Ep. 520 - Cory Raggi – How to Stay Grounded and Lead with Trust

Summary

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)

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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.

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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.

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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)

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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

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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.

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Where to Connect with Corey

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

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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)

Transcript

[Corey Raggy]

I spent 17 years at a company with, you know, 15,000 employees. Now I'm at an organization that has 80 people in the building and I was very scared that I would have to do everything. And I fortunately am somewhere where if I make a business case, we can, we can invest in a hire or a technology. And that, that was something that was important to me.

[Savannah Brewer]

Welcome to the Second in Command podcast produced by the COO alliance and brought to you by its found, Cameron Herold. In the second in command podcast, we talk to top COOs who share the insights, strategies and tactics that made them the chief behind the chief. And now here's your co host, former COO of a multi eight figure remote company and alumni member of the COO Alliance, Savannah Brewer. Today on the Second in Command podcast, we are joined by corporate Corey Raggy, COO of One rdg, the One Financial Center. Corey oversees strategy, culture and seamless operations while actively serving her community as Vice president of the RDG Foundation. She also has spent many years in HR, including working at a 15,000 person company, which is part of the conversation today about how she has transitioned from going from large, larger corporate companies to a smaller 80 person startup. We also hear how she's learned not to get stressed, really keeping herself grounded and regulated in high pressure environments and revealing the three core practices and ways of thinking to do that. We dive into her leadership principles shaped by years in hr, exploring how to build trust quickly in a new role, what she's learned about running effective meetings and keeping communication tight across the team, and how leadership shifts when managing an 80 person team versus a 15,000 person organization. So if you're looking to strengthen your operational leadership while staying grounded and people focused, you'll take away practical tools from this episode with Corey. We are live with Corey. Welcome to the show.

[Corey Raggy]

Thank you so much.

[Savannah Brewer]

It has already been a great conversation since joining in on this zoom. You have incredible energy and we've already started diving into topics where I was like, okay, wait Corey, stop, because this is going to be so good. Let's save it for the episode. And I'm really, really excited for this.

[Corey Raggy]

Me too. Thank you so much for having me.

[Savannah Brewer]

Yeah, well, let's go ahead and dive right in. Why don't you tell us a little bit about the company that you work for and I would also love to hear how you found yourself at this company because it sounds like you found yourself kind of stumbling into a COO role and you weren't maybe expecting to find yourself there.

[Corey Raggy]

Absolutely, yes. So I am COO at 1rdG, the financial center. And we are a company that began as an accounting firm 20 years ago, and our founders over the years had this vision to provide holistic guidance to business owners and slowly started adding additional products and services. So when I joined in 21, they had the beginnings of a payroll and benefits business. They had a version of a wealth management partnership in place along with the traditional accounting firm services. So since I've been here, we've really integrated service models. We've rebranded to 1rdG so that we can become the financial center and resource for business owners. And it's interesting because if you'd asked me five or 10 years ago, would you ever be a CEO, I probably would have laughed at you, like, oh, you haven't met me, Because I just did not consider that. As a matter of fact, when the opportunity came up, I was texting with a friend who was connected to one of the founders here, and I said, you know, I'm looking for new opportunities. And she said, well, you need to work here. They need a coo. And I said, I'm not a coo. And she said, I'm not even really sure what you do, but they need you.

[Savannah Brewer]

Wow.

[Corey Raggy]

And I thought, well, that's the kindest thing anybody has ever said to me. So now I need to look at it. And it turns out being a COO can mean a lot of different things. So falling into it was probably the best thing that ever happened to me personally and professionally.

[Savannah Brewer]

That's so cool. What about the role made you think that you were not fit for a COO position?

[Corey Raggy]

You know, I almost feel like we need to retitle it, like chief operating officer. Sorry, I can't even talk chief operating officer. It sounded like buildings and maintenance and vendors and logistics of things that were so far away from people. And I am a lover of all things people. And when I started interviewing and learned that the COO's role is really to become what the CEO needs, it completely shifted my understanding. They didn't need those things as much. What they needed was somebody to bring some order and some organizational structure and some process to a company that had really great talent, but they were missing that kind of connector that wasn't focused on the client. That was focused on the business and the people. And so, you know, I very quickly learned that my. My first impression of it maybe was outdated to today's business needs. And thank God I had the opportunity to. To get past my first impression there because I was. I was so wrong. Nobody's relying on me for anything maintenance. Because they know I am not good at those things.

[Savannah Brewer]

Same. I mean, I really resonate with this a lot because I actually find myself when I'm talking about new opportunities with people, when they hear my background as a coo, they immediately think this person's going to come in and build all these systems and create automations. And I really get to go through the process with them of communicating. That is not my strong suit. But I am really good at putting the right person in place for that and building them into the culture and holding them accountable. That's what I really love to do and that can fit in the COO role. But I myself do not ask me to go put a zap together.

