Liz Landry (fromoperatortoownerbook.com [http://fromoperatortoownerbook.com/]), speaker, strategist, and author of the forthcoming book From Operator to Owner: The Entrepreneur's Guide to Running a Business That Doesn't Run You [https://lizlandry.com/fromoperatortoowner], joins host Dan Freehling (contempusleadership.com [http://contempusleadership.com/]) to explain why so many entrepreneurs end up trapped by the businesses they built. Liz argues that getting unstuck requires a shift from the "hard work" identity that gets a business off the ground to the identity of a leader (02:31) and lays out her four-stage framework for sustainable growth (10:07). Liz offers a practical test for when a solopreneur is ready to make a first hire (17:21), contrasts the wiring of entrepreneurs with the skillsets that leadership actually demands (27:16), and sheds light on the misconception that you're the only one struggling (33:24). Recommended Reading: "The Road Less Stupid" [https://www.amazon.com/Road-Less-Stupid-Keith-Cunningham/dp/0984659269] by Keith J. Cunningham and "The E-Myth Revisited" [https://bookshop.org/p/books/the-e-myth-revisited-why-most-small-businesses-don-t-work-and-what-to-do-about-it-michael-e-gerber/e748163cc1e35924] by Michael E. Gerber. Show notes at forwardlookingleadership.com [http://forwardlookingleadership.com/].

Liz Landry on the Four Stages of Business Growth and What It Really Takes to Move from Operator to Owner

Joe Davis (linkedin.com/in/joedavis1313 [https://linkedin.com/in/joedavis1313], joedavis.com) [https://joedavis.com/], former Head of Boston Consulting Group-North America and author of The Generous Leader: 7 Ways to Give of Yourself for Everyone's Gain, joins host Dan Freehling (contempusleadership.com [https://contempusleadership.com/]) to discuss what separates truly generous leadership from simply being nice. Joe draws the distinction between direct kindness and fearful 'nice' (03:05). He explains why technology, the always-on work-life blur, and the disappearance of lifetime job security have made command-and-control unworkable (06:39). Joe argues that the rise of AI raises the premium on generous leaders who can guide their teams through change (11:02), tells a vulnerable personal story about his father and explains how sharing it with colleagues deepened trust (17:52), and offers hard-won lessons on driving organizational change (26:16). Joe and Dan discuss the role of purpose in private-sector companies (30:20), Joe’s lessons on nonprofit board service (35:28), and what he hopes executives will take away from the book (37:25). Show notes at forwardlookingleadership.com [https://forwardlookingleadership.com/].

Former Head of BCG-North America Joe Davis on Generous Leadership, Why It Isn't Always Nice, and What Separates Great Executives From the Rest

Kirsten de Greling-Visman (linkedin.com/in/kirstendegrelingvisman [https://www.linkedin.com/in/kirstendegrelingvisman/], claritycompasscareercoach.com [https://www.claritycompasscareercoach.com/]), international career strategist and founder of Clarity Compass Career Coaching, joins host Dan Freehling (contempusleadership.com [https://www.contempusleadership.com/]) to share how she helps clients use AI smartly in their job search. Kirsten explains why she started building AI systems after watching clients' applications lose all personality (00:48), and walks through her “own your story” foundation, culture matching, and trigger-event research (05:07). She makes the case for using Gemini's live, Google-integrated search rather than frozen data (07:31), and breaks down her weekly strategy across the public and hidden job markets (11:01). Kirsten and Dan discuss why human connection and networking are still critical even with AI (21:21), her own path across nine countries and path to career coaching (26:02), and why most senior transitions happen before a role is ever posted (33:36). Recommended Reading: “Working Identity [https://bookshop.org/p/books/working-identity-unconventional-strategies-for-reinventing-your-career-herminia-ibarra/570a62bc3a115939]” by Herminia Ibarra. Kirsten also returns often to Brené Brown on owning your story, and points to LinkedIn and Brainz Magazine (brainzmagazine.com [https://www.brainzmagazine.com/]) as ongoing resources. Show notes at forwardlookingleadership.com [https://forwardlookingleadership.com/].

