In Episode 147 of “The Trusted Advisor,” RSPA CEO Jim Roddy talks leadership with Sandee Finley, Chief Payments officer at Paysafe Associates and the 2025 RSPA W2W Community Leader of the Year. Among the topics discussed are the value of leading with empathy, encouragement, and authenticity, why people connect with honesty and not perfection, and the importance of creating an environment where the leader is challenged. 

“The Trusted Advisor,” powered by the Retail Solutions Providers Association (RSPA), is an award-winning content series designed specifically for retail IT VARs and software providers. Our goal is to educate you on the topics of leadership, management, hiring, sales, and other small business best practices. For more insights, visit the RSPA blog at www.GoRSPA.org.

Watch Episode 147 now:

“The Trusted Advisor” is also available on Amazon Audible, Apple Podcasts, YouTube Podcasts, and Spotify, subscribe today!

Full episode transcript via Apple Podcasts:

00:00:06.973 –> 00:00:14.893
Roddy: Welcome to another episode of The Trusted Advisor podcast and video series, powered by the Retail Solutions Providers Association.

00:00:14.893 –> 00:00:20.453
Roddy: Our goal on the pod is to accelerate the success of today’s and for our leaders in the retail IT industry.

00:00:20.453 –> 00:00:21.853
Roddy: I’m Jim Roddy back with you again.

00:00:21.853 –> 00:00:23.613
Roddy: Thank you so much for joining us.

00:00:23.613 –> 00:00:29.533
Roddy: As always, we talk with leaders in the Retail IT channel about their leadership journeys and what they’ve learned along the way.

00:00:29.533 –> 00:00:32.233
Roddy: In this episode, we’ll talk with Sandee Finley.

00:00:32.233 –> 00:00:35.953
Roddy: She’s the Chief Payments Officer at RSPA member Paysafe Associates.

00:00:36.333 –> 00:00:44.353
Roddy: She’s also the SVP of Executive Partnerships at Trident One POS Software and the VP of Business Development at I Hate Receipts.

00:00:44.353 –> 00:00:55.993
Roddy: Prior to those roles, Sandee served as EVP at Up Payments, Senior Director of Customer and Technical Support at Merchant’s Choice Payments Solution Partners, and as a Relationship Manager at Merchant’s Choice Card Services.

00:00:55.993 –> 00:01:00.853
Roddy: Sandee’s earned and maintained her certified payments professional designation through ETA.

00:01:00.853 –> 00:01:12.433
Roddy: She’s co-chair of the Paytech Women Houston chapter and Paytech Women’s LGBTQ chapter, and she’s an active member of the RSPA VAR Business Growth and Development Community and W2W Community.

00:01:12.433 –> 00:01:21.173
Roddy: And to put a cherry on top of all those accomplishments at RetailNOW 2025, Sandee was named the RSPA Women to Women Community Leader of the Year.

00:01:21.173 –> 00:01:25.453
Roddy: Sandee, congratulations on the award and welcome to The Trusted Advisor.

00:01:25.453 –> 00:01:26.353
Finley: Thank you very much, Jim.

00:01:26.353 –> 00:01:28.433
Finley: I’m happy to be here with you today.

00:01:28.433 –> 00:01:30.533
Roddy: Always a pleasure to connect with you.

00:01:30.533 –> 00:01:33.013
Roddy: So let’s talk about your leadership journey.

00:01:33.073 –> 00:01:35.673
Roddy: I kind of mapped out all the positions you’ve held over time.

00:01:35.673 –> 00:01:42.073
Roddy: But can you talk about how did you find your way into the payments industry and into the Retail IT channel?

00:01:42.073 –> 00:01:52.973
Finley: Quite honestly, about over 20 years ago, coming straight out of college, just trying something different to gain some experience in the technology field.

00:01:52.973 –> 00:01:56.973
Finley: You know, you know somebody that knows somebody that can get you that starting position.

00:01:56.973 –> 00:01:59.053
Finley: And that’s how I kind of got into payments.

00:01:59.053 –> 00:02:01.553
Finley: I didn’t even know what payments was and what it entailed.

00:02:01.993 –> 00:02:09.853
Finley: I just knew I was starting in this call center, running, you know, doing technical support and customer support for customers, for merchants.

00:02:09.853 –> 00:02:20.153
Finley: Little did I know that I was going to be breaking down statements and batches and deposits and then, you know, troubleshooting credit card machines that don’t even exist anymore.

00:02:20.153 –> 00:02:27.373
Finley: But it quickly developed into a passion and something I was actually quite good at and I liked doing.

00:02:28.813 –> 00:02:43.773
Finley: Just quickly excelled into becoming the trainer of the department, the supervisor of the department, you know, after, you know, about seven or eight years of doing, you know, supervising that department, I wanted to move into something bigger and do more.

00:02:43.773 –> 00:03:02.133
Finley: So I got into relationship management, managing the ISOs, helping them grow, helping them grow their businesses, you know, strategic planning on different types of solutions that were available through the acquirer and comparing them to other acquirers and why we were better, obviously.

00:03:02.133 –> 00:03:06.413
Finley: A little bit after that, I decided, you know, it’s time for me to go and be that person.

00:03:06.413 –> 00:03:11.493
Finley: So I came to work for an ISO and understand the sales side of everything.

00:03:11.493 –> 00:03:23.313
Finley: And I’ve just been here ever since for about a decade now, and I’ve grown to just love everything about it, including not just payments, but now in fintech and software.

00:03:23.313 –> 00:03:46.033
Finley: And, you know, and in meeting you with you guys, what, over five years ago, Jim, at the RSPA in San Antonio, was just, you know, an eye opener for me on how I can get into the space where I started originally in technology and how we can help merchants better run their businesses, other than just a credit card machine, but give them an all-in-one sweet solution.

00:03:46.033 –> 00:03:55.853
Finley: So just years and years of teaching myself and meeting all of these other great leaders through the RSPA has just been an eye opener for me.

00:03:55.853 –> 00:04:03.233
Finley: And it’s just so overwhelming sometimes because you think you know enough to run your business and then you learn something new.

00:04:03.233 –> 00:04:06.453
Finley: And you’re just like, yeah, let’s go do this too, you know?

00:04:06.453 –> 00:04:09.073
Finley: Or let’s partner with this guy and let’s do this too.

00:04:09.713 –> 00:04:11.673
Finley: It’s just been a great journey for me.

00:04:11.973 –> 00:04:17.893
Finley: And I’m just looking forward to the next 10 years of it because I’m way too young to give up yet.

00:04:17.893 –> 00:04:19.733
Finley: I want to know more.

00:04:19.733 –> 00:04:20.773
Finley: But yeah.

00:04:20.773 –> 00:04:21.473
Roddy: No, thank you for that.

00:04:21.473 –> 00:04:23.353
Roddy: And what you mentioned, passion, right?

00:04:23.353 –> 00:04:24.953
Roddy: And you found passion in it.

00:04:24.953 –> 00:04:26.373
Roddy: What sparked the passion?

00:04:26.493 –> 00:04:30.893
Roddy: What were you particularly passionate about in the payment space?

00:04:31.973 –> 00:04:40.573
Finley: Just teaching, honestly, it was just learning new skills and then teaching, paying it forward to somebody else.

00:04:41.553 –> 00:05:00.433
Finley: Teaching the next generation how to handle the situation better or easier, whether that was additional training, one-on-one training, or mentoring, or if it was group mentoring, where we can all be open and talking to each other about certain situations.

00:05:00.433 –> 00:05:02.333
Finley: That was passion there.

00:05:02.333 –> 00:05:02.673
Roddy: Very good.

00:05:02.673 –> 00:05:10.073
Roddy: Yeah, it seems like it’s a very complicated industry, but if you could simplify it for somebody and teach them and guide them, that’s where a lot of the teaching will come in.

00:05:10.973 –> 00:05:11.393
Roddy: All right.

00:05:11.393 –> 00:05:13.693
Roddy: I want to dive into some leadership principles.

