Work Should Feel Good with Diana Alt

What can leaders and business owners learn from moonshiners? More than you might think. Jon Umstead has spent more than 30 years leading teams and organizations, from startups to Fortune 500 companies, in roles ranging from COO and CMO to transformation leader. In this episode, Jon and Diana reconnect after working together more than 17 years ago to talk about leadership, navigating change, entrep...

AI is changing how companies hire, but trying to beat AI with more AI isn't the answer. Diana talks with Jeremy Schifeling, founder of The Job Insiders and author of Unbreakable, about the human skills that matter most, how to build trust in your job search, and how to use AI without losing what makes you valuable. Why human skills matter more in the age of AI How referrals build trust in a job se...

Diana talks with Adrienne Dorison about building teams and businesses that don't depend on one person to keep everything moving. They explore better delegation, decision-making, and how leaders can give people the autonomy to do great work. Teaching people how to think, not just what to do Building better judgment and decision-making Using vision and values as decision-making tools Reducing owner...

As AI becomes part of everyday work, genuine human connection matters more than ever. Diana talks with Jim Morris, author of Connect or Die: How to Survive AI, about building stronger relationships through curiosity, integrity, vulnerability, and a willingness to help without making every interaction transactional. Building relationships without transactional networking Why authenticity matters mo...

What happens when your leadership gets tested and your team suddenly has to function without you? Ian Ng joins Diana to talk about his transition from individual contributor to manager and how unexpected triple bypass surgery put his approach to leadership to the test. They explore delegation, self-sufficient teams, boundaries, and why making yourself indispensable isn't necessarily good leadershi...

Diana sits down with brand strategist, entrepreneur, and Second Wind Women podcast host Karen Spies for a candid conversation about career reinvention, entrepreneurship, and the messy moments that push us toward change. They explore why your experience comes with you into a new chapter, why entrepreneurship isn't necessarily the easier path, and how sometimes moving forward means moving sideways o...

Todd joins Diana to talk about the unexpected career path that took him from movie theaters and Disney to working as a flight attendant, winning Survivor: China, rebuilding his life after alcoholism, and eventually discovering an artistic talent he didn't know he had until his 30s. Today, he and his husband create custom artwork through Todd's Pop Shop, a business Todd built around creativity, com...

What happens when life completely derails the plan and forces you to rethink how you work, lead, and let other people help? Terry Weaver returns to Work Should Feel Good to share how a sudden case of sepsis landed him in the ICU just as The Thing was beginning. Diana and Terry talk about the community that stepped in to keep the event going, his long recovery, and how the experience changed his th...

What if your appearance is either reinforcing or quietly undermining the credibility you've already earned? In this episode, Diana sits down with image strategist Eden Oates to explore how visual authority builds trust, confidence, and connection without feeling fake or performative. Whether you're a corporate leader, entrepreneur, or professional looking to strengthen your personal brand, you'll...

In this episode, Diana sits down with interview expert Lili Foggle to explore why interviewing is really about strategic communication, authentic connection, and understanding what employers are actually looking for. From AI's impact on hiring to practical interview preparation strategies, this conversation is packed with insights that will help you interview with greater confidence and clarity. W...

What does it really take to build authentic professional relationships in a world increasingly dominated by AI and transactional networking? In this conversation, Diana sits down with Michael Roderick, CEO of Small Pond Enterprise LLC and host of the Access to Anyone podcast, to explore how clarity, curiosity, and memorable communication create opportunities that traditional networking never will....

What does it actually mean to have influence and do you really need to become an "influencer" to make an impact? In this episode, Diana sits down with digital strategist Mark Lebrun to unpack why genuine influence has far more to do with trust, service, and credibility than follower counts or viral content. Whether you're a corporate professional, business owner, or aspiring thought leader, you'll...

What happens when your career is driven by purpose instead of titles? In this episode, Diana sits down with workplace experience and food systems leader Lucy Norris to explore the importance of knowing the deeper "why" behind your career choices. From building healthier workplaces to navigating a long job search with intention, Lucy shares practical wisdom on creating meaningful work without letti...

