Work Shouldn't Suck is for people who refuse to accept that work has to be soul-crushing and stuck in dusty, outdated systems.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.
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Are Non-Linear Careers The New Linear?
2026/07/28
Emil Kang became the head of one of the largest orchestras in the U.S. at 31. He went on to direct arts grantmaking at The Mellon Foundation, where he helped imagine Creatives Rebuild New York, a $125 million workforce development initiative during the heart of the pandemic. Now he's an arts consultant, writer, and educator based in New York City, and his Substack, The Reprise, has become required reading for people working in and around arts institutions.
In this episode, host Tim Cynova and Emil trace what all those vantage points reveal about careers, hiring, and the institutions we build. They start with the question behind one of Emil's essays: who are you without the title? From there, the conversation moves through nonlinear careers, the relational job search most people skip, what search committees often get wrong before a search even launches, and why nonprofit governance often operates with so little accountability.
Whether you're navigating your own next move, serving on a search committee, or wondering why a nonprofit board works the way it does, we explore all of those things and more.
Links & ResourcesThe Reprise, Emil's SubstackEmil’s website, emilkang.comCreatives Rebuild New York
Related Podcast EpisodesHiring with Intention: An Executive Search Case Study (EP.93)Inside the Search: What Executive Hiring Actually Looks Like (EP.91)Hiring in the Age of A.I. (EP.90)Hiring as Improv: Embracing the Unscripted in Job Searches (EP.85)Values-Based Hiring: Re-Imagining the Search Process (EP.58)Inclusive Hiring Practices (EP.45)
About the GuestsEmil J. Kang is a cultural strategist, leader, and educator, working at the intersection of arts, philanthropy, and public policy. He has an active consulting practice working with arts leaders and organizations driving change.
Previously, Kang served as Program Director for Arts and Culture at The Mellon Foundation—the nation's largest arts funder—where he led a $120 million annual portfolio and conceived Creatives Rebuild New York, the largest guaranteed income program for artists in U.S. history. He founded and led Carolina Performing Arts at UNC-Chapel Hill, building it into one of the country's premier university-based performing arts programs while commissioning over 60 new works from internationally renowned artists. While at UNC, he also served as Professor of the Practice in the Department of Music and Special Assistant to the Chancellor for the Arts.
He continues to serve on the National Council on the Arts, having been appointed in 2012 by President Barack Obama. Kang currently serves as Entrepreneur-in-Residence at the Yale Ventures Cultural Innovation Lab at Yale University. Previously, he served as the Agnes Gund Visiting Professor of the Practice of Arts at Brown University.
Earlier in his career, Kang served as President and Executive Director of the Detroit Symphony Orchestra, becoming the youngest and first Asian-American CEO of a major American symphony orchestra.
Kang currently serves on the boards of directors of several arts organizations including Silkroad, National Sawdust, GYOPO, and Mutual Mentorship for Musicians, and is a member of the Council of Korean Americans. He serves as Vice Chair of the New York City Cultural Affairs Advisory Commission. A sought-after speaker on cultural leadership and institutional transformation, he writes provocatively about the future of arts institutions, leadership, and philanthropic practice on his substack, The Reprise.
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, 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. More at timcynova.com.
Hiring with Intention: An Executive Search Case Study
2026/05/30
Most hiring processes were built in a different era, carried forward by inertia without much consideration, and optimized for the organization’s convenience rather than a candidate’s experience.
This episode is about what happens when a team decides to proactively reimagine that dynamic.
WSS host Tim Cynova is joined by Katrina Donald (Ever-so-curious), Julie Mae Lopez (People Power Solutions), and guest host for the episode, Jodi Cobalt (Yerba Buena Center for the Arts). The four of them collaborated on a search at YBCA in 2022-23 for an executive-level Head of External Relations role. This episode is a detailed reflection of what they and the organization tried, what surprised them, and what they’d do again.
