Leading Your AP Team Through Automation: Managing the Human Side of AI

In this episode, AP leader and consultant Nicole returns to join host Grace Berube to discuss how leaders can guide their teams through automation and AI. Nicole explains why this wave of automation feels different from earlier ones like OCR and workflow: instead of replacing discrete tasks, AI is moving into judgment, exception handling, and decision-making, which feels closer to people’s identity. She describes the quiet anxiety leaders often encounter when automation is announced, why pushback is better treated as data than defiance, and how honest, consistent communication builds trust. Nicole also shares ways to keep teams engaged, how to handle a leader’s own nerves, and four steps to take now if a rollout is coming.

WHAT YOU’LL LEARN IN THIS EPISODE

• Why today’s automation wave raises different questions than earlier ones, shifting from “what do I do all day” to “what am I here for” as AI, including agentic AI, takes on judgment and decision-making.
• What to expect when automation is announced, including the quiet anxiety that often shows up as silence, and why leaders should plan their messaging for skepticism and concern about personal security.
• How to reframe pushback as data rather than defiance, since nitpicking a new process is often anxiety about role and identity that has nowhere else to go.
• How to have honest conversations about changing roles, including saying what you know, what you don’t, and what you will find out, and why silence and ambiguity invite worst-case assumptions.
• How to keep a team engaged through change by using influencers as peer champions, delivering small, visible wins, and checking in on how people feel rather than only on training completion.
• How leaders can handle their own nerves by being open about their concerns, and by shifting the question from “will I be needed” to “what will I need to be good at going forward.”
• Four steps to take before a rollout: start the conversation early, ask your team what automation means for their roles, identify and empower a champion, and set up a recurring check-in.

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 Berube
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 Berube: Welcome to the IOFM podcast, the go-to show for accounts payable professionals who want to stay ahead of the curve. Whether it's automation, artificial intelligence, career growth, compliance, leadership, or the trends shaping the future of AP, we're bringing you the real conversations with the professionals driving this industry forward.

Hey Nicole, how's it going?

Nicole Caley: I'm fantastic, Grace. How are you?

Grace Berube: I am doing great. Great to have you back on another episode. Today, we're going to switch it up a little bit, still on a leadership topic, but talking about leading through automation. I know a lot of AP teams now and AP leaders are going through a lot of different phases of automation, and automation in general in AP has taken a lot of different forms in the past two, three, five years. So, I'd love to hear your perspectives on how you've grown in your automation journey, how other leaders can, and just get your opinions on things.

00:00:57

Nicole Caley: Yeah. No, you are absolutely correct. This is going to be a great topic to step through, especially because we really started with the earlier waves being what changed about what people did all day. So, if you think about taking data entry and making it OCR or putting in workflow, now this new wave of automation is really raising questions about not what do I do all day, but what am I here for?

Grace Berube: Right. Yeah, and I think that the biggest thing, when I think about automation now, I think about AI obviously. So, you've watched, like you said, you go in through OCR and now we're at AI. So, what's different about right now versus how it's been, again, two, three, five years? What feels different about this wave of the automation journey?

Nicole Caley: Yeah. Again, it's because before, we were touching tasks, very discrete tasks, data entry, routing, matching, and now we are talking about judgment.

00:02:01 

We're talking about exception handling. We're talking about decision-making. We're talking about things, AI. Especially when you talk agentic AI, which anybody you talk to about AI now, if they're not talking agentic AI, that's what they need to be talking about. But that's when you're really getting into what do people use their brains for and not just their hands. 

So, when you get closer to judgment and decision-making, you're now shifting to something that feels closer to people's identity and you can't just shrug that off. Because it's not just a scanner that's replacing manual entry, but it's AI making decisions that—and it just hits differently. It hits people differently.

Grace Berube: Yeah. And I think that when we started to introduce AI to AP teams and started to talk about it at conferences, or on our webinars or our podcast, something that we like to say is it's replacing the manual tasks that you're doing every day, but it's allowing you to have more decision-making ability or to be a little bit more creative with your thinking. And I think all those things remain true.

