Work. Shouldnt. Suck.

Tim Cynova
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Work Shouldn't Suck is for people who refuse to accept that work has to be soul-crushing and stuck in dusty, outdated systems. It’s for those building the future. Hosted by Tim Cynova, SPHR and COO/CHRO of WSS HR Labs, this podcast brings you honest, practical conversations with leaders, innovators, and changemakers redesigning work for the better—and proving it's possible, even in the messiest, most resource-constrained environments. Exploring questions like: How do you build organizations where people actually thrive? How do you design for humans in an AI-accelerated world? How do you translate values into resilient, scaleable systems? What does it take to make real change when resources are tight? Field reports from people building what comes next. Subscribe now.

  1. Hiring in the Age of A.I.

    10/28/2025

    Hiring in the Age of A.I.

    Artificial intelligence isn’t just changing how we work—it’s reshaping how we hire. In this episode, hosts Tim Cynova and Katrina Donald explore the impact of AI on hiring practices. Joined by their unique, algorithmic guest—Chad Geepet (pronounced GPT 😉), part thought partner, part mirror, and all algorithm—they unpack what AI is really doing to hiring systems, not just in headlines but in the messy middle where résumés, interviews, and algorithms now mingle. Drawing on eight recent studies and articles, they explore: Learning to Speak Algorithm: How job seekers and employers are adapting to (and gaming) A.I. systems — and what that reveals about a hiring culture that prizes efficiency over connection.A.I. Interviews and the Illusion of Fairness: Exploring why structured doesn’t always mean just, and how transparency can restore trust in the interview process.Invisible Filters: Where bias hides in plain sight — inside the data, the design choices, and even our definitions of “professionalism.”Trust and Transparency as the New Currency: How sharing how the system works can turn skepticism into credibility.From Risk to Responsibility: Designing for Care: How bias audits, explainability, and “A.I. use statements” can shift compliance from checkbox to culture — turning care into a competitive edge. Together, Tim, Katrina, and Chad explore the tensions between efficiency and care, risk and responsibility, asking questions like: What would it look like to design hiring as an act of care? And how do we make sure that technology reflects our values—not the other way around? “AI won’t replace humans in hiring—it will amplify whatever values are already in play.” — Chad GeepetWhether you’re a job seeker navigating an algorithmic gauntlet or an HR leader experimenting with new tools, this conversation offers both insight and invitation: to build hiring processes that are transparent and deeply human. 📺 Watch the animated edition of the podcast episode! Highlights: 01:39 Meet Chad Geepet: An Algorithmic Guest02:49 The Big Story: Trust in Hiring04:03 Theme 1: Learning to Speak Algorithm06:41 Reactive Creativity in Job Seeking17:09 Theme 2: AI Interviews and the Illusion of Fairness 26:46 Theme 3: Invisible Filters: Bias in Data and Design33:16 The Importance of Bias Audits34:21 AI as a Mirror in Hiring35:05 Feedforward Loops and Cultural Impact35:59 Layers of Transparency and Accountability37:42 Theme 4: Trust and Transparency as the New Currency38:18 Transparency as a Competitive Advantage46:54 Theme 5: From Risk to Responsibility: Designing for Care in Hiring1:00:32 The Future of AI in Hiring Links & Resources"Recruiters Use A.I. to Scan Résumés. Applicants Are Trying to Trick It" by Evan Gorelick (The New York Times, Oct 2025)"Job Interviews Are Broken: People are sneaking...