It’s a behind-the-scenes account of what intentional hiring looks like in practice, with enough specifics that you can take ideas directly into your next search.
In this conversation:
Why the typical playbook fails → information flows one way, candidates are kept in the dark for weeks, and “culture fit” bias goes completely unchecked.“Dot connector” screening calls built around one prompt: Connect the dots between where you’ve been and this role. Those calls can reshuffle the entire candidate list.Treating the job posting like a marketing campaign: multiple formats, audio and video assets, detailed comp and benefits information, distributed through the varied networks and channels where candidates are located.Why a $250 honorarium Venmo’d the moment a finalist leaves the room might matter more than the dollar amount suggests.Redesigning reference checks to ask “what advice would you give this candidate’s future supervisor?” instead of “was this person a team player?”Accessibility built into the process from the start: contrast ratios, audio versions of postings, empathy mapping for sourcing, feedback loops through the process.Building the case story bank: a practical tool for candidates navigating searches in the age of AI-generated everything.
Plus: using Critical Response Process for final interviews, giving care packages to finalists, sending search committee bios to candidates in advance, starting interviews with an ice breaker question, asking candidates to predict their own reference feedback, designing the search to feed directly into onboarding, calibrating the ask of candidates to where they are in the process, and how to not ghost people when the answer is no.
Want to go deeper on navigating your own search? Career Camp — the online program Katrina and Tim created — is designed to help you get unstuck, map your next move, and build a job search strategy that reflects how hiring actually works.
Links & ResourcesOnline Courses
Inclusive Hiring: Building a Search Process from Job Description to Onboarding [FREE]Building a Core Curriculum [FREE]Career Camp “Prepare for Your Next Career Move” [$99]
Tools
Download the 100-page Search Playbook for this searchTemplate for Executive Search Process | 130-item Project Management ChartYBCA Search | Social Sharing KitLiberating StructuresThe Behavior DashboardCritical Response Process
Related Podcast Episodes
Inside the Search: What Executive Hiring Actually Looks Like (EP.91)Hiring in the Age of A.I. (EP.90)Hiring as Improv: Embracing the Unscripted in Job Searches (EP.85)Values-Based Hiring: Re-Imagining the Search Process (EP.58)Inclusive Hiring Practices (EP.45)
About the GuestsJodi Cobalt (she/her), a Co-Founder of Thought Partner, is a seasoned theater manager with over two decades of experience in the industry. Her unique blend of leadership, hands-on knowledge, and a thorough understanding of theater give her a wealth of insight from which to draw on. After earning her BFA in Theater at Emerson College she moved to the Bay Area, finding work in a variety of venues as a Lighting Designer, Performer, Educator and Production Manager. At Yerba Buena Center for the Arts, Jodi has held the roles of Director of Production and Chief of Operations and was the General Manager of The Shalleck Collaborative where she contributed to the operational, communications and management side of the business. More at heythoughtpartner.
Katrina Donald (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. More at Ever-so-curious.
Julie Mae Lopez (she/her) is a human resources leader and consultant with 15+ years of experience working with small to mid-sized for-profit and non-profit mission-driven organizations. Early in her career, Julie Mae managed people and culture operations for non-profits in the education and arts sectors. In 2018, she earned a Senior HR Professional certification from SHRM, and in 2023, a workplace certification in Diversity, Equity, & Inclusion from USF, fueling her passion for designing people programs that foster inclusive workplaces. She specializes in building human-centered practices where inclusive values are integrated into the entire employee lifecycle—from recruitment and performance management to professional development and offboarding. Through her consultancy, People Power Solutions, she provides expert guidance to help companies build environments where every individual is empowered to thrive and contribute meaningfully to their organization's success. Julie Mae received a BS in Sociology from University of California, Santa Cruz. A proud Oakland resident and Bay Area native, she is an avid thrifter and enjoys Saturday mornings at the park with her dog, Sampa. More at People Power Solutions.
Tim Cynova (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, 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...
