What It Takes to Be a Great COO

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This is Greg Bartalis for Barron's The Way Forward. My guest today is Allison Felix, COO of Cassiday and Company. Today we're going to focus on operations and how advisors can ensure that their businesses are being run optimally. Allison, welcome.

Thank you. Appreciate being here.

Well, my pleasure. I'm glad you could make it. You've been with Cassiday for over 20 years. And you have seen a lot. You know the institution very well, its history and whatnot, personnel. You've seen it through all forms of its existence. Tell me about what it's like being COO, what your job's like, and importantly, too, what listeners should know for hiring a COO. And also, if they don't have a COO, how can they delegate those responsibilities? So there's a lot to tackle, but it's just going to be a deep dive in all things operations.

OK, well, I'm in that space. I hope I know it well and can speak to all of those questions. And so, you know, the first question is, you know, how do you approach being a COO? And for me, if everything in the firm is operating as it should, then goal attainment should be your number one objective. And so, whether it's the firm goals, the team's goals, or individual role and position goals, the COO is there to make sure all of that's happening, understanding key performance indicators, understanding what people need and what might be getting in the way of that. That coupled with taking the operational management off of whether it be a CEO role, a founder, a lead advisor. The COO is there to be, you know, the yin to the yang for that person. And so if you recognize that you're equivalent as a need in the firm, but that your strengths play off their weaknesses and vice versa. And so, for me, that's how I tackle the operations and COO role is it's, you know, it's so critical to the firm, and yet for many, many years, I was not that title. And so, you know, I can kind of speak to your question about if firms are smaller, practices don't have that titling, you know, how do you make somebody, not make them, but, you know, how do you accommodate the needs of the practice. So, for me, I came in with a dual role. I was the administrative assistant to our then CEO and was also what they called at the time the business manager. I did the bills and the payroll and sort of an amalgamation of accounting and HR and sort of all those detail things that just need to be done. So, what's critical for the firm and for what we look for in quality employees employees is innate abilities that can't be trained because you can train them on the technical skills. And so finding someone who is willing to, you know, push up their sleeves and get in there and just do what's asked of them, and when that happens, you start developing a trust between you and that employee, and you start looking at them with a different mindset. You know, we at Cassidy and Company are really honed in on who we believe future leaders of the firm are.. And so that may not be tomorrow or next year, but within the next 5 years. And so how do we embrace that? How do we talk to them about their career pathing? What interests them? If you can ask somebody, what do they enjoy doing? And they hear in your voice that it's not just about what you need them to do, you've created an entirely different relationship there. And that's what Steve Cassaday did with me. I may have had a title that was administrative assistant, but I was well beyond that. And so, So, us working together and him eventually approaching me, you know, a decade or so into the role and saying, you know, hey, I think you'd be really good for this as we continue to grow. That was really just the push that I needed. You know, entered next MBA program and sort of those more technical, you know, educational skills that come along with developing just a confidence level and trust from your peers, you know, others in the firm who might have seen you come up from a different position. So that's a little bit about sort of my story, but also a little bit about how a COO at a firm can be developed even if you are not yet ready to have a position titled that.

Right, right. You look for the characteristics, but to put a finer point on those characteristics, you mentioned future leaders. What are some other things that you would see in a potential future leader? Which, what attributes, you know, might be hustle, intelligence, high EQ, etc.? Sure.

I mean, all of those things combined. You know, for, for us, it's willing to go that extra mile. We often will bring people in and say, here's the general framework of what we need from you, but we're not going to micromanage you, and we want to see how you tackle that role and what do you put of yourself into it. We have a unique structure at Cassidy and Company where everyone in the firm is paid a percent of our firm revenue. When you compensate people like entrepreneurs, they start thinking and leaning towards a more entrepreneurial mindset. And so the people who take to that way of operating, they're invested. They put in their all. They don't look at the clock, right? They're interested in a career, not a job. And so for us, it's just those people start shining. They go above and beyond. They say, you know what's not being done? But wasn't assigned to me and I'm just going to make it happen. You know, that's that grit and that, you know, sort of ownership is what we like to call it, and just making the role your own, and really why we have so many people at the firm who, like myself, have gone from one role into a much more graduated role and have significant tenure at a firm that, you know, has rewarded them for those kinds of behaviors.