Employee benefits are often treated as paperwork and perks, but what if they could become one of the most powerful tools for improving employee retention and helping people build the lives they actually want?   In this episode, Diana sits down with Larry Salazar to discuss why employers need to think beyond traditional benefits and invest in the whole person—not just the employee. From financial w...

What if creativity isn't something you have, it's something you practice? In this conversation, Diana Alt sits down with artist, speaker, and creative mentor Mike Brennan to explore how a simple daily creative habit transformed his life after burnout and depression. Together, they unpack why creativity matters far beyond the arts and how consistent creative practice can fuel innovation, resilience...

Burnout isn't a personal failure, it's a systems problem. In this episode, Diana sits down with Cass Cooper to unpack how high performance often masks exhaustion, why "fixing yourself" won't solve burnout, and what actually needs to change at work. Why burnout is a systems issue, not an individual weakness How high performers unknowingly mask exhaustion The role of meeting culture and notification...

What happens when a historian becomes an AI consultant? In this episode, Diana Alt sits down with Rob Voss to explore the real-world impact of AI on work, education, business, and how we think. Rather than focusing on futuristic hype, Rob shares practical insights on how AI is already changing the way people learn, make decisions, and solve problems. Whether you're AI-curious, leading a team, or w...

Why do so many successful people still feel stuck, anxious, disconnected, or unfulfilled? In this episode, Diana Alt sits down with brain health expert and licensed therapist Dr. Ketam Hamdan to explore the hidden patterns driving our thoughts, emotions, and behaviors. Drawing on her background in consulting, psychology, neuroscience, and brain mapping, Dr. Hamdan explains why understanding your "...

What happens when you stop trying to do everything yourself? In this episode, Diana sits down with Louise Sandoval, founder of Virtual Staff Pro, to talk about outsourcing, delegation, and building a support system that helps entrepreneurs grow sustainably. Louise shares how she went from medical laboratory science to running a global outsourcing agency and explains what business owners get wrong...

What actually separates high performers from the people who get promoted into leadership? In this episode, Diana Alt sits down with workforce strategist and founder Grace McCarrick to unpack the real-world value of soft skills, discernment, communication, and professional polish in today's workplace. Why soft skills matter more in the AI era The real meaning of discernment at work How leaders eval...

AI is changing hiring fast, but not always in the ways people think. In this conversation, Diana Alt sits down with recruiter and content creator Bonnie Dilber to unpack what's really happening behind the scenes in modern hiring, from AI-powered screening tools to the realities of career pivots in today's market. Transitioning from education into recruiting and tech Why strategic career pivots wor...

Networking doesn't have to mean awkward events or forced small talk. In this episode, Diana sits down with Greg Roche to break down a practical, low-pressure approach to building meaningful professional relationships especially for introverts.   Rethinking what "networking" actually means Why traditional networking advice doesn't work for introverts How Greg built his approach after being laid off...

What happens when you stop waiting for permission and start betting on yourself? Diana sits down with Kenny Booth to explore his unconventional path into tech, entrepreneurship, and landing a role at his dream company. If you've ever hesitated to take a risk, this episode will challenge how you think about failure and opportunity.  Kenny's nontraditional path into tech and business intelligence Tu...

In this milestone 50th episode, Diana reconnects with Angie Callen to explore how confidence is built through action not before it. They unpack the realities of entrepreneurship, creative risk-taking, and how embracing imperfection leads to meaningful growth in both work and life. ⏳ Timestamps 01:00 Meet Angie Callen & her new book 03:00 Confidence through action vs. perfection 07:00 The trap of...

In this episode of Work Should Feel Good, Diana sits down with product leader and consultant Michael Hirsch to explore what real product leadership looks like, especially as AI reshapes how product teams work. They discuss the difference between product management and product leadership, why most companies fail to prepare new leaders, and how AI can free product managers from tactical work so they...