Unhooking from Norms
2026/05/15
What happens when the people an organization exists to serve are also the ones designing it?
On this episode, host Tim Cynova is in conversation with Lu Zhang, Gregory Sale, and Diya Vij of A Blade of Grass to discuss what it looks like to approach your organization as a living experiment.
A Blade of Grass supports socially engaged artists through a grants program, an in-fellowship cohort, and a digital publication called Landscapes. But their work goes well beyond their program design. They're actively questioning whether competition-based, project-focused philanthropy actually serves artists. They pay their board members. They use a randomized selection process for small grants. They talk openly about sunsetting the organization in the same breath they discuss 100-year plans. These are not things most organizations do.
This conversation explores practitioner-led governance, the gap between what socially engaged artists need and what traditional arts infrastructure delivers, how to build for responsiveness and long-term strategy at the same time, and what it means to make an organization that doesn't require artists to check their creativity at the door.
If you're a leader questioning default organizational norms, a funder trying to align your grantmaking practices with what artists need, or anyone building infrastructure in a sector that keeps treating creativity as something that happens somewhere else, this one is worth your time.
In this conversation:
What "practitioner-led" really means when it extends from staff to boardThe case for randomized grant-makingWhy A Blade of Grass paused programming for a full year to do field researchBuilding a paid, working board and what that changes about governanceHow socially engaged artists think about entering and exiting community work and what organizations can learn from thatHolding grief, iteration, and ambition without getting precious about any of it
Links & Resources
A Blade of Grass — Website, Newsletter, Instagram, Facebook, Landscapes
2025 In Fellowship Cohort:
Great LeapWhat Would an HIV Doula Do?Wild Path CollectiveReflections on the first year of In Fellowship
About the Guests
Diya Vij was the Vice President of Curatorial and Arts Programs at Powerhouse Arts in Brooklyn, NY when this episode was recorded, and is committed to critically investigating the evolving role of art in politics and civic life. Most recently, she served as the Curator at Creative Time where she commissioned and stewarded large-scale public art work, launched the public programming space CTHQ, re-launched the Creative Time Summit, and initiated the R&D Fellowship for socially engaged artists. Over the past decade, she has held programming, curatorial, and communications positions at major New York City Institutions. As the Associate Curator of Public Programs at the High Line, she organized dozens of live events and performances with artists, activists, practitioners, and healers. At the New York City Department of Cultural Affairs, Vij launched and co-directed the Public Artists in Residence (PAIR) program. Additionally, she helped lead the Agency’s citywide Diversity, Equity, and Inclusion initiative, and played an active role in public monument efforts, as well as CreateNYC—New York City’s first strategic long-term plan for culture. She was a curatorial fellow and the communications manager at the Queens Museum from 2010–2014. She currently serves on the Boards of A Blade of Grass, the Laundromat Project and the Poetry Project and was co-curator of the Counterpublic Triennial 2023 in St. Louis, MO. [After this episode was recorded in 2026, Diya was appointed the Commissioner of NYC’s Department of Cultural Affairs.]
Gregory Sale is an artist, curator, educator, and community organizer whose work uses creativity as a tool for transformation. His socially engaged practice is grounded in collective experience, relationship-building, and shared authorship to create large-scale, often long-term public projects that address social challenges. For over two decades, Sale’s projects have focused on mass incarceration, reentry, and civic life, centering system-impacted individuals as creative collaborators and leaders. Notably It’s not just black and white (2011) and Future IDs at Alcatraz (2018–19) – a yearlong exhibition and series of community programs developed in partnership with the National Park Service, the Golden Gate National Parks Conservancy, and more than 20 community organizations. Reaching hundreds of thousands of visitors, Future IDs at Alcatraz created an evolving civic space for open dialogue and stories of trauma, transformation, and resilience. Sale co-founded the Future IDs Art and Justice Leadership Cohort, which works with justice-involved leaders and allies to explore how art can support leadership, civic participation, and systemic change. Participants have co-created projects such as Justice + Art Jam (2025), a day of art, advocacy, and resource sharing in Los Angeles. Sale also co-leads initiatives about voting and love as social and political strategies, including #ArtistsWhoVote and the Love for Love series. His work has been supported by Creative Capital, Kenneth Rainin Foundation, A Blade of Grass/David Rockefeller Fund, Art Matters, Center for Artistic Activism, and Andy Warhol Foundation for the Visual Arts. Sale is Professor of Expanded Arts and Public Practice at Arizona State University and serves on the board of A Blade of Grass. He is based in Phoenix and Los Angeles. Gregory’s website and his project Future IDs website.