And what do some of the best COOs do today, which might overlap a little with what we just talked about, but in terms of execution on a fairly high level, any other things you could add to that?

I'll try. I'll tell you that I mentioned this earlier today to somebody else. It's— the COO role is tough because there's no peer equivalent at your firm, and so you have to seek those people out, whether it's at a Barron's conference. In 2008, I started a group of female COOs COOs in the local Washington, D.C. area. So, getting people together and talking about those experiences, but regardless of industry, I have found that the core skills of a COO are, I'm just going to do it. You know, I don't look to someone else to do it until it's time to say, okay, here's a delegation opportunity, here's a role change opportunity. You know, you have to be willing to do everything, you know, that is asked of you operationally, back office, technology, marketing, and everything in between. But I would say that again, I'll go back to the achievement of goals. If you are a firm who is looking to be not only successful, but successful enough to have someone in a COO position, it's because you set the goals that got you there, and you had the team rally around those goals to get there. And so the COO is the one who is making sure those don't get tossed by the wayside. You know, we all get busy with our day-to-day. Clients are calling in, tax season rolls around, year-end comes, you know, to fruition. And so, you know, we find that if we're not really diligent about having our goals being managed, and this is where a leadership team for the firm has come into play, executive coaching has come into play. And so I find that regardless of industry, when I'm talking to COOs, it's how are they just making sure that everything is still, you know, continuing forward, the train doesn't have the wheels falling off, you know, sort of all of those objectives.

So based on what you said, it seems that one constant in this position over the years is being a self-starter, being organized, being thorough, paying attention to detail. But I'm curious now what has changed and maybe to what extent, if any, has technology made the job easier and/or harder? There are many more moving parts, right? There are.

Yeah. Yeah. So it's a great question. There is technology in the sense that, you know, my IT guy comes when I can't figure out why my computer is not working. And then we've gone a whole nother route, which is frankly data management and databases. And so when you couple those things, you're talking about technology in a pretty expansive space. We have found that though there are a lot of great technologies, especially for this industry, they don't always do what we want them to do, right? They're built for the mass. And if you want a customized product, you really have to kind of define that yourself. So we've brought some people in who know how to code, know how to, you know, manage data. And so, you know, back to those skills of diligence, attention to detail, you know, really being kind of in the weeds on some things. As a COO, you're often, like I said, the yin to the yang of the other person. And so if you're dealing with someone who's a salesperson, a people person, a rainmaker, they're, they're not the type of person you want in the weeds and managing the details.

Right.

So, I would say that technology has vastly improved how we run as a firm. I think that anyone who, you know, came out of the pandemic unscathed, if you will, not traumatized by the amount of working from home and schooling our children and those kinds of things, realizes that actually technology has made so much more possible for us. We had one of our best years ever, and we weren't even able to do the vast majority of in-person marketing that we had ever done in previous this year. So, to the credit of IT teams who said, you know, maybe you're not comfortable meeting with a client over a camera, but we had that introduction years ago. And so, when the pandemic rolled around, we were already prepared. Now, maybe some were more comfortable than others, but technology has also brought so many more systems, you know, to the landscape. And so, whether it's a CRM system, a portfolio trading rebalancing system, a client portal, Somebody was mentioning today how they use Teams in conjunction with a Zoom meeting. I mean, there's just, there's so much there, but as an ops person, you have to know enough to be dangerous in all of those areas so that you can help manage the people who are doing that. And I find that the subject matter is less important than being a sounding board, someone to help them weed through their emotions and the priorities. If you come to me and say, here are the 6 things that people are demanding of me, Okay, well, let's talk through why those are important, who are they important to, and what's the timeline we're working with. Regardless of subject matter, a COO can do that. A good COO can do that because it's really more about the emotional intelligence and the organizational intelligence, you know, in terms of managing people.

And having a holistic awareness of the organization, its history, the values, all of it, right?

