Second in Command: The Chief Behind the Chief with Cameron Herold

Episode 520 - How to Stay Grounded and Lead with Trust with Corey Raggy

Date: October 21, 2025
Guest: Corey Raggy, COO of One rdg, The One Financial Center
Host: Savannah Brewer (for Cameron Herold)

Episode Overview

In this episode, host Savannah Brewer sits down with Corey Raggy, COO of One rdg, to discuss the art of operational leadership—from managing teams in massive corporations to leading a nimble, people-focused mid-sized company. Corey delves into her transition from a 15,000-employee organization to an 80-person financial services firm, sharing insights on building trust quickly, grounding oneself under professional pressure, hiring and leading outside one's subject expertise, and the essential leadership habits that keep her—and her team—centered and targeted on what matters.

Key Discussion Points & Insights

1. Corey’s Journey: From Large Corporate HR to Small Company COO

• Unexpected Path to COO: Corey initially doubted the COO role was right for her, believing it to be all about logistics and maintenance, far from her people-centric strengths. However, the reality was different:
  • “It sounded like buildings and maintenance and vendors and logistics...I am a lover of all things people.” (04:35, Corey Raggy)
• Culture Fit Over Technical Fit: Corey was recruited for her ability to bring structure and build connective tissue among a talented team, not for technical expertise.
• Transitioning Company Sizes: Going from a massive company to a much smaller one required “deprogramming”—letting go of asking permission for everything and embracing more informal, flexible processes.
  • “I had to drop some of that people pleaser permission mentality. Nobody has time for that in a small business.” (10:21, Corey Raggy)

2. Leadership Principles: Trust, Authenticity, and Relationships

• Building Trust Quickly:
  • Trust with the CEO and partners was developed over “almost three months” during interviewing, grounded in real conversations about pushing back and honest communication.
  • Initial six months: Corey focused on listening and proving value, not just executing tasks but improving processes.
    • “Not an order taker, but like a...‘yes, and’ person.” (09:10, Corey Raggy)
• Admitting Weaknesses and Encouraging Directness:
  • Corey advocates open self-deprecation and upfront honesty about her own quirks to foster a transparent environment.
    • “Here’s what’s going to drive you crazy about me…I want you to have permission to call me out.” (16:45, Corey Raggy)
• The Power of Relationship-Building:
  • “So much of the COO role is relationships...The secret is the relationships that will allow you to implement.” (18:42, Corey Raggy)

3. Leading Outside Your Expertise

• Hiring for Strengths:
  • Corey and her partners split duties in interviews—Corey screens for culture and fit, while partners handle technical skills.
    • “You screen for culture, fit, motivation, career planning. You screen for technical, and we just divide and conquer together.” (14:26, Corey Raggy)
• Continuous Learning:
  • She humbly learned industry jargon and acronyms on the job, encouraging leaders to admit what they don’t know and ask for help.

4. Effective Meetings and Communication

• Reshaping Meetings for Clarity:
  • Corey established distinct meetings for partners, department leads, managers, and teams, each with a clear objective and cadence.
    • “We have staff meetings and said what’s the objective and who needs to be there and what’s the scope…” (24:15, Corey Raggy)
  • The partner meetings focus on discussing—not just reporting—metrics, approaching numbers with “curiosity,” and distinguishing between qualitative and quantitative causes.
• Practical Meeting Tips:
  • Only include the right people, use agendas, and keep meetings concise.

5. Core Leadership & Change Management Lessons

• Key Practices for Staying Grounded:
  1. Know Your Kryptonite:
     • Identify personal basics that keep you well—sleep, nutrition, etc.
     • “For me I have to have upwards of six to seven hours of sleep. If I get sleep, I can handle anything.” (35:32, Corey Raggy)
  2. Interrupt Stress Spirals:
     • Recognize personal stress signals, stop, and address the immediate next step to regain control.
  3. Proactive, Constructive Conflict:
     • View conflict as addressing issues early, not as negative confrontation. Don’t address issues if emotional state is too high or low—wait and reflect first.
  4. Emotional Intelligence & Self-Reflection:
     • “Studying Emotional intelligence and crucial conversations…game changers for me in stress management.” (38:37, Corey Raggy)
• Feedback and Development:
  • Regular, “uncomplicated” feedback is fundamental:
    • “Get great at helping people get better. And don’t avoid those conversations, or you’re missing the power of the team.” (33:16, Corey Raggy)
• Leading Middle Managers:
  • Don’t try to mold managers in your own image—help them become their own best version.
  • Leadership is coordination—“like being a drummer”—and requires learning to ‘drum’ many rhythms at once.