Lu Zhang is an artist and arts worker. She is the Executive Director of A Blade of Grass (ABoG), an artist-run nonprofit dedicated to socially engaged art. In collaboration with a paid board of artists and practitioners, Lu guides programs rooted in co-creation and dialogue that provide flexible, responsive resources to artists. Under her leadership, ABoG continues to evolve as a nimble organization that adapts its structure and programs to meet the changing needs of socially engaged artists. Before joining ABoG, Lu served as Initiatives Director at United States Artists (USA), a national arts funder supporting artists across all disciplines. There, she launched a new department to expand holistic support for artists, including landmark programs such as Disability Futures and Artist Relief. Previously, Lu was Deputy Director of The Contemporary, a nomadic museum in Baltimore, where she provided strategic oversight and led initiatives to strengthen the local arts ecosystem. As an artist, Lu’s work spans books, drawings, installations, and interventions. She has partnered with Press Press to produce publications, with the George Peabody Library to launch a studio residency program, and founded the Institute for Expanded Research, which activates sites and resources for artist projects. Lu holds an MFA in Painting from the Frank Mohr Institute in the Netherlands and a BFA from the Maryland Institute College of Art in Baltimore. Listen to more with Lu on episode 11 of the body is the brain.
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. More at a href="https://www.timcynova.com/" rel="noopener...
Inside the Search
2026/04/28
What does an executive search actually look like from the inside?
This episode brings together two people who know the process from different vantage points: Pamela Bol Riess, CEO of PBR Executive Search, and Deeksha Gaur, Executive Director of Theater Development Fund, who was a candidate in a search Pamela led in 2023.
Together, we discuss how executive hiring really works right now — what search committees are actually evaluating, why the boldest candidates tend to win, and how to show up in a competitive market without losing yourself in the process.
In this conversation:
Why you usually can't get everything in one hire, and how smart organizations identify their true must-haves before the search begins.How candidates are being evaluated from the first email they send, not just in the interview room.Why "the answers are in the position description" and what it looks like when candidates use them.Deeksha's approach to her own search: researching every search committee member, preparing a strategic deck, and giving herself the freedom to show up authentically. Why the boldest candidates tend to win and what "leading in the room" actually looks like.How post-pandemic uncertainty has shifted what organizations are really hiring for: pattern recognition, comfort with failure, and judgment over credentials alone.How to stay resilient as a finalist who doesn't get the offer.
Whether you're navigating a search, hiring into complexity, or doing search work yourself, this one's full of practical insight and rare candor from both sides of the table.
