The authentic leader asks 'Is this it?': Choosing heart over armor with Katherine Dudtschak

Scaling empathy moments that matter: Building inclusive cultures from day one with Brooke Sullivan

What happens when you take fifteen years of startup chaos, a front row seat to the exact moment culture either takes root or falls apart, and a leader who gets excited about the hard conversations most people run from? You get this conversation with Brooke Sullivan, Director of People and Talent at Banyan Software, and a leader building belonging inside fast-moving companies. Brooke has spent her career inside software startups, building people functions from zero, from the "we do not even have an org chart yet" phase, and turning that scrappiness into something real. She has a gift for what she calls scaling moments, that critical twenty-to-one-hundred-person inflection point where inclusive culture either becomes the foundation or something you wish you had built. In this episode, Brooke shares the practices and small everyday moments that create workplace belonging long before a handbook ever could. She walks us through her Exercising Empathy programming, the one-on-one design choice that changed how leaders showed up for their teams, and the moment she realized the language a company uses for its people reveals everything. This is a conversation about authentic leadership, human-centered innovation, and what it takes to foster a sense of belonging at work when speed and scale are pulling in opposite directions. Brooke gives listeners practical language for belonging, grounded in fifteen years of building people experience. Must-hear insights and key moments * Why the twenty-to-one-hundred-person window is the make-or-break moment for inclusive culture in scaling startups * The Exercising Empathy programming Brooke built to give teams permission to talk about the hard things at work * A one-on-one design choice, a green or red box at the top of the doc, that lets leaders see what is distracting their people without forcing the conversation * The Bechdel test for meetings and the question Brooke uses to surface who is missing from the room * How the words a company uses for its people reveal whether belonging is real or performative * Why friendship at work is one of the strongest signals of workplace belonging * The story behind Brooke's name and what it taught her about honoring the people who shape us Brooke's standout quotes * "There's a human sitting across from you, whether it's virtual or in person, and sometimes you're the first person that listened to them all day." * "If someone had a friend at work, they felt a deeper sense of belonging." * "You are gifted to care for these people." * "We talk about hard things here. We hold space for each other here." * "If you don't have people, you have nothing." * "My belonging comes from myself until it comes from that organization or that community." * "I know I belong when someone shares something really personal with me." Why this episode matters Building a sense of belonging in fast-scaling companies is not a side project. It is the work. Brooke shows leaders, HR practitioners, and founders how strategic inclusion lives in the smallest design choices: the language we use, the questions we ask, the connection moments we engineer on purpose. This episode reframes belonging vs inclusion in plain terms and gives listeners a working vocabulary for creating belonging at work inside teams that are moving fast and figuring it out in real time. Who should listen People leaders, founders, HR and talent professionals, DEI practitioners, and managers building inclusive culture inside startups, scaleups, and hybrid or remote teams. This episode is for anyone scaling a team through that twenty-to-one-hundred-person window, anyone creating belonging at work without a playbook, and anyone who wants stronger language to talk about belonging in the workplace, authentic leadership, and people experience in ways their teams can feel. An Innovation Unbiased Production https://www.iknowibelongwhen.com/about-the-show [https://www.iknowibelongwhen.com/about-the-show]

Mother Nature humbles, AI exposes: Authentic leadership in motion with Sarah A. Scala