[Corey Raggy]

No. And I'd say, like if somebody said, what's your number one like mantra or rule that you live by? It's right people, right seats. Like, that's the. That's where I start with solving every problem. And one of the things that I've been able to talk to people about over the years is different. Either accounting firm, managing partners, or even other businesses. People have come to me and said, should I hire a coo? How do I know if I should hire a coo? And it requires a degree of humility, I think, to be able to look at yourself and say, what is the business missing because of the skills I'm lacking? Or maybe where my focus is and can you let somebody in and trust them enough to make some business decisions on your behalf, to look at the business in a way that you would want them to, but also be open to their point of view. It's a personal decision. It's maybe the most personal hire a managing partner could ever make or a CEO could ever make. But it can really be what you need it to be. So that match, I think is super important. And then the COO's role is similarly, you're not going to know everything about everything. You have to know where the strengths are that you have that domain expertise and where the areas are that you don't and hire for them. And fortunately I joined an organization that allowed me to do that. That was one of my fears too, especially being at a smaller company. I spent 17 years at a company with 15,000 employees. Now I'm at an organization that has 80 people in the building. And I was very scared that I would have to do everything. And I fortunately am somewhere where if I make a business case, we can invest in a hire or a technology. And that was something that was important to me.

[Savannah Brewer]

What Was that process like of building the trust with the CEO? Did you guys have a relationship before?

[Corey Raggy]

A very surface one. You know, I would say more of the trust was built during the interview process. I talked with them for probably almost three months before I started in person. Different members of the partner group, different perspectives. And I really tried to see can I see myself working with them on a daily basis and being honest. And they asked me a lot, are you comfortable pushing back? And I loved that they asked me that because it gave me permission. But I will say, you know, my first six months specifically, I listened and I learned and I did what I was asked and I tried to take every task as an opportunity to prove that I could execute but build value in the process. Not an order taker, but like a.

[Savannah Brewer]

Yes and person or we love yes and people.

[Corey Raggy]

Right. Like I'm going to bring additional value to that. And over time, I would say I was given a little bit greater scope. A little bit greater scope. A little bit greater scope. And my confidence increased too because, you know, I'm not an accountant, I'm not a finance professional, I'm not a wealth management advisor. So I, we had to quickly sort of agree that, like, you know your strengths and I'll trust you in those. And I hope that you grow to respect my strengths and trust me in those. And that's been, I would say, the vibe of our relationship and building trust over the years. I still think I'm growing trust every day. I hope I am. You know, as we continue to grow and our challenges change.

[Savannah Brewer]

Yeah. With the change from a 15,000 person company to 80, what was that difference like for you? Were there things where you came into this company and it was like, oh, this isn't actually how they do things and kind of bringing over past. I've never worked at a company bigger than the one that I helped build. And that was 108 people at the time that I left. So I've been curious about what would it be like to go work at a bigger company. What were the differences for you?

[Corey Raggy]

Huge. I had to deprogram. I mean everything from. I laugh about this to this day because I remember like I always felt like I needed to ask permission when I first started. When you're part of a big company and there's a ton of structure and processes, you know, if you're leaving for a dentist appointment, people need to know. And I remember saying to John, our managing partner, I have a dentist appointment in the morning, do you want to know that? And he was like, no, okay, you know, very. I had to drop some of that people pleaser permission mentality. Nobody has time for that in a small business. A B. I wanted to communicate via PowerPoint all the time. Like, my brain only worked in PowerPoint. I had to let that go because nobody wants to see a deck every single time. They just want to know the point.

[Cameron Herold]

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[Corey Raggy]

You know the worry all the time. Like, this is a really funny, specific story, but the COVID restrictions were being lifted about a month after I started and it was the first day in New York State, at least, that people didn't need to like, get their temperature taken at work. And you do all these things. And we weren't super tightly following all of the things, but we, you know, we're, we were in the ballpark of it. So the first day those were lifted, our HR admin at the time came to me and said, hey, I was thinking tomorrow that since we don't have to greet people with a thermometer, what if we greeted them with a mimosa? I was like, can we do that? And she goes, well, why not? I'm like, well, who would you ask? She says, I'm asking you. Like, oh God. Like, who would you have asked before me? I mean, it's okay to do some of those fun off the beaten path things in a smaller company where in a larger company you would just never consider it. So just freeing up my, like, rule following, compliance seeking part of me and just being, getting to be a little bit more human was fun. But yes, it took me years to drop the, like, perfection need. You know, nobody expected me to be perfect here. And I love, I still love that because fortunately I'm very good at not being perfect. I excel.

