loader from loading.io

CEO Ray Schiavone, Learning from Executive Mistakes & Perservence

CXO Conversations

Release Date: 12/24/2019

2 Min CxO Clip- John Oechsle show art 2 Min CxO Clip- John Oechsle

CXO Conversations

What does it take to plan a career all the way to the CEO chair? In this episode of CXO Conversations, John Oechsle discusses the strategic decisions that helped him rise from technology leadership at J&J and IHS to CEO of Derive Systems. He reflects on how international assignments shaped his leadership style, why embracing “crackpot projects” at Kellogg’s accelerated his growth, and the importance of taking roles for the right reasons—not just for compensation. For aspiring executives, John’s story is a roadmap on career planning, resilience, and the values that define strong...

info_outline
10 Min CxO Clip- John Oechsle show art 10 Min CxO Clip- John Oechsle

CXO Conversations

In “Career Planning and Strategic Decisions to Become CEO,” was CEO of Derive Systems and now Bolt On Technology, shares how purposeful choices shaped his path from CIO roles at Johnson & Johnson and IHS to leading multiple organizations, including Swiftpage and now Derive. John explains how he set a goal early to become a CEO, took on challenging assignments others avoided, and leveraged international experiences across Europe, Latin America, and Asia to expand his leadership perspective. He also offers candid insights on why money is the wrong reason to pursue the C-suite and why...

info_outline
2 Min CxO Clip- Craig Cummings show art 2 Min CxO Clip- Craig Cummings

CXO Conversations

What does it take to transition from the battlefield to the boardroom? In this episode of CXO Conversations, Craig Cummings—Army veteran, Bronze Star recipient, and co-founder of Moonshots Capital—discusses the lessons he’s carried from 17 years of military service into the world of startups and venture capital. He shares practical advice on creating a career-defining elevator pitch, supporting veteran entrepreneurs, and building strong networks that accelerate growth. From deploying with Special Operations to scaling tech startups and investing in extraordinary leaders, Craig’s...

info_outline
10 Min CxO Clip- Craig Cummings show art 10 Min CxO Clip- Craig Cummings

CXO Conversations

In “Building Your Career Transition Elevator Pitch,” shares how his journey from Army Intelligence Officer in Afghanistan to General Partner at Moonshots Capital shaped his approach to leadership, entrepreneurship, and investing. A Bronze Star recipient and West Point graduate with a Ph.D. from Columbia, Craig explains how veterans can craft an elevator pitch that opens doors, the importance of building strong entrepreneurship communities like Austin’s, and why investing in talented veteran founders is a mission for him. His story is a powerful reminder that clarity, curiosity, and...

info_outline
2 Min CxO Clip- Chris Younger show art 2 Min CxO Clip- Chris Younger

CXO Conversations

What can hundreds of transactions and decades of leadership teach us about CEOs? In this episode of CXO Conversations, Chris Younger, CEO of Class VI Partners, reflects on buying, selling, and leading companies across industries. He shares candid insights on managing the stress of leadership, why presence and transparency matter, and how servant leadership builds lasting teams. From his experience acquiring 27 companies to guiding CEOs through exits and growth strategies, Chris highlights both the rewards and the realities of C-suite life—and why prioritizing self-care is as important as...

info_outline
10 Min CxO Clip- Chris Younger show art 10 Min CxO Clip- Chris Younger

CXO Conversations

In “CEO Insights & Self Care with Chris Younger,” shares lessons from a career spanning telecom, private equity, and advisory leadership. As President of Expanets, he acquired 27 companies in just 3 years before selling to Avaya, and today, as CEO of Class VI Partners, he advises middle-market businesses and family offices on transactions and growth. Chris opens up about the physical toll of overwork, the importance of managing stress, and why diet, sleep, and exercise are critical for executives. He also explains his “Dinner Test” for CEOs and why executive presence sets the tone...

info_outline
2 Min CxO Clip- Christine Gagnon show art 2 Min CxO Clip- Christine Gagnon

CXO Conversations

What does it mean to be truly intellectually curious as a leader? In this episode of CXO Conversations, Christine Gagnon, CFO of African Asset Finance Company at time of interview, discusses the value of continuous learning and the global perspective she’s gained from international assignments and advanced education at top institutions. From her early career at PwC and EY to her current role financing critical sectors across Africa, Christine shares how ongoing education enriches her work, enhances strategic planning, and opens new angles of business she would have never seen otherwise. Her...

info_outline
10 Min CxO Clip- Christine Gagnon show art 10 Min CxO Clip- Christine Gagnon

CXO Conversations

In “Christine Gagnon CFO, the Importance of Being Intellectually Curious,” shares how a lifelong passion for learning has shaped her global career. During recording, she was the CFO of African Asset Finance Company, she reflects on her journey through leadership roles at EY, PwC, and OneWest Bank, as well as earning multiple advanced degrees and executive certifications from Harvard, Stanford, and Washington University. Christine explains how international experiences, from Johannesburg to London, shaped her global market perspective, and why intellectual curiosity allows her to better...