Highlights:
01:40 Meet Pamela and Deeksha02:34 Career Origins and Paths03:50 What Hiring Gets Wrong06:11 Judgment and Fit at Exec Level07:42 Defining the Right Leader10:04 Showing Up as a Candidate12:28 Bold Interviews That Win14:45 Testing Thinking and Ego17:36 Practical Interview Prep19:51 Signal Commitment and Research23:49 Authenticity and the Current Job Market27:04 Cover Letters and Owning Your Gaps29:24 Everything Is Data33:28 Bravery and Joyful Leadership37:17 Networks and References38:34 Encouragement and Relationships
Links & Resources
PBR Executive Search including their Active Searches and Recent PlacementsPBR's Job Search GuidePamela's Succession Planning SeriesTheatre Development Fund (TDF)
About the Guests
Pamela Bol Riess has been in the search business for more than 25 years, focusing exclusively on the nonprofit sector. During her career, she has led hundreds of leadership searches for a wide variety of nonprofit clients based in the US and abroad. Through this work, she has developed an extensive network of relationships with nonprofit leaders, a deep understanding of the skills and experiences that make candidates successful, and knowledge of the institutional conditions necessary for supporting that success. She is particularly adept at understanding the culture of a client organization and identifying people who will thrive there. She has a BA in English from Brown University and an MFA in Fiction Writing from New York University.
Deeksha Gaur is Executive Director at Theatre Development Fund (TDF), a non-profit that is building the future audience for the performing arts by removing financial, physical, and invisible barriers to attendance. Prior to this, Deeksha spent eight years at the nexus of theatre and tech at Show-Score, a consumer reviews platform that she co-founded. Following its acquisition in 2020, she ran the incubated brand for TodayTix Group. With TDF, she returns to the non-profit arts world, where she has previously held senior marketing and PR positions at Woolly Mammoth Theatre Company, Two River Theater Company, and Long Wharf Theatre. She serves as Treasurer and a founding board member of Kaleidoscope Dreams Foundation, chaired by Alicia Keys, and has previously served on the boards of the award-winning Second Stage Theater, Ars Nova, and Space on Ryder Farm, where she was also Treasurer. She is an adjunct professor at Fordham University and guest lecturer at Yale University's David Geffen School of Drama. Deeksha is also a Tony Nominator and a published crossword constructor.
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. More at timcynova.com.
Hiring in the Age of A.I.
2025/10/28
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.
Building Justice: Rethinking Construction, Climate, and Care
2025/10/15
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.
Deep Democracy at Work
2025/09/17
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.
Nonprofit Governance in Uncertain Times
2025/09/09
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.
Thera-Coaching Through Uncertainty
2025/08/28
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.
Hiring as Improv: Embracing the Unscripted in Job Searches
2025/08/21
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.
Co-CEO Chronicles: Navigating Growth, Change, and Complexity
2025/08/18
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.
Socrates Sculpture Park: Exploring Art, Community, and Experimentation
2025/06/10
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...
Democracy and Creative Practice
2025/02/25
In this episode of Work Shouldn’t Suck, host Tim Cynova connects with the ever-awesome Shannon Litzenberger to explore the intersections of democracy, creative practice, and collective thriving. Together, they dive into how artistic methodologies can expand leadership frameworks and help shape more caring, equitable communities.
In this episode:
How creative practice informs leadership and systems changeThe importance of mutual care and collective thrivingSensory attunement, attentional awareness, and improvisational leadershipDisrupting default systems and embracing world-making as a practice
Fresh from the national tour of her production World After Dark and moments away from presenting at a social theory, politics, and the arts conference in Spain, Shannon shares insights on how creative practice can serve as a catalyst for personal and societal transformation. They discuss the power of mutual care, the significance of sensory attunement, and the need to reimagine default patterns in both the workplace and society.
This episode also touches on the enduring influence of Shannon’s friendship and collaboration with the late Diane Ragsdale, their shared exploration of aesthetics and embodiment, and their co-authored chapter in Democracy as Creative Practice. Plus, hear how Shannon is bringing her artistic ethos into unexpected spaces—like reimagining an academic panel as an improvisational score.
Tune in for a conversation packed with practical wisdom, unexpected insights, and a reminder that thriving workplaces and thriving communities are built on mutual care, relational leadership, and a willingness to embrace the unfamiliar.
