Work. Shouldnt. Suck.

Tim Cynova

Work Shouldn't Suck is for people who refuse to accept that work has to be soul-crushing and stuck in dusty, outdated systems.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 answers from AI, and who can blame them?" by Ian Bogost (The Atlantic, Oct 2025)"AI Did The Job Interview. The Results Shocked Everyone" by Marc Ethier (Poets & Quants, Oct 2025)"Voice AI in Firms: A Natural Field Experiment on Automated Job Interviews" by Brian Jabarian and Luca Henkel"Why might AI-enabled interviews reduce candidates’ job application intention? The role of procedural justice and organizational attractiveness" by Wenhao Luo, Yuelin Zhang, and Maona Mu (Humanities and Social Sciences Communications, 2025)"Age and gender distortion in online media and large language models" by Douglas Guilbeault, Solène Delecourt, and Srinivasa Desikan (Nature, 2025)"Invisible Filters: Cultural Bias in Hiring Evaluations Using Large Language Models" by Pooja S. B. Rao, Laxminarayen Nagarajan Venkatesan, Mauro Cherubini, and Dinesh Babu Jayagopi (arXiv, 2025)"How AI-powered recruitment defies expectations about inclusion and transparency" by Mark Esposito and Ava Fitoussy (World Economic Forum, Sept 2025)"NYC Set to Enforce Law to Regulate Use of Automated Hiring Tools Starting July 5, 2023" by Joseph O’Keefe & William GreyArtificial Intelligence Legal Roundup: Colorado Postpones Implementation of AI Law as California Finalizes New Employment Discrimination Regulations and Illinois Disclosure Law Set to Take Effect (Seyfarth Shaw LLP, Sept 2025) About the GuestsABOUT CHAD GEEPET Chad Geepet is Work Shouldn’t Suck’s resident AI collaborator — a reflective analyst with a knack for connecting data, design, and humanity. Trained on far too many résumés and research papers, Chad brings curiosity (and occasional existential humor) to conversations about how technology is reshaping hiring and the future of work. They’re especially interested in what happens when we design systems that amplify care instead of bias — and in helping humans stay at the center of innovation. ABOUT KATRINA DONALD Katrina (she/her) is a regenerative systems designer, developmental strategist, thriving workplace practitioner, and both a certified recruiter and coach. She has become a trusted guide for individuals, teams, and organizations facilitating pivotal developmental moments, sparking curiosity in service of innovation, and supporting emergent change. With two decades of experience working across sectors, Katrina has helped folks develop their capacity to lead through complex challenges, embrace experimentation, make informed decisions, and design adaptive strategies that flow with the ever-changing dynamics of their work. She’s worked with community foundations and other non-profits, health agencies, post secondaries, arts and culture organizations, start-ups, social enterprises, family businesses, and more. This work spans everything from organizational design and learning, people and culture processes (including hiring, onboarding, training, coaching, and leadership development), to strategic evaluation, R&D, and system change and mission impact initiatives. Through her own consulting and coaching company, Ever-so-curious, and her collaboration with great partners like Shift Consulting and WSS HR Labs, Katrina works with the brave and the curious — those who are daring to bring forth what is new, what is next, and address what needs to change. Learn more at Ever-so-curious. ABOUT TIM CYNOVA Tim (he/him) is the host of the Work Shouldn’t Suck podcast, where he and guests explore bold ideas and practical strategies for creating workplaces where people thrive. At the consulting firm WSS HR Labs, he draws on deep experience leading and advising mission-driven organizations through growth, change, and complexity to help them dust off outdated policies, challenge default approaches, and design values-centered workplaces that align people strategy, organizational culture, and operational infrastructure. A certified Senior Professional in Human Resources (SPHR) and trained mediator, Tim’s path has taken him from orchestral trombonist to C-level roles in multiple $25M+ nonprofits around the globe. Whether consulting, teaching, or recording, he brings curiosity, candor, and a knack for making workplace design engaging and actionable.

