The Jasmine Star Show

Finding Your Dream COO and Defining Success for Their Role

• Jasmine Star

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Ever feel like your business is outgrowing you?

Like you’re stuck in the daily grind, managing everyone and everything, and somehow still have no time to think big?

Been there. 🙋🏻‍♀️

In this episode, I’m pulling back the curtain on how I hired my right hand: our Chief Operating Officer (COO)—and what that decision has meant for scaling our business beyond 7 figures.

It all started with a simple question Jade (now our COO) asked me:

“What would make you fire me?”

😳 Cue the mic drop.

And in that moment, I realized… if I couldn’t answer that, I wasn’t leading with clarity.

So we’re diving deep into:

  • How I knew it was time to hire an integrator
  • What role I hired for before calling her “COO” (hint: humility check)
  • The Harvard Business Review article that changed the way I viewed operational leadership
  • The one KPI I gave her (yes, one)—and why it works like magic
  • The real reason I trust her to lead even when I’m not looking
  • How we define success together, not just in numbers but in execution

Whether you’re a 7-figure founder looking to scale to 8, or you're dreaming of finding someone to help carry the load of building a big business with heart—this episode is your guide to making that vision a reality.

Spoiler alert: It’s less about resumes and more about trust, alignment, and execution.

Grab your notebook—you’ll want to jot this down.

Click >>PLAY<< to hear all of this and:

[00:02] How the question “What would make you fire me?” sparked a leadership reflection

[00:08] When I knew I needed a COO—and the chaos that led me there

[00:13] The Harvard Business Review insight that changed how I hire

[00:21] The unusual path I used to test and promote our COO

[00:31] Why I only gave her one KPI—and how it works better than a spreadsheet

[00:38] What my COO does that I could never do myself

[00:44] Questions you should ask yourself before hiring your right hand

[00:54] What would make you fire your COO? Define it—before you need to

Listen to Related Episodes:

>>Harvard Business Review Article Mentioned<<

📧 Join my Newsletter for a weekly cocktail of insider business strategy, personal reflections, and the journey of being a thought leader. 📧

Click >>PLAY<< to listen now!

For full show notes, visit jasminestar.com/podcast/episode539

Jasmine Star 00:00:00  Have you made a list of what you need from a COO or an integrator? Having a list empowers you to create a job description that allows you to define and attract the right person for your needs. All right. We're going to start with tea. She sat across from me and she said, can I ask what would make you fire me? that caught me off guard. So let me back up a little bit. I work with a woman by the name of Jade, and she is our CEO. And she has become such an integral part of my business. And I also host a mastermind now inside of the mastermind. People are asking me questions around how they begin their scaling process from 7 to 8 figures, and they asking questions that I had faced in a previous journey of me building a business. Now, inside of the slack channel, this is how we communicate with the mastermind. A couple people were asking questions around operations, around hiring a CEO, or sometimes it's called an integrator. Essentially, how do they hire the best right hand for their business? And so we're asking these questions in slack.

Jasmine Star 00:01:07  And so I started answering them from my perspective of working with our CEO. This meant that our CEO went into that slack channel and read about this experience from a third person narrative. She was reading about herself from herself. So let's go back to the story. What would make me fire my CEO? Well, I'll answer that in a bit. But what I want to do is set the stage for how and when I started thinking about hiring a CEO. But before I do that, I want to take a second to shout out a friend of the show who left a five star review. Jay Winer, 2010 wrote, Jasmine's podcast always has what I'm looking for as an entrepreneur mindset, operations, marketing, leadership, tech, inspiration the list goes on. Whenever I have an obstacle or need advice, I find what I need in Jasmine's podcast. Okay. Thank you. Jay Wiesner 2010. You will never know how much it means for myself and the team to read those reviews. Thank you so much.