Quotables
“This is where I find a lot of fertile ground for transformation, and why I feel it's so important for creative practice methodologies to gain purchase in this conversation around change, because they're practice-based, and practice is how we change habits. We can have lots of fruitful conversations that evoke ways of knowing that we understand, but to actually become something different than what we've already been conditioned to be requires practice, not just a kind of conceptual knowing.” – Shannon Litzenberger
“ Practice is the pathway to change. If you want to be able to expand your repertoire of being and doing, you have to practice things that are unfamiliar.” – Shannon Litzenberger
“Identity is a very powerful organizing construct in society. The pandemic especially I think really highlighted identity significantly as an organizing structure, as a way of revealing structural harms and inequities. It also started to deepen the way that we are relating in these identity-based affinity groups, and in a sense, this is a challenge when it comes to developing practices that are supportive of a pluralistic democracy. Because, in a pluralistic democracy, we need to develop an ability to be together in ways that are not so strictly codified that we are all twisting ourselves in a knot to try to belong, that actually we need to be able to embrace differences within a dynamic whole in order to work well and co-create well together.” – Shannon Litzenberger
Highlights:Values in Creative Practice (02:14)Exploring “World After Dark” (04:08)Leadership and Collective Action (09:32)Navigating Post-Pandemic Challenges (11:10)Creative Practice in Organizations (17:43)Improvisational Leadership (27:09)Collaboration with Diane Ragsdale (35:33)Improvisational Score as Panel Discussion (42:29)Final Thoughts and Reflections (45:52)
Related Resources:Shannon's SubstackDemocracy as Creative Practice: Weaving a Culture of Civic Life Edited By Tom Borrup and Andrew Zitcer“The Snapback: Why Workplaces Are Reverting and What We Can Do About It” by Tim Cynova“Beyond the Snapback: Designing Change That Lasts” A Facilitator’s Guide
Bios
Shannon Litzenberger (she/her, Tkaronto) is an award-winning choreographer, director, researcher and embodiment facilitator. She creates sensory-rich multi-disciplinary performance experiences that animate our relationship to land, community and the forgotten wisdom of the body. Her imaginative collaborations connect art forms and communities, centering participatory experiences in artistic processes. Throughout her 25+ year career, her work has been presented across Canada and the U.S., in collaboration with many of Canada’s leading artists across disciplines.
The creative principles and embodied practices she works with regularly in the studio are also central to her work in relational leadership, organizational development, and systems change. Her approach to personal and collective transformation focuses on recovering our capacity to sense and make shared meaning of our complex, rapidly changing world. The collective experiences she designs focus on strengthening our ability to respond generatively to what a moment is asking of us, in service of mutual thriving. They invite a conscious recovery of embodied capacities like sensory attunement, expanded attentional awareness, reciprocity, imagination, collaborative play and worldmaking.
She works frequently across corporate, academic and non-profit spaces in support of creating a healthier, more interconnected, caring and resilient society. She is currently a Public Imagination Network Fellow and Artist Researcher in Residence at Creative Community Commons, within University of Toronto’s School of Cities. www.shannonlitzenberger.com
Tim Cynova, SPHR (he/him) is the Principal 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 trombonist, musicologist, and for five years in his youth he delivered newspapers for the Evansville, Indiana Courier-Press. Learn more on LinkedIn.
Climate Justice HR | Part 1
2025/01/17
In this episode of the Work Shouldn’t Suck podcast, host Tim Cynova begins an exploration into the crucial intersection of Human Resources (HR) and climate emergencies. Recorded amidst recent natural disasters, the discussion explores how workplaces can prepare for and respond to climate-related challenges, underscoring the importance of planning for the unexpected, building resilient systems, and supporting employee well-being in the midst of these emergencies.
Joining the conversation are Jenna Ringelheim and Jillian Wright, bringing their insights on meaningful HR and organizational design practices rooted in equity, anti-racism, and compassion. They emphasize the importance of proactive planning, values-based workplace design, and the integration of equity, empathy, and integrity in HR practices. This spirited discussion highlights the evolving nature of workplace challenges posed by climate change and the need for resilient, people-centered organizational frameworks.
