Julie Harris Oliver welcomes Dr. Kim Stepanski, an executive coach and organizational psychologist, to explore what leadership feels like right now amid rapid change, AI disruption, geopolitical volatility, and polarization. They discuss how leaders face loneliness, pressure to have answers, and the challenge of guiding teams whose perspectives are shaped by narrowing information "echo chambers." Kim emphasizes building capacity to see beyond one's own lens, getting comfortable with not knowing, and using reflection, connection, and community to stay grounded and humane. Julie shares practices such as acknowledging heaviness, simple meeting check-ins (e.g., green/yellow/red), and creating space for people to share what they're carrying without leaders needing to fix it. Kim describes using small experiments, grounding tools, and peer groups—especially for senior women—to build vulnerability, perspective-taking, and support, and closes with ways to connect with her online.

00:00 Welcome to Deep Work

00:33 Meet Kim Stepanski

02:17 Why Kim Chose Coaching

04:16 Leading Right Now

06:56 Filters and Echo Chambers

09:30 Simple Human Check Ins

12:26 Coaching Tools and Experiments

15:07 Practicing the Uncomfortable

15:53 Building Leader Community

20:37 Systems and Human Centered Work

26:42 Staying Grounded and Closing

Host Julie Harris Oliver welcomes transition and emerging leaders coach Ben Basilan, who shares how layoffs in his industry and his background in counseling and UX research led him to coaching. They explore identity as a root issue in major transitions such as becoming a manager or small business owner, experiencing layoffs, divorce, aging, and retirement, focusing on what feels fixed versus changeable and how "inner saboteurs" formed in childhood can stop serving us. Ben describes growing up as a Filipino immigrant kid navigating cultural and emotional silence, moving states, and realizing he was gay, then later finding greater openness through grad school and counseling training. They discuss authenticity at work as a spectrum tied to psychological safety and how integrating Ben's identities as coach and researcher improved his motivation and communication. They also address identity clashes with loved ones amid polarized beliefs and the role of coaching in healing.

00:00 Welcome to Deep Work

00:31 Meet Ben Basilan

01:19 Why Ben Chose Coaching

02:10 Identity as a Theme

02:53 Transitions Trigger Identity

06:01 What Can Change

07:15 Roots of Rationality

09:33 Move South and Isolation

12:48 Coming Out and Becoming Whole

14:51 Authenticity at Work

18:40 Merging Work Identities

23:26 Life Stages and Reinvention

28:43 When Identities Clash

32:53 Coaching as Healing Purpose

33:54 Where to Find Ben

34:26 Closing Invitation

Host Julie Harris Oliver welcomes executive coach and former CFO Heather Pomerantz to discuss living your authentic self through clarifying core values and purpose. Heather shares how her early love of listening and connection, a long achievement-driven finance career, and a Unilever purpose program led her to coaching when she realized she was in physical pain from misalignment. They outline steps: identify core values from a word list, narrow them, define what each means personally, translate them into "I am" statements, assess alignment, and decide what must shift to integrate joy now rather than waiting for "someday." They explore freedom as a sample value, signs of misalignment like anxiety and Sunday dread, authenticity in interviewing, and how leaders can improve results and retention by understanding employees' values and reshaping responsibilities.

00:00 Welcome to Deep Work

00:36 Meet Heather Pomerantz

02:23 Heather's Coaching Origin

03:32 Achievement to Purpose

06:20 CFO Misalignment Wakeup

08:17 Living Authentic Self

08:53 Find Your Core Values

11:36 Define Values and Freedom

13:47 Check Alignment and Shift

15:23 Why Wait Integrate

19:29 Lead Through Values

22:04 Strengths Versus Values

28:15 Values in Career Transitions

30:56 Somatic Signs of Alignment

34:19 Closing Takeaways and Links

Dr. Matt Kodsi's book: A Story Tale - ABC's of the stories we tell ourselves