Jasmine Star 00:02:08  Okay, now let's get back to the process of finding and hiring my crew Chief Operating Officer. I realized that I needed a CFO, an integrator. Once I had seven people reporting to me, okay, seven people were reporting to me as the CFO. I had no time to work on the business because I was still in the business. People were asking me questions, and I felt like I have less time to do and or think because I'm helping them solve their problems. And it's not a bad thing. That is my job as a CEO. But the minute I had seven people asking me, I said, okay, this is not helpful because I went from doing all of the work to managing people, do all of the work, and I didn't feel like I had more time. I mostly felt more drained, and so I did not know how to hire a CFO. But I came across a Harvard Business Review article that helped me so much. Now, what I want to do right now is I want to read a tiny bit of that article.

Jasmine Star 00:03:07  You can find the link to the full article in the show notes. It would be definitely worth your while if you're looking to hire a right hand person. So I'm going to begin reading a portion of that article now. Quote asking the question what makes a great CEO is like asking what makes a great candidate for U.S. Vice president? It all depends on the first name on the ticket the CEO. After in-depth conversations with dozens of executives, there are seven basic reasons why companies decide to hire a CEO. Number one to implement the CEO strategy. Number two, to lead a particular initiative, maybe something like a turnaround. Number three, to mentor a young, inexperienced CEO. Number four, to complement the strengths or makeup weaknesses in or of the CEO five. To provide a partner to the CEO. Number six to test out possible successors. Number seven to stave off deflection of a highly valuable executive. Maybe two losing them to a rival. Those are seven reasons why or how they're looking for a CEO. What are they going to do? So this is a tremendous variation.

Jasmine Star 00:04:21  And it implies that there is no standard set for great CEO attributes, which makes finding suitable candidates for companies difficult. Pause. End quote. I want to stop here for a second because CEOs and I'm largely talking to CEOs, founders of companies right now. You all need. We all need different things. So if you are looking for a CMO, a chief marketing officer, well, you need that person to understand marketing. If you're looking for a CTO. Chief Tech officer, where you're looking for somebody to understand and own tech, right? But for CEOs, that is such a role that has so much variance that it really depends on what the CEO needs. I just want to make sure we're all on the same page. Let's go back to the article. Quote. Still, certain common success factors came up consistently in the interviews, the most important being a high level of trust between the CEO and the CEO. Trust comes from meeting obligations on both sides. The CEO must truly support the CEO's vision, keep the ego in check, and exhibit strong execution, coaching and coordination skills.

Jasmine Star 00:05:31  The CEO must communicate faithfully, grant real authority and decision rights, and not stymie the CEO's career. End quote. Okay, I wanted to share that perspective from the Harvard Business Review article because it really changed everything how I hired my current CEO. So let's start with that story. How I hired I was looking for a CEO to, number one, implement my strategy and to ensure that everybody on the team was executing their respective roles. Now, here's the thing. Because I didn't know what I was doing, I didn't want to over title that person, right. I didn't want to hire a CEO. And I was like, I don't really know what I'm looking for. I didn't want to over title them in case it didn't work out. Maybe I thought that were great, but maybe not great as a CEO. So what I did was I created a job title and a description for an executive project manager. Why? I wanted to see their attention to detail. I wanted to see the humility and see if they would get their hands dirty.

Jasmine Star 00:06:29  And I wanted to see how they thought. Essentially, I wanted to see how did their brain work? Was it compatible? Was it different to mine? What actually were they expecting? I did this also because I wanted to know how they communicated. So I hired my first executive project manager in July of 2019. So in the first three months, all she did was watch. She was learning. And she asked why? Why did we have those meetings? Why were those people on those meetings? Why did I have seven direct reports? Why were we organizing some files on Dropbox and others on G-Drive? Why didn't we have an official way to request time off? After her 90 days, her first 90 days, she began creating projects on my behalf. Let's pause here. She was an executive project manager who just sat and watched the entirety of the business after 90 days, because she was such a sharp thinker, she came to me and said, as your executive project manager, can I take on projects like an employee handbook? Within 90 days, she started off with the employee handbook.

