How The Best New Fractional CFOs Lead | Alex Judd

Why do you think it is that so many people have a hard time with just kind of embracing that role or that realization that I'm a leader?

Good leaders give answers to people. Great leaders extract answers from people. I feel as though leaders fail because they think competency alone wins the battle. And there is a really healthy, life giving way to exercise leadership that actually looks a lot like influence resulting in positive impact.

Alex, you've had a lot of different roles at different companies from the Dave Ramsey organization to all the way to running your own company. Now for the past three years or so, you've been exposed to a lot of some of the world's best and most well known leaders. What is a leader?

Mm, I so appreciate that question. And it's, it's also a little bit comical that you would comment on the multiple roles that I've played because you're the only person I know that has CFO in their resume and also submarine in their resume as well. So we could, we could talk about that for a while. But, but let's jump into that question of what is a leader? I heard a gentleman that's actually a mutual connection of ours say this over 10 years ago and this is where it clicked for me. I'll never forget he is a retired Navy SEAL for former NFL player. His name's Clint Bruce. He lives here in Dallas and he was speaking at a leadership development event. I was 20 something at the time. And I'll never forget, he paused and he just looked at the room and he has this commanding presence about him and he said, I want you to listen to me. And he pointed and he scanned the room and he looked everyone dead in the eyes and he said, if someone depends on you, then you are a leader. And for me, that was the moment that it clicked. Right. Leadership isn't position, it's not authority, it's not a stack of accomplishments. It's certainly not perks and privileges. Although leadership often does come associated with many of those things. Leadership is the reality that people depend on you. And what's crazy is now over the course of my career that I've dedicated to the topic of growing and learning to be a better leader. What I've learned is more, more often than not the greatest limiting lid to people's leadership ability and growth is often their inability to view themselves as one. And that's why I think it's so crucial that we start with this question that you're talking about is who's a leader? Well, if someone depends on you, then you are A leader. And so therefore I would kind of say, well, you are a leader, right? And your entire audience, like they are leaders. And it's such a powerful day when we reckon with that identity and then live into that identity.

Why do you think it is that so many people have a hard time with just kind of embracing that, that role or that realization that I'm a leader?

That's such a good question. Why, like, why do we resist that, right? Why do we push back against the title of leader? Maybe we're even not just pushing back on against other people calling us that, but maybe we're pushing back against us calling ourselves that. Why? I think there's two things, right? Number one is leadership, we know, demands responsibility. That like, we have that in our bones. We have that in our, in our mental understanding subconsciously or consciously. Like we know if I adopt the, the essence or title of leadership or the responsibility of leadership, then what I'm taking on is a lot of work. And sometimes we're shunning or trying to skirt away from the responsibility. But then I think the other piece that keeps us from identifying with that title of leader is just probably previous experience. I think we've all had bosses that carried the title of leader but didn't act like one, right? They were brash, they were bombastic, they were micromanagers, right. They were anxious, they were prideful, some combination of all of these things. And we see that from our past experience and we said, oh, that was a leader. And, and so now if I'm being expected to lead, I don't want anything to do with that, right? So I don't want to take on the title of leadership. And you know, the mission that our team is on is just basically saying that is not leadership. And there is a really healthy, life giving way to exercise leadership that actually looks a lot like influence resulting in positive impact.

When you think about a, an online business owner and as an online business owner yourself that you offer coaching to, to other business leaders, we're talking to fractional CFOs today. But by and large with, with few exceptions, the, the role that we play is, is online. And so what are the challenges and how do you overcome those challenges when it comes to being a leader in the online game?

What are the challenges associated with leading in the online game and how do.

You overcome those challenges? Any advice?

Yeah, well, I am in the game, right. And I'm actively learning as we go. Right. So I think this will be a great question for us to explore together because I'd love to know what you've learned on this topic as well. But if we're talking about leading in an online environment, the first thing that we have to remember is, is that leadership always starts with relationship. And a functional definition of leadership that I like to use is leadership is taking people from here to there. The first part of that definition is taking people. And we've got to remember that if you're going to opt into leadership, whether it's with customers or with team members or in any relationship that you're in, you're opting in for a relationship, we got to remember that people are the point. And we were talking about this at breakfast today, that remote work can often stymie or, or if we're not careful, even put resistance to the building of authentic, genuine, real relationship. And so what does that mean we've got to do? It means that we've got to accelerate intentionality in relationship building on the front end and make sure that we're really getting to care about the person and know the person and understand the person's context and get into their world on the front end, whether that's remote or in. Right. So that we can effectively take them or work with them to go to a worthwhile destination. But if we're not careful, zoom calls don't. Aren't often conducive to building relationship.

So how can we be intentional about that? So I love the theory of it. Yeah, but what's the practicality of it? How do you, how do you do that in, in a virtual environment?

