Leading with Confidence: Real-World Lessons for AP Leaders

What does confidence really look like in a leadership role? Hint: It’s not about having all the answers, it’s about showing up with clarity, courage, and consistency, even in the face of chaos.

In this episode, seasoned AP leader Nicole Caley shares the lessons she’s learned over two decades in the trenches of finance operations—offering real talk on confident decision-making, leading during change, and helping new managers find their footing.

Whether you’re newly promoted, managing a growing team, or mentoring future leaders, this episode offers actionable takeaways you can start using right away.

If you're leading (or want to lead) in AP, AR, or finance ops, this conversation will help you step into that role with confidence and authenticity.

Nicole Caley

Nicole Caley stands at the forefront of the Operational Accounting world, bringing over 25 years of diverse and extensive experience, using her results- oriented, entrepreneurial mindset and leadership ability to drive change. As current Director Accounts Payable Shared Services with Aspen Dental Management Inc and Founder & President of Payables Solutions Partners, LLC, she not only leads a 16-person remote team that ensures the accuracy over $1.5 billion in payments annually, she also consults AP teams across the country creating world class AP departments and processes. In her roles, Nicole concentrates intensively on Organizational Leadership, staff development, training, and using technology to advance the world of operational accounting.

As a valued speaker and partner of The Institute of Finance and Management (IOFM), Nicole focuses her workshops on Leadership with sessions focusing on Emotional Intelligence, Conflict management, building and motivating high performing teams, how to make leadership a habit, and the essential soft skills of leadership. In additional to being a respected speaker in the industry, Nicole also teaches certification courses with IOFM for accounts payable, accounts receivable, procure-to-pay, and order-to-cash.

Nicole earned her BA in Accounting, with a Certificate in Forensic Accounting, and then her MBA with a concentration in Organization Development, from Benedictine University. She has served for the last 4 years as the President of the Board of the Illinois Chapter of IOFM. In 2016 she was awarded AP Director of the Year for companies over $1 billion by the Institute of Finance & Management. In 2018 Nicole was awarded Top Professional of the Year in Finance & Management by The International Association of Top Professionals (IAOTP), and in 2019 was awarded Empowered Woman of the Year by IAOTP where she was featured in Top Industry Professional Magazine. 

Grace Chlosta
Senior Content Manager, IOFM

Grace is the Senior Content Manager at the Institute of Finance & Management (IOFM), where she has led content strategy and development since 2022. In this role, she oversees all aspects of IOFM’s digital and event-based content, ensuring it remains timely, relevant, and actionable for all financial operations professionals.

Grace manages IOFM’s robust library of site content, leads the organization’s editorial and member webinar programming, and hosts IOFM’s podcast series. She also oversees a team of subject matter experts who contribute thought leadership and educational articles. In additional, Grace curates and manages all speaker content for IOFM’s in-person and virtual events, ensuring consistency and quality across every touchpoint. With nearly three years in the role, Grace brings a deep understanding of the financial operations landscape and a passion for delivering content that empowers professionals to excel in their roles.

Transcription

Grace Chlosta: Welcome to the IOFM podcast. This is a podcast for accounts payable and accounts receivable professionals who want to stay in the know with current AP and AR trends and ideas. We'll be interviewing professionals in this space on a wide variety of subjects, including automation, artificial intelligence, career growth, compliance, leadership, and much more.

Hey, Nicole. How's it going? 

00:00:33

Nicole Caley: Oh, fantastic. How are you?

Grace Chlosta: I'm doing good. So happy to have you on the podcast today. This is your first time on the podcast, isn't it?

Nicole Caley: It is. It is. I'm super happy to be here.

Grace Chlosta: That's crazy. That is wild. I mean, you're such a staple at our IOFM events. We're so happy to have you. We're on site at IOFM Spring right now. How's everything going so far?

Nicole Caley: Oh, it's been fantastic. Yesterday, I taught certification. Today, I've had a few sessions. The sessions have been jam-packed, full of super-exciting people. Just wrapped up one that was a new one for the conference, got some great feedback on that, so it's been a joy. I think everyone is having a really good time, enjoying all the content.

00:01:05

Grace Chlosta: That's amazing. I mean, I've only heard good things about the conference and your sessions, so we're super excited to have you, as always. I think most people who are up on IOFM content known who you are, but if they don't, you want to give us a little, brief overview of who you are, what you do, and your journey with IOFM a little bit?