00:03:12

Nicole Caley: I would agree that they remain true, but I don't think people are necessarily at a place where they've wrapped their brain around that yet. I think the big change with automation today versus three, five years ago is that it feels different. And we can't ignore the fact that this now, it just feels different.

Grace Berube: It does. So, I think in general, AI is causing a lot of this, a little bit of emotional turbulence. So, if you're a leader and you're thinking about introducing if it's not AI even, just a new form of automation, when something like that gets announced to your team, what are you seeing with an emotional reaction from your team and how do you start to handle those emotions?

00:04:03

Nicole Caley: Yeah. No, this is a great question because I think as leaders, we want to expect that people are going to be curious and that maybe they'll feel a mild inconvenience. And reality is, that is not what happens. Typically, when you announce some sort of automation, what you're going to get is anxiety and it is not a loud anxiety. It is a very quiet anxiety, where people are in the meeting and they are not asking questions, and they are kind of just sitting in their thoughts.

And I think the gap between what we expect, which is people to be curious and people to maybe feel like this isn't going to affect me that much, and what's really happening, which is this very quiet anxiety, is something that we have to talk about, we have to plan for as leaders.

00:04:56 

We need to plan our messaging for skepticism around the tool, for that anxiety around whatever message it is that you just delivered and what that real reaction is about personal security. Because remember, I just talked about the biggest change we have right now is that we went from tasks to now, the what it could do to what am I actually here for? Because this feels like it is closer to my identity. 

Grace Berube: Yeah. That was going to be my next point, my next question. I think that a lot of directors or leaders could see pushback or interpret that anxiety as resistance to change. But what's going on for someone? I think it's that they're afraid that they're going to be pushed out of their current role based on the new automation AI that might be coming in.

00:05:51 

Nicole Caley: Yeah, absolutely. I think in my career and in my experience, pushback is rarely about the tool itself. It's usually a proxy for the real unspoken question that people are feeling, which is if this task is automated, what am I for or what am I going to do? And oftentimes, what people end up doing is they end up nitpicking the new process when really, that nitpicking is the anxiety with nowhere else to go. Oftentimes we displace things, we displace our feelings and emotions. So, people push on the process details because they don't know how to ask that identity question specifically.

So, as a director and as a leader, you've got to figure out how to reframe that. So, I often reframe that and I'm like okay, pushback is the data, it's not defiance. So, what is it telling me about where the fear is actually living and what do I really need to listen for? And then, how do I need to have those conversations about what it really is versus maybe what it's presenting as?

00:07:00  

Because again, rarely is it about the tool itself. It's more about the uncertainty that is existing in the person or the people that may be pushing back the hardest about what their future really looks like.

Grace Berube: Yeah. And I think that sometimes, someone who's been in a role for a long time, things have stayed the same. When these tools come in, it does change what their role looks like or what their daily duties are. So, I'm sure you've probably had to have conversations with a team member about their role changing or—I don't want to say shrinking but kind of, less than what they had previously been doing, but making room for something else. But what did you learn from those sorts of conversations or what can a leader do to have those tough conversations with someone who, again, just has a lot of anxiety, but that anxiety might be warranted in a sense?

00:07:50

Nicole Caley: Yeah, I think here, it's just very important to have an honest conversation. To have the honest conversation because if you give generic answers, people are going to see right through that. So, you need to be able to have very honest conversations about what it is, and understand that people are going to forgive hard news that you deliver honestly more than they are going to forgive false things or false reassurances that you try to give them that turn out to be wrong later because now you've lost their trust. And trust is such a key component any time you're going through a change. It doesn't even have to be an automation change. It can be any change in your organization. Trust is going to be critical. So, I think you just need to have honest conversations.

You also have to be willing to say what you know, and maybe what you don't know, and what you'll find out. But if it's something that you're going to find out, you also have to make sure you follow back up because that's part of closing that trust circle.

00:08:58

Grace Berube: Yeah. And I was going to say, is there any sense of overcommunication at all? So, if decisions aren't necessarily finished being made or the tool isn't finalized, is there ever a situation where overcommunication might cause more disruption than necessary?