Yeah, I, I appreciate the question of, like, practicality of building relationship in a virtual environment. We always teach our one on one coaches. That's our kind of specialty as a business is one on one coaching. Right. Really, really strong, intentional, deep, trusting relationships with executives over an extended period of time is what we do. And we always say there's five qualities of an effective coach. Relational, curious, assertive, directional, and principle based. The one that I would focus on is curious in response to your question or I always think to myself, good leaders give answers to people. Great leaders extract answers from people. And I'll never forget when I heard Henry Cloud say, recognize that your goal as a listener is not for you to understand. And I heard that. I was like, what? That doesn't make any sense. I always thought the whole point of listening was you're listening to understand. Right. This doesn't make any sense. But then he explained, your goal as a listener is not for you to understand. Your goal as a listener is for Them to, to understand that you understand. And so the thing that we've got to remember is that good leaders ask great questions. And the goal is not just for you to extract a bunch of information from these people. That, that's good. Right? But what's so powerful is if you can ask questions that makes the other person have a sense of assurance and confidence that, oh, they see me, oh, they get me, oh, even though they're on a zoom seven states away from me, thousands of miles, they actually know what it feels like in this office. And what I had to learn over the course of my career is that I was building narratives about people based on assumptions that were totally incorrect. And what I've learned to do as a practice to overcome that pitfall is ask so many questions, enter into every single call thinking, I have no clue. I have no clue what it's like to walk in this person's shoes. I have no clue what this person's office is like. I have no clue what their day to day stress level is like. I have no clue what their books look like.

Right.

If it's yalls. And don't assume that you know, ask questions because you might confirm your assumptions. But the biggest thing that you're going to do in that is you're going to give them the healthy assurance that, oh, I can trust this person because they've done the hard work to understand where I'm coming from.

Can you give me an example of where you saw that play out?

Yeah, for sure. I'll give you an example of a mistake of how I saw it play out. I worked with a manufacturing company one time and had spent a year working with this organization in a completely online capacity. And a lot of that year I didn't know. This at the time was built on some assumptions that I had. And because I was making assumptions about where things were today, right. We were walking on a path that was taking them in a specific direction. Right. And we had done that for about a year and it was at that time that they actually brought me in for a team training that we were going to do for their team and I was going to come in and teach their team on a topic called ownership mentality. It's a team training that we do. And I went into the business and before we did the team training, we toured the facility, got to meet the team members and everything like this. And I toured the facility. I was like, this is not at all what I've been picturing this entire time. We've been working together for A year. And then I. I met some of the people, and I was like, oh, I've heard your name said before. And I had this image of what you look like and what your personality was like based on, you know, things that I assume, and you're not like that at all. And. And I just started to realize, like, man, all these assumptions are off. And what was so cool is I actually was very honest with them. And I said, you know, it's been so helpful for me to be here in person because I've learned that some of the things that I've been assuming were correct about y' all were actually incorrect. And. And I said, I think we're going to be able to work together better on the back side of this team training. And sure enough, I basically re onboarded with them, right? I basically said, I. I'm gonna start from a blank slate and just get rid of all of my assumptions. And now that I've been here, I think I've got better visibility into the right questions to ask. And it was like I took a blank canvas and I started filling it in with right information. And we did more in the next three months than we did in the previous year. And so from that, now we train all of our coaches. You start with a blank canvas. You always start with a blank canvas. Do not fill anything in on the canvas until you hear the customer that you're working with, the team that you're working with, confirm that your assumption is correct. And it just makes you so much more effective at actually serving people.

One of the comments that you just dropped in there that I think is so important is confirm that the assumptions are correct. How do you do that? Is it as simple as just saying, hey, I don't want to assume this, but what I'm seeing is xyz. Is that correct, or is there a better way to do it?