Most leadership advice about artificial intelligence promises the machine will solve your people problems. Sarah A. Scala is in the other room telling executives the opposite. Artificial intelligence will expose them, and she is staying long enough to help fix what surfaces. That is the conversation that Christopher Bylone, host of I Know I Belong When, has on this episode. Sarah is an award-winning diverse supplier, a global speaker, and a leadership consultant who has spent more than two decades turning inclusion into measurable performance. Not aspirational. Not vibes. Measurable. Fortune 10 companies have hired her. Out and Equal and Lesbians Who Tech have put her on their stages. Her work sits at the intersection most executives are quietly panicking about: emotional intelligence, psychological safety, and how a human leader keeps both alive in the age of artificial intelligence. This is a working session on authentic leadership, inclusive culture, and how building belonging in the workplace shows up on the bottom line. Sarah walks through what shifts when a coach treats strategic inclusion as a performance strategy rather than a values conversation, why bite-sized trust changes teams faster than any policy rewrite, and what kayaking, hiking, and Nordic skiing teach her about people experience that no boardroom can. Mother Nature humbles. Artificial intelligence exposes. Authentic leadership stays in motion through both. Must-hear insights and key moments * Why Sarah stopped treating inclusion as values work and started treating it as a measurable performance strategy * The new question executives are asking now, and what it signals about people experience in the age of AI * How artificial intelligence exposes the people problems leaders thought they had hidden, and why empathy is the differentiator * Why accuracy does not equal care when machines write your emails, and what that means for creating belonging at work * The smallest inclusion behavior that creates the biggest team shift, with a real example from a pharma executive * What changed when Sarah came out as a certified LGBT business enterprise and stopped translating herself in the room * What Mother Nature, a kayak, and 50 books a year teach about authentic leadership that no boardroom ever will Sarah's standout quotes * "With my clients, I measure outcomes, not intentions" * "AI can be a super speedy and helpful tool, and it can never replace people and effective leaders" * "Accuracy doesn't always equal care" * "It lacks that human behavior. It also can lack accountability" * "Look at it as more of a sidekick" * "What's most important is that everyone in that room knows I am safe to be themselves around" * "When my voice changes outcomes, that's the end game" Why this episode matters Most conversations about artificial intelligence at work treat people experience as the soft thing the technology will replace. Sarah names the opposite. The machine accelerates everything, including gaps in trust, missed names, and leaders who never learned to recover from a mistake. Authentic leadership in this moment is the practice of staying human and measurable at the same time. For anyone building belonging, leading remote teams, or working through belonging vs inclusion, Sarah hands you language and a next step you can use Monday morning. Who should listen This one is for executives, HR and people leaders, learning and development professionals, DEI and IDEA practitioners, and team managers who want a practical view on creating a sense of belonging at work in the age of artificial intelligence. It is for leaders coaching senior teams through trust and psychological safety. It is for founders and small business owners building inclusive culture from the ground up. It is for anyone caught between business savvy and empathetic, and ready to be both. An Innovation Unbiased Production https://www.iknowibelongwhen.com/about-the-show [https://www.iknowibelongwhen.com/about-the-show]

Accessibility never meant lowering the bar: The win-win case for inclusion with Daniel Hodges