[Savannah Brewer]

That's great. Well, and this is really helpful for me because hearing you say that, I'm like, man, maybe going to a bigger company is not for me because I like to break the rules. I don't want to ask questions. I need a lot of photo.

[Corey Raggy]

Yeah, I mean, and listen, not all cult. I came from a company with a pretty conservative culture. Amazing company. I learned everything there. But conservative. Like, I'm sure there's like super cool startups that are bigger now that are, that are looser. I just didn't work at any of them, so who knows?

[Savannah Brewer]

Well, one of the other things that you had mentioned a little bit earlier that I would love to know is with being in a CEO position at a financial company, but not having a financial background, what has it been like trying to hire and build and lead people in departments that you don't have expertise in?

[Corey Raggy]

So, you know, it's. I'm so fortunate because our partners are so open to the fact that like we can say going into an interview, for example, I'm going to screen for culture, fit, motivation, career planning. You screen for technical, and we just divide and conquer together. And I'm so lucky that I work with a team that's like, okay, cool. Because frankly, they don't always want to screen for culture fit, career planning, all those pieces either. So we just leverage each other's strengths that, you know, back to that right people, right seats piece. You know, we're constantly looking at each other going, what are you best suited for? What's the highest level of value that you can bring to this project, this solution, this meeting, this interview and, and what's left lacking there and who can we bring in? We are constantly looking at every situation like that. So, you know, we just, we focus on each other's strengths and I bring what I can and they bring what they can. Now along the way, I have learned so much. You know, I had to ask for all the vocabulary and acronym words when I started. I don't have to ask those anymore. I can talk a good game. I know enough to be dangerous and I know when enough to ask for help.

[Savannah Brewer]

That's great. The acronym thing makes me think back to this conference I went to with my dad and I was just like, I want to go to something that's outside of the world that I live in. And so he brought me to a, like an E commerce conference because he runs an E commerce agency and people like every conversation I was in, I was hearing the term CPG and I had this moment of like, do I want to look like I'm cool here and just keep nodding my head or am I going to be brave and ask what does that stand for? And then what I heard is like, consumer package. Good. I'm like, oh, that makes so much sense. I can't believe I didn't know that. But it takes humility to come into a company, especially when you're being brought in as a coo. I just really admire you for having the humility to go into a space that you don't know and learn the acronyms and the terminology and all these things that are so new to you. I don't, I don't think many people are courageous enough to go into a totally different sphere and really put aside some of that, you know, the, the ego that wants to show up in the workplace sometimes.

[Corey Raggy]

Thank you for that. And, and I, I, it's interesting. I think I'm also a big fan of sort of like authentic self deprecation in the workplace. Right. Like when somebody's working for me, I'm the first one to tell them, here's what's going to drive you crazy about me. And I don't want that to get in your way. That's not an excuse. If, if me being a little flighty or disorganized on something or kind of all over the board and what we're talking about impacts you. I want you have perish to call me out. You know, I want to tell you what's wrong with me before you think about it behind my back. So maybe there's a little face saving there. Um, but I also find it ramps up that trust so quickly too. Because I don't want you to worry. I don't want you to think like, boy, that really drives me crazy about Corey. Now I have to work around that. I'd rather tell you up front, don't work around it. I know that about myself. Just go, Corey, you're doing it. And remind me a little bit. I'm still working on it. It's not a. I'm not asking for a pass on it, but you know, they. The first accounting term I learned was retained earnings rolling did retain something like that. I don't, I still don't know what it means. But every once in a while I'll walk by one of their desk and I'll just ask them if they rolled. And people laugh because they know I don't know what I mean. And it just, it just makes it like fair game to talk about.

[Savannah Brewer]

Yeah, the trust piece is really important, especially in the beginning parts of a hiring process. I mean, I think sometimes people in the hiring process and onboarding, they're trying to seem so serious and put together and they want to make a good impression that they miss out on just the fact that we're all human. And the quicker you can just get on a human, human level, it really helps build the trust. And you're going to have topics raised up quicker than you would. If people are trying to act all perfect and seem like, you know, none of us have any issues, it's just not true.

[Corey Raggy]

And you think about that, you know that concept in the book Speed of Trust, Right. I want to get there as quick as I can. I want us to be comfortable with each other authentically, as quick as we can, because that's what our working relationship is going to get, really productive. And I think so much of the COO role is relationships. Like back to our beginning conversation. It's like 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? Do they trust to come back to you when the thing's not working and saying to you, hey, I tried what you said. The secret is not the answer. The secret is the relationships that will allow you to implement. And I would give that advice to any COO relationships.