00:05:13.693 –> 00:05:18.373
Roddy: Your LinkedIn profile, it really focuses on leadership and stewardship.

00:05:18.373 –> 00:05:25.173
Roddy: One line says, Sandee uplifts those around her with empathy, encouragement, and authenticity.

00:05:25.173 –> 00:05:29.613
Roddy: I’m hoping we can dive deep into the importance of each of those traits as a leader.

00:05:29.613 –> 00:05:37.193
Roddy: If you can start with empathy, that’s having the ability to understand the feelings of others is foundational to successful leadership.

00:05:37.593 –> 00:05:45.573
Roddy: Talk about empathy and why you see that’s important for a leader and why it’s been important in your career and how you integrate that into how you lead.

00:05:45.573 –> 00:05:46.953
Finley: Sure.

00:05:46.953 –> 00:05:56.073
Finley: For me, empathy started becoming real when life handed me moments that forced me to slow down and see people differently.

00:05:56.073 –> 00:06:11.413
Finley: When you go through loss, challenges, or major shifts in your life, you learn quickly that not everyone around you is, you know, that everyone around you is actually carrying something different and something similar at the same time.

00:06:11.413 –> 00:06:14.453
Finley: That awareness completely reshaped how I lead.

00:06:14.453 –> 00:06:18.573
Finley: You know, empathy doesn’t mean lowering standards or avoiding hard decision.

00:06:18.573 –> 00:06:21.253
Finley: It means understanding the human side of work.

00:06:21.253 –> 00:06:28.093
Finley: It’s taking a minute to ask, you know, your employees or your coworkers, you know, how are you really doing?

00:06:28.093 –> 00:06:32.433
Finley: You know, it’s listening before reacting, put that way.

00:06:33.213 –> 00:06:38.013
Finley: It’s recognizing when someone needs support versus when they need a push.

00:06:38.013 –> 00:06:42.993
Finley: In my experience, empathy builds trust faster, you know, than anything else.

00:06:42.993 –> 00:06:49.213
Finley: People open up, they collaborate more, they take on risk.

00:06:49.213 –> 00:06:51.893
Finley: They feel safe enough to grow, basically.

00:06:51.893 –> 00:06:54.853
Finley: And honestly, teams led with empathy are just stronger.

00:06:54.853 –> 00:06:58.093
Finley: They handle challenges better because they know they’re not alone.

00:06:59.333 –> 00:07:10.473
Finley: You know, in my 20 plus years, I, you know, I’ve learned that when your team feels seen and valued as humans first, they’ll give you their best as professionals.

00:07:10.473 –> 00:07:16.173
Finley: So as a leader, empathy keeps you grounded, but it also keeps you connected and keeps you human.

00:07:16.173 –> 00:07:19.373
Finley: So to me, it’s not a soft skill, Jim.

00:07:19.373 –> 00:07:21.213
Finley: It’s more of a strategic advantage.

00:07:21.213 –> 00:07:25.193
Finley: And it’s one of the most powerful tools that a leader can have.

00:07:25.193 –> 00:07:28.973
Roddy: Yeah, I used to work down the hallway in a business park from a psychotherapist.

00:07:28.973 –> 00:07:31.313
Roddy: And we would joke, I don’t know anything about psychotherapy.

00:07:31.313 –> 00:07:32.853
Roddy: She didn’t know anything about business.

00:07:32.853 –> 00:07:35.833
Roddy: But then the more that we talked, we realized the crossover.

00:07:35.833 –> 00:07:42.233
Roddy: And one was if somebody was acting a certain way, my reaction was, what a jerk, like don’t want to work with that person anymore.

00:07:42.233 –> 00:07:46.333
Roddy: And hers was, I wonder what happened in their life that would cause them to behave this way.

00:07:46.333 –> 00:07:48.653
Roddy: And I’m like, sure, be empathetic, right?

00:07:48.653 –> 00:07:50.373
Roddy: Like I knew that was the right way to go.

00:07:50.373 –> 00:07:56.833
Roddy: But I’m interested, you said something about, a lot of times people think empathy just means, oh, let me give you a hug, put your head on my shoulder.

00:07:56.893 –> 00:08:00.913
Roddy: But you said, sometimes you have to support them, sometimes you have to push them.

00:08:00.913 –> 00:08:06.273
Roddy: And so the empathy is really getting to know them and where they are, and then giving them what they need.

00:08:06.273 –> 00:08:12.333
Roddy: So empathy doesn’t always have to be something that is necessarily soft, or let me relieve the pressure.

00:08:12.333 –> 00:08:15.173
Roddy: Sometimes you got to push the person outside their comfort zone.

00:08:15.173 –> 00:08:16.493
Roddy: Am I understanding that correctly?

00:08:16.493 –> 00:08:18.293
Roddy: Is that how you view empathy?

00:08:18.293 –> 00:08:18.773
Finley: I do.

00:08:18.773 –> 00:08:19.233
Finley: I do that.

00:08:19.233 –> 00:08:21.313
Finley: And I do that in my personal life too.

00:08:21.413 –> 00:08:23.933
Finley: I told you, I have a 15-year-old boy right now.

00:08:23.933 –> 00:08:31.593
Finley: And sometimes you have to push them just a little bit and show them a little bit of perspective, because they might not be seeing everything through somebody else’s eyes.

00:08:31.593 –> 00:08:41.253
Finley: So you want them to walk in somebody else’s shoes, to understand what they’re going through, so that you can know how to lead them or how to guide them.

00:08:41.253 –> 00:08:42.333
Roddy: Very well said.

00:08:42.333 –> 00:08:47.113
Roddy: The first ever Women-to-Women Community Leader of the Year was Abby Sorensen.

00:08:47.113 –> 00:08:49.413
Roddy: I actually worked with her at Business Solutions Magazine.

00:08:49.413 –> 00:08:53.153
Roddy: Her first day on the job, she put up on her bulletin board three giant letters.

00:08:53.213 –> 00:08:57.113
Roddy: They said FIO, and I was like, what is FIO?

00:08:57.253 –> 00:09:01.453
Roddy: She said her college golf coach would tell them, figure it out.

00:09:01.453 –> 00:09:03.533
Roddy: They would come to him, I need you to solve this for me.

00:09:03.533 –> 00:09:05.933
Roddy: He’d be like, sounds like you need to figure it out.

00:09:05.933 –> 00:09:08.573
Roddy: She saw that as very empowering for her.

00:09:08.573 –> 00:09:12.413
Roddy: Instead of getting the answers, there were times where you had to figure it out for yourself.

00:09:12.413 –> 00:09:14.453
Roddy: I guess you see that as part empathy as well.

00:09:14.453 –> 00:09:19.813
Roddy: It’s not always being there to give the answer to the person, it’s sometimes they have to figure it out on their own.

00:09:20.333 –> 00:09:23.213
Finley: No, because you’re not teaching, you’re just doing their job for them.

00:09:23.213 –> 00:09:32.253
Finley: You have to be able to teach them not to just give them the answers, but know how to find the answers as well and learn how to grow from that and then pay it forward to teach someone else.

00:09:32.253 –> 00:09:34.893
Finley: So if you’re not teaching, you’re doing.

00:09:34.893 –> 00:09:35.493
Roddy: Very well said.

00:09:35.493 –> 00:09:36.413
Roddy: So that was empathy.

00:09:36.413 –> 00:09:38.593
Roddy: Now we want to talk about encouragement.

00:09:38.593 –> 00:09:41.753
Roddy: And I think that’s very much an overlooked leadership action.

00:09:41.753 –> 00:09:46.953
Roddy: I know a lot of folks who I talk with and they seem like they’re gritty and they’ll fight through anything and everything.

00:09:46.953 –> 00:09:52.013
Roddy: There were times where they were thinking about giving up but somebody offered them a word of encouragement.

00:09:52.013 –> 00:09:58.513
Roddy: Can you share with our audience, what are some tactics you’ve embraced to offer sincere encouragement, right?

