Shameless Leadership

Sara Dean
undefined
Oct 7, 2025 • 35min

960: LEADERSHIP STORIES: Top Struggles of My Business Coaching Clients Right Now

This episode is especially for business owners and consultants, but the themes will resonate with anyone navigating leadership in challenging times. No matter your role, the struggles we face are often more similar than different, and there’s always something to learn from the stories of others. Recently, my business coaching clients and entrepreneurial colleagues have been sharing struggles that might feel familiar:  "What sold before is not selling now." "I am ready to make a pivot, but I'm feeling nervous and unsure about how to do so." "With the online space feeling loud and saturated, I'm feeling less confident in making myself more visible." "I need to grow my team, but I'm nervous about finding the right people and/or giving up control." "I'm struggling with boundaries and communication with my team." "I'm overwhelmed and exhausted by my business + the state of the world!" Over my 22 years as a business owner, the state of the world has forced me to reimagine (and sometimes rapidly pivot) my business, my offers, and my team multiple times. After a few moments (or days) of "WTF?! Why is this happening to me?!", I've always been able to find a path forward and often have found a stronger sense of purpose and drive because of this driving mantra: I know what I'm good at. I know I can create incredible outcomes for people. I have proven that I can be endlessly adaptable and resilient in my 49 years on this planet. This time is no different. LFG. In this episode, I’ll share 3 steps you can take right now to address these struggles head-on. Because the world being extra loud and extra messy does not diminish the need for your work. In fact, it amplifies it. Interested in becoming a sponsor of the Shameless Mom Academy? Email our sales team at sales@adalystmedia.com. Links Mentioned: Attend Sara’s Influence & Ignite Retreat for Women Business Owners: saradean.com/retreat Join Sara’s Next Business Coaching Cohort: https://saradean.com/influence-ignite-business-group-coaching/ Hire me to speak: saradean.com/speaking Coach with me: https://saradean.com/executive-coaching-services Connect with me on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Learn more about your ad choices. Visit podcastchoices.com/adchoices
undefined
Sep 30, 2025 • 51min

959: Michelle Desmond: Why We Need to Talk About Death, Loss, and Grief at Work

I met Michelle Desmond a few months ago at a birthday gathering for a mutual friend.  As Michelle started talking about her work in dying, death, and grief, I had question after question. I realized quickly I had to get her on the pod. I was so excited and grateful when she said yes. This is such an important topic that impacts every single human, yet very few ever talk about it. Michelle is a corporate executive turned thanatologist (expert in dying, death, and bereavement). After experiencing extensive personal losses, she chose to leave a career that included leadership roles in marketing, innovation, and line-of-business management at Verizon, T-Mobile, and Starbucks to pursue a Master of Science degree in the study of thanatology. She is passionate about bringing education, guidance, and innovation to the modern experiences of death and grief. She founded On Grief and Death LLC, through which she offers workshops and classes, 1:1 grief guidance, and consulting to businesses. She has led group and individual programs at companies, as well as the world-renowned Miraval Resort in Tucson. Michelle is an adjunct professor at Marian University, teaching master’s degree students about the role of technology in how we die and grieve. Listen in to hear Michelle share: What thanatology is and why she left a successful corporate career to go into this field The costs of living in a culture that leaves us utterly unprepared for experiencing loss, death, dying, and grief The biggest myths (and corresponding truths) about grief The costs of us not speaking more openly about grief - especially in professional spaces What would be different if we were to normalize talking about grief and loss  How companies and individuals can support others through experiences of death and loss of all types Links Mentioned:  Connect with Michelle: www.ongriefanddeath.com Michelle on LinkedIn: https://www.linkedin.com/in/michelle-desmond-811410/ Michelle on Substack: Death and Other Stories Get Michelle’s Book: Death and Other Stories Attend Sara’s October Retreat for Women Business Owners: saradean.com/retreat Join Sara’s Next Business Coaching Cohort (Oct-May): https://saradean.com/influence-ignite-business-group-coaching/ Hire me to speak: saradean.com/speaking Coach with me: https://saradean.com/executive-coaching-services Connect with me on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Interested in becoming a sponsor of the Shameless Mom Academy? Email our sales team at sales@adalystmedia.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices
undefined
Sep 23, 2025 • 27min