Nicole Caley: Yeah, sure. So I'm Nicole Caley, for those that don't know. I'm currently director of AP shared services for the Aspen Group, but also have my own consulting company, Payable Solutions Partners, where I help not only organizations that are looking for help with people, processes and solutions, but also some of the vendor partners that are here. I've worked with some of them to help develop new content or new solutions and new products, and get those to market.

00:01:43

IOFM? Man, it's been a long time. We were trying to figure out how many years it's been. We know for sure it's been over 10 -- we think 11, maybe even 12 -- that I've been working with the organization. And I started, I think, with one session maybe on some leadership topic and then was asked to do APS certification.

Now, at this point, I think maybe one of the only people that can do every certification that IOFM offers, which is a lot of them. So it has been a long journey. I mean, I've even seen a lot of staff changes, right? When I first joined, Brian Cuthbert was leading this conference, and there have been changes there, and now Josh is leading the conference. Just the overall change -- transformation. It's had a transformation just in how things go and how it's set up and the staff. Even staff -- there are so many more people here now.

Grace Chlosta: So many people. I know. If you're not on site or haven't been, this is our biggest event staff-wise we've ever had. We have like 20-soomething people here, helping us. It's an amazing team, but it's really running smoothly because we have so many people, and we're in communication at all times. So, yeah, I'm sure it's crazy to see how much has changed over a decade.

00:02:54

Nicole Caley: Absolutely. I want to say there might have been three people on site in my first ever conference.

Grace Chlosta: Oh, my gosh. That wouldn't work for me. Even I would struggle with that.

Nicole Caley: Yeah, it was nuts. It was nuts, but we made it work. That's the crazy thing: it worked. Somehow, it worked.

Grace Chlosta: Yeah, and it's only gotten better. And there's still so much to do, I feel like, still so many things we're still learning. So one of the topics -- well, you and I speak on a women's panel, a Women in Leadership panel. That's going to be tomorrow morning. And I feel like one of the common questions we get asked is how to be confident in your role. Tell me a little bit about what conference in leadership looks like to you, just as a brief overview, and we'll get into a deep dive of some of the questions that I have.

Nicole Caley: Yeah. I think confidence is such a tough thing, right, because I just finished a session on imposter syndrome, and we know how women face it more than men, first, to start. And then how it can kind of present itself, right? Reality is, is that it presents itself mostly in successful, overachieving women. People look at me even and they're like, "You're so confident. You can't be suffering from this." And I'm like, "Well, jokes on you because I do and we all do."

00:04:02

Confidence is just something that I think is a constant practice. We all get knocked down, and we all have to kind of figure it out. And maybe in certain areas we excel or we feel more confident, but I think it's figuring out how to trust and believe in your own abilities, right? Knowing what you value, knowing what matters to you, and then trusting and believing in that. There have been a lot of times where I've been tested. My values have been tested and I've had to ascertain that confidence to be like, "No. You know what? This is not okay with me." And it can be tough because you can have people against you, where they don't see eye to eye, and you have to stand true in it. I just think it's kind of knowing that. It's what you value, what you believe in, staying true to that. But I think when it comes to your team, it's more of: How do you instill that in them? 

00:04:52

Grace Chlosta: Right. How do you instill that in them?

Nicole Caley: Oh, goodness. I should've known that was coming. [chuckles]

Grace Chlosta: Immediate followup.

Nicole Caley: Yeah. No, it's a fair question. I think it's empowerment. I feel like -- I've been told, at least, [that] I have this gift of seeing in people what they don't see in themselves, and I think, when you can do that, you can help bring that out of people. When you can bring things out of people that they didn't even know existed in themselves in the first place, that, in and of itself, can be a confidence boost to people.

Grace Chlosta: Yeah, absolutely.

00:05:23

Nicole Caley: But I do a lot of empowering people to build their own relationships. I know some leaders maybe decide, "I want everything to go through me," or they kind of want to be a catalyst for most things. That could not be further from who I am. I may have someone on my team, a lead analyst, who is empowered and I am an advocate for them, going straight to the source of who they need to build a relationship with, and helping advocate for them to kind of build and establish that. Those types of things build their confidence because they take full ownership of something.