Back to the goals, right? Yeah. Annual goals that everybody participates in. Our entire firm has a role in that, and so when you can keep that forefront to everybody's mind and ask the question, does this support the goal that we're trying to achieve, then it becomes that much more clear. But people have to— sometimes they just need someone to help them get out of their own way. There's a coaching element to the COO role.

It's amazing how many jobs seem embedded in the COO role. You wear so many hats. You're a psychologist, you're a strategist, you're this, you're that, and and it all comes together. It's got to make the job interesting, I guess, because every day you're going to lean on different skills.

100%. And I often tell people who— I never know quite how to react when people say to me, I would never want your job. And, you know, I think, but I wouldn't want any of the other jobs. You know, I enjoy coming in and maybe not knowing what the day is going to present me. It never looks the same. I am, you know, I literally can go from one meeting about technology to the next meeting about a client experience to the next meeting about, you know, our accounting and where our financials are. And so having to have that level of oversight for the organization and strategic thinking and saying, how do these all play a role together? And then how do you get those people to work together? So I do think jack of all trades is a great way to describe it. And most of the time, that's why I think that internally promoting your COO is of some greater value than bringing it from the outside. And I'm not knocking bringing in outside experience., but there has to be a level of trust in your COO at having experienced, you know, boots on the ground. I mean, for years I sat within earshot of our directors of client service. I never did their job, but I learned enough by being around them and picking up from them what the job entailed to be able to not only manage client service, but also when we We developed a distinct onboarding team exclusively for bringing in new assets, adding a financial planning team, an insurance and annuities team, an estate planning team. You know, all of that goes back to service and keeping the clients happy. So I just think that there's a real level of importance of having somebody knowing your culture and your mission regardless of where they come from.

Right. I mean, I think the argument of having a fresh set of eyes in a business Does make sense. There is a lot to be said for that, but I would say up to a point, because you can have someone parachute into a new business they don't know, and in 2 weeks think they understand it and have all the answers, and they come out guns blazing with proposals and ideas, and then if their ideas are not instituted, they think, "Oh, these fuddy-duddies aren't hip to my brilliance," and in reality, there are often some political realities. There's some— you have to understand what's a reach, what's a given, what's a no-go, and navigate all that while trying to improve. So it's that whole figuring out that tension, and with a little time, you'll know how to navigate and get stuff done. You can be far more effective than not knowing who are the power players, who are centers of influence, and whatnot.

And so education is just another component of a COO, you know, role. You're educating a new person and a new hire saying, well, how am I able to get my ideas implemented? You know, why are my decisions not going the way that I want them when we're, you know, at that ownership decision-maker level? We are thoroughly embedded with outside coaches. And so when you talk about that extant viewpoint, we think that's critical, whether it's on our sales process, just interpersonal dealings, or, you know, the formation of our leadership team. We also have a client advisory board. You can't take enough from outside influence. But when it comes to making sure everybody's rallied around doing the same thing, and that doesn't mean that everything I try to get done is supported, but you figure out how to work within the framework and with the personality types and the limits. And maybe there's a compliance reason that something can't get done. But yeah, Yeah, for sure, trust is huge in that role.

For each firm, there's a unique corporate DNA and value system, etc. So what works and doesn't work might vary, but are there more hard and fast rules of things that do and don't work, or consider common mistakes that COOs make over and over that are entirely preventable? Can you think of anything high level that you see?

I think it could go both ways. I think, as you mentioned, coming in like a bull in a china shop and trying to get your plans implemented with a very short window of experience and trust is certainly something that's not going to work for you. I'm not going to say that there are people who get to the COO level who are often of that ilk, because I think that you have to work towards the trust levels that would even get you into that category of consideration. I think it goes the other way. I think there can be opportunities where a COO type might think that they're backseat to the owner, the founder, you know, name, name sort of the leader at the organization. And I actually think that those seats are on par. I think that you are there as the COO to challenge the person who has been there for a long time and give them sanity checks and really develop a relationship where you can be brutally honest. And that's, that's what has worked with myself and our CEO. And if you don't feel that confidence, that you can challenge someone else's ideas, all within the right time, the right opportunity, right? I, you know, I have enough sense to know when I should bring something up and when I shouldn't. And I think that it's the personal dealings, it's understanding the people you're dealing with, that will get your operational objectives, you know.

