How a Failed Application Led to a Successful Chief of Staff Career
Sometimes the best opportunities come when you least expect them. That’s what happened to Kalen Stanton. He showed up for an interview, only to find the job he applied for no longer existed. But instead of walking away, he walked into a new role that shaped his career—the Chief of Staff.
Key Takeaways
Opportunities often look different than expected. Kalen didn’t plan on becoming a Chief of Staff. The role came up when the CEO realized he needed someone to help manage the growing demands of leadership.
Curiosity and relationship-building are essential. Walking the halls, asking questions, and connecting across teams helped Kalen spot problems and build trust.
The role blends structure with flexibility. Plans are important, but Chiefs of Staff must adapt quickly when things change.
Notable Quotes
“I had to walk in every day thinking about the whole company.”
“You’re not just building trust with others but also breaking down silos across the organization.”
“Leadership is often very hard because it’s not black and white—you have to serve two customers and find the balance.”
Real-World Applications
Stay open to surprise opportunities.
Example: If a planned project is canceled, ask where else you can contribute instead of stepping back.Build trust by being present.
Example: Walk the floor or join casual team conversations to hear concerns that may not come up in formal meetings.Act as a connector.
Example: Notice when two teams are struggling with the same issue and bring them together to solve it.
Kalen’s story shows that a “failed” application can lead to something far better than expected. The Chief of Staff role is less about a fixed job description and more about trust, curiosity, and flexibility. When done well, it strengthens not just the CEO but the entire company.
00:53 Guest Introduction: Kalen Stanton
02:23 Kalen's Journey to Chief of Staff
07:18 The Role of Chief of Staff in Building Relationships
17:33 The Importance of Culture in Leadership
19:45 The Chief of Staff as a Specialist vs. Generalist
27:30 Kalen's Experience in East Africa
32:33 Conclusion and Final Thoughts
Connect with Kalen on LinkedIn
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About The Author
Emily Sander is an ICF-certified leadership coach with more than 15 years of experience in the business world and the author of Hacking Executive Leadership. She’s been featured in several print publications, online articles, and podcasts, including CEO Today Magazine, Leading to Fulfillment, and Leadership Powered by Common Sense.
Emily has a passion for helping business leaders reach their full potential. Go here to read her story from seasoned executive to knowledgeable coach. If you want to send Emily a quick message, then visit her contact page here.