Getting the senior role is one challenge. Surviving the transition into it is another.

In this episode of BizBlend, Sana sits down with Stephen "Steve" Moss, founder of Executive Springboard and a four-time former Chief Marketing Officer, for a candid conversation about why highly capable executives can struggle after stepping into new leadership roles.

For Steve, the question became personal after his fourth CMO position lasted only around 18 months. Rather than simply blaming the economy, the organization or himself, he began researching what causes senior leadership transitions to break down.

One of his central conclusions is particularly important: executive failure is often not about functional competence. The harder problems involve people, relationships, organizational dynamics and culture.

Steve explains why new executives need to stop "selling themselves" once they have the job. Instead of immediately trying to prove why they were hired, their early focus should be listening, asking questions, understanding how decisions really get made and learning the organization's cultural rhythm.

The conversation also explores why external hires can face greater transition challenges than internal promotions, how to recognize trouble during the first 90 days, and why incoming leaders should be cautious about making sweeping changes before understanding why existing systems operate the way they do.

Steve offers two especially practical tools: keep a journal and conduct a listening tour. Document what you're observing, revisit those observations regularly, and talk to people across the organization about what they do, why they do it and what they would change.

Finally, Sana and Steve explore the difference between executive coaching and mentoring, and why having someone who has already "sat in the chair" can provide a different kind of perspective when the stakes become higher.

About Stephen Moss:

Stephen Moss is the founder of Executive Springboard and an experienced global marketing executive. He has held senior marketing leadership roles at Gilbey Canada, Pillsbury International, Nestlé Ice Cream and Imation, working with brands including Smirnoff, Green Giant, Häagen-Dazs and Drumstick.

Executive Springboard now has a network of 100+ experienced executive mentors and focuses on supporting leaders through pivotal career moments, including new-role onboarding, succession and broader leadership development.

Key Takeaways:

• Executive failure isn't automatically a competence problem. People and organizational dynamics can be decisive.
• Once you get the job, stop selling yourself and start learning.
• Humility and curiosity matter during the first 90 days.
• External executives need time to understand the culture that internal hires already know.
• Cultural agility means learning how decisions are made, how people interact and what behaviors the organization rewards.
• Don't rush into sweeping changes before understanding why existing processes developed.
• Keep a journal during your transition and review it regularly.
• Conduct a listening tour across the organization before assuming you understand the problem.
• Executive mentoring differs from coaching because mentors can bring experience from having faced comparable leadership situations.
• The best mentors don't make the relationship about their accomplishments. Their success is reflected in the person they help develop.

Chapters:

00:06 The 18-month CMO experience that changed Steve's career

01:47 Why Steve researched executive failure

03:23 How risk changes across executive transitions

04:58 Why the statistics shouldn't stop leaders from stepping up

06:06 Why senior leaders fail for reasons beyond competence

08:43 Warning signs during the first 90 days

11:06 Cultural agility and the advantage of internal hires

12:24 Navigating broken processes as an external executive

13:44 Why new executives should journal and conduct listening tours

15:50 Executive mentoring versus executive coaching

18:36 What makes an effective executive mentor

20:46 Leadership without ego

21:34 Connecting with Executive Springboard

22:43 Executive Springboard's international reach

🎙️ Want to Be a Guest on Healthy Mind, Healthy Life?

Send me a direct message on PodMatch.

👉 DM Me Here: https://www.podmatch.com/hostdetailpreview/avik

🌱 About Healthy Mind By Avik™️

Healthy Mind By Avik™️ Global Mental Wellness Podcast Network - focused, credible, no more identity clutter.

👉 Subscribe and be part of this healing journey.

Refer a Guest

Know someone who would be a great fit for one of our podcast shows? Email us at [email protected] with the subject line “Refer a Guest.” Requests without this subject line cannot be catered to.

Support Our Podcast: Support this Podcast

📬 Contact & Links

Brand: Healthy Mind By Avik™️

Contact Us

Based in: India & USA

🎧 All Podcast Shows

🤝 Be a Guest

📩 Newsletter Substack

👉 Join the LinkedIn Community

📌 Disclaimer - This episode is produced for educational and informational purposes only. All views expressed by the guest are their personal opinions alone and do not represent the views of the host or Healthy Mind by Avik™. The Network does not verify, endorse, or assume responsibility for any guest statements. Nothing in this episode constitutes medical, legal, financial, or professional advice, please consult a qualified professional before making any decisions. Listeners are encouraged to engage critically and independently with all content do not consume blindly. Use this content as a starting point for your own reflection and research, not as a substitute for professional guidance. Third-party content is referenced under fair use for informational purposes only. Guest speakers are solely responsible for their own statements.

If you have concerns about any content, please contact us here

By listening, you acknowledge and accept this disclaimer in full. Read detailed disclaimer here.

#BizBlend #StephenMoss #ExecutiveSpringboard #ExecutiveLeadership #ExecutiveMentoring #ExecutiveOnboarding #First90Days #CSuite #LeadershipDevelopment #Mentorship #CorporateCulture #CareerGrowth #SeniorLeadership #BusinessLeadership #Leadership