00:09:58.513 –> 00:10:02.493
Roddy: Not the fake, I’m sure you’re going to get this thing done like no matter what.

00:10:02.493 –> 00:10:05.733
Roddy: How have you offered sincere encouragement to others?

00:10:05.733 –> 00:10:08.413
Finley: Well, first and foremost, I completely agree with you.

00:10:08.413 –> 00:10:13.933
Finley: Encouragement is just hugely overlooked and yet, it’s one of the most powerful things that a leader can give.

00:10:13.933 –> 00:10:15.933
Finley: You have something but you can also give something.

00:10:16.433 –> 00:10:21.193
Finley: For me, sincere encouragement starts with actually paying attention to people.

00:10:21.193 –> 00:10:27.493
Finley: You can’t encourage someone if you don’t know who they are or what they’re walking through.

00:10:27.513 –> 00:10:33.373
Finley: One thing I’ve embraced is calling out specific strengths in ICM people.

00:10:33.373 –> 00:10:39.233
Finley: Not just saying great job, like you just said Jim, but saying why it was great.

00:10:39.233 –> 00:10:44.233
Finley: When someone feels seen for something real and personal, then it hits a little bit differently.

00:10:45.053 –> 00:10:49.573
Finley: I also try to encourage people in the moments they least expect it.

00:10:49.573 –> 00:10:59.053
Finley: Sometimes it’s a quiet check-in after a hard day or a quick message reminding them that their work actually matters.

00:10:59.053 –> 00:11:06.633
Finley: I’ve had leaders do that for me during my most difficult times, chapters in my life where I just felt like I can’t do this.

00:11:07.293 –> 00:11:10.773
Finley: Because they did that for me, it changed the way that I showed up for work.

00:11:10.773 –> 00:11:12.153
Finley: I try to pay that forward as well.

00:11:13.153 –> 00:11:20.733
Finley: Another tactic is creating a space for people to voice their worries or their doubts without feeling judged.

00:11:20.733 –> 00:11:28.253
Finley: When someone trusts you enough to be vulnerable, encouragement becomes more meaningful because it’s rooted in understanding and not assumptions.

00:11:29.073 –> 00:11:29.473
Roddy: Yes.

00:11:29.473 –> 00:11:30.173
Roddy: Talk about that.

00:11:30.173 –> 00:11:39.573
Roddy: How do you get somebody to be that vulnerable with you and not feel like it’s a sign of, oh, I can’t do all this stuff or I haven’t figured out, I don’t have all the answers.

00:11:39.693 –> 00:11:40.353
Roddy: How do you do that?

00:11:41.013 –> 00:11:43.433
Finley: Well, I mean, you got to be vulnerable yourself too.

00:11:43.433 –> 00:11:47.753
Finley: So you got to be able to open up about yourself too and not just let them open up.

00:11:47.753 –> 00:11:50.153
Finley: So sharing.

00:11:50.153 –> 00:11:52.673
Finley: It’s about connection.

00:11:52.673 –> 00:12:03.293
Finley: So it’s letting people know, I see you, I value you, I believe in you, let me tell you a little bit about me and my journey so that they can find a way to relate with them.

00:12:03.293 –> 00:12:04.673
Finley: They’re not alone.

00:12:04.673 –> 00:12:06.673
Finley: You’ve been through it yourself.

00:12:06.673 –> 00:12:07.633
Finley: You got through it.

00:12:08.033 –> 00:12:10.933
Finley: You got to where you were because you went through all these things.

00:12:10.933 –> 00:12:15.773
Finley: So let me encourage you to probably look at life the same way.

00:12:15.773 –> 00:12:17.053
Finley: You will get through this.

00:12:17.053 –> 00:12:19.913
Finley: I will help you get through this because I’ve been through it.

00:12:19.913 –> 00:12:24.233
Finley: You know, so that’s where encouragement for me comes into play.

00:12:24.233 –> 00:12:25.193
Roddy: And thank you for that.

00:12:25.193 –> 00:12:29.933
Roddy: And how do you this is maybe explaining a personal shortcoming of mine.

00:12:29.933 –> 00:12:37.093
Roddy: I tend to move on, solve that problem, move on to the next one, solve that problem, move on to the next one and don’t pause to say thank you or job well done.

00:12:37.093 –> 00:12:43.733
Roddy: And to the point of where I actually ordered for myself a whole bunch of thank you and job well done notes back when I worked in an office.

00:12:43.733 –> 00:12:49.133
Roddy: And then I’d open up my drawer, like I actually have some over here, I got some right here for the folks watching on YouTube, right?

00:12:49.133 –> 00:12:51.133
Roddy: It says big thanks on it.

00:12:51.133 –> 00:12:52.773
Roddy: And so I’d open up my drawer to grab a pen.

00:12:52.773 –> 00:12:55.233
Roddy: I’m like, I haven’t given out one of those notes in a while.

00:12:55.233 –> 00:12:58.113
Roddy: Like it was something, is this something that comes to you naturally?

00:12:58.113 –> 00:13:02.993
Roddy: Or is this something that you can have to hardwire to make sure you’re offering encouragement?

00:13:02.993 –> 00:13:05.533
Finley: No, I think it’s more natural for me.

00:13:06.433 –> 00:13:14.053
Finley: I grew up, you know, I’m from Texas, so we have that southern hospitality of yes, ma’am, no, ma’am, thank you, no, thank you, et cetera.

00:13:14.053 –> 00:13:18.313
Finley: I was raised to be well-mannered and always say yes, thank you.

00:13:18.313 –> 00:13:21.113
Finley: And actually say thank you with meaning, thank you with purpose.

00:13:21.113 –> 00:13:23.493
Finley: Like really, I am grateful for what you did today.

00:13:23.493 –> 00:13:27.473
Finley: I am grateful for what you’ve accomplished today.

00:13:27.473 –> 00:13:29.973
Finley: I’m here for you if you need anything else.

00:13:29.973 –> 00:13:32.573
Finley: So I think that’s a more natural thing for me.

00:13:32.573 –> 00:13:39.253
Finley: But for those that it doesn’t come natural, then what you’re doing is perfect because you have to have to say thank you right there.

00:13:39.253 –> 00:13:43.313
Finley: You know, again, my son is a little bit more literal.

00:13:43.313 –> 00:13:45.533
Finley: So he sometimes doesn’t know how to say thank you.

00:13:45.533 –> 00:13:48.753
Finley: So I have to shoot him a reminder, say, hey, say thank you.

00:13:48.753 –> 00:13:51.773
Finley: You know, say you appreciate it because don’t you appreciate it?

00:13:52.213 –> 00:13:54.173
Finley: And he’ll say, yes, I do.

00:13:54.173 –> 00:13:55.233
Finley: Vocalize it.

00:13:55.233 –> 00:13:56.513
Finley: That’s all you have to do.

00:13:56.513 –> 00:13:56.953
Finley: So yeah.

00:13:56.953 –> 00:14:00.073
Finley: So, you know, everybody does whatever works for you, Jim.

00:14:00.073 –> 00:14:06.773
Finley: If that’s what works, then just make sure you’re doing it because it does make someone’s day when you say thank you.

00:14:06.773 –> 00:14:07.193
Roddy: For sure.

00:14:07.193 –> 00:14:07.573
Roddy: And it’s funny.

00:14:07.573 –> 00:14:12.413
Roddy: So you have a 15 year old son, I have a 20 year old daughter who you’ve met at RetailNOW.

00:14:12.413 –> 00:14:13.693
Roddy: And that was a big thing growing up.

00:14:13.693 –> 00:14:14.593
Roddy: Somebody would do something.

00:14:14.593 –> 00:14:15.713
Roddy: You’re always whispering in their ear.

00:14:15.713 –> 00:14:16.633
Roddy: Did you say thank you?

00:14:16.633 –> 00:14:17.793
Roddy: Yes, I said thank you.

00:14:17.793 –> 00:14:18.333
Roddy: Right.

00:14:18.373 –> 00:14:21.553
Roddy: And you want to remind them over and over to do that again.