[Savannah Brewer]

First, are there any particular pieces in building trust? Especially like when you're outside of the initial kind of onboarding, but when you've got KPIs to hit and there's pressure and people are bringing up ideas, or maybe they're scared to bring up ideas, like what is. What are some principles or some ways of thinking in your leadership style that allow you to continue keeping the trust even when things might start feeling a little stickier?

[Corey Raggy]

So I I I 1 I 1 answer I would say is I try to look at my environment as some form of a mirror of myself. So if something is off in that meeting, I have to ask myself, what environment are you creating? Are you modeling the behavior that you want to see? So if they're defensive, is it because I look like I'm attacking? If they're reticent to share something, is it because I appear judgmental, so I might have to role model it first so that they can respond in kind? So to give a specific example, let's say there's a KPI we're missing and I need us to think, I need us to get better at it. I'll probably open up that meeting and say this number's off. I want to brainstorm together ideas for how we can hit it. Not all ideas are going to be great. I'm going to write in pencil out loud right now. These are not fact. Right. These are just ideas. Here's some thoughts that went through my mind. What else? And so you have to set the tone that you want replicated. And back to that humility thing. If the vibe is off, it might be you take responsibility for it and reset it if needed. The more I do that, and I can think of very specific examples right now of things my team is going through that I have to constantly do that. You have to be willing to take accountability first for that vibe.

[Savannah Brewer]

If the vibe you feel like genuinely isn't you and you're showing up as a leader, your best every day, you're continuing to pour into this person and things are still just not where they're at. What's your process for handling those tough conversations?

[Corey Raggy]

So I recently went through exactly what you're describing and I brought the team members that I felt like we were off with and I brought them in my office and I said, I want to share something with you all. And I'll admit half of this is self serving because I don't know what to do and I'm not sure that my intentions are making their way to you. So let me share with you what I'm trying to do and let's talk about where we are. And I did get feedback. It didn't make me happy. It wasn't awesome. We might end up with some shifts talent wise there, maybe not all my choice. But that happens. And in those moments you try to connect emotionally, but then you have to go back to what does the business need and you keep balancing the business and the people. The business and the people. I had a mentor once that said, you know, it's two sides of a coin and your job is to roll on the edge and I keep that visual there. So I want to connect with people. I want to get into that vibe and I want to understand it. But I also need to get back to the business and look at what it's telling me. Are there moves we need to make that might not be popular? Talent wise, process wise, staffing wise, whatever. And keep asking yourself, am I on the rim?

[Savannah Brewer]

The metaphor being on the rim is so perfect.

[Corey Raggy]

It. I thank him every day for that. It might be one of my most Used guiding posts, you know, in, in, in what somebody taught me and I'm, I am forever grateful for him. His name's Jeff Grenzer, as a matter of fact, and he was my director in organizational development and he taught that to me.

[Savannah Brewer]

Beautiful. And yeah, that'll be passed on to me. I feel like the visual is so easy to think about.

[Corey Raggy]

Right.

[Savannah Brewer]

In terms of maybe some more practical ways to do that, is there any way that you and your leadership team or you and the company as a whole try to keep everyone on the same page of what does that look like? How do we take care of the people and where's the business going? What's important? Do you guys have monthly meetings? Are there reports that people are reading? How do you guys go about that?

[Corey Raggy]

Yeah, great question. I'd say that's probably one of the more tangible things I've implemented in my role. When I started, I would say our partner meetings were finance meetings and those were the only meetings that happened. And they were every two weeks since then we have restaffed meetings and said what's the objective of what's the objective and who needs to be there and what's the scope of the content? Because you can't talk about everything at every meeting and every level shouldn't be involved in everything. So now we have partner meetings, we have department leadership meetings, we have manager meetings, we have department meetings. Now somebody might say, is that meeting overkill? You have to monitor for that. You have to watch how much of your time is spent in meetings. But for us we're very clear that there is a clear objective and then you establish the cadence. Is it monthly? Is it bi Weekly, is it 30 minutes, is it an hour? Like. And it's different for all of them. Right. Some of the things that have allowed us to. And I'll take our partner meeting as an example. Two things help us. One is we have metrics that we discuss with curiosity. We don't let them tell the whole story. So this person or this department is behind does anybody know why? Instead of just making decisions on it. And if we don't know why, we go back and we find out. So we make sure the qualitative and quantitative information is there. Because two departments could be off for very different reasons. So we, we discuss, we don't just send out a report and decide. We discuss a B, our strategic goals. Whenever I feel like I'm flailing a little bit or at a lack of focus, I go back to our 18 month plan, which we are 12 months into and I say, I look at them and go did we move the ball? It always recenters me. And then I bring that update to our partner meeting and I'll say as an FYI, if anybody's feeling like we're all over the board, let's go back to kind of ground zero for a minute. This is what we said we wanted to do 12 months ago. In 18 months, here's our status and fortunately this year all of our efforts keep driving those five initiatives forward. If you've got a lot of initiatives that are outside of that, you have to go where our initiatives wrong or is our effort wrong or has it just changed and do we need to re agree? But you as coo, I think you've got to be the pulse keeper of your strategic energy and make sure that it's kind of going that direction. So I'd say discussion around KPIs and strategic goal updates, those two things are huge in deciding all of those things.