    1h 5m
  2. Building Justice: Rethinking Construction, Climate, and Care

    10/15/2025

    Building Justice: Rethinking Construction, Climate, and Care

    Construction sits at the intersection of some of today’s most urgent challenges—workforce shortages, climate change, housing insecurity, and culture change. It’s also where solutions are being built, literally and figuratively. In this episode, host Tim Cynova continues the Climate Justice HR series with Mel Baiser and Kate Stephenson, co-founders of HELM Construction Solutions, a people- and planet-forward consulting firm helping construction companies transform their culture, strengthen business resilience, and lead on climate action. They explore: What it means to embed justice, care, and clarity into hiring, leadership, and everyday operations.Why construction’s cultural transformation could unlock lessons for every sector.How HELM helps companies evolve from “chaotic job sites” to thriving, values-aligned workplaces.The industry’s overlapping crises—from labor shortages and mental-health challenges to ICE raids and climate emergencies.How coaching, community-building, and shared learning can shift entire systems, not just individual job sites. Despite the gravity of the challenges, Mel and Kate also share a deep sense of hope—that by centering connection, humility, and interdependence, we can build not only structures but the systems that sustain us. Highlights:01:06 Meet the Guests: Kate Stephenson and Mel Baiser02:19 Personal Backgrounds and Career Paths07:30 The Origin and Vision of HELM Construction Solutions12:55 Challenges in the Construction Industry16:38 HELM's Approach to Addressing Industry Challenges28:09 Leadership and Business Development41:51 Climate Justice and Workforce Issues51:11 Client Success Stories and Future Vision Links & ResourcesRecording of the event “Building Solidarity: Construction Workers, Jobsite Safety, and ICE” mentioned during the episode.HELM Resource Library containing a wealth of materials to inform, support (and occasionally entertain) you as you develop your company.HELM Job Board if you're looking to join a forward-looking company with a great work culture. About the GuestsABOUT MEL BAISER | Co-Founder & Director of Vision & Strategy, HELM Mel (they/them) believes in the transformative potential of the construction sector. This industry, which contributes nearly 40% of the carbon emissions wreaking havoc on our planet, is well positioned to become a catalyst for change in the movement for climate justice. Mel is passionate about making that happen. One could say Mel was destined to enter the construction trades. A 7th-generation Vermonter, they come from a long line of builders and homesteaders. After years working as a residential carpenter, project manager, and estimator in both the San Francisco Bay Area and New England, Mel couldn’t ignore the tremendous opportunities for improvement they saw for the industry. With a degree in sociology, decades of organizing experience, and a desire to engage with the building world, Mel co-founded HELM to provide a

    59 min
  3. Deep Democracy at Work

    09/17/2025

    Deep Democracy at Work

    Nonprofit teams. City governments. Unionizing workplaces. Pet pics in the team Slack thread. No matter the setting, one thing is certain: conflict is going to show up. But what if conflict isn’t the problem—it’s the way we relate to it that matters? In this episode, Tim Cynova is joined by facilitators, coaches, and organizational practitioners Navida Nuraney and Camille Dumond to explore the Lewis Method of Deep Democracy, a practical and surprisingly playful framework for navigating disagreement, surfacing unspoken truths, and building real relational capacity in teams. We explore what makes Deep Democracy distinct from traditional facilitation approaches, why it matters more than ever in today’s complex workplaces, and how even seemingly small tensions—like whether your team’s Slack channel should be for logistics or life updates—can benefit from the tools and mindset Deep Democracy offers. And in true WSS style, we don’t just talk about the framework—we try it out! Together, Tim, Navida, and Camille take the “Debate Tool” for a spin, exploring the polarity between “Just do the job” and “Bring your whole(ish) self to work.” Spoiler: You might agree with both. Highlights:03:55 Understanding the Lewis Method of Deep Democracy05:47 Practical Tools for Navigating Conflict10:30 Personal Experiences with Deep Democracy17:07 Applying Deep Democracy in Organizations20:41 The Importance of Addressing Conflict Now23:50 Exploring the Debate Tool24:34 Exploring the Polarity of Bringing Your Whole Self to Work29:58 Debating the “Just Do the Job” Perspective33:16 Balancing Both Sides: Insights and Reflections37:03 Practical Applications and Tools for Conflict Resolution41:00 Upcoming Opportunities Links & ResourcesLewis Deep DemocracyWaterline Co-opRole Theory Companion: Applying Deep Democracy ($16 CAD) Camille Dumond's book exploring the secret sauce behind the method; includes a number of leadership applications.International Association of Process Oriented PsychologyWork Won’t Love You Back by Sarah Jaffe About the GuestsABOUT CAMILLE DUMOND Camille (she/they) is a settler of Indo-Caribbean and French-Irish descent living on unceded territories of the xwməθkwəy̓əm (Musqueam), Sḵwx̱wú7mesh (Squamish) and səlil̓ilw̓ətaʔɬ (Tsleil-Waututh) peoples. Her practice is as a somatic therapist, conflict and group facilitator. With over 20 years experience facilitating change processes, she brings depth psychology, social movement analysis, and embodied spirituality to organizational change. This allows her to support a sense of center and even playfulness in complex, emergent situations.  Camille co-founded the Refugee Livelihood Lab with Nada Elmasry to amplify the impact and transformational influence of racialized leaders with lived experience of forced displacement and migration. She is principal at Dignity Facilitation.  ABOUT a...