958: LEADERSHIP TIPS: What Emerging Leaders Really Need—But Aren’t Getting

"Sara, some of my newer leaders are really struggling. I know they want to shine, but they need support, and I don't have the time or skills to give them. Can you help?"  This is a conversation I've found myself in more and more over the last year. So, how did we get here?  More and more managers are being promoted into leadership roles without the training or support to succeed. In this episode, I unpack why so many emerging leaders are struggling: rapid reorgs, leaner teams, and the disappearance of formal leadership development. Then, I outline four key areas where new leaders need the most support. If you are an emerging leader in your organization, this episode will help you identify the skills you can develop to improve your leadership competence and confidence. If you are leading emerging leaders, this episode will help you more deeply understand how and why emerging leaders are struggling (often through no fault of their own) and what you can do to help them thrive. Whether you’re an executive watching your emerging leaders flounder or a brand-new manager looking for your footing, this episode offers practical insights you can use right away. The hidden forces pushing people into leadership before they’re ready The skill gaps most first-time leaders don’t even know they have Four core areas every new leader needs to master: clarity & confidence, communication, coaching and people development, and leadership resilience How to spot when your rising leaders need extra support—and how to get it for them Links Mentioned: Attend my Influence & Ignite Retreat for Women Business Owners: saradean.com/retreat Hire me to speak: saradean.com/speaking Coach with me: https://saradean.com/executive-coaching-services Connect with me on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks What You’ll LearnInterested in becoming a sponsor of the Shameless Mom Academy? Email our sales team at sales@adalystmedia.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices
undefined
Sep 16, 2025 • 53min

957: Jamie Lee: How to Amplify Self-Advocacy to Claim Your Power

Jamie Lee is an executive coach who specializes in women and underrepresented leaders who are "allergic" to risky conversations and office politics. She focuses on helping them get promoted and better paid without compromising their integrity or throwing anyone under the bus. In her practice, she blends proven self-advocacy strategies with evidence-based neuroplasticity tools. For over a decade, Jamie has trained thousands of professionals in effective self-advocacy at leading organizations, including Citi, Unilever, Association of Corporate Counsel, American College of Cardiologists, UC Berkeley School of Business, and Smith College. She's also the host of the Risky Conversations podcast, where she has honest talks with thought leaders on topics often considered taboo or "too risky" at work -- negotiation, mental and reproductive health, office politics, social injustices, and unconventional ways smart women navigate their path forward despite a flawed workplace. Listen in to hear Jamie share: How deepening her understanding of herself and her identity as a Korean immigrant woman helped her become a better self-advocate when she realized she was being significantly underpaid at work How our development of self-advocacy is not just about us, but also an act of service How she overcame the assumption that women need to earn their power in order to see that women actually need to claim their power The connection between self-advocacy, shame, and power How women can use anger to activate motivation The science of successful negotiation by decentering yourself How to use Zen practices and neuroscience to inform to rewrite your internal narratives and unlock your greatest potential  Links Mentioned: Connect with Jamie: https://www.jamieleecoach.com Jamie on LinkedIn: https://www.linkedin.com/in/leejieunjamie Jamie on Instagram: https://www.instagram.com/jamieleecoach Listen to Jamie’s interview with Sara on Risky Conversations: https://podcast.jamieleecoach.com/ Book: The Heart Sutra Book: Open Focus Brain Connect with Sara: saradean.com Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Interested in becoming a sponsor of the Shameless Mom Academy? Email our sales team at sales@adalystmedia.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices
undefined
Sep 9, 2025 • 31min

956: LEADERSHIP MINDSET: The Leadership Advantage of Owning Your Failures & Fumbles

