One big question, asked at the start and end of the show—with the last answer being much deeper than the first. On Ask It Like You Mean It, Aaron Barlin commits to asking his deepest questions, and his guests commit to giving their deepest answers. Authors, consultants, and organizational leaders are guided to give their most hard-hitting insights into their industry's hardest questions.
That's a wrap on Season 1! Many thanks to our wonderful guests this season: together, they offer a robust range of different and in-depth expertise. We asked them hard questions like we meant it -- and they all answered like they meant it, too!
Presented by Elynndí (http://elynndi.com), and hosted by Aaron Barlin (https://www.linkedin.com/in/aaron-barlin/). See elynndi.com to learn how we "think like a teacher" to create the show.
10 Nov 2025
Sarah Kagan helps us rediscover ourselves through grief
Sarah Kagan (https://www.linkedin.com/in/sarah-kagan), grief coach and consultant at Keriah Grief Coaching & Consulting (https://www.keriahcoaching.com/), helps people and organizations rebuild the capacity to grieve together—openly, skillfully, and with ritual. Sarah examines what our loss of common grief practice reveals about community and emotional life today.
Sarah shares insights on:
How her lived experienced called upon her to become a grief coach
What distinguishes grief coaching from therapy
How to design grief-literate teams and organizations—and avoid delaying the work we know is healthy but uncomfortable
When grief fuses with identity and how to transition toward “building a life that fits who you’ve become”
Presented by Elynndí (http://elynndi.com), and hosted by Aaron Barlin (https://www.linkedin.com/in/aaron-barlin/). See elynndi.com to learn how we "think like a teacher" to create the show.
3 Nov 2025
Maria Morukian explains what it means to lead lovingly
Maria Morukian (https://www.linkedin.com/in/maria-morukian), founder and CEO of MSM Global Consulting (https://msmglobalconsulting.com/about/about-maria-morukian/), has spent over 18 years guiding leaders and organizations through culture change, intercultural competence, and leadership development.
Maria reframes leadership not as a position of power but as an act of loving stewardship—setting the tone for what organizations and people can become when they work alongside each other, rather than "for" their respective superiors.
Maria shares insights on:
What motivates her to challenge traditional organizational norms and leadership approaches she sees repeatedly across cultures and industries
The underlying cultural and structural mechanisms that perpetuate the same old leadership models over and over
Pitfalls that even well-intentioned leaders stumble into when trying to evolve their practices toward more inclusive, belonging-oriented leadership
What it looks like when belonging truly sits at the heart of organizational achievement—and the real-world examples that show it in action
Presented by Elynndí (https://elynndi.com/), and hosted by Aaron Barlin (https://www.linkedin.com/in/aaron-barlin/). See elynndi.com to learn how we “think like a teacher” to create the show.
27 Oct 2025
Wallis Mills helps us stay modern in our own way, instead of following the herd
Wallis Mills (https://www.linkedin.com/in/wallismills)—Founder & Principal Advisor at Modern Enterprise (https://modernenterprise.ai/)—helps C-suites separate real modernity from trend-chasing. Drawing on executive roles at AMD and NVIDIA, she advises on AI readiness, go-to-market, and narrative strategy that builds durable advantage instead of “shiny object syndrome."
Wallis shares insights on:
Why she left her previous roles to build an independent strategic studio
Lessons from big-chip playbooks (AMD, NVIDIA): strategies worth emulating, as well as common missteps to avoid
How and why she identifies an organization's identity and direction before strategies and tactics
Differentiating helpful collective wisdom from unhelpful groupthink when it comes to the "new shiny thing" like AI
Presented by Elynndí (https://elynndi.com/), and hosted by Aaron Barlin (https://www.linkedin.com/in/aaron-barlin/). See elynndi.com to learn how we "think like a teacher" to create the show.
20 Oct 2025
Ellen Raim helps Gen Z and Gen X finally understand each other
Ellen Raim (https://www.linkedin.com/in/raimprofile), founder of People Matter LLC (https://peoplematterllc.com/), is a "generational interpreter" in the workplace, helping companies and young professionals bridge the divide between Gen Z, Gen X, and all in-between.
In this episode, Ellen invites us to rethink how age-based differences in the workplace are about more than just our years of life: they’re about how we handle change and difference in general, as well as how we play—or not play—by "rules of the game" that organizations often leave unwritten.
Ellen Raim shares insights on:
What sparked her shift from employment attorney and HR leader to "organizational whisperer" who decodes how young professionals adapt to established cultures
Why thinking of generational divides as “speaking different languages” or “playing by different rules” can help older and younger colleagues interpret each other more effectively
The subtle (and not so subtle) behaviors in workplaces that say “people don’t matter”—and how those behaviors cut across generations
How our resistance to change and our comfort with familiar patterns keep old generation gaps alive, even when the workforce is evolving
Presented by Elynndí, and hosted by Aaron Barlin (https://www.linkedin.com/in/aaron-barlin/). See elynndi.com (https://elynndi.com/) to learn how we “think like a teacher” to create the show.
13 Oct 2025
Rachael G provides a deep dive on toxic workplaces
Rachael G describes herself as a “Big Law refugee,” and she joins us to pull back the veil on some of the most toxic workplaces in her industry (while keeping the most sensitive details confidential along the way). Our conversation is about how walking away from toxicity is the start, not the end, of a new and more fulfilling phase of work and life.