Yeah, I. One of the things that we train is avoid yes or no questions, right? Because I'm a big believer in the idea, because I've seen this play out over the course of my career. Specific questions yield specific answers. And so if I'm looking for a yes or no answer, then ask a yes or no question. But more often than not, what I'm actually looking for is perspective. And it's crazy how much people will tell you if you just give them the time to share it with you. And so to answer your question of how do you confirm your assumptions, or how do you see if your assumptions are correct? First of all, I think one thing that I've gotten better at is get rid of the assumptions in the first place, if I can stop making assumptions. But then sometimes you don't even realize you're making them. And that would lead to the second point, which is become aware of the assumptions that you're making. First of all, like actually acknowledge these are the assumptions that I'm making, right? And this is, this is what I'm believing about this place. And then ask more, more broad questions about, about whether or not that's true. So if, if I was in the position of a fractional cfo, right, maybe one of the assumptions that I could have is this person feels really frantic and frazzled and stressed about the financial state of their company. Now I could just generally operate with that assumption and treat that person like a person that's frantic, frazzled or stressed. But if they're not actually in that mental state and emotional state, I'm basically giving them medicine at that point for a disease that they don't have. And they could actually be served by something much different than that. And so instead of just saying, hey, are you frantic? Are you frazzled? Are you stressed? That's kind of like leading the witness. If I'm in a one on one conversation with someone and I'm a fractional cfo, I would do what you do so well is I would ask an open ended question and sit back and listen. So something like, hey, can you tell me about your mental state surrounding the finances of your business? And one of the really practical takeaways that I've learned from coaching is don't be disturbed by awkward silence. There is always gold on the other side of awkward. That's what I've learned. And so ask people, tell me about the mental or emotional state of your finances right now. They're going to give you an answer really, really fast, most likely. And that's going to be their scripted answer that they tell everyone that they have coffee with, right? And, and then to that, what you want to do is you want to say, can you tell me more about that? Or can you dive a little bit deeper into that? Or can you double click on that? And now you've got them, you've got them off script, right? Because no one at coffee is asking them, tell me more about that. And they're going to struggle with an answer and you're going to feel really tempted and to give them the words to say you're going to jump in for them, you're going to lead the witness and give them an answer that they Want to give, don't do it. Let them talk. Give them space to talk. That's going to be so that's serving them really, really well because you're giving them space to actually talk about what's really going on and in that place actually recognize for themselves and garner self awareness about what's going on. But it's also going to be so helpful for you because you're getting past the initial scripted layer of what's going on in their business and that's where you can actually serv from.

Couple thoughts that, that I'd love to share on that is I think there's, there's a lot of wisdom and, and experience packed into that answer. Where I've seen that play out with, with our clients is, you know, even starting that, that question line during the sales process so you know, where is their head at? And then during onboarding and if you're not intentional about going beyond that surface level answer, what ends up happening, I would say more times than not is they give you an answer. It's a surface level answer. You take for granted that that is the real answer. And then what do we do? We start formulating our financial strategies and tactics and action items around those surface level answers. We put together a meaningful strategy that will help resolve whatever that surface level answer was. And then the client is dissatisfied. And it's like you sit back and you're like, oh my gosh, I literally put together a plan that totally addressed what they've been sharing with me. And what we realized is, well, that wasn't what I call the for real reel. That wasn't the real frustration or fear or anxiety inducer or stress inducer. And so what we've done is crafted a great plan that doesn't solve the real problem or address the real issue. And so now we have a client that's not a client any longer. And so what we've got to do to your point is we've got to get better at finding those, those different strategies and tactics to, to peel the onion back a little bit further to make sure that we're addressing the for real real. And to your point, I think that a lot of times it's ask that next question or the question after that and then just shut up and, and let there be awkward silence. Don't fill in the blanks. Don't think. I think what, what's true for me is a lot of times I start to worry that they think that I'm dumb. Like, why would you ask this? I just Told you the answer. And so I. My ego ends up wanting me to fill in the blanks because I'm worried about the narrative that they're telling themselves about me, when really it's not about me at all. And it's giving them the space to formulate an answer, to really gather their thoughts and to organize their thoughts and to come up with a way to articulate it that doesn't make them feel excessively vulnerable. And I think when we can do that, then that. That accelerates that trust process. The amount of time it takes to. To get trust and rapport and like, okay, this guy or this lady, she sees me. She sees through the. The curtain of the. The. The answer we give at coffee or at the bar on the golf course with. With our buddies.

And.

And, wow, I'm gonna have to show up different when I'm with him or when I'm with her.

Can I mention something on that now?

Of course.

It's one of the things that I really appreciate about you and your team is y' all are tactically excellent, right? No one can spend any amount of time on any of your programs online or reading any of Yalls content or even just having conversations with your team members and not leave saying, wow, they really know their stuff. They're very competent. Right? But so often I feel as though leaders fail because they think competency alone, alone wins the battle. And we write off the things that many people would probably refer to as soft skills. The thing that I would really love for people to take away from this conversation that I think in so many ways is one of the key indicators of why you and your team have been so wildly successful at serving people is soft skills create hard results. Right? And, man, I know it can be a little bit like, okay, so I'm just going to trust you that if I get good at this, it will create the results that I want. It's a little bit less measurable. But what I see over and over and over again is that when you pair unbelievable competency with a desire and a commitment to always improving and getting better at the soft skills, like greeting people and making a great first impression, like listening, like asking great questions, like learning the difference of when to be curious and when to be assertive, like how to establish direction in a conversation, like how to end a conversation well, like how to position a next conversation, these are all things that we could call soft skills that create the environment and the framework for your competency to be displayed.