Public failures and fumbles are painful to say the least.  I’ve recently had a handful of clients come to me feeling crushed after making a mistake, fumbling, or failing publicly. The most prominent outcome in all of their stories? SHAME. Their instinctual behavior to manage the shame? Hide, deny, or deflect. Fun fact, people don't actually trust leaders who never admit to making mistakes. Mistakes are a demonstration of humanity, authenticity, and vulnerability. We trust people who we see as human, fallible, and REAL. We trust people who aren't afraid to take accountability. We trust people who don't shy away from saying sorry. At the end of the day, our public mistakes don’t have to be the end of our credibility. In fact, they can become a powerful part of the evolution of our growth and credibility as a leader. In this episode, I’m digging into how public fumbles can actually make you a better leader, and I’ll walk you through the four steps (borrowed from restorative justice practices) to move through mistakes in a way that builds, rather than breaks, your credibility: Take responsibility for your part in the mess. Apologize for any harm done. Share and demonstrate what you’ve learned. Commit to the steps you’ll take to do better next time. By taking these steps, you are modeling humility, integrity, strength, grace, and a healthy sense of ego. When you model these things, people trust you MORE. People see you as more credible and authentic. People feel more connected to you. You become the kind of leader people remember and emulate.  I’ll also talk about how to let go of the shame of failure as an essential step for moving forward. The reality is, being a great leader is far more about being real than being perfect. Processing the shame is part of being real and giving yourself the grace to be imperfect. If you’ve ever found yourself in the spotlight for the wrong reasons—or feared what might happen if you do—this conversation will give you a roadmap for navigating those moments with integrity, humility, and strength. Links Mentioned: Attend my Influence & Ignite Retreat for Women Business Owners: saradean.com/retreat Hire me to speak: saradean.com/speaking Coach with me: https://saradean.com/executive-coaching-services Connect with me on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Interested in becoming a sponsor of the Shameless Mom Academy? Email our sales team at sales@adalystmedia.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices
undefined
Sep 2, 2025 • 35min

955: LEADERSHIP STRATEGIES: What Actually Makes Someone a Thought Leader?

When you hear the phrase thought leader, what comes to mind? For a lot of people, it’s someone with a massive following, a bestselling book, or a keynote spot at a big conference. But here’s the truth: thought leadership isn’t about popularity, perfection, or being the smartest (or loudest!) person in the room. It’s about having the courage to share ideas that shape or shift how others think, act, or lead. In this episode, I’m pulling back the curtain on what actually makes someone a thought leader—and what doesn’t. I’ll walk you through some of the biggest myths about thought leadership, like the idea that you need a huge audience, massive expertise, or flawless content before you can make an impact. Spoiler: you don’t. Then, I’ll break down the traits that really define thought leadership—clarity, consistency, courage, and a commitment to service. I’ll also share examples of leaders (many without fancy titles) who are shaping culture and conversations right where they are. If you’ve ever wondered whether your voice matters enough to share publicly, or if you’ve doubted whether you’re “qualified” to be seen as a thought leader, this episode is for you. You’ll leave with practical ways to start building credibility and influence, even if you’re starting small. Thought leadership isn’t about ego or self-promotion. It’s about generosity, contribution, and showing up consistently with ideas that matter.  Anyone can be a thought leader, and your path to thought leadership can begin today! Episode Highlights: Why thought leadership is about service, not self-promotion The biggest myths (and truths!) about thought leadership The four traits that make someone a trusted and influential voice How to know if you’re already showing up as a thought leader without realizing it 5 practical steps you can take to begin sharing your ideas with more confidence and consistency Links Mentioned: Jalonni Weaver on IG: https://www.linkedin.com/in/jalonniweaver/ Attend my Influence & Ignite Retreat for Women Business Owners: saradean.com/retreat Hire me to speak: saradean.com/speaking Coach with me: https://saradean.com/executive-coaching-services Connect with me on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Interested in becoming a sponsor of the Shameless Mom Academy? Email our sales team at sales@adalystmedia.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices
undefined
Aug 26, 2025 • 32min