    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 much-needed service—while simultaneously disrupting business as usual. They became a BPI- and PHIUS-certified professional, are an ICF PCC-accredited coach, and have been providing business consulting, coaching, and project management services to companies throughout North America over the past ten years. As Director of Vision and Strategy, Mel leads the effort to generate and hold HELM’s vision of making a positive impact on the world in the areas of climate change and social justice. They live in Brattleboro, VT, with their wife and son where they enjoy monthly hikes on big mountains, speaking Spanish, and listening to music. ABOUT KATE STEPHENSON | Co-Founder & Director of Training & Finance, HELM Kate (she/her) is an experienced leader in the fields of green building, professional education, sustainability, and business management. She’s worked with established and emerging businesses and non-profits to achieve triple bottom line metrics, develop business systems, and plan for a dynamic and resilient future. She has deep experience in post-secondary education, and led the Yestermorrow Design/Build School for over thirteen years. Kate helped to develop and is a facilitator for NESEA’s BuildingEnergy Bottom Lines program. Kate is a Senior Fellow of the Environmental Leadership Program, a member of the Montpelier Energy Advisory Committee, and serves on the Boards of NESEA and the Studio for High Performance Design and Construction. She holds a MS in Management from Antioch University New England and a BA in Anthropology and Environmental Science from Haverford College. ABOUT TIM CYNOVA Tim (he/him) is the host of the Work Shouldn’t Suck podcast, where he and guests explore bold ideas and practical strategies for creating workplaces where people thrive. At the consulting firm WSS HR Labs, he draws on deep experience leading and advising mission-driven organizations through growth, change, and complexity to help them dust off outdated policies, challenge default approaches, and design values-centered workplaces that align people strategy, organizational culture, and operational infrastructure. A certified Senior Professional in Human Resources (SPHR) and trained mediator, Tim’s path has taken him from orchestral trombonist to C-level roles in multiple $25M+ nonprofits around the globe. Whether consulting, teaching, or recording, he brings curiosity, candor, and a knack for making workplace design engaging and actionable.

    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 NAVIDA NURANEY Navida (she/her) is a liberatory coach, facilitator and organizational consultant. At the heart of her life and work is a commitment to nourishing people through practices that center love, justice and liberation. She has held leadership roles across start-ups, nonprofits, and municipal government, always with a commitment to fostering healthier, more creative, and relationally alive workplaces. She holds an MBA from the University of British Columbia with a focus on Human Resources and Organizational Development. Her early studies in architecture and graphic design enabled her to see how beauty and aesthetics shape experience. Navida has ancestral roots in Gujarat, India and was born on the unceded lands of the xwməθkwəy̓əm (Musqueam), Sḵwx̱wú7mesh (Squamish) and səlil̓ilw̓ətaʔɬ (Tsleil-Waututh) Peoples in so called Vancouver, Canada. Discover more at www.navida.ca. ABOUT TIM CYNOVA Tim (he/him) is the host of the Work Shouldn’t Suck podcast, where he and guests explore bold ideas and practical strategies for creating workplaces where people thrive. At the consulting firm WSS HR Labs, he draws on deep experience leading and advising mission-driven organizations through growth, change, and complexity to help them dust off outdated policies, challenge default approaches, and design values-centered workplaces that align people strategy, organizational culture, and operational infrastructure. A certified Senior Professional in Human Resources (SPHR) and trained mediator, Tim’s path has taken him from orchestral trombonist to C-level roles in multiple $25M+ nonprofits around the globe. Whether consulting, teaching, or recording, he brings curiosity, candor, and a knack for making workplace design engaging and actionable.

    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 for The Journal of Arts Management, Law, and Society, and a co-editor of Artivate, a journal on arts entrepreneurship. His book, The Artful Manager: Notes on the Business of Arts and Culture, is available from arts axis press. And he's producing an array of free and public resources to support Arts Management practitioners – online textbook, weekly newsletter, short video series – all available at ArtsManaged.org. ABOUT TIM CYNOVA Tim Cynova is the host of the Work Shouldn’t Suck podcast, where he and guests explore bold ideas and practical strategies for creating workplaces where people thrive. At the consulting firm WSS HR Labs, he draws on deep experience leading and advising mission-driven organizations through growth, change, and complexity to help them dust off outdated policies, challenge default approaches, and design values-centered workplaces that align people strategy, organizational culture, and operational infrastructure. A certified Senior Professional in Human Resources (SPHR) and trained mediator, Tim’s path has taken him from orchestral trombonist to C-level roles in multiple $25M+ nonprofits around the globe. Whether consulting, teaching, or recording, he brings curiosity, candor, and a knack for making workplace design engaging and actionable.