[Cameron Herold]

Hey, it's Cameron Herald, your high energy leadership guru here to pump you up on the Second Command podcast. If you get frustrated because your managers aren't leading like you want them to be, check out my game changing leadership [e-mail] that's investinyourleaders.com for just 347 per liter. You get 30 years my proven experience straight from taking 1,800 got junk from 2 million to 106 million as CEO and it's packed with 12 easy modules. Learn situational leadership coaching, delegation, conflict management and more all in under six [e-mail] with straight to the point videos, worksheets and real life scenarios. Your team will master time management, be able to hire a players and get aligned with your vision. It's all backed by a 30 day money back guarantee and raved about by hundreds of CEOs and thousands of managers already learning from the content. Grab this now and watch your business soar.

[Savannah Brewer]

A big thing that's coming up for me is just avoiding assumptions when it comes to data and people. But like you said, really being curious and asking questions. I've talked about this a lot on the podcast because I just experienced so early on in my COO role of making assumptions and trying to figure out how do I lead people. I was so new and trying to figure out how do I protect the business. And you know, you see these numbers, you're like okay, low number, you know, why is this person not hitting it? We need to get them out. But really taking the Time to slow down. And here, because all these things can be connected to other places and unless you really go investigating, you know, you can make the wrong decisions, you can move people, fire people, and then end up regretting it later. And the other thing that you mentioned was the importance of having meetings with an agenda and a clear outcome, which we at our company, at Closers, there was a point where we got just. I felt like I was on meetings all the time. And so Cameron actually has a book called Meetings Suck. And I believe this was even before I had even worked with Cameron as hiring him as my mentor. But I read his book Meeting Suck and it was so helpful for me on, you know, one, one thing was condensing the time and then figuring out how do you create an agenda that works for that? Because everyone will book like an hour long meeting and then, you know, it might go over. It's like you might as well get 20 minute meeting and if you got an extra five minutes at rollover, awesome. But really cutting it down and you're only focused on the most important things really.

[Corey Raggy]

And do you have the right people at it? Like staffing meetings appropriately is a whole skill in and of itself. You know, and I'd say too, you know, back to the thing about leading people, I'm grateful. I've got a, A good chunk of my prior life was in HR disciplines. You know, employee development, hr, leadership development, and so much of business challenges come back to leadership. And I'm so grateful that I have that I was given the opportunity to focus so much in that because it's my number one tool to look at it. Good leadership solves so many things. And I very often go right back to that. Like, what is leadership doing when there's a problem? It's not a process problem. You've probably built the process five times, but nobody's enforced it, nobody's trained it, nobody's inspected it, nobody's given feedback on it. The process is less often the problem. The people are usually the ones in need of attention more than the process. And if you still point at the process, well, who's managing the process? Then it still goes back to a person every single time.

[Savannah Brewer]

Right.

[Corey Raggy]

I keep waiting to think I'm wrong about that, but I just, I can't find it yet.

[Savannah Brewer]

Well, what are some other leadership breakdowns or challenges that you find are the most common with maybe people in middle management that you're leading and kind of training up? What are some of the most common mistakes or challenges that you're seeing?

[Corey Raggy]

Oh, My God. Okay, so I could do a whole.

[Savannah Brewer]

Talk, Just be a whole episode.

[Corey Raggy]

Sure, yeah. I mean, but number one is any time you feel yourself comparing someone to what you would have done, like, I want you to. I want it to go like. Your job is not to make them like you. That's an old, bad management habit. Our job as leaders is to find talent that we believe has the potential to be great and help them become the best versions of themselves, not of you. So you should be hiring people that you can see that in. So when you get that. When I was your age, when I started. No, no, no. Nope, nope, nope, nope, nope. Big mistake. Two, underestimating the challenge of it. I actually had the analogy when I was driving this morning, and I have no idea where this came from, but I don't know if you've ever tried to be a drummer before.

[Savannah Brewer]

I've taken three drum lessons in Nashville.

