Work. Shouldnt. Suck.

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

56 min · 30. touko 2026
jakson Hiring with Intention: An Executive Search Case Study (EP.93) kansikuva

Kuvaus

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 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 [timcynova.com].

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

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 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 [timcynova.com].

30. touko 202656 min
jakson Unhooking from Norms (EP.92) kansikuva

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 & 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&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 timcynova.com [https://www.timcynova.com/]

15. touko 202653 min
jakson Inside the Search (EP.91) kansikuva

Inside the Search (EP.91)

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 Deeksha * 02:34 Career Origins and Paths * 03:50 What Hiring Gets Wrong * 06:11 Judgment and Fit at Exec Level * 07:42 Defining the Right Leader * 10:04 Showing Up as a Candidate * 12:28 Bold Interviews That Win * 14:45 Testing Thinking and Ego * 17:36 Practical Interview Prep * 19:51 Signal Commitment and Research * 23:49 Authenticity and the Current Job Market * 27:04 Cover Letters and Owning Your Gaps * 29:24 Everything Is Data * 33:28 Bravery and Joyful Leadership * 37:17 Networks and References * 38:34 Encouragement and Relationships Links & Resources * PBR Executive Search [https://www.pbrsearch.com/] including their Active Searches [https://www.pbrsearch.com/active-searches/] and Recent Placements [https://www.pbrsearch.com/active-searches/] * PBR's Job Search Guide [https://www.pbrsearch.com/wps/wp-content/uploads/2026/02/PBR-Executive-Search-Job-Search-Guide.pdf] * Pamela's Succession Planning Series [https://www.planaadvisors.com/wisdom/succession-planning/] * Theatre Development Fund (TDF) [https://www.tdf.org/] 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 [timcynova.com].

28. huhti 202645 min
jakson Hiring in the Age of A.I. (EP.90) kansikuva

Hiring in the Age of A.I. (EP.90)

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 Geepet Whether 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 [https://youtu.be/sLMd0NfaVO4?si=gMS5DWP2tVmdkia5] of the podcast episode! Highlights: * 01:39 Meet Chad Geepet: An Algorithmic Guest * 02:49 The Big Story: Trust in Hiring * 04:03 Theme 1: Learning to Speak Algorithm * 06:41 Reactive Creativity in Job Seeking * 17:09 Theme 2: AI Interviews and the Illusion of Fairness * 26:46 Theme 3: Invisible Filters: Bias in Data and Design * 33:16 The Importance of Bias Audits * 34:21 AI as a Mirror in Hiring * 35:05 Feedforward Loops and Cultural Impact * 35:59 Layers of Transparency and Accountability * 37:42 Theme 4: Trust and Transparency as the New Currency * 38:18 Transparency as a Competitive Advantage * 46:54 Theme 5: From Risk to Responsibility: Designing for Care in Hiring * 1:00:32 The Future of AI in Hiring LINKS & RESOURCES * "Recruiters Use A.I. to Scan Résumés. Applicants Are Trying to Trick It [https://www.nytimes.com/2025/10/07/business/ai-chatbot-prompts-resumes.html/]" by Evan Gorelick (The New York Times, Oct 2025) * "Job Interviews Are Broken: People are sneaking answers from AI, and who can blame them? [https://www.theatlantic.com/technology/2025/10/ai-cheating-job-interviews-fraud/684568/]" by Ian Bogost (The Atlantic, Oct 2025) * "AI Did The Job Interview. The Results Shocked Everyone [https://poetsandquantsforexecs.com/news/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 [https://papers.ssrn.com/sol3/papers.cfm?abstract_id=5395709]" by Brian Jabarian and Luca Henkel * "Why might AI-enabled interviews reduce candidates’ job application intention? The role of procedural justice and organizational attractiveness [https://www.nature.com/articles/s41599-025-05607-z]" 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 [https://www.nature.com/articles/s41586-025-09581-z]" by Douglas Guilbeault, Solène Delecourt, and Srinivasa Desikan (Nature, 2025) * "Invisible Filters: Cultural Bias in Hiring Evaluations Using Large Language Models [https://arxiv.org/abs/2508.16673?]" 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 [https://www.weforum.org/stories/2025/09/ai-powered-recruitment-inclusion-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 [https://www.lawandtheworkplace.com/2023/04/nyc-set-to-enforce-law-to-regulate-use-of-automated-hiring-tools-starting-july-5/]" by Joseph O’Keefe & William Grey * Artificial Intelligence Legal Roundup: Colorado Postpones Implementation of AI Law as California Finalizes New Employment Discrimination Regulations and Illinois Disclosure Law Set to Take Effect [https://www.seyfarth.com/news-insights/artificial-intelligence-legal-roundup-colorado-postpones-implementation-of-ai-law-as-california-finalizes-new-employment-discrimination-regulations-and-illinois-disclosure-law-set-to-take-effect.html] (Seyfarth Shaw LLP, Sept 2025) ABOUT THE GUESTS ABOUT 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 [https://www.linkedin.com/in/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 [https://www.eversocurious.ca/]. ABOUT TIM CYNOVA [https://www.linkedin.com/in/timcynova/] 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.

28. loka 20251 h 4 min
jakson Building Justice: Rethinking Construction, Climate, and Care (EP.89) kansikuva

Building Justice: Rethinking Construction, Climate, and Care (EP.89)

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 [https://www.buildhelm.com/], 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 Baiser * 02:19 Personal Backgrounds and Career Paths * 07:30 The Origin and Vision of HELM Construction Solutions * 12:55 Challenges in the Construction Industry * 16:38 HELM's Approach to Addressing Industry Challenges * 28:09 Leadership and Business Development * 41:51 Climate Justice and Workforce Issues * 51:11 Client Success Stories and Future Vision LINKS & RESOURCES * Recording of the event “Building Solidarity: Construction Workers, Jobsite Safety, and ICE [https://www.buildhelm.com/ice]” mentioned during the episode. * HELM Resource Library [https://www.buildhelm.com/library] containing a wealth of materials to inform, support (and occasionally entertain) you as you develop your company. * HELM Job Board [https://www.buildhelm.com/jobs] if you're looking to join a forward-looking company with a great work culture. ABOUT THE GUESTS ABOUT MEL BAISER [https://www.linkedin.com/in/mel-baiser-ab056411/] | 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 [https://www.linkedin.com/in/kategstephenson/] | 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 [https://www.linkedin.com/in/timcynova/] 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.

15. loka 202558 min