954: LEADERSHIP STORIES: A New Me: My Personal Menopause & HRT Follow Up

A few months ago, I shared some of my personal experiences in perimenopause.  Today I am back with a big update. Since the last episode on this topic, I had a severe shift in my mental health, including a raging comeback of my lifelong anxiety and panic.  On top of this, I started having emotional responses to situations that I could tell were very much disproportionate to the situation, yet I couldn’t seem to talk myself out of severe and dark emotional states. Initially, I thought this was all due to general life stress and the relentless state of the world. After a few months of waking up in sheer panic night after night, I asked my doctor if we could recheck my hormones. WOW, did those lab results paint a picture!  I received my lab results via email on a Friday afternoon. Since my follow-up with my doctor wasn’t until the next week, I did what any anxiety-ridden perimenopausal 49-year-old woman would do. I went straight to my pal, Chatty (ie: ChatGPT). Chatty broke everything down for me and told me that, based on my lab work, I was very likely in the final stages of perimenopause or early stages of menopause. Chatty also noted that my lack of estrogen (which was so low it literally did not register on the lab work) may have me experiencing the following: Tearfulness or crying more easily Feeling raw, edgy, or like your “emotional skin is thinner” Mood crashes that feel out of proportion to the trigger Moments of despair or hopelessness that feel unfamiliar Feeling more reactive or “on edge” without clear cause Loss of resilience in situations you used to handle with ease CHECK. CHECK. CHECK. CHECK. I didn’t even realize how incredibly awful I had been feeling until I saw this list and realized that every single item was ME! I took the list to my husband, who lovingly verified that he had seen this all in me in recent months and shared, “You really haven’t been yourself for a while.” The next week, I had my lab review appointment with my doctor, who told me, “We are going to fast-track HRT for you. You need estrogen asap!” She called in my prescription and warned me that it would take a few weeks, maybe longer, before I noticed any significant changes in how I felt.   I put on my first hormone patch at 4 pm on a Tuesday. By Wednesday at 8 am, I felt like a new woman! I felt energetic, optimistic, motivated, and at ease. No panic, no anxiety. The sun shone brighter, the chirping birds made me smile (instead of annoying me), I didn’t want to scream at my family for no reason, and I couldn’t wait to tackle my To Do List for the day. I immediately realized how horrible my quality of life had become over the last few months. In short, HRT brought me back to myself in 16 hours.   In this episode, I share more of my story and provide a few recommendations for you to get the proper support during your own perimenopause/menopause journey. I’m so lucky to have a fantastic doctor, which I know is not the case for so many women. I hope my story will help you find the support you need during this season. If you are a woman between the ages of 35 and 55, this episode is for you!  Links Mentioned: Join my Influence & Ignite Retreat for Women Business Owners: saradean.com/retreat Shameless Leadership Ep 924: More Talking About Menopause Please Dr. Mary Claire Haver on IG: https://www.instagram.com/drmaryclaire Hire me to speak: saradean.com/speaking Coach with me: https://saradean.com/executive-coaching-services Connect with me on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Interested in becoming a sponsor of the Shameless Mom Academy? Email our sales team at sales@adalystmedia.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices
undefined
Aug 19, 2025 • 27min

953: INCLUSIVE LEADERSHIP: The Empathy Tightrope: How Much is Too Much (or Too Little?)

Empathy is one of the most critical leadership skills we can have—but like any strength, it can become a liability when it’s out of balance. In this episode, I’m diving into the dangers of both too much and too little empathy as a leader. Because here’s the truth: leaders without enough empathy lose trust, connection, and team cohesion… but leaders with too much empathy risk burnout, decision fatigue, and losing their leadership edge. We will dig into what happens when empathy turns into emotional over-functioning, when we’re not just feeling with our people, but we’re carrying their feelings as our own. This is especially common for leaders who are natural caretakers or people-pleasers, or who’ve been taught that being liked equals being effective. I’ll also break down how leaders with too little empathy often miss opportunities to connect, inspire, and build loyalty. Most importantly, I’ll walk you through practical ways to find your Goldilocks “just right” empathy zone. You’ll learn how to be compassionate without losing your boundaries, how to acknowledge people’s experiences without absorbing their emotions, and how to lead with both heart and backbone. This is the work of becoming a leader who is deeply human and deeply effective. If you’ve ever wondered whether you’re caring too much—or not enough—about the emotional side of leadership, this conversation will help you recalibrate so you can lead with clarity, confidence, and courage. Links Mentioned: Register for Sara’s October Influence & Ignite Retreat for Women Business Owners: saradean.com/retreat Hire me to speak: saradean.com/speaking Coach with me: https://saradean.com/executive-coaching-services Connect with me on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Interested in becoming a sponsor of the Shameless Mom Academy? Email our sales team at sales@adalystmedia.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices
undefined
Aug 12, 2025 • 52min