Kirsten de Greling – Visman on Using AI Smartly in Your Job Search

Stephe McMahon (boardbridge.com [https://www.boardbridge.com/], linkedin.com/in/stephe-mcmahon-3b2750/ [https://www.linkedin.com/in/stephe-mcmahon-3b2750/]), co-founder and Chief BridgeBuilder at BoardBridge, which empowers corporate employees to serve on nonprofit boards, joins host Dan Freehling (contempusleadership.com [https://www.contempusleadership.com/]) to dig into why there are more than a million open seats on nonprofit boards and how to close the gap. Stephe explains why the on-ramp to board service is so unclear and how BoardBridge lowers the barrier for individuals and nonprofits alike (01:18). He shares his advice for aspiring board members (07:55) and gives a crash course on board service (14:20). Stephe and Dan discuss board service as a form of leadership development, including new Taproot Foundation and PwC research showing pro bono service outperforms traditional training on human skills (17:44). Stephe makes the case for using your "new kid card" and what good governance actually looks like (32:25) and walks through the BoardBridge process end to end (38:10). Recommended Reading: BoardSource's resources [https://boardsource.org/] and Taproot Foundation and PwC's "Human Skills at Work [https://taprootfoundation.org/tools/human-skills-at-work-pro-bono-service-driving-development-in-a-changing-world-of-work/]" report. Show notes at forwardlookingleadership.com [https://forwardlookingleadership.com/].

BoardBridge Co-Founder Stephe McMahon on How to Join a Nonprofit Board, Why It Beats Traditional Leadership Development, and the Power of Your 'New Kid Card'

Lauren Goldberg (laurengoldbergcoaching.com [http://laurengoldbergcoaching.com/], linkedin.com/in/lauren-e-goldberg/ [https://www.linkedin.com/in/lauren-e-goldberg/]), a career self-discovery and leadership coach for changemakers working with their ADHD instead of against it, joins host Dan Freehling (contempusleadership.com [http://contempusleadership.com/]). Lauren explains why the ADHD label is just bad branding and what leaders can actually do to support neurodivergent team members (00:39). She unpacks internalized ableism and what it looks like to turn down the volume on the inner critic and work with your natural wiring rather than against it (03:50). Lauren and Dan explore why overconfidence and under-confidence so often come from the same place, and how to build confidence that is not rooted in self-judgment (08:33). Lauren describes the exhausting cost of masking and the freedom of embracing the unique shape that school never made room for (13:03). She also shares how she is rethinking her own inner bully and inner best friend language through the lens of parts work (20:24). The conversation turns to the new frontiers she’s exploring in her practice, from nonviolent communication and decolonizing the framework to moving from canceling toward calling people in (24:03). Lauren lays out the crux of Marshall Rosenberg's nonviolent communication (29:12) and closes with book recommendations through a disability justice lens (31:58). Recommended Reading: "Nonviolent Communication" [https://bookshop.org/p/books/nonviolent-communication-a-language-of-life-life-changing-tools-for-healthy-relationships-marshall-b-rosenberg/10180253?ean=9781892005281] by Marshall B. Rosenberg, "D [https://bookshop.org/p/books/nonviolent-communication-a-language-of-life-life-changing-tools-for-healthy-relationships-marshall-b-rosenberg/10180253?ean=9781892005281]ecolonizing Nonviolent Communication" [https://www.meenadchi.com/] by Meenadchi, "Calling In: How to Start M [https://www.meenadchi.com/]aking Change with Those You'd Rather Cancel" [https://bookshop.org/p/books/calling-in-how-to-start-making-change-with-those-you-d-rather-cancel-loretta-j-ross/3628632975c0d0e8] by Loretta Ross, "The Body Is Not an Apology" [https://bookshop.org/p/books/calling-in-how-to-start-making-change-with-those-you-d-rather-cancel-loretta-j-ross/3628632975c0d0e8] by Sonya Renee Taylor, "Being [https://bookshop.org/p/books/the-body-is-not-an-apology-second-edition-the-power-of-radical-self-love-sonya-renee-taylor/fa663e923147ae53]Heumann" [https://bookshop.org/p/books/being-heumann-an-unrepentant-memoir-of-a-disability-rights-activist-judith-heumann/15281048] by Judy Heumann, and "Care Work: Dreaming Disability Justice" [https://bookshop.org/p/books/care-work-dreaming-disability-justice-leah-lakshmi-piepzna-samarasinha/16603798] by Leah Lakshmi Piepzna-Samarasinha. Show notes at forwardlookingleadership.com [http://forwardlookingleadership.com/].