[Corey Raggy]

All right, so you know how hard it is to make your left foot do one thing, your right foot do another, Right? Leadership is the same thing. You need to have your pulse and your hand on different people doing different things all the time. It takes coordination. It takes, like, multiple monitoring all at the same time to make this whole thing work together. And I think people think leadership sometimes is just telling people what to do. And it's not. It is separate functions, especially in a CEO role, because you're not managing 12 people that are doing the same job. If you're like me, you know, I've got a shared services division. IT marketing, HR operations, they don't have a lot in common. So underestimating the challenge of leadership and not considering it a skill to get great at huge miss. Read the books, watch the videos, spend the time on it. Like, don't underestimate that. And the third one I'll say, just so that I don't take up the entire time, is get great at feedback. Like, at not making it a big deal. You know, somehow if you're the coach of a team, like an athletic team, you know, your job is to say, hey, that was great, but next time, try this, and somehow you get into the working world and that ease of feedback goes away. Get great at helping people get better. And don't avoid those conversations, or you're just. You're missing the power of the team. The whole point of this is to scale and to get everybody being great, not just you. So I could. I could talk about that one.

[Savannah Brewer]

Those are phenomenal. Really good.

[Corey Raggy]

I'm passionate about it. I just love it. It's my favorite thing.

[Savannah Brewer]

I can tell. And I have very similar energy on these topics. So it's, it's really amazing to feel that passion that you have.

[Corey Raggy]

I feel the same way. Like the second we got on the phone I'm like, oh God, we get this going.

[Savannah Brewer]

Be fun.

[Corey Raggy]

Yeah.

[Savannah Brewer]

There was something that you said in there that kind of ties back to when we first got on the call and we were just kind of shooting back and forth which is when you are managing multiple different departments and like you said, you got to keep your finger on the pulse of so many different pieces and people. That takes up a lot of mental bandwidth. It's a lot of energy. And especially, I mean coming from a company with 15,000 people and being in charge of HR, I can imagine just the amount of complexity or challenge even in that space versus the role that you're in now and how they all probably have such a different opportunities for stress. So I'd be curious to hear if you would share some of the things that we were talking about earlier around you had mentioned you just don't feel stressed anymore. Which to me I'm like, how do I take what is in your nervous system and your brain into me? Because that has been hands down my number one challenge is being able to stay regulated and calm while handling absolute chaos.

[Corey Raggy]

Yes, I man, you know, I share this and this is coming from someone who 10 years ago, like major challenges handling stress, anxious like it was manifesting physically. Like I remember going to the doctor and tell him I thought I had something in an organ and he's like that's not where that organ is. Like I was dressed. And I will say in full disclosure, like it started with like I went to therapy to understand all of that, all of these pieces and then, and then I learned a lot. And now I'd say, you know, after a lot of self reflection and taking accountability for, you know, for a lot of those pieces, which it sounds weird to say taking accountability for being stressed, but you have to, 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? And now I would say, you know, a few things. One, know, know where your Achilles heel is going to be, know where, know what's your kryptonite. For me I have to have upwards of six to seven hours of sleep. If I get sleep, I can handle anything. If I don't, I can have nothing. And so everybody's might be different. Like one of my daughters says hers is nutrition. She doesn't need all the sleep, but she needs to eat good. So know what yours is? Mine is sleep. 2. When you feel that stress hit and everybody gets that feeling different. For some people it's a pit in their stomach. From some people, it's distraction. Later on, you might find yourself scrolling on your phone and tuning out more like you, you. Everybody has their tell. When I see mine, I stop and I go, where? Where is this coming from? What's causing this? And what's the one next right thing I can do to get control of the situation? Don't spiral past that. Just what's one the one next thing I can do. And I use that at home if I'm worried about something with my kids, I use it at work. If I feel like a project's going off or if I feel like a staff member's in a weird spot or like whatever that root of the worry is, what's the one next right thing I can do? The third thing is I am not a conflict avoider. I started to share that with you earlier. I don't view conflict is like negative and starting a fight. I view it. I view it as addressing the elephant in the room before it's that big. And so whoever I need to talk to. And by the way, sometimes it's just yourself you need to have a talk with. But whoever I need to talk to, I might do it. My only disclaimer to that is, if you're too high or too low, don't do it yet. Like, just recognize like, I'm worried about what so and so is thinking of me right now. Let's just say that that's where a lot of stress comes from. I screwed up. So and so is going to think less of me. I'm not saying go run in there and. And go, hey, are you mad at me? Like, do not create that. But think about that for a minute. Why am I worried about that? Do they. Did I met? Did I mess something up that I need to own up to? Is there a way I can correct that? And go, Guys, after that last meeting, I had one more thought that I think will shore up where we landed that I wanted to share with you. Don't let the paranoia feed who you talk to. But what's the one next right thing? And is there a group I need to talk to about it? You'll be amazed at what your central nervous system will do. And if you don't let it spiral and don't get emotionally hijacked, I'll share it. Studying Emotional intelligence and crucial conversations. Those two topics, game changers for me in stress management. This is another one I could probably talk about for a long time, but know your trigger, do the next right thing and don't avoid the situation.

