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What if the biggest mistake organizations make in a leadership search isn't choosing the wrong person — but asking the wrong questions before they begin? Emil Kang, former head of arts grantmaking at the Mellon Foundation, on nonlinear careers, the relational job search, and why governance may be the nonprofit sector's most unregulated corner.

What happens when the people an organization exists to serve are also the ones designing it?

On this episode of the Work Shouldn’t Suck podcast, 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.

What does the nonprofit executive search process actually look like? In this episode, executive search professional Pamela Bol Riess and Executive Director Deeksha Gaur break down how C-suite hiring works right now — from how search firms build candidate pools to what boards are really looking for in their interviews. If you're preparing for an executive director search, hiring into a leadership role, or just trying to understand how the process works, this conversation is essential listening.

This episode explores the impact of A.I. on hiring practices with the hosts joined by a unique, algorithmic guest—Chad Geepet (pronounced GPT 😉). Chad is part thought partner, part mirror, and all algorithm. They unpack what A.I. is really doing to hiring systems, not just in headlines, but in the messy middle where résumés, interviews, and algorithms now mingle.

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.

What if conflict isn’t something to avoid—but something to practice? In this episode, facilitators Navida Nuraney and Camille Dumond introduce the Lewis Method of Deep Democracy, a practical framework for navigating tension, surfacing unspoken truths, and building real relational capacity at work. Plus, we try one of their favorite tools live.

Nonprofit board governance has never felt more complex—or more important.

In this episode, host Tim Cynova sits down with Andrew Taylor—professor, researcher, consultant, and board chair—to explore what boards are really for, why bylaws matter more than most people think, and how values-driven governance can thrive in unpredictable times. From OpenAI to the Kennedy Center, they unpack high-profile governance challenges, reframe the role of boards as servant leaders, and offer practical wisdom for navigating risk, resilience, and collaboration.

Whether you’re considering your first board role, leading alongside a board as an executive, or simply curious about what governance looks like today, this conversation will spark fresh thinking about how boards can evolve to meet the moment.

Licensed therapist and executive coach Chantel Cohen joins the Work Shouldn’t Suck podcast to explore how mental wellness, identity, and relationships shape the way we lead at work and in life. From managing ADHD and anxiety to navigating career transitions and co-leadership dynamics, this episode offers a grounded, holistic take on thriving through change.

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.

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 eight-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.

In this episode, host Tim Cynova records is joined by co-directors of Socrates Sculpture Park, Katie Dixon and Shaun Leonardo, to discuss the park's transformation from a landfill to a creative haven, its role as a space for community and artistic experimentation, and the unique dynamics of their co-directorship model. The conversation considers the intersection of art, community, and leadership in crafting thriving urban spaces, particularly at this moment in history.

In this episode of Work Shouldn’t Suck, host Tim Cynova and guest Shannon Litzenberger explore how creative practice and relational leadership can cultivate collective thriving and drive societal transformation.

The conversation explores the crucial intersection of Human Resources (HR) and climate emergencies, discussing 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.

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.

The Bridge Live Arts team shares the origins of its distributed leadership model, how their particular model works, how engaging with community informs and evolves the model, some of their “ahas” and lessons learned along the way, and where to from here.

In organizations dedicated to creative expression and innovation, why is it that so many have workplace practices and policies that are dusty? This episode explores reimagining of value-centered workplaces through Creative Administration.

If you’ve ever wondered about the ins-and-outs of executive coaches – how does it work, how do you find out; I’m not an “executive,” is it still for me? – this is an episode for you! Host Tim Cynova is in conversation with Farah Bala, a certified executive coach and founder of Farsight, an agency dedicated to leadership and organizational development with a focus on equity, diversity, inclusion, and anti-oppression practices. Their conversation covers a lot of ground, from the philosophical to the practice, with some highlights from the discussion below.