Highlights:
Introduction to Climate Emergency and HR (00:00)Unplanned vs. Unexpected Events (01:06)Climate Justice HR: A New Approach (02:31)Guest Introductions and Their Work (03:04)Values-Centered Work in HR (04:08)Climate Justice HR in Practice (10:39)Real-World Examples and Challenges (12:43)Developing Compassionate Leave Policies (18:18)Building Resilient and Supportive Workplaces (22:16)The Importance of Flexibility and Empathy (34:28)Final Thoughts and Takeaways (44:22)
Related Resources:
The Resilient Organization: A Guide to Nonprofit Disaster Preparedness by the Center for Disaster PhilanthropyScarcity and the Non-Profit People Paradox Example 2 delves into the St. John’s case study and how they approached the unplanned versus the unexpectedClimate Emotions Wheel including a Guide to Climate EmotionsPhases of Disaster Response from the Institute for Collective Trauma and GrowthUniversity of California’s Center for Climate Justice “What is Climate Justice“ and the Six Pillars of Climate Justice.Tulane University’s “What Is a Disaster Management Cycle?”Crisis Relief & Recovery on “What is Disaster Leadership?”“How to Lead Through a Crisis” by the Center for Creative Leadership“The connection between the climate crisis and outdated leadership models” by the Academy for Sustainable Innovation“Five Critical Questions Every Nonprofit Must Address for Disaster Preparedness” by OneStar
BIOS
JENNA RINGELHEIM (she/her) is a skilled facilitator, coach, and HR practitioner that is passionate about igniting liberatory leadership practices within workplaces. She has a keen interest in program and curriculum design, supporting equity-centered people and culture efforts, network weaving and building communities of practice. Jenna is happiest when she is co-creating systems and structures that allow for greater agency, transparency, and shared learning. In her previous work as nonprofit executive, Jenna catalyzed a network of over 2,000 environmental and social change leaders as the Deputy Director of the Environmental Leadership Program. She also served as the Executive Director of Wild Gift, a wilderness-based leadership development program and international network of social impact entrepreneurs. Jenna has a BA in Environmental Studies and Anthropology from Skidmore College, an MA in Urban and Environmental Policy and Planning from Tufts University, an MBA in Sustainable Systems from Pinchot University, and a Certificate in Human Resource Management from Portland State University. Most importantly, she is a proud parent, partner, pet matchmaker, foodie, and e-bike enthusiast living in Portland, Oregon. Learn more on LinkedIn.
JILLIAN WRIGHT, PHR (she/her) spends her days as an HR consultant, but she’s also a dancer, mother, gardener, and puzzle finisher who enjoys helping small businesses succeed. For over 18 years, she’s had the privilege of working with and learning from some amazing folx who have taught her so much about how to facilitate people support BETTER – and she wants to share what she’s learned with other value-driven companies who are ready to do things differently. Her passion for people-support and behavioral psychology in the workplace along with her deep personal commitment to social justice as a member of the queer community has fueled her desire to help leaders create inclusive places to work. Jillian’s background in small non-profit and mission-driven workplaces has gained her valuable skills in the art of prioritization, efficient use of time, and understanding how to make things happen on a shoestring budget, and she’s worked hard to apply those principles to creating affordable, time-conscious, impact-centered consulting projects tailored to a variety companies specific goals, opportunities, and challenges. Learn more on LinkedIn.
Tim Cynova, SPHR (he/him) is the Principal 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 trombonist, musicologist, and for five years in his youth he delivered newspapers for the Evansville, Indiana Courier-Press. Learn more on LinkedIn.
Startups & Scaling
2024/11/14
In this episode of Work Shouldn’t Suck, host Tim Cynova is rejoined by co-host Lauren Ruffin and special guest Adam Huttler, the founder of Fractured Atlas and current head of product and technology at MonkeyPod, another company he founded. Together, they dive into the nuances of starting and scaling organizations, drawing from their shared experiences at Fractured Atlas and beyond.