info_outline
21 Min CxO- Gen. Kevin 21 Min CxO- Gen. Kevin "Chili" Chilton

CXO Conversations

In “General Kevin ‘Chili’ Chilton, Board Member, Astronaut and Flying the Space Shuttle,” shares lessons from his extraordinary 34½ years in the U.S. Air Force and his successful transition into corporate leadership. On this episode of CXO Conversations, Chili reflects on problem-solving and leadership training, the astronaut band Max Q, and the experience of flying three space shuttle missions. From serving as Deputy Program Manager of Operations for the International Space Station to becoming the only astronaut to achieve the rank of 4-star General, Chili’s story is a powerful...

info_outline
2 Min CxO Clip- David Cox show art 2 Min CxO Clip- David Cox

CXO Conversations

What does it take to transform one of the world’s most respected publications without losing its identity? In this episode of CXO Conversations, David Cox discusses his 14 years at The Economist, including his role as CFO and COO, where he spearheaded the company’s global shift from print to digital and live events. He explains how he balanced editorial independence with client demands, why pricing digital at the same level as print was a pivotal decision, and what he learned about storytelling, teamwork, and leading large-scale transformation. David’s lessons remain invaluable for...

info_outline
 
More Episodes

Welcome to Part 2 of this discussion with CEO Ray Schiavone. During this episode, we dive into what drives CEO turnover, what working for PE-owned companies is like, where good ideas come from, and the importance of doing whatever it takes. Ray also shares a heap of tips for aspiring CEOs and current C-level professionals.

 

ABOUT OUR GUEST

Ray Schiavone started his career at G.E., during the then-CEO Jack Welch’s tenure. He then moved on to act as a tech company CEO twice over and has since settled into running his own firm.

 

Ray is a graduate of Syracuse University and subsequently earned an MBA from the University of Maryland where he serves as a board member for the A. James Clark School of Engineering. He has been recognized for his accomplishments with numerous awards including the Michigan Venture Capital Association’s Entrepreneur of the Year Award, Crain’s Detroit Business 40 Under 40 and the Ernst and Young Entrepreneur of the Year Award.

 

GET IN TOUCH WITH RAY ON LINKEDIN

 

THANKS TO OUR SPONSORS

Podfly Productions: Podfly.net

Veterans of Foreign Wars: VFWpost1.org

OC Executive Search: OCExecutiveSearch.com

 

KEY TAKEAWAYS

[1:50] Michael opens up Part 2 of this discussion with Ray Schiavone with a question on CEO departures.

 

KING-CEO [5:22] Ray speaks to working with larger-than-life people and what a company needs to build around such big personalities in order to foster the best out of their people and protect their assets.

 

SO YOUR FIRM’S BEEN BOUGHT? [8:51] Ray shares his experience with being bought out by a private equity firm, the first discussions he had with the new owners, the relationship before, during, and after the transaction as well as the factors that made them keep him onboard. Ray shares his advice for CEOs who may be going into this kind of situation and the type of work structure they can expect.

 

WHEN OUTCOMES DON’T MEET EXPECTATIONS [14:50] Admitting failure is the toughest part of life. Ray shares a professional story of failure.

 

LEARNING FROM JACK WELCH AND GE [17:16] Good ideas come from everywhere is what Ray remembers first, he gives a few examples and explains how he integrated what he learned from Jack into his own management style. He also speaks to the influence Jack had on corporate America.

 

[21:22] Ray unpacks the toolkit he inherited from GE and explains what he still uses and what he had to change.

 

MENTORSHIP [24:18] Ray gives tips on how to be mentored.

 

REWARDS, SURPRISES, AND CULTURE [26:27] Setting a company culture starts with leading by example; Ray also shares what surprised him about being in a leading position.

 

LEGACY [30:23] Learning and being a good human is the legacy Ray hopes he has. He shares the aspects he enjoyed the most and the least about being a CEO — they’re the same!

 

IS THE OLD STILL NEW? [33:11] Giving people the power to make decisions is something Ray saw at GE and still sees today. However, decentralization and the increase in remote work make it harder to stand out.

 

DIVERSITY [36:51] Corporate America still has a long way to go, but diversity has increased; Ray speaks to simple things that can be done to improve flexibility.

 

[39:30] Motivating younger generations is a challenge that Ray thinks can be tackled with empowerment, ownership, and flexibility; he details why.

 

MILITARY SPOUSE [40:48] Ray speaks to his wife having been on active duty in the Air Force and the challenges related to juggling two careers, a military commitment, a family, and multiple deployments and countries!

 

WORK HABITS [45:20] Ray breaks down his usual routine.

 

RAY’S ADVICE FOR HIS YOUNGER SELF [47:12] Don’t worry, it’ll all work out.

 

BEST WORST JOB RAY EVER HAD [48:37] Ray shares his experience working at a circus and what it taught him!

 

[52:47] Michael thanks Ray for coming on the podcast to share his insight and closes out the podcast with his favorite takeaways.

 

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

 

MENTIONED IN THIS EPISODE

Book: Good to Great: Why Some Companies Make the Leap and Others Don't, by Jim Collins

Six Sigma

ROTC

 

SPECIAL THANKS TO

Jalan Crossland for the music

Angela Johnson at OC Executive Search

Joseph Batty at Podfly

Corey Coates at Podfly