00:14:21.553 –> 00:14:24.393
Roddy: Hopefully our kids perform better than we do.

00:14:24.393 –> 00:14:26.373
Roddy: So that’s our purpose here, right?

00:14:26.373 –> 00:14:29.533
Finley: Is to make the next generation better than we are.

00:14:29.533 –> 00:14:30.813
Roddy: Amen.

00:14:30.813 –> 00:14:31.513
Roddy: Amen.

00:14:31.513 –> 00:14:35.993
Roddy: Now, before we take a commercial break, one more element we want to talk about is authenticity.

00:14:35.993 –> 00:14:41.113
Roddy: And so a great book on that is Authentic Leadership by Bill George.

00:14:41.113 –> 00:14:45.453
Roddy: And so in it, he writes, leadership begins and ends with authenticity.

00:14:45.453 –> 00:14:49.193
Roddy: It’s being yourself, being the person you were created to be.

00:14:49.193 –> 00:14:54.673
Roddy: So can you share with our audience your perspective on authentic leadership?

00:14:54.673 –> 00:15:00.653
Finley: Well, it really comes down to showing up as a human being, not a title, not a resume, just me.

00:15:01.733 –> 00:15:07.113
Finley: I’ve learned that people connect with honesty more than perfection.

00:15:07.113 –> 00:15:09.693
Finley: So a lot of that comes from my own experiences.

00:15:09.693 –> 00:15:21.613
Finley: In my hardest moments in my life, the leaders who’ve made the biggest impact on me were the ones who didn’t pretend to have it all together and they listened, they saw me and they met me where I was.

00:15:22.693 –> 00:15:27.913
Finley: They taught me that leadership should feel like a family.

00:15:29.373 –> 00:15:34.453
Finley: Like family talking to you, not just an employer talking to you.

00:15:34.453 –> 00:15:39.033
Finley: You want to feel like yourself and you don’t have to hide yourself.

00:15:39.033 –> 00:15:44.253
Finley: So I try to bring the same energy to every team and every conversation.

00:15:44.253 –> 00:15:50.113
Finley: I focus on empathy first, understanding what they’re carrying, what fuels them and what might be weighing them down.

00:15:50.793 –> 00:15:57.093
Finley: I don’t mind being more vulnerable myself, like I said, because I think that’s what gives the permission to be honest as well.

00:15:58.153 –> 00:16:12.013
Finley: Authentic leadership to me is staying grounded in your values and when it gets messy, be willing to say, I don’t have all the answers, but I’m here and we’ll figure it out together, right?

00:16:12.013 –> 00:16:15.693
Finley: So I mean, honestly, at the end of the day, I want people to feel supported.

00:16:15.693 –> 00:16:19.213
Finley: I want them to feel seen and inspired to grow.

00:16:19.273 –> 00:16:20.853
Finley: I can do that.

00:16:22.073 –> 00:16:26.893
Finley: Then I feel like I am leading in that way.

00:16:26.893 –> 00:16:28.633
Finley: That is true to me.

00:16:28.633 –> 00:16:30.073
Finley: I want to be myself.

00:16:30.073 –> 00:16:31.593
Finley: I want to be open about myself.

00:16:31.593 –> 00:16:35.473
Finley: I don’t want to hide myself because that’s going to inspire them to do the same.

00:16:35.473 –> 00:16:44.133
Finley: Then that becomes this great relationship, whether it’s work or life, because that trust is built, and loyalty is built.

00:16:45.993 –> 00:16:47.673
Finley: That’s authenticity to me.

00:16:47.673 –> 00:16:48.633
Finley: Just be yourself.

00:16:48.633 –> 00:16:49.613
Finley: Don’t hide.

00:16:49.613 –> 00:16:50.993
Finley: There’s no reason to.

00:16:50.993 –> 00:16:51.253
Roddy: Yeah.

00:16:51.253 –> 00:16:51.973
Roddy: Well said.

00:16:51.973 –> 00:16:57.473
Roddy: Especially like Ty, you said people connect more with honesty than they do perfection.

00:16:57.473 –> 00:17:01.133
Roddy: Can you expand upon that a little bit?

00:17:01.133 –> 00:17:05.133
Roddy: For folks who might think, no, leaders are supposed to be follow me.

00:17:05.133 –> 00:17:06.153
Roddy: I have the answers.

00:17:06.153 –> 00:17:09.893
Roddy: Talk about what it means to people connect more with honesty than perfection.

00:17:10.553 –> 00:17:11.953
Finley: Oh, I wish.

00:17:11.953 –> 00:17:15.813
Finley: No, I’ve never met anybody who’s perfect, Jim.

00:17:15.813 –> 00:17:18.113
Finley: You come pretty close, but come on.

00:17:19.973 –> 00:17:25.433
Roddy: You’re too kind and obviously, you’re not aware of a lot of other shortcomings I have, but go on.

00:17:25.433 –> 00:17:26.293
Finley: Well, no.

00:17:26.293 –> 00:17:30.413
Finley: I mean, a perfect leader, there’s no such thing as a perfect leader.

00:17:31.033 –> 00:17:37.093
Finley: If you think you’re a perfect leader, then you’re making a mistake right then and there, because you are going to make mistakes.

00:17:37.093 –> 00:17:41.613
Finley: Things are going to happen, and then when that mistake happens, then what does that say about you?

00:17:41.653 –> 00:17:45.413
Finley: You and you’re supposed to be this perfect leader that doesn’t make any mistakes.

00:17:46.593 –> 00:17:50.253
Finley: I tear myself down when I make a typo in an email.

00:17:51.033 –> 00:17:55.313
Finley: That’s just too funny for me sometimes because I don’t do typos.

00:17:55.313 –> 00:17:57.873
Finley: I use everything to try not to do a typo.

00:17:57.873 –> 00:18:00.573
Finley: But you cannot look at yourself as perfect.

00:18:00.573 –> 00:18:02.373
Finley: You cannot look at the world as perfect.

00:18:02.373 –> 00:18:04.933
Finley: You got to look at it as a lesson every single time.

00:18:05.933 –> 00:18:12.393
Finley: And room to grow and be better for the ones that you’re leading so that they can be better.

00:18:12.393 –> 00:18:12.633
Roddy: Yes.

00:18:12.633 –> 00:18:33.853
Roddy: And even if you’re leading at a high level, it’s important, I think, to remind people of here’s where I learned this lesson and going back to something, whether it’s six months a year, 10 years, 20 years ago to say, here’s when I stubbed my toe or fell flat on my face and what I learned from it so people realize it’s not just, yeah, I just have this magic dust or things of that nature.

00:18:33.853 –> 00:18:37.713
Roddy: You have to say, here’s the mistakes that I made and it could be the same situation.

00:18:37.713 –> 00:18:44.973
Roddy: I’m wondering if you feel that same way, like bringing up times where how you’ve learned from it and why you believe what you do as a leader.

00:18:44.973 –> 00:18:52.913
Finley: Well, yeah, one thing I do tell my mentees that I go, that I talk to you is don’t trip over the same stone.

00:18:53.513 –> 00:18:59.113
Finley: You saw it, you see it coming, you learn from it.

00:18:59.113 –> 00:19:08.913
Finley: Do what you gotta do to learn from it, whether that’s going to your mentors, whether that’s doing further research or just not trying to make that same mistake over again.

00:19:08.913 –> 00:19:12.633
Finley: Because if you do make the mistake, then obviously you didn’t learn the first time.

00:19:12.633 –> 00:19:15.593
Finley: And sometimes people need to learn two or three times.

00:19:16.053 –> 00:19:22.033
Finley: Don’t overestimate someone just because of who they are, because of their title.

00:19:22.033 –> 00:19:23.453
Finley: They will make the mistake over time.

00:19:23.453 –> 00:19:24.773
Finley: And that’s okay to do that.

00:19:24.893 –> 00:19:29.973
Finley: As long as you are learning from that experience and moving forward with it.

00:19:29.973 –> 00:19:31.473
Finley: And then pay it forward.