The conversation explores the intricacies of startups and scaling, including the critical transition points, calibrating risk between staff and boards, the importance of intellectual honesty, and the role slack plays in supporting a culture of learning.
Key Highlights:
Product-Market Fit [02:09]Startup Phase Challenges [02:56]Transitioning to Scaling Mode [03:22]Experimentation & Intellectual Honesty [04:45]Evaluating Team & Leadership [08:35]Nonprofit Sector Dynamics [13:51]Risk Calibration in Nonprofits [20:08]Strategic Planning & Strategic Thinking in Organizations [26:11]Hybrid Workplace & Organizational Culture [32:27]Building High-Performing Teams [36:30]Creating Space for Learning & Growth [44:55]
BIOS
ADAM HUTTLER is the founder and head of product of MonkeyPod, an all-in-one software platform for nonprofit organizations that supports accounting, donor management, fundraising, collaboration, and more. A serial entrepreneur at the intersection of technology, culture, and social justice, his career emphasizes developing innovative business models and revenue strategies for mission-driven companies, in both the for-profit and non-profit sectors.
In 1997, Adam founded Fractured Atlas, a non-profit technology company that helps artists with the business aspects of their work. During Adam's twenty years as CEO, the organization grew from a one-man-band housed in an East Harlem studio apartment to a broad-based service organization with an annual budget of $25 million. When he left in 2017, Fractured Atlas's services had grown to reach over 1.5 million artists across North America and distributed over $250 million to support their work.
From 2003-2013, Adam also ran Gemini SBS, a software development firm serving the nonprofit and public sectors. Before being acquired by Fractured Atlas in 2013, Gemini worked with clients such as the US Department of Education, New York University, and the University of North Carolina, among many others.
In 2017, Adam left Fractured Atlas to launch Exponential Creativity Ventures, a boutique venture capital fund backing early-stage technology companies that support human creative capacity. ECV was fully deployed as of late 2019, but Adam continues to support and advise ECV's 18 portfolio companies.
In 2019, a personal side project became a bona fide startup when Adam publicly launched MonkeyPod.
Adam has a B.A. in theater from Sarah Lawrence College, an M.B.A. from New York University, and is a self-taught software developer. In 2011, he was recruited for the inaugural class of National Arts Strategies' Chief Executive Program. He is also an alumnus of Singularity University's Executive Program and the University of California at Berkeley's Venture Capital Executive Program.
Adam was named to Crain's New York Business's 2016 "40 Under Forty" class and was listed by Barry's Blog as one of the "Top 50 Most Powerful and Influential Leaders in Nonprofit Arts" for five consecutive years.
LAUREN RUFFIN (she/her) is the Director and Lead Strategist of Art & Culture at Michigan Central. An expert in responsible innovation, her work centers on defining and implementing best practices for organizations reshaping the world through technology to ensure their platforms are safe, equitable and beneficial for all users. From 2016-2021 she served as Chief External Relations Officer and co-CEO of Fractured Atlas, the largest association of independent artists in the United States, where she oversaw marketing, communications, community engagement and fundraising for the nonprofit. In 2017 Ruffin co-founded CRUX, an immersive storytelling cooperative that collaborated with Black artists creating content in virtual and augmented reality (XR). In addition to her work as co-director at Michigan Centra, Ruffin is an Associate Professor of Worldbuilding and Visualizing Futures at Arizona State University where she explores the unprecedented and rapid political and social changes taking place in every facet of modern life due to advances in technology. Ruffin has held various positions at the NAACP Legal Defense Fund, Children’s Defense Fund, New Leaders and AAUW and has served on the governing and advisory boards of Black Innovation Alliance, Black Girls Code, ArtUp, Black Girl Ventures and Main Street Phoenix Cooperative. She graduated from Mount Holyoke College with a degree in Political Science and obtained her J.D. from the Howard University School of Law.