952: Themba Dayton: The Power of Diversity In Building Effective and Successful Teams

I was thrilled to interview Themba Dayton, whom I was introduced to by Elena Joy Thurston, a past guest of the show and a friend. When I learned about Themba’s track record in building and guiding diverse teams, I immediately had a ton of questions for him. This conversation is a treasure trove of sage advice around the power of diversity in professional environments and why diverse teams will always have a leg up, no matter the state of the world.   Themba Dayton is a 30-year insurance professional in the employee benefits industry, living in the Pacific Northwest. In an industry that is known for being overwhelmingly male, Themba has been a part of and has had the honor of leading extremely diverse and dynamic teams that have been innovative and successful in their roles. Teams at their best are varied, have full engagement, and the group is committed to the success of the whole more often than the success of the individual. In his current role, Themba looks for opportunities to ensure all voices are allowed to be heard, to allow for more robust discussions, and to pave the way for more meaningful outcomes. Listen in to hear Themba share: How to leverage diversity to build effective and successful teams His secret in helping each member of diverse teams feel seen, heard, held, and valued - getting to know each person individually, developing strong 1:1 relationships How he is sensitive to his industry being “pale, male, and stale” and how he, as a Black man, leads with this sensitivity in mind How he looks for opportunities to amplify women’s voices How highlighting someone else not only amplifies their voice but also helps you shine brighter as a strong leader Links Mentioned: Connect with Themba on LinkedIn: https://www.linkedin.com/in/themba-dayton-ab956b5/ Register for Sara’s October Influence & Ignite Retreat for Women Business Owners: saradean.com/retreat Hire me to speak: saradean.com/speaking Coach with me: https://saradean.com/executive-coaching-services Connect with me on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Interested in becoming a sponsor of the Shameless Mom Academy? Email our sales team at sales@adalystmedia.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices
undefined
Aug 5, 2025 • 33min

951: LEADERSHIP STRATEGIES: 4 Questions to Ask Before Making a Decision

Have you ever found yourself staring down a big decision, maybe making a move, a new job offer, a promotion, or even staying in a role that no longer fits — and thought, “How do I know if this is the right move?” In this episode, I walk you through four powerful questions I ask myself (and my clients) before making a big personal or professional decision. These questions help cut through the noise, slow down the overthinking spiral, and get you grounded in what you truly want and need. I will walk you through these questions, applying them to an example from my personal life, and then use a professional example that will likely be familiar to you. This episode will help you become a better decision maker and action taker, providing objective clarity to get you through tough decisions. Being able to make value-aligned decisions, guided by simple questions, will enhance your leadership, save you a ton of decision fatigue and mental energy, and open up space for you to do more of your best work.  In this episode, you will learn: The question I ask that always brings me back to clarity How to assess if a decision is additive or draining Why getting honest about the costs of a yes is just as important as the benefits How to make choices from purpose, not pressure Whether you’re weighing a big move or a small shift, this episode will help you trust yourself more in the process. Links Mentioned: Register for Sara’s October Influence & Ignite Retreat for Women Business Owners: saradean.com/retreat Hire me to speak: saradean.com/speaking Coach with me: https://saradean.com/executive-coaching-services Connect with me on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Interested in becoming a sponsor of the Shameless Mom Academy? Email our sales team at sales@adalystmedia.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app