    47 min
  4. Nonprofit Governance in Uncertain Times

    09/09/2025

    Nonprofit Governance in Uncertain Times

    In this episode, host Tim Cynova is joined by E. Andrew Taylor—professor, researcher, consultant, board chair, and longtime colleague—to explore the messy, meaningful, and often misunderstood world of nonprofit boards. Together, they take a fresh look at what boards are really for, why bylaws matter more than most people realize, and how values-based governance can meet the challenges of an unpredictable world. Dispelling common myths, Andrew reframes the governing board as a servant leader to the public it represents. The conversation spans recent high-profile governance stories at institutions like OpenAI and the Kennedy Center for the Performing Arts, the importance of stress-testing bylaws, and the unique hurdles boards face in today’s rapidly shifting environment. Spoiler Alert: Instead of seeing risk as threat, this episode invites us to (re)imagine governance as a space for resilience, creativity, and collective leadership. Whether you’re curious about joining your first nonprofit board, navigating one as an executive, or rethinking governance structures in your own organization, this conversation will spark fresh thinking about how boards can evolve to meet the moment. Highlights: 01:11 Current Issues in Nonprofit Governance06:01 The Role and Challenges of Nonprofit Boards07:36 Understanding Nonprofit Organizations17:22 The Importance of Bylaws21:13 Revising Bylaws for Modern Governance21:35 The Concept of Minimum Viable Everything22:32 Using AI for Policy Development24:57 The Role of the Board in Nonprofits25:37 Bridging the Gap Between Board and Staff29:32 Navigating Risk and Collaboration35:45 The Importance of Collective Action Related ResourcesArtsManaged Field Guide, E. Andrew Taylor’s online "textbook"ArtsManaged Field Notes, E. Andrew Taylor’s weekly newsletter, which includes a page dedicated to governance-relevant posts“Trump has purged the Kennedy Center’s board, which in turn made him its chair – why does that matter?” by E. Andrew Taylor published in The Conversation“OpenAI and Nonprofit-Money Collaborations” by Gene Takagi via NEO Law Group“Facing Trump threat, Corporation for Public Broadcasting amends bylaws to protect directors from removal” by Austin Fuller BiosABOUT E. ANDREW TAYLOR Andrew Taylor thinks (a bit too much) about organizational structure, strategy, and management practice in the nonprofit arts. An Associate Professor and Director of Arts Management at American University, he also consults for cultural, educational, and support organizations throughout North America. Andrew is past president of the Association of Arts Administration Educators, board chair for Fractured Atlas, consulting editor...