00:05:59

And when they take full ownership of something and they see the success of their full ownership of something -- and maybe, again, something they didn't even know they could do, but you've put the belief in them that you believe in them, and they have confidence in you because you've shown that you're a great leader. 

Grace Chlosta: Absolutely.

Nicole Caley: They then just kind of follow suit. We've had great success with it in my organization. It's been powerful. We've promoted from within so many times because people are developing those soft skills that maybe they didn't even know they had. But trust is so huge. They have to trust you, and they have to know that you trust them. And when that falls, the whole kind of thing falls apart.

Grace Chlosta: Do you have like a turning point or a memorable moment where you first kind of had this revelation about leading with confidence, or something that had happened to you where you felt like there was a turning point in your career -- honestly, like as a leader -- and you finally felt that confidence within you? Or do you feel like it's always been something?

00:06:54

I know that you just said, "I'm not always confident. Who is?" But have you always felt like that was in you anyway? 

Nicole Caley: Yeah, fair enough. So it's funny because I think as a kid I knew I was destined to be a leader. I don't know if I knew I was going to lead people. I don't know if I knew I was going to lead politics. I don't know if I knew I was going to lead a church group or I was going to lead kids I mentor. Who knows? But I think I always knew I was going to be a leader. I remember, even being a kid, I was friends with -- let's call 'em the nerdy kids. But I was always friends with the jocks and the really popular kids.

Even in junior high school/middle school, I had this ability to bring those two groups together. And I think -- so very early on, I learned I have this skill that a lot of people didn't have. So, again, didn't know what it was going to turn into, but I think I knew I had it. 

00:07:41

For me, though, from a career perspective, I definitely had a turning point. I was a director at a fairly young age. I was in my very early 30s in my first director role, and I was the youngest person on my team of 51 people. I had 51 people. When I joined, I would hear them talking so much trash about me -- so much trash. "There's no way she can do this. She was in diapers since I've been doing this job." Some of the people on my team had even been with the company since I was in like third grade, so their tenure was almost exceeding from when I was a child. 

Yeah, yeah, so they had zero confidence in me, and I had to really rely on the fact that my CFO, who hired me, was very successful and had a really good reputation, and I had to kind of keep falling back on the fact of like, "He sees something in me." So it kind of goes back to what I was saying about me seeing something in my team and in my people, maybe what they can't see in themselves, and just realizing, like: Well, he didn't put me in this job if he didn't think I could do this job. So even if I was struggling from imposter syndrome at that moment, because I wasn't sure how I was going to do that job and I didn't know how I was going to lead 51 people. 

00:08:52

Somebody knew I was going to be able to do it. But they talked so much trash -- so much trash. 

Grace Chlosta: How did that turn around? Or did it?

Nicole Caley: It did. It did. I was hired because the year before my team had the lowest employee engagement scores in the entire company, and they ended up tanking the company from winning a Top Workplace in Chicago. The company was not okay with it. So my background is also in organization leadership, and I have a track record of turning teams around from an engagement perspective, so that's really why I was hired. That's kind of what I went to work on immediately. The team was in shambles. Nobody liked each other. Engagement was down. Morale was down. Everybody was kind of just complacent and not in a good place, and I was like, you know what? I'm not going to prove to them that I'm good at this from doing AP technical tasks. I'm going to prove to them that I am good at this by turning the morale around and getting people to understand that I may be young, but I am genuine in the way I care for people. I am genuine in the way I lead. I'm genuine in the way I communicate, and all of those things. And that's really what I did. I just started.

00:09:54

I had one-on-ones with everybody on the team, very genuine one-on-ones to learn about them as people, and then I started putting those things I learned into every single person. The next year -- or it wasn't even a full year later, I think, it was like eight months later -- we did another employee engagement score. My team had the top scores in the entire company, and I think that was my turning point. That's when I was like, "Don't tell me what I can't do," right? "I've got this." 

Grace Chlosta: Look at this.

Nicole Caley: Yeah.

Grace Chlosta: That's so -- you probably felt so good.

Nicole Caley: Oh, I did. I did. And then it wasn't even that, but then my CEO invited me to like a board dinner because there was all of these kind of awards and accolades and things. I didn't really care as much about the awards. It was such a huge transformation. I even got invited to Soldier Field in Chicago, where they did the Top Places to Work awards ceremony.

Grace Chlosta: Cool. Sweet. That's awesome.