[Savannah Brewer]

Those are so huge. I mean, emotional intelligence, I think is like, it's the one of the most number one things that I'm looking for in people on my team. Because if, if you don't have it, if people around you don't have it, it becomes very difficult to make any progress. Stuck in victim and it's their fault. And what are they thinking of me and all these external things versus just focusing on the thing that we can control. And I, I thought of this. I don't remember who told me this, but the concept of open and closed loops where, you know, maybe that you, you felt this like little tiny weirdness on a call with one of your coworkers and you let it go. But every time you talk to them, there's this tiny little open loop in your brain. And over time, when you've got hundreds or even thousands of those with the people in your life, it takes up so much mental capacity. The amount of times that I've, like, felt something and like, I was worried about it and worried about it and I let it build and build and then I'm so nervous about it. I'm thinking about how this person's going to respond and I'm going to get fired or whatever the case. And then I finally get to my breaking point. Like, I have to talk about it. And 90%, 99% of the time, it is not that bad. It's actually really good. And I walk away being like, wow, I cannot believe I didn't just give that feedback faster or receive that feedback faster. So I think that is such an important part.

[Corey Raggy]

Well, and you know, you, you just painted such a great picture of all those, like, micro interactions, right? And it becomes clutter. And so, you know, the same way clutter on your countertop in your kitchen like, suffocates you and adds up. So do all those little unfinished things. So being able to stay in the moment and deal with them as they come, instead of, like hoarding them all, it just takes away that weight and removes that stress that wakes you up in the middle of the night, which is really what we're all trying to avoid. We just want to sleep through the night. Big deal.

[Savannah Brewer]

Totally. This is something that I was just talking about with my roommate because he has a YouTube channel called Wellness Daddy and talks a lot about sleep. But his first question, when I tell him, I'm like, oh, I got a horrible night of sleep. He's not asking if I ate before too close to bed, or, you know, if I put my boulevard blockers on. His first question is always, is there something on your mind that you need to clear? Like, yeah, it's true.

[Corey Raggy]

Because that's what wakes you up with that start. And you know, it's funny because now if I wake up with that start. I mentioned to you earlier that I like to do a lot of mindless listening to books, you know, like murder mystery, true crime, ish type. Which does not sound light. But my point being, stuff that's not stimulating to me, it's like a form of meditation and like a regulating calm that just listening to a story does for me. And so it's not uncommon. If I wake up at a start and people don't know how to get back to sleep. You've heard about 4, 7, 8, breathing. You've heard all of these things. I've tried them all. I listen to something in the middle of the night. I will turn it on. And it just calms me back down. Because how big something seems in the middle of the night is not real. It's like when you're little and you see a big shadow and it was a little toy. Same thing with stress in the middle of the night. It's not that big. You need to go back to sleep and think about it tomorrow. Sleep will help you deal with it the right way. I love sleep.

[Savannah Brewer]

Sleep is the best. It's impressive that you only need like 7 hours of sleep though, because I'm like, my baseline is nine, which I'm like, man, I'm getting like two hours less life to live day than some other people. But, you know, we're all different.

[Corey Raggy]

Well, and. And I also, like, I might be at like a sevenish, but I'm also not afraid to take a nap like on a Saturday afternoon. So we might average out. Right. Like, naps are magic too. When you need them, take them. They aren't. I love them.

[Savannah Brewer]

Incredible. Especially on a Saturday or like a Sunday nap brunch.

[Corey Raggy]

Yes.

[Savannah Brewer]

The best. Take it a little bit of a kind of pivot here. I remember reading in some of the form that you filled out before was around some of the isolation that comes with being a CEO. I'd be curious to hear you just expand a little bit on what that means for you.

[Corey Raggy]

Yeah. So it's really weird. And I. This is a. I find this to Be odd about myself. I actually have never liked Jobs where there was a ton of people doing what I was doing. I always found it distracting because you compare, you know, maybe some, maybe that's a mountain I will need to climb someday to get okay with that. But when I was in Jobs where it was easy to compare, it distracted me. I like to run my own race. I do. I like to go, are you doing your best? And just black out the rest of it. And it's easy to do in a role where you're the only one of it or it's different enough that you can't compare it. Maybe it's self preservation. I don't know if this is a good thing or a bad thing, but it just is. So I will say I like that part about being a coo is that I'm the only one. But it's hard to ask for advice because you have to be the ultimate unbiased human being in your organization. You can't really let yourself be overly influenced by any one person except in certain areas where they're the superpower. Right? Like, I know I want to go to this partner when I want to know about this, and I know I want to go to that partner when I want to know about that. But at the end of the day I feel the need to be very unbiased. So that level of like kind of mental separation you need to always keep for yourself. It's, there's times where you just feel like a little bit the odd man out. Nobody really gets what you're trying to do and to even the CEO, because he's one of the people or she is one of the people that you're trying to do that with. So you know, I think you have to, you have to find your outside board of directors and, and for. I think that's what's kept me sane over the years is that I've, I have probably six or seven people that I will still reach out to that I can just talk freely and confidentially with and get some perspective because you don't, you don't really have that safe place within your building.

