https://www.linkedin.com/in/damonlembi/ Follow Damon on Instagram: https://www.instagram.com/damonlembi/ 

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