Nicole Caley: So it was just such an accomplishment. I think at that point I was like, "Nobody will ever be able to again tell me what I'm not capable of doing."

Grace Chlosta: Yeah, absolutely. Yeah, never again. You're like, "No, thank you." I feel like emotional intelligence is really tied into leadership. Tell me a little bit about that and how you practice it as a leader.

00:11:04

Nicole Caley: Yeah. Such a big part of emotional intelligence, obviously, is self-awareness, right? We have to be so aware of who we are and how we affect and impact other people, but we have to be socially aware, right? We have to be aware with everybody on our team, and everybody receives things differently. Everybody has different needs. Everybody has different backgrounds. Everybody has different experiences. We can't just like -- I say peanut butter spread. We can't just peanut butter spread leadership. You have to take an individualized approach to everyone, and that's really been kind of my focus always is: How do I take all of those components of emotional intelligence -- obviously, like social awareness and those things and social influence -- and really figure out? Empathy is a huge part of emotional intelligence, right?

Grace Chlosta: It is.

00:11:48

Nicole Caley: Again, it goes back to everybody has their own experiences and you have to be so aware of that, even in today's day and age. I know we talked about this a little bit last conference, because I think last conference was the day after the election, right?

Grace Chlosta: It was, yeah.

Nicole Caley: And the day after the election was a sensitive day for folks and our country as a whole.

Grace Chlosta: Absolutely. Yeah.

Nicole Caley: We don't need to get into that, but no matter which side of it you were on, it was a sensitive day for people.

Grace Chlosta: A crazy day. And it's hard to be in a group of people and not really know what to say or do. Yeah, it's a scary time.

Nicole Caley: And I know we talked about the fact that I was the conference, but I did a check-in on Teams with my whole team to say, "Hey, folks. I know today is a sensitive day for folks. I just want to check in with everyone, make sure everyone is feeling okay, and let you know that if anybody needs to chat or if anybody needs some time, just let me know."

Grace Chlosta: That's awesome.

Nicole Caley: Right? Like, "I'm here. Let me know and we can step through it." Because I think what we don't do a lot of times as leaders is we don't face things head on. We pretend that something didn't happen, or that something isn't affecting and impacting people, and it is.

00:12:48

Grace Chlosta: Especially if it's uncomfortable, right?

Nicole Caley: Yeah, especially if it's uncomfortable and it's one of those topics we're not supposed to talk about at work.

Grace Chlosta: Right. It could be anything. Anything that's going on in the world, I feel like it's important. Or, in someone's personal life, I feel like, as you get to grow your team and you know people, you realize what people are going through. So just having that understanding and knowing them on a personal level really makes a big difference, yeah, absolutely. So how do you feel like -- if someone's new in their leadership role, how do you help them take on that confidence, take on the growth that they need to do in order to grow and find their own voice?

Nicole Caley: Yeah, you know, my first bit of advice -- and this just comes -- again, for those that may know me, I've got a pretty strong voice, right? And one thing that I find happens most frequently is that people try to emulate me or people try to mimic me; people try to be me. So the first bit of advice I give everyone is: "Don't be me. Don't try to be me. Be your authentic self, and whatever that looks like, it's perfect. It is perfect to be you." Because when you're trying to be someone else, it shows up as inauthentic. If there's one thing people hate, it's inauthenticity in anyone.

Grace Chlosta: Sure.

00:14:01

Nicole Caley: So that's my first bit of advice, always, is just, in order to find your own voice, it needs to be your own voice. It can't be the voice you're trying to mimic of me or of anyone else.

Grace Chlosta: Yeah and that's enough. People are going to love you because you're your own person.

Nicole Caley: Exactly, exactly. I actually had someone on my team who was -- that you would pick up on bits and pieces of times when they were trying to be like me, I'll say, right? And it wasn't working and people picked up on it, to your point, and called out on it. They were like, "Just stop. This is not you. It doesn't work well for you and it actually backfires a lot." So that's always my first bit of advice.

But then the second thing is really just to empower them and let them know that things aren't always going to be perfect, and then guide and coach as we go, right? So sometimes you have to give people feedback, constructive feedback and let them know there are going to be situations where maybe you need to pause, and that's okay. Maybe there are going to be situations where you need to know your audience and when your comments aren't meant for that audience. It's okay because you just hold them and have the proper conversation later. 

