Tim Cynova

Work. Shouldnt. Suck.

Business EN ↓ 93 episodes

Work Shouldn't Suck is for people who refuse to accept that work has to be soul-crushing and stuck in dusty, outdated systems.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 d...

Author

Tim Cynova

Category

Business

Podcast website

workshouldntsuck.co

Latest episode

May 30, 2026

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Episodes

Sunsetting Organizations (EP.68) 15.02.2023

Whether you refer to it as "sunsetting" or "supernova’ing," what’s true is that there are few resources to guide those wanting to intentionally shutdown an organization’s operations. While a multitude of resources exist dedicated to starting and scaling ventures, the same can’t be said when one finds themself on the other end of the organizational life cycle. In this episode, host Tim Cynova conne...

Into the future with Yerba Buena Center for the Arts (EP.67) 29.12.2022

In this episode, we’re exploring uncertainty, transitions, and moving forward in ambiguity – something most of us probably feel like we’re getting pretty used to having lived the past several years amid a global pandemic. We’ll be exploring how these things show up in organizations, and in one organization in particular – San Francisco’s Yerba Buena Center for the Arts. And we’ll discuss how they’...

Journey Towards Anti-Racism Ep13: Conversation with a Peer Support Circle (EP.66) 13.09.2022

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 the...

Journey Towards Anti-Racism Ep12: Conversation with Jared Fishman (EP.65) 09.09.2022

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 ques...

Journey Towards Anti-Racism Ep11: Conversation with Ted & Rooney Castle (EP.64) 04.09.2022

In episode eleven of the 12-part podcast series, " White Men & the Journey Towards Anti-Racism ," Tim interviews Ted Castle (Founder & President) and Rooney Castle (Vice President) of Rhino Foods , the birthplace of the iconic cookie dough that goes into Ben & Jerry’s Cookie Dough Ice Cream. This series was created to be a resource for white men who might be wrestling with questions li...

Journey Towards Anti-Racism Ep10: Conversation with Kit Hughes (EP.63) 23.06.2022

In episode ten of the 12-part podcast series, " White Men & the Journey Towards Anti-Racism ," Tim interviews Kit Hughes, Co-Founder and CEO of Look Listen, a consulting company working at the intersection of creativity, data, and technology. 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...

Journey Towards Anti-Racism Ep9: Conversation with David Reuter (EP.62) 21.06.2022

In episode nine of the 12-part podcast series, " White Men & the Journey Towards Anti-Racism ," Tim interviews David Reuter, Partner at LLR , a private equity firm based in Philadelphia investing in technology and healthcare businesses. 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 justi...

Journey Towards Anti-Racism Ep8: Conversation with Marc Mannella (EP.61) 25.04.2022

In episode eight of the 12-part podcast series, " White Men & the Journey Towards Anti-Racism ," Tim interviews Marc Mannella formerly CEO of KIPP Philadelphia Public Schools and currently a consultant working with clients that range from professional sports teams, to charter schools, to non-profits. This series was created to be a resource for white men who might be wrestling with questions l...

Journey Towards Anti-Racism Ep7: Conversation with Raphael Bemporad & Bryan Miller (EP.60) 10.04.2022

In episode seven of the 12-part podcast series, " White Men & the Journey Towards Anti-Racism ," Tim interviews Raphael Bemporad (Founding Partner) and Bryan Miller (Chief Financial Officer) of BBMG, a branding and social impact consultancy. 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...

Journey Towards Anti-Racism Ep6: Conversation with Sydney Skybetter (EP.59) 04.04.2022

In episode six of the 12-part podcast series, " White Men & the Journey Towards Anti-Racism ," Tim interviews Sydney Skybetter choreographer and founder of the Center for Research on Choreographic Interfaces that convenes experts in dance, performance, computer science, kinesiology, anthropology, social justice, and design to explore the relationship between bodies, movement, and emerging tech...

Values-Based Hiring: Re-Imagining the Search Process (EP.58) 28.03.2022

In this episode, we dive into re-imagining the hiring process, in particular, how it might be designed if we dusted off executive search to co-create a process that centers our values of equity, inclusion, anti-racism, and anti-oppression. Find out more about Work Shouldn't Suck's hiring-based offerings here , including full-service executive search, our hiring process consultation, and our brand...

Journey Towards Anti-Racism Ep5: Conversation with Ron Carucci (EP.57) 23.03.2022

In episode five of the 12-part podcast series, " White Men & the Journey Towards Anti-Racism ," Tim interviews Ron Carucci, an author and Co-Founder & Managing Partner at Navalent , a firm that works with CEOs and executives who are pursuing transformational change for their organizations and industries. This series was created to be a resource for white men who might be wrestling with que...

Journey Towards Anti-Racism Ep4: Conversation with Jay Coen Gilbert (EP.56) 19.03.2022

In episode four of the 12-part podcast series, " White Men & the Journey Towards Anti-Racism ," Tim interviews Jay Coen Gilbert, CEO of Imperative21 and Co-Founder of B Lab. 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 migh...