Nicole Caley: Yeah, perhaps, for sure. But I want to say this first before I fully answer your question. We always have to remember, silence will get filled with worst-case assumptions. So, when you say nothing, you are setting yourself up for people to fill in that gap with the absolute worst-case assumption. Ambiguity is also worse than incomplete information every single time.

So yes, we can absolutely overcommunicate. You don't want to overcommunicate maybe what's being discussed, when decisions will land, things that have undecided outcomes. There are certain things that don't need to be shared.

00:09:56

But you always have to make sure that you are sharing things that allow for, again, that trust circle to be closed, your team to feel confident in what you're providing, but making sure that you're not leaving gap for false assumptions and even really scary assumptions because our brains always go to the worst. That's just something that as humans we do. We always go to the worst assumption. And we need to make sure that we are walking this line between not being worried about saying too much, but also feeling like we're not having our team in a position where they're going to feel like they're the last to know something.

So, what is the balance? And as a leader, it's going to be tough and it's also going to be situational. So, every single thing that you go through, whether it's automation again or each project that you're working on may have a different level of that. So, there's nothing wrong with saying, here's what I know today. Here are the things that we still need to make decisions on. And if they start asking questions that you don't have an answer on, it's okay to say, you know what? We've got about three options in that. Here are the three options.

00:11:02 

At this point, I don't have a we're leaning towards one more than the other. If you have concerns with each of the options, I'm more than happy to hear them, so we can bring those back to the conversation. 

Grace Berube: Yeah, and I think that limiting ambiguity and just being honest, I think all of what you just said goes for more than just an automation journey too. I think that's great advice for any decision or any communication that a leader or director has to make in big conversations with their teams.

Nicole Caley: Oh, absolutely.

Grace Berube: So, honest conversations, making sure that people know the full picture, feel like they're a part of the process from the beginning. So, if you've made that decision and you're going through with it, how do you keep a team engaged and motivated through an automation journey? Because I'm sure you've been through a few in your time. So, what does that look like? I'm sure that there's different team members who have different feelings about things. Maybe there's a squeaky wheel who's complaining a lot. How do you keep people engaged and motivated, and your team ready to take on a journey like this?

00:12:03

Nicole Caley: Yeah, this is a really loaded question. And I know I refer to DISC personality profiling a lot, but here is where that can also help you a ton or hurt you a ton, if you don't understand the different personalities on your team. So, if you know DISC, you have your I personality styles, which is your influencers. We love to use influencers to our advantage when we are going through a massive change. If you can get your influencers on board, they will help you with the peer-to-peer motivation on the team.

But what's most important is small wins. So, small wins rather than big promises. So, you've got to show early proof that whatever it is you're doing is working. And not only is it working, but it's freeing people for better work, or work they're more interested in, or work that's more analytical, or work that makes them feel like they're adding more value to the organization.

00:13:00 

Don't just say it. It goes back to the trust thing. You have to do what you say you're going to do or prove that the tool does what you said it was going to do, and figure out how to make that very, very visible. I also think that it's really more about noticing people than it is giving these big speeches. So, checking in on how someone's actually doing. 

So, you talked about maybe a couple of people are really struggling. So, checking in with how someone's doing with the change. Not just whether they've completed the training on what you asked them to do or whether they're stepping through the motions on what you've asked them to do, but how are they really feeling? And this is, again, where those peers can really help you. So, if you've got someone that's really motivated also with you and they happen to be a peer to the team members, they can be highly influential even in spaces that you can't be.

00:13:54

Grace Berube: Yeah, I think that's really great advice, taking the hard, honest conversations, checking in with people, and giving praise and maybe a little bit more responsibility to the people that feel positive about it, and letting them be a peer leader among their group, I think is great.

We talk a lot about teams and team building through a change, but I feel like sometimes a leader would have maybe a little bit of their own nerves about a journey like this, too, and having to feel confident in front of your team to make them feel confident. But how do you handle your own personal hesitations with a new journey? How do you handle your own emotions through something like this?

Nicole Caley: You know, I think part of it is just communicating, too, because I've always been a firm believer that there is nothing wrong with showing your vulnerability to your team. Why not let your team know that you also have valid worries? Why not share that with your team, that they're not alone in this and that you guys sit in the same space when it comes to this.

