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CPO Michelle Anastasi, Pros & Cons of Long Tenure at Same Company

CXO Conversations

Release Date: 01/28/2020

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Today we’re going to discuss the pros and cons of staying with the same company for an extended period, creating an HR organization from scratch, and the lessons that Michelle Anastasi has learned throughout her career.



Michelle is an outgoing CPO who has worked at CompSych, GiveForward, Dell and ASAP Software. She earned her Business Administration degree from the Indiana University Kelley School of Business and an MBA from Northwestern University’s Kellogg School of Management.





Podfly Productions: Podfly.net

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OC Executive Search: OCExecutiveSearch.com



[1:52] Michael introduces Michelle Anastasi and asks her to share an interesting tidbit about herself — She has had a bear visit her kitchen while she was home!


[4:00] Michelle touches on the roles she embodied and the mentors that guided her during her 16-year stint at the same software company, from the accounting department to building an HR department from scratch.


BUILDING HR FROM THE GROUND UP [6:18] Michelle breaks down how she went about tackling the HR department build with very little experience from establishing priority lists to finding the right mentors.


REGRETS? [11:50] Michelle admits to having made her share of mistakes, but she wouldn’t trade any of them — she does share the one thing she would have done differently: networks and relationships.


STARTING FROM SCRATCH [12:36] Michelle packs so much advice in a minute, you won’t believe it — we counted 11 really important and insightful tips.


SHAKING ASSUMPTIONS [15:30] Behaviors can help in preventing people from pigeonholing you — think about your executive presence and be strategic.


WHY SO LONG? [18:46] Michelle opens up on the reasons why she stayed so long at ASAP, the first of which is that she kept having opportunities to learn and be challenged. She touches on the increasingly short windows companies get to show how engaging they can be to new hires.


THE DELL MERGER [22:21] She did work through a few mergers, but Dell was at a different scale! She talks us through the ups and downs of the experience.


C-SUITE, CPO VS CHRO [25:38] Though there seems to be a push away from the human resources terminology, Michelle sees very little difference between the roles themselves. She delves into what best prepared her for the C-Suite, including a tough boss that knows how to push you outside your comfort zone.


GETTING TO THE C-SUITE [30:04] Michelle hands out fistfuls of advice for aspiring CPOs.


SURPRISES AND REWARDS [33:22] Michelle shares the aspects of being a CPO that she finds surprising and rewarding — even if a lot of the work is covered by NDA!


OVERSEAS EXPERIENCE [33:50] Michelle’s approach to HR is influenced by having lived overseas and being culturally aware.


A BAD CALL [35:18] Michelle shares the time she joined a company led by a narcissist.


MBA [36:56] Michelle touches on the value her MBA has had in her career.


CANDIDATE ATTRIBUTES [38:15] What are the things Michelle looks for in a successful candidate to hire.


BEST WORST JOB MICHELLE EVER HAD [39:19] Waitressing is such a good background for everything in life!


FINAL THOUGHTS AND GOOD READS [42:02] Michelle shares a very generous amount of titles to read and a recap of her tips for emerging CXOs.


[44:20] Michael thanks Michelle for coming on the podcast to share her insight and closes out the podcast with his favorite takeaways.


We hope you learned something today and enjoyed the conversation. Please give us 5 stars on iTunes and share your comments so we can improve and ask the questions you want to hear.



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Turn the Ship Around!: A True Story of Turning Followers into Leaders, by L. David Marquet

Start with Why: How Great Leaders Inspire Everyone to Take Action, by Simon Sinek

The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers,
by Ben Horowitz



Jalan Crossland for the music

Angela Johnson at OC Executive Search

Joseph Batty at Podfly

Corey Coates at Podfly