Lauren Goldberg on Working With Your ADHD Instead of Against It, Leading Neurodivergent Teams, and When Overconfidence Is Insecurity in Disguise

Navid Ladha (linkedin.com/in/navidladha/ [https://www.linkedin.com/in/navidladha/], onpurposecareers.org [https://onpurposecareers.org/]), founder of OnPurpose Careers, joins host Dan Freehling (contempusleadership.com [https://www.contempusleadership.com/]) to challenge the notion that purpose-driven work has to come with lower pay. Navid and Dan discuss why underpaying social impact staff creates wealth inequity that disconnects organizations from the communities they serve (02:53) and walk through what job seekers, board members, and executive leaders can each do to shift this (04:10). Navid shares his take on what AI-driven workforce changes may mean for the social sector (08:44) and the policy levers that could bring more people into this work (12:09). Navid and Dan talk about the growing demand for strategic fundraisers and the case for nonprofits to define an "end game" rather than operate in perpetuity (24:32). Navid identifies the highest-paying, most active subsectors right now (27:38) and Dan describes what he calls the "new social sector" (33:58). Both push back on greenwashing and performative social impact branding (37:09). On remote work, Navid shares findings from running the OnPurpose Careers job board (46:00). He also walks through how he sources hidden roles through his network and how jobseekers can train their LinkedIn algorithm to surface real opportunities (48:59). Recommended Reading: "Sparked [https://bookshop.org/p/books/sparked-discover-your-unique-imprint-for-work-that-makes-you-come-alive-jonathan-fields/15713075]" by Jonathan Fields, "Be Ready When the Luck Happens [https://bookshop.org/p/books/be-ready-when-the-luck-happens-a-memoir-ina-garten/21212711]" by Ina Garten, and "This Is Marketing [https://bookshop.org/p/books/this-is-marketing-you-can-t-be-seen-until-you-learn-to-see-seth-godin/12083742]" by Seth Godin. Show notes at forwardlookingleadership.com [https://forwardlookingleadership.com/].

Navid Ladha on Why Low Pay Is a Leadership Problem, Finding Hidden Remote Roles, and the Future of Social Impact

Logan Yonavjak (founderready.io [https://founderready.io/]), Co-Founder and CEO of Founder Readiness Institute, joins host Dan Freehling (contempusleadership.com [https://www.contempusleadership.com/]) to discuss how AI-powered assessment is giving investors, enterprises, and leaders a new window into leadership capacity. Logan explains the concept of vertical development and why it is the theoretical underpinning of Founder Readiness Institute’s work (00:08:35), addresses concerns about AI bias and shares how it can counter traditional human biases, and discusses what she learned from taking her own assessment (00:29:17). Logan makes the case for coachability as the most essential leadership construct (00:27:08) and explains why human leaders in an AI-augmented world will need to hold increasingly more complexity (00:32:42). Recommended Reading: "$100M Leads [https://bookshop.org/p/books/100m-leads-how-to-get-strangers-to-want-to-buy-your-stuff-alex-hormozi/1f16f42d4b73a7d8]" by Alex Hormozi. Show notes at forwardlookingleadership.com [https://forwardlookingleadership.com/].

Logan Yonavjak on Making Smarter People Decisions, Assessing Leader Readiness With AI, and Why Coachability Beats Pedigree Every Time