What if everything you have been told about accessibility, inclusion, and the so-called trade-off between doing good and doing well is wrong? In this episode of I Know I Belong When, host Christopher Bylone sits down with Daniel Hodges — lawyer by training, nonprofit founder by calling, and living proof that when someone tells you no road exists, that is simply the opening line of your comeback story. As a kid, Daniel was functionally illiterate. A so-called Blindness Professional once told him the best he could hope for was canning chairs for a living. He went on to earn multiple advanced degrees, launch the Pieces of Me Foundation while still in law school, and build a career dismantling the false paradigm that organizations must choose between accessibility and profit, inclusion and merit. Daniel lives with blindness, chronic pain, anxiety, and depression, and he refuses to let any of those define his ceiling. His story gives listeners new language for belonging — language rooted in lived experience, authentic leadership, and the conviction that strategic inclusion is not charity, it is good design. Whether you are an HR leader exploring how to create a sense of belonging at work, a manager rethinking belonging in remote teams, or an executive curious about belonging vs inclusion, this conversation delivers practical insight inside one of the most powerful comeback stories you will hear this year. Must-hear insights and key moments * The false paradigm myth: why accessibility and profit, inclusion and merit, were never meant to be opposing forces * Build with, not for: how co-designing alongside disabled people produces human-centered innovation no one expected * The professor moment: how one law professor's email redefined Daniel's understanding of inclusive culture and what it means to truly belong in a room of high standards * High standards plus human kindness: why lowering the bar is not inclusion, and what authentic leadership actually requires * Invisible disabilities and the toughness tax: how chronic pain, anxiety, and depression shaped Daniel's identity differently than blindness ever did * Calling people in, not calling them out: the mindset Daniel brings into every room that is not yet ready for him Daniel's standout quotes * "I try to help organizations find a way to break free of the false paradigm that makes them believe they have to choose between accessibility and profit, inclusion and merit." * "I do not want to succeed based on somebody's pity. I want to succeed and fail based on how I show up, based on my gifts and talents." * "Even failure is an opportunity to grow." * "We focus on calling people in rather than calling them out, and meeting people where they are." * "So often we are judged not by our own capabilities, but by other people's perceptions." * "I know I belong when I am able to compete and show up and be judged on my gifts and talents, my successes, my failures — not based on bias, not based on barriers, but based on my ability to compete on a level playing field." Why this episode matters This conversation reframes accessibility not as a cost center, not as a charitable add-on, though as the foundation of strategic inclusion and human-centered innovation. Daniel gives leaders, people practitioners, and culture-builders the language they have been searching for to talk about belonging vs inclusion — with clarity, credibility, and lived authority. For anyone serious about building belonging in workplaces and remote teams, Daniel offers a model that is sustainable, repeatable, and rooted in dignity. Who should listen This episode is for HR leaders, IDEA practitioners, people experience designers, and managers actively asking how to create a sense of belonging at work. It is for executives wrestling with the business case for accessibility. It is for disability advocates who want an honest first-person story about navigating school, work, and parenting through chronic pain and invisible disability. And it is for leaders committed to creating belonging at work that does not lower the bar — it raises everyone over it. An Innovation Unbiased Production https://www.iknowibelongwhen.com/about-the-show [https://www.iknowibelongwhen.com/about-the-show]

The authentic leader asks 'Is this it?': Choosing heart over armor with Katherine Dudtschak

"What does authentic leadership look like when the person in the corner office decides that the boldest move available is telling the truth about who she is? In this episode of I Know I Belong When, host Christopher Bylone sits down with Katherine Dudtschak, former president and CEO of Home Equity Bank and former executive vice president at RBC, to explore what happens when more than thirty years of elite corporate performance meet a choice to integrate rather than fragment. Katherine is the creator of the Sincerely framework and a conscious leadership advisor who guides executives and founders from survival-based identity to essence-led leadership. She serves the leader who has the title, the resume, the followers, and is still quietly asking, "Is this it?" In this conversation, Katherine walks listeners through the moment she publicly came out as a woman in front of 80,000 colleagues while still in executive leadership, and what that decision unlocked for her, the people around her, and the culture she helped shape. She speaks plainly about command-and-control giving way to heart-centered leadership, vulnerability as strategic power, and why an inclusive culture is built from the inside of the leader outward. This is a master class in authentic leadership, workplace belonging, and the cost of leading from armor rather than essence. Must-hear insights and key moments * Why heart-centered leadership creates psychological safety that policies alone cannot deliver * The Sincerely framework explained: holding space for human stories so others find language for their own becoming * How vulnerability operates as a strategic asset for senior leaders, and what shifted when employees began trusting Katherine with their stories * The three layers of identity Katherine names: essential self, physical and inherited self, and lived experience self * Why the future of work favors regenerative leaders over performative ones, and what that means for building belonging in remote and hybrid teams * The five points Katherine wants every executive quietly fragmenting in a corner office to hear before their next decision * What it takes to bring your whole self to work, and why belonging to yourself first is the foundation for every other room you enter Katherine's standout quotes * "I'm a human being. I'm a human being first and foremost." * "Opening your heart and being vulnerable is a gift. It's not a weakness." * "It is moving forward in the face of profound, crippling fear because you're trying to be true to something deep within you." * "No human journey to wholeness happens in thirty seconds or thirty minutes or thirty days." * "There's a better world available to us. One that is truly inclusive from a place of kindness and curiosity." * "The best is yet to come." * "I know I belong when I find self-love within me." Why this episode matters This conversation gives leaders practical language for belonging in the workplace at a moment when teams are tired of performance and ready for presence. Katherine names the cost of fragmentation, the power of vulnerability, and the difference between inclusive culture as policy and inclusive culture as practice. For anyone navigating belonging vs inclusion, this is a first-person blueprint grounded in real executive experience. Who should listen CEOs and senior leaders are asking whether the title is enough. HR and people experience practitioners building strategic inclusion programs and seeking stories that land beyond the slide deck. DEI consultants, founders, and team managers are learning how to create a sense of belonging at work. Coaches and conscious leadership advisors are developing their own frameworks. If you are leading a company, a team, or yourself through a season asking more of you than you thought you had, this one is for you." An Innovation Unbiased Production https://www.iknowibelongwhen.com/about-the-show [https://www.iknowibelongwhen.com/about-the-show]