Journey Towards Anti-Racism Ep3: Conversation with John Orr (EP.55) 17.03.2022

In episode three of the 12-part podcast series, " White Men & the Journey Towards Anti-Racism ," Tim interviews John Orr, Executive Director of the Philadelphia-based Art-Reach . 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...

White Men & the Journey Towards Anti-Racism Series Introduction (EP.54) 17.03.2022

In this episode, co-hosts Tim Cynova and Lauren Ruffin introduce a new 12-part podcast series, " White Men & the Journey Towards Anti-Racism ," where Tim interviews white men in positions of leadership whose companies are engaged in understanding how racism and oppression are at play in their organizations and the work they do. Download the accompanying series study guide . Series guests inclu...

Re-Imagining the Role of the Art Center (EP.53) 13.01.2022

This conversation was recorded as part of Work Shouldn't Suck's Ethical Re-Opening Summit that took place on April 27, 2021. What does it look like to co-create a future where everyone thrives? We explore re-imagining the role of the art center as a canvas and place to play and explore, and how to transform society by transforming organizations and the systems and structures that built and sustain...

Alternate Power and Decision Making Models (EP.52) 27.12.2021

This conversation was recorded as part of Work Shouldn't Suck's Ethical Re-Opening Summit that took place on April 27, 2021. There are a multitude of ways to share power, decision making, and leadership in organizations. In this episode, Aja Couchois Duncan, Hop Hopkins, Lauren Ruffin, and Jason Wiener explore several, as well as discuss what companies should keep in mind as they consider differen...

Policies and Practices for Hybrid Org Arrangements (EP.51) 13.12.2021

This conversation was recorded as part of Work Shouldn't Suck's Ethical Re-Opening Summit that took place on April 27, 2021. How do you create and maintain equitable policies and practices when your team works across differing onsite and remote arrangements? Resources mentioned during session: Results-Only Work Environment The People’s Institute for Survival and Beyond (PISAB) Team Dynamics’s Beha...

Liberating Workplaces (EP.50) 02.12.2021

This conversation was recorded as part of Work Shouldn't Suck's Ethical Re-Opening Summit that took place on April 27, 2021. Co-host Lauren Ruffin facilitates a discussion with Vanessa Roanhorse and Syrus Marcus Ware on how organizations can center those most vulnerable to craft workplaces where everyone can thrive. Their discussion explores recently announced changes at Basecamp, and also the wor...

Employment Law and COVID (EP.49) 23.11.2021

This conversation was recorded as part of Work Shouldn't Suck's Ethical Re-Opening Summit that took place on April 27, 2021. Coming off a year that has echoed sentiments of feeling out of control, leaders from across sectors and industries have questions about employment law, safety, and other areas impacting how we earn a living in the wake of COVID. Those in smaller organizations or independent...

Intentionality and Environmental Impacts (EP.48) 10.11.2021

This conversation was recorded as part of Work Shouldn't Suck's Ethical Re-Opening Summit that took place on April 27, 2021. This past year saw the environmental impacts of the workplace shift dramatically. For many, travel for work was completely erased, both commuting and related business travel. Conferences that traditionally attracted hundreds or thousands of in-person attendees shifted to onl...

Mental Health and Well-Being Amid a Global Pandemic (EP.47) 04.11.2021

This conversation was recorded as part of Work Shouldn't Suck's Ethical Re-Opening Summit that took place on April 27, 2021. How can we and our organizations acknowledge and support the well-being of everyone as we continue to live and work through a global pandemic? Resources mentioned during session: Project Include’s Remote Work Report & Executive Summary “ What Does It Mean to Be a Manager...

New(ish) to Organizational Anti-Racism Work (EP.46) 23.10.2021

This conversation was recorded as part of Work Shouldn't Suck's Ethical Re-Opening Summit that took place on April 27, 2021. This unprecedented time has become a time of learning (and relearning) for many. But what is the process for turning knowledge into action in and out of our organizations? Thinking about organizational anti-racism work begins with a clear understanding of what “the work” is....

Inclusive Hiring Practices (EP.45) 06.10.2021

Three members of the Toronto-based company Generator discuss their approach to inclusive hiring practices as recently demonstrated during their call for new organizational leadership. While the search has concluded with their recent appointment , you can still check out the archived position posting here . Two consultants mentioned during the episode include: Zainab Amadahy and Angela Sun . SEDINA...

Race-based Caucusing in the Workplace (EP.44) 21.09.2021

Courtney Harge (CEO, OF/BY/FOR ALL) and Nicola Carpenter (Director of People Operations, Fractured Atlas) sit down with Tim Cynova to answer the 30 questions they most frequently receive when speaking with individuals and organizations about race-based caucusing in the workplace. Want to learn more? Join them for their brand new course "Race-Based Caucusing in the Workplace: The Why & How" tak...

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