Eirik Gislason (archwaypartnersinc.com [https://archwaypartnersinc.com/]), founder of Archway Partners Coaching, leader of the Excelsior Team at Brown Harris Stevens, and host of the Shear Line: Negotiation Mastery podcast, joins host Dan Freehling (contempusleadership.com [https://www.contempusleadership.com/]) to discuss how to get more of what you want without bullying, hard bargaining, or leaving value on the table. Eirik explains why hiring the meanest broker backfires and what strength in negotiation actually looks like (00:42), how collaborative negotiators grow the pie in a real estate deal rather than splitting it (06:05), and the upside and hidden downside of “Minnesota nice” (12:03). He walks through how to prepare for a negotiation with a Trump-style hard bargainer, including anchoring, BATNAs, and process before substance (15:47). Eirik also shares takeaways from the Harvard Law School negotiation program (41:20), unpacks the five most common negotiation mistakes (47:42), and breaks down the four decision-maker types (53:23). Recommended reading: “Getting to Yes [https://a.co/d/0aVjkrYu]” by Roger Fisher and William Ury, “Getting to Yes with Yourself [https://a.co/d/0c9OChZp]” by William Ury, “Think Again [https://a.co/d/0fOPaIOC]” by Adam Grant, “Never Split the Difference [https://a.co/d/03mkXwo5]” by Chris Voss, and “Negotiating the Impossible [https://a.co/d/0ifm0cFZ]” by Deepak Malhotra. Show notes at forwardlookingleadership.com [https://forwardlookingleadership.com].

Eirik Gislason on Hard-Won Negotiation Lessons from NYC Real Estate, Outmaneuvering Hard Bargainers, and Getting Paid What You Deserve

Jermaine Ee, founder of Heirlight (heirlight.com [https://heirlight.com/en]), an AI-powered estate planning app, joins host Dan Freehling (contempusleadership.com [https://contempusleadership.com]) to discuss what it takes to make one of life's most avoided conversations easier. Jermaine shares how a dinner with his parents about retirement planted the seed for Heirlight (02:37) and how the app uses guided AI conversation rather than a laundry list of assets to build an estate plan around the user (04:53). He also describes his deliberate choice to stay bootstrapped and away from the venture treadmill (15:35), the mentality required to run a product-driven startup (21:38), and how losing his mother gave his mission a clarity he didn't ask for but can't ignore (22:56). Recommended reading: “Essentialism [https://a.co/d/001O2HPa]” by Greg McKeown, “Die with Zero [https://a.co/d/02hNK2NS]” by Bill Perkins, and “Predictably Irrational [https://a.co/d/0dMxZII4]” by Dan Ariely. Show notes at forwardlookingleadership.com [https://forwardlookingleadership.com].

Jermaine Ee on Scaling an AI-Powered Startup, Designing for the 70%, and Not Getting to Choose Your Founder Story

Ang Richard (angrichard.com [https://www.angrichard.com/], linkedin.com/in/angela-richard/ [https://www.linkedin.com/in/angela-richard/]), a Gen Z career coach, TEDx speaker, LinkedIn Top Voice, and PhD candidate in higher education, joins host Dan Freehling (contempusleadership.com [https://contempusleadership.com]) to examine how Gen Z is navigating a rapidly changing world of work. Angela reflects on shares guidance for early career professionals on handling criticism and staying grounded in impact rather than online noise (03:35). She explores how generational differences in communication styles and values, especially around feedback, work-life balance, and career development, are often misinterpreted as deficiencies rather than differences (06:56). Angela also discusses the current labor market and its disproportionate impact on early career professionals, emphasizing the importance of realistic, data-informed coaching that acknowledges structural barriers alongside individual agency (13:22). The conversation also covers Angela’s approach to LinkedIn as a space for authentic thought leadership, where sharing failures and uncertainty builds trust and community rather than personal branding polish (21:44). Angela shares insights from her doctoral research on the school-to-work transition, sense of belonging, and intersectionality, as well as her work examining how federal workforce policy connects unevenly to community colleges across states (32:07). Recommended reading: “The Privileged Poor [https://a.co/d/6ldETcz]” and “Class Dismissed [https://a.co/d/by1Z17w]” by Anthony Abraham Jack, “The Unspoken Rules [https://a.co/d/5vm40M7]” by Gorick Ng, “Careers by the People [https://a.co/d/jficRqx]” by Mike Wysocki. Show notes at forwardlookingleadership.com [https://forwardlookingleadership.com].

Ang Richard on Coaching Gen Z, Becoming a LinkedIn Top Voice, and Reimagining the Campus-to-Career Playbook

Dan Freehling (@contempusleadership) · Zencastr

Dan Freehling (@contempusleadership)

This is a podcast for visionary leaders building future-ready organizations. You’ll come away from each episode with fresh, in-depth insights on all things leadership and career development.

Forward-Looking Leadership