Everyday Bias, rewritten: AI, attention, and the next generation with Jake Ross

Last week, you met the father. This week, meet the son who did not just inherit a mission. He built his own lane inside of it. In this episode of I Know I Belong When, Christopher sits down with Jake Ross, founder and CEO of Belong Together, banjo player, former COO of an AI startup, and co-author of the second edition of Everyday Bias with his father, Howard J. Ross. Jake holds a bachelor's degree from UC Berkeley in interdisciplinary studies, a master's in applied positive psychology from the University of Pennsylvania, and a thesis called Building Belonging that reads more like a mission statement than an academic paper. In part two of this father-and-son series, Jake brings the next-generation vantage point. His chapters in the new edition of Everyday Bias take on what most belonging conversations still avoid: the attention economy, the algorithms that decide what we see, and the emotional relationships people are quietly forming with artificial intelligence. Jake describes it all honestly, as someone who has sat on both sides of the question. Jake also opens up about the recovery community that first showed him what belonging feels like when you cannot earn it, and the friends who see him so completely that his identity stays steady in any room. If last week's conversation offered a half-century of perspective, this one offers the map forward. Must-hear insights and key moments: * How a recovery community in California taught Jake what a real sense of belonging at work and in life actually feels like * Why the death of the public third place matters more now than it did when Robert Putnam first wrote about it * What the attention economy is costing us, and how algorithms quietly engineer outrage on every side of the political spectrum * The hidden cost of non-belonging inside tech teams, and why isolated builders tend to create isolating systems * Jake's father-to-colleague moment from his side of the table, and why it changed how he shows up professionally * Why the Lego collection, the banjo, and the fire dancing are not side quests; they are the practice of authentic leadership in full expression Jake's standout quotes: * "Belonging is not about being good enough to be in a group. It comes when you and those around you decide that you belong, simply because you do." * "When the people building those systems are lonely and not connected to their broader self, the influences of that loneliness get baked into the algorithms." * "Who we are paints the glasses." * "If I can help one person feel like they really matter, that is my life's work in action." * "I know I belong when the world around me celebrates my desire to be in full expression." Why this episode matters: Belonging is not a soft concept, and it is not an HR initiative. It is the infrastructure of how humans show up at work, with each other, and online. Jake offers the next-generation view on what is shifting under our feet: algorithms trained to agree with us, a tech industry building interpersonal products from inside deep isolation, and a culture slowly losing its public third places. His work bridges positive psychology research and practical human-centered innovation. If you lead a remote team, a product team, or an inclusive culture strategy, Jake names what the next five years will actually require. Who should listen: This episode is for founders and product leaders thinking seriously about bias baked into AI systems, people leaders designing inclusive culture for a hybrid and AI-augmented workplace, DEI practitioners looking for fresh language on belonging versus inclusion, positive psychology students and practitioners, HR and people experience strategists navigating belonging in remote teams, and anyone raising, mentoring, or working alongside the next generation of leaders. If last week Howard gave you the long view, this week Jake gives you the fieldwork. An Innovation Unbiased Production https://www.iknowibelongwhen.com/about-the-show [https://www.iknowibelongwhen.com/about-the-show]