6. Navigating Isolation in the COO Role

• Solo Role, Mental Separation:
  • COO is often a lonely job—"You have to be the ultimate unbiased human being in your organization." (44:09, Corey Raggy)
• Find Your ‘Outside Board of Directors’:
  • “I have probably six or seven people that I will still reach out to that I can just talk freely and confidentially with...” (45:54, Corey Raggy)
• Communicating Value:
  • Emphasize to the company that the better you do your job, the less visible it becomes—role clarity and recognition are crucial.

Notable Quotes & Memorable Moments

• On Transitioning to COO:
  • "Falling into it was probably the best thing that ever happened to me personally and professionally.” (04:12, Corey Raggy)
• On ‘Right People, Right Seats’ Mantra:
  • “That's where I start with solving every problem.” (06:26, Corey Raggy)
• On Relationship Over Process:
  • "If you're only focused on process, if you're only focused on data, on systems, on automation, that's not the secret sauce. The secret sauce is do people trust you to implement together?" (18:42, Corey Raggy)
• On Handling Stress:
  • “You have to be willing to look in the mirror and go like, but really why? And how hard am I willing to work on it?” (35:52, Corey Raggy)
  • “What’s the one next right thing I can do to get control of the situation? Don’t spiral past that.” (36:35, Corey Raggy)
• On Emotional Clutter:
  • “All those little unfinished things...take away that weight and removes that stress that wakes you up in the middle of the night.” (40:58, Corey Raggy)
• On the Isolation of COO:
  • “You have to find your outside board of directors…because you don’t really have that safe place within your building." (45:54, Corey Raggy)
• On The Duality of Leadership - The ‘Rim’ Metaphor:
  • “It’s two sides of a coin and your job is to roll on the edge and I keep that visual there…am I on the rim?” (22:00, Corey Raggy)

Timestamps for Key Segments

• [02:56] Corey’s unconventional path into the COO role
• [05:49] Right people, right seats—hiring and self-awareness
• [08:20] Building trust with the CEO/partners
• [10:21] Deprogramming big-company habits for a small firm
• [14:26] Hiring and leading outside your technical expertise
• [16:45] Encouraging honesty, transparency, and “giving permission”
• [18:42] Relationships as the secret sauce to successful operations
• [21:51] Handling tough conversations and balancing business with people—the ‘coin/rim’ metaphor
• [24:15] Designing meetings and operational communication for clarity
• [31:17] Leadership lessons for middle management: avoid comparison, embrace coaching
• [35:32] Corey's personal system for stress management and maintaining calm
• [44:09] The isolation of the COO and importance of external advisors

Practical Tools and Takeaways

• Don’t operate from outdated assumptions about roles—COO is as people-oriented as you make it.
• Invest in trust from the start; build it through listening, proving value, and showing humility.
• Structure meetings with intention—objectives, the right participants, and outcome-focused agendas.
• Prioritize emotional intelligence and honest feedback, especially under pressure.
• Cultivate a personal ‘board of directors' for maintaining perspective and handling the C-suite isolation.
• Stay grounded by knowing your personal Achilles heel (sleep, nutrition, etc.), acting on stress quickly, and never avoiding constructive conflict.

Where to Connect with Corey

• LinkedIn: Most responsive for professional networking
• Podcast: Rippled Radio—about to launch season 2

Final Thought

“The COO job is probably the coolest job in the world. Anybody in it is blessed. Anybody considering it should run after it. And any CEO thinking about hiring one should do it. It’s magic. I love it.” (50:25, Corey Raggy)