    43 min
  5. Thera-Coaching Through Uncertainty

    08/28/2025

    Thera-Coaching Through Uncertainty

    In this episode of the Work Shouldn’t Suck podcast, host Tim Cynova is joined by Chantel Cohen—licensed therapist, executive coach, and founder of CWC Coaching and Therapy—for a powerful conversation at the intersection of career and mental wellness. Chantel works with entrepreneurs and corporate leaders to help them navigate the messy, magical overlap of identity, leadership, stress, relationships, and purpose. Through coaching and therapy, she supports individuals and teams in showing up more fully—for themselves, for each other, and for the work they believe in. We explore: Why founders and professionals benefit from support beyond the workplaceThe role of relationships in shaping how we lead and liveWhat couples therapy can teach us about co-leadership and team dynamicsHow to stay grounded when facing burnout, job transitions, or identity detachment from workWhy it’s worth asking: “What is this all for?”—and how that question can change your relationship to career, purpose, and community Whether you’re curious about how to navigate big career shifts, wondering why work feels lonelier than it used to, or looking for ways to lead with more compassion and clarity, this episode offers both practical tools and soulful reminders. 🎧 Listen in for stories, strategies, and truth-telling about the emotional labor of leadership—and the joy and fun that can come from not doing it alone. Highlights Chantel's Journey and Approach to Coaching (01:17)Understanding and Managing Mental Wellness (02:39)The Importance of Relationships and Support Systems (06:03)Work, Identity, and Values (10:05)Staying Grounded and Finding Meaning (19:20)Balancing Personal and Professional Dynamics (23:18)Conclusion and Final Thoughts (25:02) BiosABOUT CHANTEL COHEN Chantel Cohen is a therapist, life coach, and executive communications coach dedicated to helping individuals, couples, and groups in their journeys of self-improvement, career advancement, and relationship enhancement. She specializes in Emotionally Focused Therapy (EFT) for couples and created the Become One Again™ Method to address every aspect of a client’s life, including their mental wellness, their career or business, and their significant relationships both personally and professionally. After earning her undergraduate degree from the University of California, Los Angeles, Chantel worked as a program specialist for individuals with psychiatric and physical challenges. She then moved to New York City, where she earned a Master’s degree and Coaching Certification in Executive Coaching and Counseling from Columbia University. At St. Luke’s Hospital in New York, Chantel focused on counseling young adults facing depression, anxiety, suicidal ideation, and ADHD. In 2011, Chantel founded CWC Coaching & Therapy in Atlanta, Georgia, where she and her team provide mental health services with a business coaching lens. While her clients are from all walks of life, she works extensively with couples in relationship distress, individuals managing anxiety, ADHD, and depression, and those seeking career transitions or professional growth. Her compassionate approach and use of tools like the Myers-Briggs Type Indicator and the DISC help clients gain self-awareness and improve their communication skills. Chantel particularly works with business leaders in individual sessions or larger groups in corporate settings. Her roster of clients includes Google, Coca-Cola, Lenovo, Coursera, Village...

    29 min
  6. Hiring as Improv: Embracing the Unscripted in Job Searches

    08/21/2025

    Hiring as Improv: Embracing the Unscripted in Job Searches

    In this episode, we explore what it means to approach hiring as improvisation—especially from the perspective of job seekers navigating ambiguous, pressure-filled, and often inequitable processes. Joining host Tim Cynova are two brilliant minds who live at the intersection of the performing arts and organizational transformation: Courtney Harge, founder of CHarge Advisory Hub and Kate Stadel, General Manager of Arts at YMCA Calgary. Both bring deep experience in theater and arts leadership—and share how their training has shaped how they build teams, lead organizations, and show up in interviews. We explore: Why job seekers rarely get a full script—and how to adapt when you’re handed a vague promptHow theater skills like reading a room, holding tension, and embracing failure help candidates and hiring managers alikeWhat hiring managers can do to reduce unnecessary ambiguity and bring more care and intention into the processWhy “just be yourself” is both true and insufficient advice—and how to pick which version of yourself to show up asWhy sometimes the goal is to “interview to get fired”—so you and the organization can learn quickly if it’s a fit Whether you’re hiring, job seeking, or just rethinking the systems we all move through, this episode offers insight, laughter, and plenty of permission to improvise. Highlights: Meet the Guests (01:28)Theater Skills in Leadership and Hiring (02:50)The Art of Storytelling in Job Interviews (07:05)Embracing Feedback and Authenticity (08:54)Reimagining the Job Seeking Process (20:03)Evaluating Candidates Beyond Skills (22:53)The Purpose of Interview Questions (23:42)Challenging Traditional Hiring Practices (24:49)Authenticity in Job Interviews (27:17)The Importance of Values and Kindness (28:05)Navigating Interview Dynamics (29:40)The Role of Improvisation in Interviews (38:07) BIOS ABOUT COURTNEY HARGE Courtney is a Midwest-made, Brooklyn-refined, theater maker, facilitator, creative leader, and cultural strategist. She has been working in the service of artists, art-making, and healthy organizations for the last fifteen years. Recently, she was the CEO of OF/BY/FOR ALL, a nonprofit dedicated to improving arts, civic, and cultural institutions through community-centered strategizing. She is the Founder and Producing Artistic Director of Colloquy Collective. Her work on anti-lynching plays was featured on NPR in 2015. She’s also the Lead Consultant for CHarge Advisory Hub, a consulting service offering human-centered, tech-supported solutions for mission-driven organizations. She holds an MPS with Distinction in Arts and Cultural Management from Pratt Institute and a BFA with Honors from the University of Michigan in Theater Performance. Courtney is also an alum of APAP’s Emerging Leaders Institute, artEquity’s Facilitator Training, and Lead for Liberation’s Conscious Executive program. Learn more about her and her work at courtneyharge.com and chargeadvisoryhub.com. ABOUT KATE STADEL Currently the General Manager of Arts for YMCA Calgary, Kate is a dedicated community leader and arts administrator with a wealth of experience spanning 20 years. Her passion lies in leveraging the transformative