00:19:31.473 –> 00:19:32.593
Finley: Like you said, pay it forward.

00:19:32.593 –> 00:19:36.133
Finley: Teach somebody else, because you don’t want them tripping over that same stone either.

00:19:36.613 –> 00:19:37.533
Roddy: That’s right.

00:19:37.533 –> 00:19:39.793
Roddy: Sometimes they can learn the hardware and they have to.

00:19:39.793 –> 00:19:44.473
Roddy: But if sometimes you can avoid them from a calamity by giving them some guidance of what you’ve done.

00:19:44.473 –> 00:19:45.953
Roddy: So, all right, very good.

00:19:45.953 –> 00:19:50.813
Roddy: Well, let’s pause here and let our listeners and viewers know about the Retail Solutions Providers Association.

00:19:50.813 –> 00:19:57.433
Roddy: The RSPA is North America’s largest community of retail technology VARs, software providers, vendors and distributors.

00:19:57.433 –> 00:20:03.433
Roddy: To accelerate your success through an RSPA membership, email membership at gorspa.org.

00:20:03.433 –> 00:20:09.593
Roddy: Also, we want to say thanks to these companies who support the RSPA community and make this podcast and video series possible.

00:20:09.593 –> 00:20:12.613
Roddy: For 2025, our Platinum sponsor is Blue Star.

00:20:12.613 –> 00:20:17.673
Roddy: Our gold sponsors are Cocard, Epson, Heartland and ScanSource.

00:20:17.673 –> 00:20:21.873
Roddy: And then finally, we want to make sure everybody is aware registration is open for Inspire 2026.

00:20:22.453 –> 00:20:30.153
Roddy: The Retail IT channel’s premier leadership conference, RSPA Inspire is set for February 1st through 4th on the beautiful island of Kauai, Hawaii.

00:20:30.153 –> 00:20:38.293
Roddy: For more information, visit gorspa.org/inspire so you can experience networking nirvana.

00:20:38.293 –> 00:20:39.573
Roddy: All right, let’s dive in.

00:20:39.573 –> 00:20:43.133
Roddy: Thank you for talking about those core leadership traits.

00:20:43.133 –> 00:20:45.533
Roddy: Let’s talk about some of your experience as a leader.

00:20:45.533 –> 00:20:50.753
Roddy: Who are some leaders that you look up to as mentors and have helped you shape your leadership approach?

00:20:51.073 –> 00:20:52.753
Roddy: I’m curious, what did they do?

00:20:52.753 –> 00:20:56.393
Roddy: What did they say that’s really had a lasting impact on you?

00:20:56.393 –> 00:21:04.753
Finley: Well, without throwing names out there, my two employers are my biggest mentors and advocates in my personal life and in my career.

00:21:04.753 –> 00:21:17.573
Finley: They encourage me to keep learning and to keep teaching, but to also bring all of that into our environment to better our organization in whatever we have to do.

00:21:17.573 –> 00:21:22.453
Finley: Some of the things that they’ve always told me is, it’s not what you know, it’s who you know.

00:21:22.453 –> 00:21:32.873
Finley: You don’t have to know everything, but at least know someone, expand your network, know somebody that knows a little bit about it to be able to help you.

00:21:32.873 –> 00:21:41.333
Finley: As far as mentors are concerned, I have about a handful of mentors myself that I still go to, that some of them have been my mentors for about 15 years.

00:21:42.053 –> 00:21:48.873
Finley: We cross-mentor each other now, because I’ve learned certain things, this person has learned certain things, so now we’re cross-mentoring each other.

00:21:49.353 –> 00:21:53.513
Finley: It becomes more of a conversation, and it’s a trustful conversation.

00:21:53.513 –> 00:22:09.253
Finley: But I have a handful of women mentors by design, because women leaders to me are a little bit more encouraging on my side, and they encourage me to keep going, and they push me to keep going.

00:22:09.253 –> 00:22:15.413
Finley: They push me to try something new every single time that I may not feel comfortable with.

00:22:15.413 –> 00:22:22.493
Finley: They will push me to get out of my comfort zone, and, hey, let’s go bungee jumping.

00:22:22.493 –> 00:22:23.593
Finley: Okay.

00:22:23.593 –> 00:22:30.273
Finley: Whether it’s something physical, or if it’s something brand new, that I may fail at.

00:22:30.273 –> 00:22:34.873
Finley: It’s okay, because that failure, again, it’s a lesson, and I’m going to move forward with it.

00:22:34.873 –> 00:22:39.493
Finley: Again, I trip over the same stone, but at least I tried it.

00:22:39.493 –> 00:22:48.293
Finley: Quite honestly, and not to throw it back at you, Jim, but you, your tenacity alone is inspiring, and it’s why we call you an icon.

00:22:51.313 –> 00:22:52.153
Roddy: I appreciate that.

00:22:52.153 –> 00:22:54.753
Roddy: That’s a very kind of you.

00:22:54.753 –> 00:23:06.733
Roddy: From a mentoring standpoint, I’m hoping you get help because we have, RSPA is a next-gen leadership community, and oftentimes, there are folks there saying, hey, let’s put together a mentoring program and do all this matchmaking and things of that nature.

00:23:06.733 –> 00:23:11.073
Roddy: There’s another school of thought of, there’s no real formal program to it.

00:23:11.073 –> 00:23:14.613
Roddy: Just throw yourself out there and start asking people questions.

00:23:14.993 –> 00:23:18.213
Roddy: Can you talk about what is your experience from a mentoring standpoint?

00:23:18.213 –> 00:23:19.673
Roddy: Is it more formal?

00:23:19.673 –> 00:23:20.633
Roddy: Is it informal?

00:23:20.633 –> 00:23:22.033
Roddy: Has it been a mix?

00:23:22.153 –> 00:23:23.453
Roddy: I’m just curious.

00:23:23.453 –> 00:23:27.193
Roddy: Some folks are looking for a mentor, but it’s like how do you even start down that path?

00:23:27.193 –> 00:23:31.373
Finley: Well, it can be both formal and informal.

00:23:31.373 –> 00:23:39.993
Finley: What you want it to be is a relationship, a long-lasting relationship where you build that trust with your mentee or your mentor.

00:23:41.713 –> 00:23:49.353
Finley: Honestly, the way that I would start it is, like you said, matching them, personalities, because not all personalities are going to mesh.

00:23:49.353 –> 00:23:54.133
Finley: I’ve had mentees where we’ve had one conversation and we said, okay, this is not going to work.

00:23:54.133 –> 00:23:56.253
Finley: Obviously, I’m not the right person for you.

00:23:56.253 –> 00:24:00.753
Finley: But it’s okay because we can admit that and honesty.

00:24:00.753 –> 00:24:16.593
Finley: But you want to make sure that they are looking for, what they’re looking for is actually what they’re looking for to learn or to lead with, and that what you have is going to be what they actually need, because that’s the only way it’s going to be successful.

00:24:17.673 –> 00:24:26.093
Finley: If it’s something where you’re going to come to me and you want to learn about AI, I’m not that person for you, Jim, but I can refer you to somebody that can help you with that.

00:24:26.093 –> 00:24:28.833
Finley: But if you want to learn about payments, then sure, I’m that person.

00:24:28.833 –> 00:24:31.393
Finley: I will sit with you and I will guide you and I will help you.

00:24:31.393 –> 00:24:34.673
Finley: So you want to match make that relationship.

00:24:34.673 –> 00:24:46.173
Finley: If it’s a good relationship, again, it can last for decades and years and decades to come, where it becomes a personal relationship and now it’s a trusting relationship.

00:24:46.293 –> 00:24:48.893
Finley: Now you can go to that person for whatever you want.

00:24:48.893 –> 00:24:57.993
Finley: I can pick up the phone and call one of my mentors right now, she’ll pick up the phone right away or text me and say, I’ll call you back in 10 minutes because she knows I’m coming to her for something that I actually need.

00:24:59.093 –> 00:25:04.153
Finley: But at the same time, I can call her and say, hey, let’s go have lunch, let’s just go catch up on life.