A former attorney at one of New York’s billion-dollar law firms, Rachael clerked for a federal judge before finding her way to the firm she's at now: a workplace haven known for its more balanced culture and humane pace. Reflecting on her and her colleagues' challenges with unhealthy culture, she explores what it takes to rebuild professional agency and personal fulfillment after toxicity takes its toll.
Rachael shares insights on:
The earliest red flags shared across her toxic workplaces
The difference between a toxic moment and a toxic culture
The turning points that finally broke the cycle of toxicity
How to detox from the lingering effects of unhealthy professional systems
While respecting confidentiality, Rachael offers a rare inside view of Big Law’s pressures and the deeper recovery that begins only after you leave. Whether you’ve endured a toxic workplace yourself or simply want to recognize the warning signs sooner, this conversation reframes “quitting” as a new beginning rather than a finish line.
Presented by Elynndí, and hosted by Aaron Barlin (https://www.linkedin.com/in/aaron-barlin/). See elynndi.com (https://elynndi.com/) to learn how we "think like a teacher" to create the show.
6 Oct 2025
Charlotte Safran knows strong health starts with strong community
Charlotte Safran (https://www.linkedin.com/in/charlotte-safran-a4608772/), Program Manager at Vermont Department of Health (https://www.healthvermont.gov/), has built her career around transforming healthcare into a system of genuine partnership. Her work bridges hospitals, families, and communities—grounded in both her lived experience as a parent and her professional mission to center empathy, equity, and collaboration in care.
Charlotte shares insights on:
What “patient- and family-centered care” means
How community storytelling reshapes empathy and policy in healthcare
The entrenched philosophies that still compete with partnership models
How partnership as a principle could transform healthcare’s culture
Whether you’re a provider, policymaker, patient advocate, or simply someone who’s ever interacted with the health system, this conversation with Charlotte Safran offers a vision of care that far departs from the reality of care today—and positively so!
Presented by Elynndí, and hosted by Aaron Barlin (https://www.linkedin.com/in/aaron-barlin/). See elynndi.com (https://elynndi.com/) to learn how we "think like a teacher" to create the show.
6 Oct 2025
Lani Matsumura explains how to make learning its own lifestyle
Lani Matsumura (https://www.linkedin.com/in/lanimatsumura), Director of Social Services Training & Development at The Salvation Army (https://shoutoutla.com/meet-lani-matsumura-director-of-training-development/), brings her background as a teacher, instructional designer, and believer in lifelong learning to this conversation. In this episode, she offers a fresh perspective on embracing a learning lifestyle—one rooted in growth, rest, and integrity, not in pressure, perfectionism, or burnout.
Lani shares insights on:
Her professional pivots and how each transition signaled a deeper call to learn
The teaching tools and design strategies she still leans on in her own personal growth
The tension between productive growth and rest, and how she honors learning even in stillness
Stories from her work at The Salvation Army and past roles
If you’re balancing ambition with well-being, seeking a more sustainable way to grow, or curious how learning shows up in all seasons of life, this conversation with Lani Matsumura is for you!
Presented by Elynndí, and hosted by Aaron Barlin (https://www.linkedin.com/in/aaron-barlin/). See elynndi.com (https://elynndi.com/) to learn how we "think like a teacher" to create the show.
6 Oct 2025
Ianna Raim coahces us to unlearn what holds us back
Business and executive coach Ianna Raim, MBA, PCC (https://iannaraimcoaching.com/) of Ianna Raim Coaching (https://iannaraimcoaching.com/) helps leaders and professionals stop sabotaging themselves and build careers that feel authentic, resilient, and fulfilling. In this episode, she breaks down how to get out of our own way and grow in both business and life.
Ianna Raim shares insights on:
What it really means to “get out of our own way” in career and leadership
Why professionals often mistake self-advancement for self-sabotage
Common challenges her clients face—and the root causes behind them
Defining coaching moments that reveal what transformation looks like in action
Whether you’re a senior leader, an emerging professional, or simply trying to create more fulfillment in your career, Ianna's answers to our deepest questions offer clarity, practical guidance, and stories of change that resonate within and beyond the workplace!
Presented by Elynndí, and hosted by Aaron Barlin (https://www.linkedin.com/in/aaron-barlin/). See elynndi.com (https://elynndi.com/) to learn how we "think like a teacher" to create the show.
29 Sept 2025
Trailer — "Today's deepest question is..."
Think of the show “Hot Ones,” but instead of pop icons, we’re putting industry leaders in the hot seat to ask them spicy questions about their expertise—from consultants, to educators, to healthcare professionals, and more.
The first 3 episodes of Season 1 drop on Monday, October 6, with new episodes released on Mondays after that.
We start with our "deepest" question—a question that makes you go, "Woah." It's relatively unanswerable, but the process of trying to answer it matters more than the answer itself. The guest gives their initial response at the start of the show.
Then we move onto our "digging" questions—the kind that make you go, "That's such a good question!" They're related to our "deepest question," but they're more exploratory: they ask about a range of topics from the guest's upbringing, reflections on current events, behind-the-scenes looks into their work, and their cutting-edge insights.
We end the show by returning to our "deepest" question from the top of the show—and the guest re-attempts their answer to it, now that they've had a chance to "deepen" their thinking.
Hosted by Aaron Barlin from Elynndi (http://elynndi.com)
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