[Savannah Brewer]

I feel this and I have so deeply and a lot, a lot of CEOs feel this way. And I remember being in, you know, at closers and feeling like, man, I don't know who to go to to ask for help. And I also felt that me trying to communicate to people what all was on my plate because I had, I had created my role. I was the second hire. I created it over Time and people just have this idea of what they think you're doing. But there's so much more of all these little pieces. And I actually had a situation where at a company that I was at, the next person who took in my role had a conversation with me and told me that there was way more to the role than they expected or that other people on the leadership team had told them and was asking for my support on a couple things. Because there is just pieces that you cannot see if you're not in the role yourself. And.

[Corey Raggy]

And nobody wants to know either. Nobody wants my update. It's like so many pieces of it are boring and it's detail and so it's. And it's so all over the board that it's also isolating that way because they don't even want to know it all. That's why you're there.

[Savannah Brewer]

Yeah.

[Corey Raggy]

And so, you know, when you're looking for performance feedback, you know, I'd give this advice to CEOs too. Like, you have to have a really clear conversation with your team to say, like, my job is to make your job easier. But the better I do, the less you see what I do. So how do we make sure that I'm. That you know, the value I'm hopefully bringing to the organization? Those were conversations I had to have.

[Savannah Brewer]

Love that. Well, and if anyone is listening who really resonates with this and you're in a role where you feel like you don't really have anyone to reach out to or you don't have that board of directors, I mean, just gonna shamelessly plug Cameron, because that is exactly. That's how I built a relationship with Cameron. It's how I ended up hosting this podcast. Now after joining the COO alliance and being able to be in rooms with other people who knew way more than I did about the problems I was trying to solve. So if that is, you look that look into that, there's a lot of resources online.

[Corey Raggy]

Incredible resources.

[Savannah Brewer]

Cameron Herald, the last question that I would have for you is, I love asking, what is the most exciting thing that you're looking forward to both in business and personally in the next six months?

[Corey Raggy]

Oh, goodness. So I say in business, we are as a team, super focused on, you know, what is our next set of goals. As I mentioned, we had an 18 month plan. We're 12 months into it and we've really kind of executed on the dream of our founders as one rdg. And so we have built all of these things that are going to position us for success. And I feel like I joined at just the right time. And now I feel like I really get to be part of a team and we get to run now. And I am very, very, very excited to just like, feel the proverbial wind in our hair and execute on, on these plans that we've been working so hard on. We're just at the most exciting possible time. And personally, I have two daughters that will be in high school together, a freshman and a senior. And I adore them. I'm obsessed with them. I make every decision for them. And they're going to be in the same school for the last time before my oldest goes and graduates. So I am planning on soaking up every single second of time with these, these two lovely young ladies that I was blessed with and trying not to cry my whole way through it. But enjoy it. If anybody has advice on that.

[Savannah Brewer]

Let her know. I mean, speaking of, if anyone wants to reach out to you, where would they find you? I know that you also, I think, have a podcast, so let us know. How can we get in touch.

[Corey Raggy]

So I love LinkedIn. That's where you and I connected, right? So I. I'm not an ignorer of LinkedIn messages at all unless it's like a, you know, pre formatted sales pitch of nothing. So I'm on LinkedIn. Rippled radio is, is my podcast fledgling. We finished one season. We're getting ready to start season two here actually this week. And I love new friends and I love connecting with people. So if anything I've said resonates with anybody, I do not have too many friends, professionally or personally. So I love meeting new people. And I just want to say thank you for having me and thank you for such an incredible platform and resource. I think the CEO 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 just. It's magic. I love it. It's my favorite thing I've ever done.

[Savannah Brewer]

Oh, Corey, this has been so fun. Thank you for saying yes. And thanks acting. All of your golden nuggets, I'm sure are going to make a massive impact on many people. So I hope so.

[Corey Raggy]

Pleasure to meet you and I fully enjoyed it. Have a wonderful day.

[Savannah Brewer]

You too. You've been listening to Second In Command, brought to you by COO alliance founder Cameron Herald. If you enjoyed this episode, please be sure to, like, share and subscribe to us on Apple Podcasts, Spotify and our other podcast streaming platforms. For more best practices from industry leading COOs, visit COOAlliance.com SA.