00:25:04.913 –> 00:25:14.393
Finley: You want that relationship built because you want that trust in that organization that’s referring you to this mentor mentee as well.

00:25:14.393 –> 00:25:21.173
Roddy: And I think that’s a good point you make is you have different mentors for different subject matters in your career, right?

00:25:21.173 –> 00:25:28.493
Roddy: Whether it’s about leadership of the industry or payments or something of that nature, it’s gonna be super, super helpful.

00:25:28.493 –> 00:25:42.993
Roddy: And it’s funny, now that you say that, I’ve had women mentor me on working with women, where guys who have mentored me on things, what are they gonna, you know, they’re not gonna tell me a whole lot, you know, in terms of, because there’s no, you know, walking a mile in their shoes, so.

00:25:42.993 –> 00:25:46.513
Finley: Well, you know what you need, and you know what you’re struggling at.

00:25:46.513 –> 00:25:51.613
Finley: So you know what you should be looking for in a mentor, and you know how to better yourself.

00:25:51.613 –> 00:25:56.813
Finley: And once you admit that and reevaluate yourself, then you know where to go to get that answer.

00:25:57.033 –> 00:26:01.633
Finley: And if the RSPA is looking to start something like that, I’d be happy to help with it.

00:26:01.633 –> 00:26:15.153
Finley: But that’s why you answer the personality test, you answer an experience test, and you match that person with the right mentee mentor, so that they can actually grow into something better, and then pay it forward later.

00:26:15.913 –> 00:26:22.273
Roddy: And a mentor doesn’t have to be somebody who’s a boss or a peer, because I think about, I showed you the note earlier about the job well done.

00:26:22.273 –> 00:26:26.373
Roddy: I had a coworker who actually reported to me, she was the operations manager, I was a general manager.

00:26:26.793 –> 00:26:29.933
Roddy: She was so good at complimenting people.

00:26:29.933 –> 00:26:35.933
Roddy: She was tough, we would always say, iron fist, velvet glove, like everybody had deadlines, she was held people to account.

00:26:35.933 –> 00:26:39.293
Roddy: But boy, was she great at praise, and I just saw how well she did.

00:26:39.293 –> 00:26:42.493
Roddy: And I was like, how can I even be one-tenth as good as her, right?

00:26:42.493 –> 00:26:44.333
Roddy: That’d be better from where I was.

00:26:44.333 –> 00:26:49.213
Roddy: So it was like drawing inspiration from her on that and kind of emulating what she did.

00:26:49.273 –> 00:26:52.513
Roddy: So all right, well, my next question is about experiences early in your career.

00:26:52.513 –> 00:26:55.773
Roddy: Here I am going on and on about experience early in my career.

00:26:55.773 –> 00:27:04.153
Roddy: I’m curious, can you share with us a learning experience or one story that’s really stuck with you and shaped you as a leader from earlier in your career?

00:27:04.153 –> 00:27:05.933
Roddy: I’d love to hear your story.

00:27:05.933 –> 00:27:11.053
Finley: Oh, yeah, I had a role where I was managing a small team.

00:27:11.053 –> 00:27:19.033
Finley: And I thought leadership was about giving direction and just making sure your tasks were done on time and accurately as possible.

00:27:19.033 –> 00:27:26.913
Finley: But one day, I was faced with a situation with a team member where they were struggling personally and professionally.

00:27:26.913 –> 00:27:30.093
Finley: And then I realized I didn’t know how to support them.

00:27:30.093 –> 00:27:32.813
Finley: I felt unprepared, very frustrated.

00:27:32.813 –> 00:27:40.153
Finley: And honestly, I was so worried about failing them as a leader that I didn’t know where to focus the attention at.

00:27:41.753 –> 00:27:45.333
Finley: They needed me and I wasn’t available for them.

00:27:45.333 –> 00:27:49.653
Finley: So that early experience kind of shaped me profoundly.

00:27:49.653 –> 00:27:59.473
Finley: It taught me that leadership is a responsibility to help people grow and that your impact is going to be measured on how others feel and succeed under your guidance.

00:27:59.473 –> 00:28:01.873
Finley: So that lesson kind of stayed with me throughout my career.

00:28:01.873 –> 00:28:05.333
Finley: And it’s pretty much the foundation of how I lead today.

00:28:05.333 –> 00:28:06.813
Finley: How you lead with purpose.

00:28:06.813 –> 00:28:15.933
Roddy: And why did you not know that person and then what actions have you taken that you know people better now that you’re working with, if you don’t mind me asking?

00:28:15.933 –> 00:28:17.413
Finley: No, I don’t.

00:28:18.153 –> 00:28:26.693
Finley: It was a situation where a lot of her personal stuff at home was impacting the professional life here and I didn’t know how to do that.

00:28:29.953 –> 00:28:43.593
Finley: I learned by self-educating myself on how to build a relationship with your employees, how to talk to your employees, how to support your employees.

00:28:43.773 –> 00:28:57.093
Finley: You seek out through mentoring, you seek out through educational courses, through other leaders, to find the best way to support your employees, to support your team.

00:28:57.333 –> 00:29:04.793
Finley: And you stop looking at them as subordinates, and you start looking at them as people.

00:29:04.793 –> 00:29:08.633
Finley: So it does change you when you start looking at something like that.

00:29:08.633 –> 00:29:08.953
Roddy: Got it.

00:29:08.953 –> 00:29:21.573
Roddy: And it seems like if we could zoom out a little bit, like a through line of a lot of your answers are, one of my favorite sayings is, there’s no substitute for a competent person, a competent leader getting closer to a situation.

00:29:21.573 –> 00:29:26.273
Roddy: That’s really what it sounds like it’s a big guidance that you have for folks who are listening to this.

00:29:26.273 –> 00:29:35.573
Roddy: Like get closer to your people, get closer to the situation, and then only then are you going to know what the next step or the appropriate range of next steps would be.

00:29:35.573 –> 00:29:41.353
Roddy: If you’re too far away, you’re going to be wrong a much higher percent of the time, if I’m understanding correctly.

00:29:41.393 –> 00:29:41.713
Finley: Right.

00:29:41.713 –> 00:29:45.133
Finley: Your title shouldn’t matter or how high up you are in the chain.

00:29:45.293 –> 00:30:00.373
Finley: You should be able to know all your subordinates on some personal level, so that you know if they need help or when they come to you, you’re ready to have that conversation with them, no matter what the conversation should be.

00:30:00.373 –> 00:30:01.093
Roddy: Got it.

00:30:01.093 –> 00:30:04.213
Roddy: Yeah, that’s the old, you go to their supervisor, did you know their kid was sick?

00:30:04.213 –> 00:30:05.453
Roddy: They’re like, I didn’t know they had kids.

00:30:05.453 –> 00:30:06.633
Roddy: Well, that’s a problem, right?

00:30:07.153 –> 00:30:11.153
Roddy: You should be aware at least at that level.

00:30:11.153 –> 00:30:13.153
Finley: Some minor details help a little bit.

00:30:14.053 –> 00:30:15.533
Roddy: Yes, for sure.

00:30:16.573 –> 00:30:19.173
Roddy: So a couple other questions for you.

00:30:19.173 –> 00:30:24.413
Roddy: Can you talk about a mistake maybe that you made as a leader, and what you learned from it?

00:30:24.413 –> 00:30:30.413
Roddy: It can be recent, it could be a long time ago, it can be fell short, a colossal disaster, some of that nature.

00:30:30.413 –> 00:30:33.493
Roddy: I’m always curious, like we talked about earlier, admitting mistakes.

00:30:33.493 –> 00:30:37.133
Roddy: Are you willing to talk about that publicly or about maybe mistake you made?

00:30:37.133 –> 00:30:40.733
Finley: Yeah, of course, it comes back to your previous question.

00:30:41.133 –> 00:30:50.973
Finley: My biggest mistake that I will never let go for anything is, it was early in my career, was calling myself a leader because I had that role.