    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 Capital, CARE, Vistage Atlanta, , Collab Capital, BIA, and the Russell Innovation Center for Entrepreneurs (RICE). In recognition of her work with couples, Chantel has been named one of the Three Best Rated Marriage Counselors in the metro Atlanta region since 2019, determined by an independent review that took into consideration factors like client reviews, customer satisfaction, and general excellence. Chantel lives in Atlanta, with her husband of 30 years, her dogs Thunder and Bourbon, and her Maine Coon cat named Ripley who thinks she’s a dog too. Chantel has three children who love to travel just as much as she does. ABOUT TIM CYNOVA Tim Cynova is the host of the Work Shouldn’t Suck podcast, where he and guests explore bold ideas and practical strategies for creating workplaces where people thrive. At the consulting firm WSS HR Labs, he draws on deep experience leading and advising mission-driven organizations through growth, change, and complexity to help them dust off outdated policies, challenge default approaches, and design values-centered workplaces that align people strategy, organizational culture, and operational infrastructure. A certified Senior Professional in Human Resources (SPHR) and trained mediator, Tim’s path has taken him from orchestral trombonist to C-level roles in multiple $25M+ nonprofits around the globe. Whether consulting, teaching, or recording, he brings curiosity, candor, and a knack for making workplace design engaging and actionable.

    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 power of the arts to foster personal and communal growth. Kate believes deeply in Art as Belonging—the idea that the arts are a vital tool for building inclusive spaces where all voices feel seen, heard, and valued. She is committed to creating environments where creativity becomes a catalyst for connection, equity, and empowerment. Kate possesses a keen ability to craft strategic business plans that yield tangible results, contributing to the development of a dynamic and lively arts community hub. Her work consistently reflects her core values of accessibility, inclusion, and community engagement. In recognition of her outstanding contributions, Kate was named as part of Avenue Magazine's prestigious Top 40 Under 40 class of 2020. katestadel.com ABOUT TIM CYNOVA Tim Cynova is the host of the Work Shouldn’t Suck podcast, where he and guests explore bold ideas and practical strategies for creating workplaces where people thrive. At the consulting firm WSS HR Labs, he draws on deep experience leading and advising mission-driven organizations through growth, change, and complexity to help them dust off outdated policies, challenge default approaches, and design values-centered workplaces that align people strategy, organizational culture, and operational infrastructure. A certified Senior Professional in Human Resources (SPHR) and trained mediator, Tim’s path has taken him from orchestral trombonist to C-level roles in multiple $25M+ nonprofits around the globe. Whether consulting, teaching, or recording, he brings curiosity, candor, and a knack for making workplace design engaging and actionable.

    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 BENNETT Jamie has been providing strategic advice through a partnership with Lord Cultural Resources to clients that include the American Museum of Natural History, the Barr Foundation, the BIG We Foundation, the Greater Columbus Arts Council, the MacArthur Foundation, PolicyLink, Starfish Accelerator, and Walk With Amal. Previously he ran ArtPlace America and worked at the National Endowment for the Arts as a political appointee in President Obama’s administration and at the NYC Department of Cultural Affairs during Mayor Bloomberg’s administration. ABOUT LAUREN RUFFIN Approaching challenges with multiple perspectives, Lauren Ruffin creates solutions bridging technology, art, and social impact. She is the Director and Lead Strategist of Arts & Cultural Programming at Michigan Central's Detroit innovation campus and teaches at Arizona State University's MIX Center. As a 2025 Lewis Latimer Fellow, she explores ethical AI applications for oral histories. Ruffin co-founded CRUX Cooperative supporting immersive artists and previously served as Fractured Atlas Co-CEO where she founded the Artist Campaign School. With a J.D. from Howard University and experience spanning arts administration and education, she remains committed to empowering creative communities while serving on the Black Innovation Alliance board. ABOUT TIM CYNOVA Tim Cynova is the host of the Work Shouldn’t Suck podcast, where he and guests explore bold ideas and practical strategies for creating workplaces where people thrive. At the consulting firm WSS HR Labs, he draws on deep experience leading and advising mission-driven organizations through growth, change, and complexity to help them dust off outdated policies, challenge default approaches, and design values-centered workplaces that align people strategy, organizational culture, and operational infrastructure. A certified Senior Professional in Human Resources (SPHR) and trained mediator, Tim’s path has taken him from orchestral trombonist to C-level roles in multiple $25M+ nonprofits around the globe. Whether consulting, teaching, or recording, he brings curiosity, candor, and a knack for making workplace design engaging and actionable.