00:15:00 

We are in this together. And guys, you have these feelings and anxieties, I have these feelings and anxieties. I don't think as leaders we should pretend to be immune to the fear. I think all that does is undercuts your credibility with anybody else that's possibly feeling it. 

Grace Berube: Yeah. And all that's going to do is, I feel like, make your team be more honest with you because they can see that you're being honest with them, right?

Nicole Caley: Absolutely. And I also think for myself especially, I've always tried to reframe it from—not to ask, will I be needed? And I even encourage my team to do this, to what will I need to be good at going forward? So, not will I be needed, but what do I need to be good at going forward?

I think it's also why a lot of my teams tend to be ahead of the curve because I'm always looking at what do we need to be good at going forward. And we tend to get ahead of things maybe a little bit before other companies.

00:15:56  

And also making sure that we are focused on skills like judgment, or people leadership, or exception handling, and the things that maybe aren't going to end up getting replaced as quickly or shifted over. I shouldn't say replaced, but shifted over to some sort of automation.

Grace Berube: Yeah. No, absolutely. I’d like to talk about action items, too, as folks have been listening and getting their tips. If a director or a leader is listening today and they know that an automation rollout is coming in the next three, four months, what should they be doing right now to start preparing their team for a change like that? Or even if they're just thinking about it, what are some action items that people can take away from this episode, if they're currently going through a journey or really anything like that?

Nicole Caley: Yeah. No, absolutely. I think that's a fantastic question. My first bit of advice would be to start the conversation now, before the tool arrives, maybe even before you know exactly what the tool is going to be. Start the conversation now. You want to mention the automation, the possibility now, because the first mention of it should never be the announcement of a rollout.

00:17:04 

You don't want your team to be surprised or taken back by the announcement of a rollout. So, I would say start the conversation today, even if it's just what you're thinking about possibly having as a project in the future. 

I would also talk to your team and open the floor because this is where, again, you've got to start to create trust early. And even though you may have trust, you need to also have trust in this change. And ask them what do they think automation means for their role before you have to correct or reassure them. You need to understand the real fear points that your team has and not your assumptions about them. You may make a whole list of what you think your team is going to be afraid of, or fearful of, or have anxiety of, and all the things, and it may not be accurate at all. So, start that conversation also. What does it mean to you? What do you think it means and what maybe are you worried about?

00:18:03

I would also figure out who on your team will probably be a champion. So, who on the team is likely to adapt the fastest and figure that out? Also, what is their personality style, and then make them a champion of it because peer credibility, again, I was just talking about that. Peer credibility is going to do so much more for you that you are not going to do in just announcements and team meetings.

The last thing I would say is just to have a simple recurring check-in, whether that's now until you get to the point of maybe actually launching or announcing. And then, not obviously from just now until then, but through the entire thing. You want to make sure that concerns have somewhere to go before they turn into disengagement. And I think the earlier you start, the better off you will be.

00:18:55

Grace Berube: That's such great advice. I feel like even just those four points sum up everything that we've been talking about. I feel like in general, you are such a leader that leads with authenticity and honesty. And in general, that creates such a bigger sense of ease within your team, and that's very obvious. So that's, I feel like, a great takeaway for me, too, just listening.

Nicole Caley: Oh. Well, thanks so much, Grace. I would hope my team would agree.

Grace Berube: I’m sure they would.

Nicole Caley: We have a really, really great job. So, my team is fantastic. I mean, they are. I know I boast about them all the time, any chance I get. But they are fantastic and they make me who I am. So, I couldn't be more proud of them.

Grace Berube: Well, thank you so much, Nicole. Always so great to have you on the podcast. And I'm sure we'll be chatting with you again soon.

Nicole Caley: Yeah, it was my pleasure, Grace. Thank you so much.

[music playing]

Grace Berube: That's a wrap for this episode of the IOFM podcast. Thank you so much for tuning in. If you enjoyed today's conversation, do us a favor and subscribe, or follow the show so you never miss an episode. And to stay up to date on everything happening in our world, including upcoming events, 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.