00:30:50.973 –> 00:30:59.673
Finley: Before I truly understood what leadership actually meant, I thought having a title or managing a team automatically made you a leader.

00:30:59.673 –> 00:31:05.073
Finley: But you quickly realize that leadership isn’t about authority or a position.

00:31:05.073 –> 00:31:11.593
Finley: I had to take a step back, like I told you, and evaluate myself and ask myself, am I showing up the way I want others to?

00:31:11.593 –> 00:31:16.973
Finley: Am I listening, guiding, supporting, or am I just managing people?

00:31:16.973 –> 00:31:20.373
Finley: The answer wasn’t always yes to these.

00:31:20.373 –> 00:31:23.713
Finley: That realization right there was humbling to me.

00:31:23.713 –> 00:31:25.093
Finley: That was my turning point.

00:31:25.193 –> 00:31:31.373
Finley: I decided, like I said, to invest in myself, learning, reflecting, growing before trying to lead others.

00:31:31.573 –> 00:31:35.653
Finley: I took a step back because I knew I wasn’t ready for it.

00:31:35.653 –> 00:31:41.513
Finley: I read books, I sought mentors, I practiced empathy, patience, and even humility.

00:31:41.513 –> 00:31:50.273
Finley: I worked on my communication, my ability to listen, and my willingness to admit that I didn’t have all the answers.

00:31:50.273 –> 00:31:59.073
Finley: I think the lesson that I learned is that you can’t truly lead others until you’ve done the work on yourself.

00:31:59.073 –> 00:32:08.633
Finley: Leadership is less about a title, like I said, and more about showing up as the best, most authentic version of yourself.

00:32:08.633 –> 00:32:12.053
Finley: That’s what inspires people to follow you as well.

00:32:12.053 –> 00:32:12.373
Roddy: Yes.

00:32:12.373 –> 00:32:13.193
Roddy: That’s what we’re reading.

00:32:13.193 –> 00:32:18.673
Roddy: The definition of a leader has nothing to do with the title is, are people following you?

00:32:18.673 –> 00:32:21.793
Roddy: You never get to anoint yourself as a leader.

00:32:21.793 –> 00:32:23.393
Roddy: It’s if people are following you, you’re a leader.

00:32:23.393 –> 00:32:24.873
Roddy: If they’re not, you’re not.

00:32:24.873 –> 00:32:26.173
Roddy: That’s really what it comes down to.

00:32:26.173 –> 00:32:28.073
Roddy: It’s for them to judge, not you.

00:32:28.073 –> 00:32:28.393
Finley: Correct.

00:32:30.293 –> 00:32:35.853
Roddy: Talk about, you mentioned the phrase, it’s not about managing people.

00:32:35.853 –> 00:32:45.693
Roddy: One of the podcasts we did earlier this year was with Bob Chapman, and so he talks about, like I even use the word management and he’s like, get rid of the word management.

00:32:45.693 –> 00:32:47.033
Roddy: We don’t manage people.

00:32:47.033 –> 00:32:48.953
Roddy: Nobody wants to be managed.

00:32:48.953 –> 00:32:50.593
Roddy: We’re leading people, we’re working with others.

00:32:50.593 –> 00:32:52.493
Roddy: I guess, is that how you view it as well?

00:32:52.493 –> 00:32:54.033
Roddy: This isn’t a management exercise.

00:32:54.033 –> 00:32:55.573
Roddy: This is working with people.

00:32:55.573 –> 00:32:58.993
Roddy: It’s leading them, helping them where they need help, and it’s them helping you where you need help.

00:32:58.993 –> 00:33:00.333
Roddy: Is that how you view this as well?

00:33:00.333 –> 00:33:02.273
Finley: I exactly how I view it as well.

00:33:02.273 –> 00:33:10.293
Finley: You don’t want to, just using the word managing people is just, it sounds like a job.

00:33:10.453 –> 00:33:13.193
Finley: And if you love what you do, it’s never work, right?

00:33:13.453 –> 00:33:16.533
Finley: You’re doing everything and you want to pay it forward.

00:33:16.533 –> 00:33:27.333
Finley: You want to teach the people that you’re managing that it’s okay to be vulnerable, that it’s okay to not know all the answers, but it’s not okay to not communicate.

00:33:27.333 –> 00:33:31.773
Finley: It’s not okay to just sit there and assume that you’re doing a great job.

00:33:31.773 –> 00:33:35.753
Finley: You want to hear it and you also want to tell your leaders they’re doing a great job too.

00:33:35.753 –> 00:33:42.033
Finley: So you kind of want to go, it has to be a back and forth conversation all the time with the people that are growing with you.

00:33:42.033 –> 00:33:42.873
Roddy: Yeah.

00:33:42.873 –> 00:33:46.913
Roddy: And this works for you and you’re in the payments industry, right?

00:33:46.913 –> 00:33:54.693
Roddy: The payments industry is very cutthroat, but it seems like you’re taking this approach that it’s not just make your numbers, hit your numbers, right?

00:33:54.693 –> 00:33:57.933
Roddy: Everything is coming down to dollars and cents.

00:33:58.773 –> 00:34:02.493
Roddy: Can you stand upon that in what is traditionally a cutthroat industry?

00:34:02.493 –> 00:34:06.853
Roddy: You can have this empathetic approach to leadership and working with people.

00:34:06.853 –> 00:34:08.593
Roddy: Can you talk about that a little bit?

00:34:08.593 –> 00:34:19.953
Finley: Well, I mean, it’s easy to get lost in the day-to-day, all the fires and the numbers, as you said, but your purpose is what keeps you centered, right?

00:34:19.953 –> 00:34:27.773
Finley: So you got to go back to that often, and it’ll keep you grounded on the hard days and grateful on the good days.

00:34:27.773 –> 00:34:43.533
Finley: So you don’t want to just be all about the end result, being the numbers and how the business, you do want to look at that obviously because that’s what’s going to help your business, but you don’t want to make that 100 percent of who you are and who your company is.

00:34:43.533 –> 00:34:52.193
Finley: You need to understand your people because your company is your people, your people are your company, and if this one succeeds, this one’s going to succeed.

00:34:52.193 –> 00:34:53.253
Finley: Does that make sense?

00:34:53.253 –> 00:34:53.973
Roddy: Yeah, very good.

00:34:53.973 –> 00:34:54.433
Roddy: Very good.

00:34:54.433 –> 00:34:55.633
Roddy: I appreciate that.

00:34:55.633 –> 00:34:56.973
Roddy: We’ve covered a lot today.

00:34:56.973 –> 00:34:59.873
Roddy: What would be your final advice for audience?

00:34:59.873 –> 00:35:02.513
Roddy: Let’s say you have a three-minute ride share.

00:35:02.513 –> 00:35:07.013
Roddy: You’re going from the conference to the hotel or conference to the airport.

00:35:07.013 –> 00:35:09.953
Roddy: You got a three-minute ride share with a small business leader.

00:35:09.953 –> 00:35:15.133
Roddy: What would be your advice for them if they said, Sandee, tell me about leadership.

00:35:15.133 –> 00:35:17.073
Roddy: What do I need to know before I hop out of this vehicle?

00:35:18.373 –> 00:35:20.393
Finley: I’d give them a lot of advice first.

00:35:22.153 –> 00:35:24.353
Finley: It’s 21 years in the industry.

00:35:24.353 –> 00:35:28.733
Finley: You learn a lot of things, so you want to bombard them with everything that you got.

00:35:28.733 –> 00:35:33.073
Finley: But the first thing I tell them is that leadership doesn’t have to be perfect to be powerful.

00:35:33.073 –> 00:35:35.013
Finley: You’re allowed to be human.

00:35:35.013 –> 00:35:37.453
Finley: In fact, your business needs you to be human.

00:35:37.453 –> 00:35:39.393
Finley: Take care of your people.

00:35:39.393 –> 00:35:41.653
Finley: See them, hear them, encourage them.

00:35:41.653 –> 00:35:46.633
Finley: Team that feels valued will move mountains for your business, especially when times get tough.