And When someone begins a COO job, I mean, would you recommend that the COO and their boss basically make all this very explicit? Like, what's your hierarchy? What are the expectations? You don't want any hurt feelings.

100%. And I think that that has come from the experiences that I've had with coaching is that, you know, when you set proper expectations for any role coming in, then you have set the stage for a far better relationship. If you're trying to be nice and tiptoe around someone's feelings, and maybe you say things that You don't want to disappoint someone. I'll say that in particular, this is off course just slightly, but in hiring post-pandemic, the inevitable question is, well, how many days do I have to be in the office? I don't want anyone to be less than truthful about that. If this is a 5-day-a-week job, but it takes us 10 weeks to find the person to find, you know, that will fill that role, then fine, because the expectation was set up upfront. I don't want to go in and tell anyone, well, you could come in 1 or 2 days a week, maybe, you know, you know, we'll work it out. That is never going to work well in your favor because you've now set a different expectation for the person on the other end than you have in your head. And with the leadership, and again, this could be, we have multiple owners at Cassidy and Company, so I'm, you know, interfacing with them at all different levels. If we're not honest with each other, then we're not going to be moving towards attaining the goals that we've set and getting them what they need from the support staff.

Earlier you've You mentioned the word trust a few times. I would think that some amount of trust might be built by virtue of how long someone has been at a firm, but that's not the only input. Besides length of tenure at a firm, what other things can a CEO do that would manifest in more trust amongst the employees?

Sure. I think meeting what you say you're going to do. You know, it goes back to those setting of expectations. If I say I'm going to deliver on something at a certain time, I need to do it. That doesn't mean life doesn't get busy. It doesn't mean that you're never going to fail at that. But if you are coming in someplace new, and you don't have the tenure on your side that has helped with that trust, it's got to be everything that you say you will do, you have to do it. So lesson learned, be careful about what you commit to. Be careful about your timelines. Be realistic. Don't come in and promise the world just to make it sound good, that you're the jack of all trades who could do everything and never sleep at night. And so it's— you have multiple ways in which trust can be developed. I find that the biggest trust development is being a confidential resource, a COO. I mean, I've mentioned HR coach, educator. You're a sounding board at multiple levels, and you have to be extremely careful and cautious around the information that you are privy to. And where you're sharing it and how and what makes the most sense. And so, again, I can only speak from being in a firm that I have been at a very long time and kind of growing into that COO role. But I can imagine that coming in from a place being brand new, those, you know, promising, delivering what you promise, not overcommitting yourself, and then, you know, adhering to those sort of confidentiality pieces are three huge components that would build trust if you don't have the tenure there to stand behind that.

Let's wrap up here with an actionable idea.

One of the things that we had not touched on, but Kasaday recently went through an M&A activity, and so we developed a partnership with an outside entity. My actionable item I think is applicable for any new project that you are approaching, whether you're COO, whether you're a business manager, or whatever whatever position you hold within a firm, ask questions. Don't assume you know anything. When you think you've exhausted all the questions, ask more questions. Get your personal and professional advisors in your life to help you ask more questions. We not only acquired a very small practice at the beginning of the pandemic, but we entered a partnership, and I would venture to say we've only scratched the surface of the things that we have begun to learn about what our future is going to look like. And so never assume anything and ask questions is really my best takeaway, you know, for your listeners, because I think it's just applicable to any, any position within the firm and all of your audience.

It's been a distinct pleasure. Thank you so much for joining.

Thanks for having me.

Well, my guest has been Allison Felix, COO of Cassiday and Company. For more advisor-specific podcasts, please check out barons.com/podcast. For The Way Forward, I'm Greg Bartalis.

This podcast was brought to you by Wells Fargo Advisors. Looking for a firm your clients can't outgrow? Wells Fargo Advisors offers financial advisors full balance sheet solutions with wealth planning, investment products, banking, and lending that meet the needs of affluent to ultra-high net worth clients. Build your practice your way and on your schedule with independent and employee model options designed to meet your needs today and tomorrow. Learn more at joinwfadvisors.com.