    44 min
  7. Co-CEO Chronicles: Navigating Growth, Change, and Complexity

    08/18/2025

    Co-CEO Chronicles: Navigating Growth, Change, and Complexity

    Discover the real-world lessons of co-leadership in this two-part conversation with Americans for the Arts’ interim Co-CEOs, Suzy Delvalle and Jamie Bennett. Recorded at the start and end of their nine-month shared leadership journey, host Tim Cynova explores how they divided responsibilities, built trust, navigated challenges, and embraced the benefits of having two leaders at the helm. From the decision to take the roles together, to the cultural shifts and surprises along the way, this episode offers candid insights for executives, boards, and organizations exploring interim leadership, shared power, and values-driven change. We explore: How the co-leadership arrangement came together and why neither would have said yes without the otherStructuring responsibilities, building trust, and navigating shared decision-making in a high-profile national nonprofitThe benefits—and surprises—of having two leaders instead of one, both internally and externallyHow interim roles can create space for experimentation, transparency, and cultural changeLessons for boards, staff, and leaders considering co-leadership or shared power models Part One captures Suzy and Jamie’s hopes, plans, and questions as they begin. Part Two—where Tim is joined by podcasting’s favorite co-host Lauren Ruffin—unpacks what worked, what didn’t, and what they wish they’d had time to do. Whether you’re curious about co-leadership, fascinated by interim executive roles, or wondering how to lead in turbulent times, this episode offers an honest, behind-the-scenes look at shared leadership in practice. Listen in and discover: How two leaders, one job, and a finite timeline reshaped an organization’s transition—and their own perspectives on leadership. Highlights: 00:00 Introduction and Podcast Episode Origins00:56 Meet the Interim Co-CEOs02:09 The Co-Leadership Journey Begins04:41 Structuring the Co-Leadership06:17 Intentional Interim Ministry08:06 Challenges and Opportunities10:23 Shared Leadership Dynamics14:51 Project Management and Organizational Goals17:39 Reflecting on Interim Leadership25:41 Future Vision and Organizational Evolution33:34 Part Two: Reflecting on the Journey35:42 Entering the Interim Role36:35 Navigating Co-CEO Dynamics37:36 Building Trust with Staff39:13 Reflections on Co-Leadership41:26 Challenges and Benefits of Shared Leadership43:18 Interim Leadership Insights45:23 Future of Leadership Models48:13 Final Thoughts and Reflections BIOS ABOUT SUZY DELVALLE Suzy is a seasoned advisor who has leveraged her expertise to drive strategic growth and stability in arts organizations, most recently through interim leadership roles at A Blade of Grass, Artadia, Socrates Sculpture Park, and United States Artists. With a proven track record of success, she previously led Creative Capital and was one of the architects of Artists Relief, a $25 million initiative that provided emergency support to artists during the COVID-19 pandemic. She was the founding executive director of The Sugar Hill Children’s Museum of Art and Storytelling following tenures at El Museo del Barrio and American Composers Orchestra. ABOUT JAMIE...