Jasmine Star 00:07:37  She started standardizing processes within our organization. She restructured our meetings for efficiency. Now, six months into her role as executive project manager, we promoted her to the Director of Marketing. Now, at the time, that was a role that I was also in. In addition to being a CEO. So I was a CEO and I was also director of marketing. But because she came in as my executive project manager, she was watching every single thing I was doing. I knew she would be able to execute. On the director of marketing. She killed it. She absolutely slayed our launches and she systematized our processes when it comes to marketing. After ten months, I promoted her to c o o, and it has been a role that she's been in since 2021. Now that sounds fast, but I knew I was looking for a c o o, but I wanted some time to watch and think. So when I think back to that Harvard Business Review article, I've seen how far I've come. I can honestly say, I thought, you know, I didn't know what I wanted, but I thought I needed a CFO to deploy on my strategy.

Jasmine Star 00:08:42  But what I think and what I can say know now, what I know now is at its core is that she strengthens my weaknesses. Our CEO remains behind the scenes. She prefers being anonymous, but she is relentless in making other people shine. She is fierce with her analytical mind, and yet she's very fair when it comes to giving feedback. But she holds no punches. She challenges everybody to step up. She challenges everybody to push harder, and she refuses to quit. So between her and my business partner JD, they also push me to think bigger and push harder. Okay, but what is this actually mean? Right. You're like okay, great. Yeah, I think I get it, but what does that mean? Let's get a little bit more specific. What I'm going to share with you with permission. We had a conversation with my mastermind in slack, and there was a mastermind member who asked the following question. Quote, I would love to hear examples of KPIs, key performance indicators you have for higher level operational roles in your organization.

Jasmine Star 00:09:38  Jasmine. The operations are the area that I have the least insight into because when I did that job in my business, aka when I used to do it, I was very simple and it's no longer simple. The business has grown and this director of operations has grown with it. Right now I have one KPI for my Director of Operations that focuses on employee satisfaction and retention, because HR is one of the Director of Operations responsibilities, but this person also oversees our operations. The role is some big picture and some execution. She has a project manager underneath her for basic execution. So I'm curious, what KPIs have you used for our operations roles? Okay. She was just saying, hey Jasmine, I have a director of ops, which is essentially for her in her organization, like a COO or an integrator. This is a person who is handling operations. And so my response to her was our CFO handle setting KPIs for all leadership, and then the leadership sets KPIs for their teams. So I set our CEO's KPIs.

Jasmine Star 00:10:50  But I made it super simple right when she says, Jasmine, what is my KPI? I'm going to tell everybody right here. I am very simple and I simply said your KPI, your key performance indicator, how you know you're winning. Stay ahead of me. That's it. And most people would hear that and say, that is so vague, Jasmine. I'm not sure how I feel about that. I understand it, but when I ask her or any other CEO I would ever work with, it's stay ahead of me. That's it. It is nearly an impossible task. But she does it. She sees around corners, she forecasts ferociously. She safeguards our money runway. She calls out my gaps. So the KPI I set for her is according to that simple ethos. Stay ahead of me. Now, what's my KPI? As a CEO now you as a CEO will likely be different. Every CEO is different. But my KPIs is I need to recruit talent. I need to get attention for the businesses in our holding company.

Jasmine Star 00:11:53  And I need to build trust. How do we know that I'm winning as a CEO is when we have a pipeline of recruiting top talent, when we are getting attention for our holding company businesses, and when I'm building trust with an audience. So if your ops person is truly focused on 100% operations, their KPI might be our 90% of all KPIs across the team being met. Like in other words, very simply speaking, they're responsible for making sure everybody gets the support they need to meet their KPIs, their goals. Another question that might be helpful to think through when it comes to having your integrator CEO. What are the things that this person can do that would make you mad or fire them. So think about this for your operations person. What would make you really mad? What would make you fire them? Maybe naming that thing and then saying, okay, you're responsible to make sure x, y, z doesn't happen and then you can make that a KPI. Now, right now we're going to pause, because right now, as I'm talking, like you founded a business and you need a right hand to come in.