In this episode, host Tim Cynova interviews Ann Le and Meg Buzzi, authors of the book "The In-Between: A Companion for Uncertain Times." The discussion brings in many of the challenges of work in the current chaotic and uncertain landscape, and offers insights on how individuals, teams, and organizations can stay engaged and motivated. At the heart of the discussion, Ann and Meg invite listeners to rethink their relationship with work and explore new possibilities.

In this episode, Tim Cynova is in conversation with Tammy Dowley-Blackman, an entrepreneur with 20+ years of experience in leadership and organizational development.  A differentiator for Tammy in this work comes in that she’s sat in many of the proverbial seats at the table: serving as a CEO and key decision-maker, a board member, a sought-after consultant, a leadership development content creator, and a key partner to corporations, nonprofits, government entities, and philanthropic institutions.

In this episode, Tim Cynova and Katrina Donald delve into the complex world of wage transparency and equitable compensation, and explore how organizations can navigate these challenges to create fair and inclusive workplaces.

This week, the world lost an amazing light of a human: Diane Ragsdale.

This episode is a previously lost and unreleased conversation that host Tim Cynova recorded with Diane at the Banff Centre in February 2020, a few weeks before the world shut down for the global pandemic... and they promptly forgot they even recorded this conversation together.

Why and how do you decolonize an organization's bylaws?

In this episode, host Tim Cynova connects with three leaders from the U.S.-based nonprofit Dance/USA about their recent and ongoing work to decolonize their organization. Joining the discussion are Kellee Edusei, Executive Director of Dance/USA, and Holly Bass and Jim Leija, two members of the Board of Directors who co-lead the process to decolonize their organizational bylaws.

How do we support leaders in the cultural sector?

In this episode, host Tim Cynova has a fun and fascinating conversation with Gail Crider (President & CEO) and Kristina Newman-Scott (Board Chair) of National Arts Strategies (NAS), an organization dedicated to building and supporting a community of arts and culture leaders who drive inspiring change for the future. We dive into the transformative work they've been doing to create more inclusive and innovative spaces and approaches within the sector through their programs and offerings.

In this episode, we explore unlimited paid time off policies: what they are, what they aren't, and items to consider when implementing this type of approach to PTO.

Tim Cynova and Lauren Ruffin dive into recent pay transparency laws and their potential to shift power and information sharing in workplaces.

How do you intentionally guide a company through the final phase of the organizational life cycle? In this episode, we connect with guests who were tasked with leading companies through that very process. We’ll hear how the decision came to be, how they’re approaching the work, and what resonates for them as they reflect on it all.

In conversation with Board Chair Renuka Kher and CEO Sara Fenske Bahat, we explore how uncertainty, transitions, and moving forward in ambiguity shows up in San Francisco’s Yerba Buena Center for the Arts.

In this special bonus episode of "White Men & the Journey Towards Anti-Racism," Tim talks with Noah Becker, Kevin Eppler, Colin Lacey, and Shannon Mudd, four members of a peer support circle that's part of the larger racial affinity group White Men for Racial Justice (WMRJ). This group of guys meet regularly to support, challenge, and hold each other accountable as they seek to live into their values and desire to help co-create an anti-racist, equitable, and just world.

This series was created to be a resource for white men who might be wrestling with questions like, “What’s my role in anti-racism, equity, inclusion, and justice work as a white man with power and privilege?” and “How might my personal commitment to do this work manifest itself in the organization I help lead?”

In episode twelve of the 12-part podcast series, "White Men & the Journey Towards Anti-Racism," Tim interviews Jared Fishman, a civil right lawyer and Founding Executive Director of Justice Innovation Lab, a company building data-driven solutions for a more equitable, effective & fair justice system.

This series was created to be a resource for white men who might be wrestling with questions like, “What’s my role in anti-racism, equity, inclusion, and justice work as a white man with power and privilege?” and “How might my personal commitment to do this work manifest itself in the organization I help lead?”