Angela Finlay is a Chief Human Capital Strategist, former CHRO, educator, and author of Skill Stacking: Taking Ownership of Your Career in Changing Times. With over 30 years leading talent strategy across Fortune 150 companies and fast-growing organizations, she helps professionals and leaders rethink what it takes to build a resilient career in a rapidly shifting world. Angela also teaches Leadership
and Human Capital Management at the graduate level, including at Columbia University, where she brings real-world clarity to the future of work.
Through her Skill Stacking framework, Angela equips individuals and organizations to move beyond outdated career paths and resume thinking. Instead of waiting to be developed, she challenges people to take ownership of their growth by intentionally building capabilities that create opportunity, mobility, and long-term relevance. In a world shaped by AI, disruption, and constant change, her message is clear: careers are no longer managed for you. They are built by you.
Angela Finlay Vroom Vroom Veer Summary
Jeff welcomes guest Angela Finlay and they laugh about the rough tech start to the session. Jeff prompts Angela to talk about what she’s excited about. Angela describes her current roles: fractional and interim CHRO/HR leader for small- to mid-sized businesses, college-level teaching (including work with Columbia University and Fairleigh Dickinson), and a passion project — her book titled Skill Stacking, Taking Ownership of Your Career in Changing Times. She frames her book’s premise: people don’t need to “start over,” they can reconfigure and combine existing skills — an evolution rather than a revolution.
Jeff and Angela briefly discuss historical job-displacement fears (Jeff mentions the example of a job to pick up horse poop) and Angela recounts a podcast episode she’d heard about the transcontinental railroad and the recurring nature of job-displacement panic in society.
Jeff asks about Angela’s background. Angela says she attended about seven schools by high school because her father worked in the newspaper industry and the family moved often; she learned to “reemerge” in new places. In high school she intentionally pushed herself out of her comfort zone (played field hockey on a losing team, joined activities) and learned to try uncomfortable things. Jeff shares a personal anecdote about his mother buying clothes for a freshman dance and how that changed his presentation. Angela mentions putting her son in a uniform/blazer changed his demeanor.
Angela describes applying to many colleges; she unexpectedly received a full scholarship to Fairleigh Dickinson and originally intended speech pathology but switched to accounting (in part because her father was an accountant). She took a job in public accounting, found the work (manual ledger work, calculators printing on paper) tedious, and left a cubicle job after about six months. Her manager had been put in charge of HR and offered it to her — she accepted, taught herself about performance evaluations via library research, and began building HR capability despite feeling underqualified.
Jeff observes that “figuring things out” is a valuable skill. Angela warns about over-reliance on instant help (Alexa) and the loss of productive struggle. They note chat AI tools are often very positive/encouraging; Jeff gives a brief anecdote of using AI to check hardware compatibility for an old computer and the AI correctly telling him “no.”
Angela traces her career: roughly eight to nine years in public accounting, then head of HR at another firm, then about ten years with a Japanese conglomerate, Mitsui. She describes cultural differences at the Japanese company: relationship-building, the “ringy” process (needing consensus from many people), and the need to engage in non-work conversation before work talk. She shares a story about a code-entry error that produced multiple memos and made her feel like she was living an “Office Space” moment. Jeff and Angela discuss how office rhythms and politeness differ across cultures and organizations. Angela says later she moved to a community bank CHRO role in Brooklyn; when the bank was sold in the pandemic she reassessed and moved toward fractional/interim CHRO work and teaching — leveraging her experience going into companies during transitions. She mentions accounting-firm sales training early in her career and that she’s “dangerous” at selling herself; also ties her teaching to early acting lessons and “interacting” skills.
They turn to the book and the skill-stacking framework. Angela explains the idea of inventorying and intentionally categorizing one’s skills instead of assuming you have no skills. She outlines categories in her stack model:
- Supportive skills: foundational expertise (examples she names include accounting and employment law).
- Tactical skills: execution skills — getting things done, project management, time/task management, resource allocation.
- Adaptive skills: ability to pivot, learn from feedback, take feedback constructively rather than fight it.
- Complementary skills: people-related abilities and emotional intelligence (EQ) — empathy, relationship-building (she gives a vivid hospital anecdote where a staffer’s comforting, practical human response mattered more than clinical intervention).
- Knowledge-seeking: ongoing learning and curiosity, the polymath concept and making connectors among different domains.
Jeff and Angela discuss AI: Angela uses AI in her work but notes it tends to be optimistic and encouraging and may not tell her when an idea is a bad one. Jeff recounts the story about AI warning him not to plug a CPU into an incompatible system. They discuss limits of AI and nuance: Angela emphasizes the human ability to read subtext, in-person dynamics, and emotional cues in organizations — things she believes AI can’t replicate. Jeff and Angela also discuss image-generation tools: Angela has experimented with them, found mixed results (about “forty percent” success in her words), and recounts trying to generate an image for a white paper and getting irrelevant outputs (a “rose” instead of the intended interconnected GROWING acronym). Angela links this back to knowledge-seeking and prompting skill development.
Angela says she’s developing a free app that will let people upload resumes to visualize their skill stacks; she invites listeners to get on the list. She gives her contact info: the website stackingyourcareer.com, LinkedIn (Angela Finlay), and a YouTube channel called Stacking Your Career where she posts videos about the concepts. Jeff repeats the site and they discuss audiences and career planning briefly: Jeff references the FIRE movement (financial independence/retire early) as context for needing ways to make money; Angela stresses building and tracking transferrable skills so people can pivot across a long career span, mentioning the idea of a “sixty year career” and the U-shaped curve of happiness (listeners are told people burn out or are bored after many years and should plan to pivot).
The interview wraps up with Jeff thanking Angela for the conversation and inviting her back. Angela agrees. Jeff jokes about “skill building” to end the recording. Tim Paige’s outro thanks listeners, points them to the show notes at vvveer.com (transcribed as “v v veer dot com / triple v v double e r dot com”), and signs off.
Connections
Podcast: Play in new window | Download | Embed
Subscribe: Apple Podcasts | Spotify | Amazon Music | Pandora | iHeartRadio | Blubrry | TuneIn | RSS | More