#257 The Three Hidden Traps That Stall New CFOs, Michael O’Reilly, GrowCFO Executive Coach
https://www.youtube.com/watch?v=FyOBP_QcsLI
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https://open.spotify.com/episode/3CrRco4GBJsnDQYaJSiPnT
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
Michael O’Reilly on LinkedIn
Kevin Appleby on LinkedIn
GrowCFO Mentoring
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
Find out more about GrowCFO
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