00:35:47.093 –> 00:35:50.353
Finley: And loyalty will develop from that.

00:35:50.393 –> 00:35:52.153
Finley: And give yourself grace.

00:35:52.153 –> 00:35:54.413
Finley: You’re going to make mistakes, and that’s OK.

00:35:54.413 –> 00:36:00.413
Finley: The real measure of leadership is how you learn, how you adjust, and how you show up afterwards.

00:36:00.413 –> 00:36:05.553
Finley: Lastly, surround yourself with people who challenge you, support you, and tell you the truth.

00:36:05.553 –> 00:36:08.473
Finley: No one leads well in isolation.

00:36:08.473 –> 00:36:19.133
Finley: So if you can stay true to who you are, care deeply about your people, and keep your eyes on your purpose, you’ll build something that is not only successful, but it lasts.

00:36:19.133 –> 00:36:21.753
Finley: You’ll grow right along with it as a person.

00:36:21.753 –> 00:36:23.293
Finley: That would be my advice.

00:36:23.613 –> 00:36:28.113
Roddy: So we’re stuck in traffic, so I have a follow-up question for him, taking on the role of that person.

00:36:28.113 –> 00:36:31.593
Roddy: You mentioned have people challenge you and tell you the truth.

00:36:31.593 –> 00:36:36.133
Roddy: How do you create the environment that makes it okay for people to challenge their boss?

00:36:36.133 –> 00:36:43.673
Roddy: Because I can say, before I came to the RSPA 17 years at Jamison Publishing, we were really candid with each other.

00:36:43.673 –> 00:36:51.293
Roddy: But I can say a lot of other work environments, people are like, I have no way saying that to my colleague or boss or owner, or anything of that nature.

00:36:51.293 –> 00:36:58.253
Roddy: How do you create the environment where challenging the leader is okay, and asking those questions and speaking the truth is okay?

00:36:58.253 –> 00:37:07.853
Finley: Well, I think it starts with the leader to be able to accept that criticism, to be able to accept that coming from someone who is not in a leadership position.

00:37:07.853 –> 00:37:11.393
Finley: You don’t know everything and you shouldn’t know everything.

00:37:14.533 –> 00:37:16.753
Finley: But think of perspective, you know?

00:37:16.753 –> 00:37:19.193
Finley: You probably are not seeing it the way that they’re seeing it.

00:37:19.193 –> 00:37:22.113
Finley: They probably have a different perspective than you do.

00:37:22.113 –> 00:37:26.033
Finley: And you didn’t see it that way, but somebody came in and showed it to me in a different way.

00:37:26.033 –> 00:37:26.893
Finley: And I said, you know what?

00:37:26.893 –> 00:37:28.173
Finley: That’s a great idea.

00:37:28.173 –> 00:37:31.913
Finley: You have to be able to accept that and not just turn around and say, oh, okay, sure.

00:37:31.913 –> 00:37:33.213
Finley: You don’t know what you’re talking about.

00:37:33.213 –> 00:37:36.813
Finley: You’re just here versus me here.

00:37:36.813 –> 00:37:37.893
Finley: It starts with leadership.

00:37:38.233 –> 00:37:48.373
Finley: If the leader can take on that type of conversation and encourage their employees to challenge them, then their employees will come to them and will challenge them.

00:37:48.373 –> 00:37:53.553
Finley: And maybe they don’t understand and maybe you need to teach them a little bit more.

00:37:53.553 –> 00:37:55.073
Finley: It’s just all about perspective.

00:37:55.073 –> 00:38:00.893
Finley: Start here and then build that trust so that everybody feels comfortable having that conversation with you.

00:38:00.893 –> 00:38:03.353
Finley: That’s how I can build it out here.

00:38:03.353 –> 00:38:07.993
Finley: That’s how I choose to build it out here because we want to have those candid conversations.

00:38:07.993 –> 00:38:15.273
Finley: We want to know what everyone is thinking because again, you grow, your employees grow, your business grows.

00:38:16.013 –> 00:38:21.893
Roddy: My boss, he used to try everything on for size and you’d give him some feedback and be like, oh, good one, good one.

00:38:21.893 –> 00:38:22.753
Roddy: Let me write that down.

00:38:22.753 –> 00:38:24.633
Roddy: Go on, tell me more about that.

00:38:24.633 –> 00:38:25.033
Roddy: What else?

00:38:25.033 –> 00:38:25.293
Roddy: What else?

00:38:25.293 –> 00:38:26.893
Roddy: And he would ask all sorts of questions.

00:38:26.893 –> 00:38:28.273
Roddy: Never get defensive.

00:38:28.273 –> 00:38:34.393
Roddy: Now, even if he disagreed with it, he was just trying to get more data, more data to go walk away and figure that out.

00:38:34.453 –> 00:38:35.213
Roddy: And that’s what it seemed like.

00:38:35.213 –> 00:38:39.853
Roddy: Any criticism, it doesn’t mean he would just be like, okay, I’m going to do whatever you tell me to.

00:38:39.853 –> 00:38:42.233
Roddy: But he was always trying it on for size and getting more data.

00:38:42.233 –> 00:38:45.273
Roddy: That’s kind of sounds like what you’re talking about, creating that kind of environment.

00:38:45.273 –> 00:38:51.213
Finley: It’s always worth the conversation to get a grab a new idea and say, okay, you know what, we tried that a year ago.

00:38:51.213 –> 00:38:52.413
Finley: It didn’t work.

00:38:52.413 –> 00:38:53.733
Finley: We’re not going to shut it down.

00:38:53.733 –> 00:38:55.273
Finley: Maybe it’ll work this year.

00:38:55.273 –> 00:38:57.613
Finley: So let’s try it again.

00:38:57.753 –> 00:39:00.513
Finley: And it’s not tripping over the same stone like I said before.

00:39:00.513 –> 00:39:03.713
Finley: It’s just your company was probably not at that point where it needed that.

00:39:04.113 –> 00:39:12.133
Finley: And then, you know, when you’re hiring even this newer, younger generation, they do know a little bit more than the older generation does.

00:39:12.133 –> 00:39:14.373
Finley: So it’s always worth listening.

00:39:14.373 –> 00:39:16.693
Finley: And it doesn’t hurt to listen to anyone.

00:39:16.693 –> 00:39:18.413
Finley: You know, it’s going to take a couple of minutes.

00:39:18.413 –> 00:39:20.373
Finley: Listen, hear them out.

00:39:20.373 –> 00:39:21.753
Finley: You may learn something, you may not.

00:39:21.753 –> 00:39:23.233
Finley: They may learn something, they may not.

00:39:23.233 –> 00:39:26.053
Finley: Either way, it serves a conversation.

00:39:26.053 –> 00:39:26.313
Roddy: Amen.

00:39:26.313 –> 00:39:32.253
Roddy: And again, there’s no substitute for a competent leader getting closer to their people, getting closer to the situation.

00:39:33.113 –> 00:39:33.513
Finley: Exactly.

00:39:33.513 –> 00:39:35.993
Roddy: Well, that does it for this episode of The Trusted Advisor.

00:39:35.993 –> 00:39:43.053
Roddy: If you enjoyed our discussion, be sure to subscribe to the RSPA YouTube channel and The Trusted Advisor podcast so you never miss an episode.

00:39:43.053 –> 00:39:47.253
Roddy: Before we go, big thanks again to Sandee Finley for sharing her wisdom with us today.

00:39:47.253 –> 00:39:55.093
Roddy: Thanks also to RSPA Marketing Director Chris Arnold for his production work, Joseph McDade for our music, and last but not least, thanks so much to you for listening.

00:39:55.093 –> 00:40:01.893
Roddy: Our goal at the RSPA is to accelerate the success of our members in the retail technology ecosystem by providing knowledge and connections.

00:40:02.193 –> 00:40:05.953
Roddy: For more information, please visit our website at gorspa.org.

00:40:05.953 –> 00:40:09.353
Roddy: Thanks for listening and goodbye everybody.