Jasmine Star 00:12:58  And this seems very nebulous. Like what we want is this is exactly the role, but it's not. And there has to be a lot of grease between that relationship between the CEO and the person who's handling your operations, your CEO, your chief, your integrator, your director of operations. Okay. Because it's so wide, I want to give you another question that a person from my mastermind had asked. This person had asked, okay, I want to follow up on that question my team will ask, but then what does success look like? Like how do you know? How do you coach to the nuances of success. When it's nebulous. When it's a little bit. A little bit yellowy. Okay. My response was that together, we clearly define what success looks like. Me and my CEO, we did this in December of 2024. She knows very specifically what success is for 2025 when a pause. I said we are successful when one, two, three happens. That's it. I said, this is how we know we're successful now.

Jasmine Star 00:14:06  Is she responsible for the outcome? No, we cannot control the outcome, but we can control the effort. Success is flawlessly executing on our stated objectives and projects. That's it. So my KPI for her is stay ahead of me. And how do we determine this success of that? Execute flawlessly. Now I know that it sounds vague, right? But here's what I know. This works for me. Every CEO, every founder. If you're listening to this and you own your business, you are wildly different than me and you need different things. One is not right and one is not wrong. Before our CEO came to work with us, she was in contention to be promoted to CEO in the company that she was working for prior. Now she saw my job listing on Facebook, and at the time, I was working with a recruiter to find that executive project manager role. So she saw the listing on Facebook that I had put out on my page, and then I had pointed her to the recruiter, and the recruiter began the process with her.

Jasmine Star 00:15:13  Jade, our CEO, took a pay cut and she took a position demotion to work at Social curator. Why? Because she believed that one day she would work her way into being the CEO of this company. She started off as an executive project manager, and she showed us her talent and skills every step of the way. Now let's make this about you. I want to ask you, have you made a list of what you need from a COO or an integrator? Having a list empowers you to create a job description that allows you to define and attract the right person for your needs. And don't worry if you think that this list is like abnormal. Like this is weird. I think that this is particular. Don't worry. The Harvard Business Review said that hiring a CEO, hiring a right hand can be abnormal since it varies so much. So don't worry, you're doing it right. Secondly, of the seven descriptions of the CEO listed in the article, I want you to focus on one as you look for qualified candidates, because it helps you assess their goals in relation to your goals.

Jasmine Star 00:16:19  Now, the third and last thing is as you set KPIs, key performance indicators for your CEO. Simply start with things that you find the most valuable to your growth and increasing your pace, and then find a way to measure it as a great way to enhance performance reviews. Right. So I tell RC, oh, this is your KPI. Stay ahead of me. And how do I know that you are being successful when you execute on our stated plans? Now let's go back to the start of this episode. My CEO sat across from me and she asked what I'd fire her for. I was caught off guard and so then I was like, whoa! So I paused and I thought about it because she said, Jasmine, I read the slack message and it was crazy that people were asking questions around performance and what would happen. And I actually don't know, what would you fire me for? And so I said, after thinking about it, I'd fire you if I couldn't trust you, if you lied to me.

Jasmine Star 00:17:28  I mean, like, if it was something like, really small or insignificant, I would lose my ability to know that the thing I value the most. I need to have it from you. And that's trust. I need to trust you won't steal. I need to trust you will speak your truth even if you know I don't like it. I need you to push back on me when you disagree with me. I need to trust that you will do what you say you will do, even when you have a hard time with it. I need to trust you. So please don't do anything that would compromise my trust. That's it. Here's the truth. This is what I told her. I was looking at her still. I mean, like, we're literally on a zoom call, and I told her, here's the truth. You know more than I do. You're better at your role than I could ever be. You set these impossible goals, and then you find a way to hit them.

Jasmine Star 00:18:28  I don't need to set those KPIs for you because yours are naturally higher than mine could ever be. So. Because we both know that this is true. I simply need you to stay ahead of me. I simply need you to make my weaknesses stronger. And please don't violate my trust. That was real and open conversations, and it makes me a little bit uncomfortable. But I'm sharing this so that you are empowered to find and hire your right hand. Somebody who is going to make your life and your business better, stronger and in flow. I hope you enjoyed this episode of The Jasmine Star Show. If you know somebody who is looking to hire a right hand, looking to hire a coach, or is in the process of needing one, share this episode with them. That would be the best thing that you could do to empower them on their journey, and help spread the word about this show. Thank you for watching and listening to The Jasmine Star Show.