GrowCFO Show #257 The Three Hidden Traps That Stall New CFOs, Michael O’Reilly, GrowCFO Executive Coach
In this insightful episode, Kevin Appleby sits down with Michael O’Reilly, a seasoned executive coach and former CFO with a diverse career spanning global finance, digital transformation, and leadership development. Together, they explore “The Three Hidden Traps That Stall New CFOs” — a candid discussion about the unseen challenges finance leaders face as they transition into enterprise leadership roles.
Michael shares his own experiences across companies like Citibank, Gap Inc., and PepsiCo, highlighting how curiosity, empowerment, and trust play crucial roles in a CFO’s success. He also explains how imposter syndrome, reluctance to delegate, and overreliance on technical mastery can prevent new CFOs from thriving in their roles. With AI reshaping the finance landscape, Michael emphasises the growing importance of emotional intelligence, adaptability, and creating psychological safety for teams navigating disruption.
The conversation goes beyond professional growth, touching on personal fulfilment and energy management — understanding what “charges or drains your batteries” as a leader. Drawing from his coaching practice and experiential leadership retreats in Ireland, Michael reveals how rediscovering purpose and flow can reignite a CFO’s impact, both in business and in life.
Key topics covered:
- How imposter syndrome can fuel curiosity and growth rather than paralysis
- Why delegating and letting go is the biggest unlock for new CFOs
- The importance of psychological safety in driving innovation and AI adoption
- Transitioning from technical expert to strategic enterprise leader
- Understanding personal “energy management” to avoid burnout
- The power of trust, empathy, and soft skills in effective CFO leadership
Links
Timestamps
- 00:40 Michael O’Reilly’s career journey from CPA to Chief Digital Officer
- 05:52 The role of imposter syndrome in a CFO’s development
- 07:52 How AI amplifies insecurity and why creating safe environments matters
- 10:07 Balancing accuracy with experimentation in finance leadership
- 16:46 What a mentoring relationship looks like with Michael
- 21:21 The critical need to delegate and empower teams
- 22:33 Michael’s experiential leadership program in Ireland
- 30:31 Finding your “flow state” and energizers outside of work
- 34:20 What kind of leaders benefit most from mentoring
- 36:16 The “ski story” — how aligning passion with leadership drives performance
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