00:15:01

But also give the feedback when it's [like], "You know what? That was outstanding. The way you handled that was fantastic. You could not have done it better, and I just want to let you know that was amazing." Kind of reinforce when they're doing things that are working really well. 

Grace Chlosta: Yeah. I feel like that's so important, too, at the event. I'm here, so I'm thinking about it. We have the women's panel tomorrow morning. I ask a question similar to what I'm asking now, and we have three or four different answers, right? And so if you're in the audience, or just listening to any panel or any conversation, and you're a new leader, you can take bits and pieces of each piece of advice that folks are saying. You might related more to what you're saying or more to what Monica is saying, and maybe that resonates with you more, but I feel like that can also help shape you based on different personality points and different ways that people lead. They can all meld into being who you want to be as a leader.

00:15:50

Nicole Caley: Oh, 100%. That's the good thing about it, right, especially with having mentors, is that you can take the good things from each person that really work for you, and you can also learn from those things. I'm never going to claim to be perfect. I will be the first person to tell you, like, "Yeah, when I did that, it wasn't really great. Don't do that. Let me be the one to just save you and tell you, 'Don't do that because that's not the way to go.'"

But you bring up a great point, that leadership panel, and you do. Monica and me have very different personalities and we go about things very differently. 

Grace Chlosta: That's great, though.

Nicole Caley: It is because leadership is also situational and there may be a point in time, no matter which thing you take from it, where you do need to handle a situation more like I would, or maybe you do need to handle a situation more like Monica would, because things are very situational all the time.

00:16:36

Grace Chlosta: Yeah, totally. And I feel like even both of you and Patty and everyone else from the panel can learn from each other and learn from your answers. I see you guys up there being like, "Oh, you know what? I wouldn't have thought of it that way," and it's interesting to see even you guys, who have been doing it for so long, really still learn and grow at these events, right?

Nicole Caley: Absolutely, yeah.

Grace Chlosta: So cool. I'll leave you with one last question. I feel like I always like to leave on one point that people can take with them. So if listeners are listening this week, even if you're at the event or you were at the event (or not), what can they do this week to lead with more confidence?

00:17:07

Nicole Caley: I would say the one thing that I would encourage everyone to do is to practice self-awareness. Write a list. Write a list of the things that you know you are strong and excel in. Write a list of the things that maybe you have an area of opportunity. I hate to call it "weakness," so I'll say you have an area of opportunity. And maybe even your biases. We all have biases, right?

Grace Chlosta: Totally.

Nicole Caley: So write that list down and figure out what those things are because the best first step to being confident is being aware. You can't really kind of step into that confidence if you're not aware.

And then I would say, just because I think it's super important, is to lead by example. People are always watching what you're doing, so you've got to do it and do it by example. 

Grace Chlosta: Yeah, that's the best way people learn, I feel like, just from watching, right?

00:17:54

Nicole Caley: Absolutely.

Grace Chlosta: Amazing. Well, thank you so much, Nicole.

Nicole Caley: Yeah, it's my pleasure.

Grace Chlosta: You have a busy afternoon and busy tomorrow, so I'll leave you to it, but we really appreciate you taking the time.

Nicole Caley: Thank you so much. It's been great.

Grace Chlosta: Thank you.

00:18:05

Thank you so much for listening to the IOFM podcast. Remember to head on over to the Member Forum to discuss today's episode and provide ideas for our next one. And to stay up to date on IOFM's current events, both in-person and virtually, head on over to IOFM.com.

Continuing Education Credits available:

Receive 1 CEU per hour of listening time towards IOFM programs:

Receive 1 CEU per hour of listening time towards maintaining any AP and P2P related program through IOFM! These programs are designed to establish standards for the profession and recognize accounts payable and procure-to-pay professionals who, by possessing related work experience and passing a comprehensive exam, have met stringent requirements for mastering the financial operations body of knowledge.

Continuing Education Credits available:

Receive 1 CEU per hour of listening time towards IOFM programs:

Receive 1 CEU per hour of listening time towards maintaining any AP and P2P related program through IOFM! These programs are designed to establish standards for the profession and recognize accounts payable and procure-to-pay professionals who, by possessing related work experience and passing a comprehensive exam, have met stringent requirements for mastering the financial operations body of knowledge.