Work. Shouldnt. Suck.

About Work. Shouldnt. Suck.

Work Shouldn't Suck is for people who refuse to accept that work has to be soul-crushing and stuck in dusty, outdated systems.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, a People + Culture infrastructure strategist, 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.

Publisher

Tim Cynova

Category

business · business · society & culture

Language

en

Explicit

No

First episode

2 Nov 2019

Latest episode

28 Jul 2026

Latest episodes

94 episodes in the feed.

1. 

   28 Jul 2026

   Are Non-Linear Careers The New Linear? (EP.94)

   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 & Resources The Reprise (https://emilkang.substack.com/), Emil's Substack Emil’s website, emilkang.com (http://www.emilkang.com/) Creatives Rebuild New York (https://www.creativesrebuildny.org/) Related Podcast Episodes Hiring with Intention: An Executive Search Case Study (https://www.workshouldntsuck.co/podcast2/ep93) (EP.93) Inside the Search: What Executive Hiring Actually Looks Like (https://www.workshouldntsuck.co/podcast2/ep91) (EP.91) Hiring in the Age of A.I. (https://www.workshouldntsuck.co/podcast2/ep90)(EP.90) Hiring as Improv: Embracing the Unscripted in Job Searches (https://www.workshouldntsuck.co/podcast2/ep85) (EP.85) Values-Based Hiring: Re-Imagining the Search Process (https://www.workshouldntsuck.co/podcast2/ep58) (EP.58) Inclusive Hiring Practices (https://www.workshouldntsuck.co/podcast2/ep45) (EP.45) About the Guests Emil 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 (https://www.timcynova.com/).

2. 

   30 May 2026

   Hiring with Intention: An Executive Search Case Study (EP.93)

   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 (https://www.workshouldntsuck.co/summer-camp-2025) — 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 & Resources Online Courses Inclusive Hiring: Building a Search Process from Job Description to Onboarding (https://youtube.com/playlist?list=PLY2yigmSNf1UiuZ6UCqb0dHcgzblI2KFA&si=sJbCyLc8nLILnw35) [FREE] Building a Core Curriculum (https://www.youtube.com/playlist?list=PLY2yigmSNf1Uurok455yF8HUYfICbwAvO) [FREE] Career Camp “Prepare for Your Next Career Move” (https://www.workshouldntsuck.co/summer-camp-2025) [$99] Tools Download the 100-page Search Playbook for this search (https://www.workshouldntsuck.co/ybca-search-playbook) Template for Executive Search Process | 130-item Project Management Chart (https://static1.squarespace.com/static/5bc7435770468008cb3e55d5/t/65bfc1614ced3f71bd78fea8/1707065697209/Executive+Search+Template.pdf) YBCA Search | Social Sharing Kit (https://www.workshouldntsuck.co/ybca-er-social-kit) Liberating Structures (https://www.liberatingstructures.com/) The Behavior Dashboard (https://www.workshouldntsuck.co/blog2/2020/03/06/the-behavior-dashboard) Critical Response Process (https://lizlerman.com/critical-response-process/) Related Podcast Episodes Inside the Search: What Executive Hiring Actually Looks Like (https://www.workshouldntsuck.co/podcast2/ep91) (EP.91) Hiring in the Age of A.I. (https://www.workshouldntsuck.co/podcast2/ep90)(EP.90) Hiring as Improv: Embracing the Unscripted in Job Searches (https://www.workshouldntsuck.co/podcast2/ep85) (EP.85) Values-Based Hiring: Re-Imagining the Search Process (https://www.workshouldntsuck.co/podcast2/ep58) (EP.58) Inclusive Hiring Practices (https://www.workshouldntsuck.co/podcast2/ep45) (EP.45) About the Guests Jodi 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 (https://www.heythoughtpartner.com/). 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 (https://www.eversocurious.ca/). 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 (https://peoplepowersolutions.net/). 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...

3. 

   15 May 2026

   Unhooking from Norms (EP.92)

   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 board The case for randomized grant-making Why A Blade of Grass paused programming for a full year to do field research Building a paid, working board and what that changes about governance How socially engaged artists think about entering and exiting community work and what organizations can learn from that Holding grief, iteration, and ambition without getting precious about any of it Links &amp; Resources A Blade of Grass — Website (https://www.abladeofgrass.org), Newsletter (https://www.abladeofgrass.org/newsletter), Instagram (https://www.instagram.com/abladeofgrassorg), Facebook (https://www.facebook.com/abladeofgrassorg/), Landscapes (https://www.abladeofgrass.pub/) 2025 In Fellowship Cohort: Great Leap (https://www.greatleap.org/) What Would an HIV Doula Do? (https://hivdoula.work/)Wild Path Collective (https://walkthewildpath.org/) Reflections on the first year of In Fellowship (https://a-blade-of-grass-fund.monkeypod.io/mailcoach/webview/campaign/427e559f-8d2d-4ba3-a2ef-cf57cc419123) About the Guests Diya Vij was the Vice President of Curatorial and Arts Programs at Powerhouse Arts (https://powerhousearts.org/) 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 (https://creativetime.org/) 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&amp;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 (https://www.nyc.gov/site/dcla/about/commissioner.pagehttps://www.nyc.gov/site/dcla/about/commissioner.page) 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 (https://gregorysaleart.com/) and his project Future IDs website (https://futureids.com/). 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 (https://www.podpage.com/thebodyisthebrain/episode-11-lu-zhang/). 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...

Who has been a guest on Work. Shouldnt. Suck.

Names identified in recent episode analyses. Showing up to five guests.

• Chad Geepet
• Mel Baiser
• Kate Stephenson
• Navida Nuraney
• Camille Dumond

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

16,315

Score snapshot 15 Sept 2025

Apple Podcasts (US)

4.9 / 5

17 ratings

Spotify

5.0 / 5

4 ratings

Podcast Authority Score: 59 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

66

Social presence

0

YouTube

76

Engagement

51

Contact Work. Shouldnt. Suck.

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.