    1h 11m
  8. Socrates Sculpture Park: Exploring Art, Community, and Experimentation

    06/10/2025

    Socrates Sculpture Park: Exploring Art, Community, and Experimentation

    In this on-location episode, host Tim Cynova visits Socrates Sculpture Park, a creative haven on along New York City’s East River. Once a landfill, Socrates is now a vibrant public space where artists and community members come together to imagine what’s possible. Co-Directors Katie Dixon and Shaun Leonardo join Tim to reflect on the park’s origins, its role in a rapidly changing neighborhood, and the creative and civic experiments it cultivates every day. Together, they explore what it means to lead an arts organization in uncertain times, how their version of co-leadership works in practice, and why places like Socrates are essential. From the artist-led programming to the practicalities of funding, from personal memories to the future vision for the park, this wide-ranging conversation is a thoughtful reminder of the value of places that are not just made for community, but by and with community. Quotables“[Places like Socrates] are not an extra, or an added-good, or a nice-but-not-necessary. They are absolutely critical to a well-functioning society and to the ability of our neighbors, our fellow New Yorkers, our fellow citizens, to have the space to interact, to practice being human together… and to be able to fail at that sometimes. That requires space, and it requires care, and it requires a kind of attention that is important and necessary, and not to be taken for granted.” —Katie Dixon “Socrates—as an arts institution and a public park—is the most democratic experiment that I've ever come to know because of our responsibility to community. Therefore, all the creative and public programming offerings that we make to our constituencies offers such a myriad of entry points to being here. I want to emphasize this idea of being the experiment is in not only the experience of art, but what art catalyzes in regards to a sense of belonging. Whether you're coming here for kayaking, the gardens, to walk your dog, to be part of some of the sculpture workshops, performances, etc., the art is unfolding whether you're conscious of it or not.” —Shaun Leonardo Highlights:Personal Histories and Inspirations (02:34)The Evolution of Socrates Sculpture Park (05:12)Community Engagement and Programming (08:01)The Importance of Cultural Nonprofits (10:06)Navigating Uncertainty and Sustaining Community Spaces (14:23)The Co-Directorship Model (27:27)Conclusion and Reflections (35:24) Related Resources:“Cultural nonprofits are the unsung stewards of NYC: Why these organizations deserve our support.” by Katie Dixon & Shaun LeonardoSocrates Sculpture ParkMark di SuveroChâteau le Woof BiosKatie Dixon, Co-Director, Socrates Sculpture Park With over two decades of experience working at the intersection of the arts, architecture, and urban planning, Katie Dixon has created cross-sector partnerships and new artist-led programming for a broad range of arts, culture and civic organizations. Her work is based in collaborative research and centers consensus-building and cooperation among many different publics, institutions, government agencies and funders. From 2014 to 2021, as the CEO of Powerhouse Arts, Dixon established the vision for a new artist-led institution and led the...

    39 min
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4.9
out of 5
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About

Work Shouldn't Suck is for people who refuse to accept that work has to be soul-crushing and stuck in dusty, outdated systems. It’s for those building the future. Hosted by Tim Cynova, SPHR and COO/CHRO of WSS HR Labs, this podcast brings you honest, practical conversations with leaders, innovators, and changemakers redesigning work for the better—and proving it's possible, even in the messiest, most resource-constrained environments. Exploring questions like: How do you build organizations where people actually thrive? How do you design for humans in an AI-accelerated world? How do you translate values into resilient, scaleable systems? What does it take to make real change when resources are tight? Field reports from people building what comes next. Subscribe now.

Information

  • Creator
    Tim Cynova
  • Years Active
    2019 - 2025
  • Episodes
    90
  • Rating
    Clean
  • Copyright
    © All rights reserved
  • Show Website
    Work. Shouldnt. Suck.