    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 redevelopment and transformation of the former BRT Power Station in Brooklyn, which was named a New York City Landmark in 2019. Dixon and her team conducted intensive workshops and consultations with artists to develop the institution’s programming, organizational structure and physical planning. Powerhouse was a response to the needs for production space, fabrication expertise and support for artists working in traditional materials that is rapidly disappearing in New York City. In addition to the institutional development, Dixon led all aspects of programming and rehabilitating the 170,000 square-foot facility designed by architecture firm Herzog & de Meuron. Dixon served as the Director of Special Projects at Brooklyn Academy of Music (BAM) from 2011 to 2014 where she established public art programming initiatives in the neighborhood, including works by KAWS and David Byrne. With BAM’s executive team, she also led capital and program planning efforts to grow and expand the institution. Prior to BAM, she was the Chief of Staff at the NYC Department of Cultural Affairs leading special initiatives for the Commissioner, as well as, overseeing the agency’s $700 million capital funding portfolio. From 2007 to 2010 as the Director of Planning and Development at the Downtown Brooklyn Partnership, she led the site development, arts program planning and administration of the Downtown Brooklyn Cultural District. Dixon holds B.A. in Architecture from Yale University and a Master of International Affairs from Columbia University. She lives with her husband and daughter in Red Hook, Brooklyn. Shaun Leonardo, Co-Director, Socrates Sculpture Park haun Leonardo has dedicated over 15 year of his professional career to arts administration at the intersection of community engagement, public programming, and experimental pedagogies. Deeply invested in processes of reciprocal exchange, Leonardo’s work flows from a belief in collaborative leadership and artistic visioning. Leonardo’s professional life began at Socrates (2005-2015) as its special events manager before expanding into the role of Socrates’ Director of Public Programs. Over 11 seasons, he envisioned and created new program initiatives and educational curriculum, including the development of the Park’s first workshop series dedicated to adults and teens and the implementation of Socrates’ first onsite and in-school high school-level, sculpture classes. His tenure was marked by collaboration with over 40 cultural and community organizations, leading to the establishment of the Park’s Healthy Living and Performance initiatives, as well as the tripling of the park’s educational offerings. From 2015-2017, Leonardo served at the New Museum’s first Manager of School, Youth & Community Programs, developing programs and accommodations for specific audience groups, both those under the umbrella of school partnerships, designed for high school teachers and students, and new initiatives in the area of community engagement. From 2018-2020, Leonardo acted as Pratt Institute’s inaugural School of Art Visiting Fellow, instigating dialogues amongst students, faculty, and staff, as well as others outside the Institute, to challenge ideas on community and belonging, while shaping possibilities of ethical community engagement. And most recently, Leonardo served as Co-Director of the Brooklyn-based Recess, helping guide the organization’s continuous evolution as an engine of social change. Shaun joined Recess in 2016, initiating the art-based diversion program Assembly as its project and curricular lead, while also acting as the project’s first facilitator. Over the course of nearly 9 years, Shaun continued to expand his role, ultimately being invited to fill the organization’s first co-directorship with founder Allison Freedman Weisberg in 2021. And during the last almost four years, Shaun took on the effort of guiding Recess through the pandemic onto thriving both programmatically and fiscally. His time was dedicated to internally operationalizing care and accountability, while pushing experimentation within the org’s external-facing programming. He is a Brooklyn-based artist from Queens. He received his MFA from the San Francisco Art Institute and is a recipient of support from Creative Capital, Guggenheim Social Practice, Art for Justice and A Blade of Grass. His work has been featured at The Guggenheim Museum, the High Line, New Museum, MASS MoCA and The Bronx Museum, and profiled in the New York Times and CNN. His first major public art commission, Between Four Freedoms, premiered at Four Freedoms Park Conservancy, in the fall of 2021. Shaun lives in Brooklyn with his wife and two daughters. Tim Cynova, SPHR (he/him) is the COO/CHRO of WSS HR LABS, an HR and org design consultancy helping to reimagine workplaces where everyone can thrive. He is a certified Senior Professional in Human Resources (SPHR) and a trained mediator, and has served on the faculty of Minneapolis College of Art & Design, the Banff Centre for Arts & Creativity (Banff, Canada) and The New School (New York City) teaching courses in People-Centric Organizational Design, and Strategic HR. In 2021, he concluded a 12-year tenure leading Fractured Atlas, a $30M, entirely virtual non-profit technology company and the largest association of independent artists in the U.S., where he served in both the Chief Operating Officer and Co-CEO roles (part of a four-person, shared, non-hierarchical leadership team), and was deeply involved in its work to become an anti-racist, anti-oppressive organization since they made that commitment in 2013. Earlier in his career, Tim was the Executive Director of The Parsons Dance Company and of High 5 Tickets to the Arts in New York City, had a memorable stint with the Cincinnati Symphony Orchestra, was a one-time classical...

    39 min

Ratings & Reviews

4.9
out of 5
17 Ratings

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.