Why Jennifer Fields Creates Conflict on Purpose

Grace at work gets read as weakness, and Jennifer Fields makes the opposite case: extending it takes more courage than bringing the hammer down, and it serves the bottom line. Jennifer Fields is Chief Delivery Officer at Acklen Avenue, where she leads an international team. She started as a software developer after a computer science advisor, Barbara Doyle, talked her out of pre-med and into one class. She talks with Ashley Russo about building trust so people tell you the truth, rewarding dissent, and why the investment you make in people is the only thing that lasts.

Chapters:

00:00 Welcome to Ask Ashley

00:43 Meeting Jennifer Fields

01:21 From pre-med to software

04:07 Being the only woman in the room

06:15 Changing the dress code at 21

07:37 Building culture with trust and empathy

09:46 Bias, triggers and pushing past them

10:35 Rewarding dissent and divergent views

12:46 Creating conflict on purpose

15:12 Community without segmentation

20:17 Why grace serves the bottom line

22:15 Retention and people who come back

24:24 How Jennifer fills her own cup

26:53 Advice to her younger self

28:38 Valuing people over the profit they bring

You can follow Jennifer Fields here:

LinkedIn - https://linkedin.com/in/jennifer-fields-0b40aa4

Learn more about Acklen Avenue:

Website - https://acklenavenue.com

What is Ask Ashley?

In Ask Ashley, Founder, Thoughtleader and award-winning media personality Ashley Russo sits down with leaders who bring purpose and humanity to business.

Each episode explores how people navigate uncertainty, lead with empathy, and create meaningful change in their organizations and lives. Listeners gain practical insights on resilience, leadership, and financially confident decision-making amid disruption.

This podcast is brought to you by Ask Ashley. If you’re interested in building a confident, purpose-driven wealth plan, reach out to Ashley at [e-mail].

00:00:01:19 - 00:00:30:00
Ashley
Welcome to Ask Ashley, the podcast, where we shine a light on the unsung heroes of the workplace. I'm your host, Ashley Russo, financial AI board member, thought leader and wealth management advisor. Each week we sit down with inspiring leaders, exploring their journeys, motivations, and the real challenges they face, from job insecurity to the evolving role of AI in a world where many feel overlooked.

00:00:30:01 - 00:00:43:06
Ashley
These guests are building hope and connection for their colleagues. Join us as we uncover their stories and discover how they're making a difference, one conversation at a time.

00:00:43:08 - 00:01:02:11
Ashley
Hello everyone, this is Ashley Russo here. I am so excited for today. I have Jennifer with us who just has such an incredible perspective, energy, outlook, a ton of amazing experience. Jennifer, will you share a little overview about yourself before we dive in?

00:01:02:11 - 00:01:19:12
Jennifer
Certainly. So I am, as she said, Jennifer Fields. I am the chief technology and Delivery Officer at Acklen Avenue, got my start in technology as a software developer and then quickly moved into leadership and found my passion in leading and developing people.

00:01:19:12 - 00:01:21:05
Jennifer
And now I get to do that every day.

00:01:21:06 - 00:01:36:06
Ashley
Loving. Love it. Can you walk us through the early years of your career? So everything from how your upbringing in values guide your decision. What drew you to software? Give us an overview there.

00:01:36:06 - 00:01:41:14
Jennifer
So I come from a very large family. My immediate family is small. It's just me and my sister.

00:01:41:14 - 00:02:09:01
Jennifer
I have an older sister and my parents, but both of my parents came from very large families, and so I grew up in a crowd of deeply loved, very faithful family and just really was taught very early on that the value system is God, family, community and then the self. And so that's sort of informed everything and has directed my life entirely.

00:02:09:01 - 00:02:33:00
Jennifer
I think I ended up in software simply because I was originally pre-med. I wanted to be a coroner. I watched a little too much Quincy, MD with my grandfather. I loved solving the puzzle of of the human body and cause of death, the investigative side of that. And so I was headed down that path until I was very naive.

00:02:33:01 - 00:03:04:23
Jennifer
I remember when the the advisor told me I would have to do clinicals and treat real patients, and I was like, I'm out. I do not have any interest in keeping people alive, especially people that are, you know, not happy with their circumstances. And so my advisor happened to be because they were all out of premed advisors when I got assigned mine, one of the first women to get a doctorate in computer science, I'm so old.

00:03:04:23 - 00:03:26:06
Jennifer
It was a new field. And so she said, what about it? Do you like what made you want to go into this? And I said, the problem solving, the investigation, the the challenge of the complexity. And she said, have you ever thought about trying computer science? Because that's what we do and we need women. Her name was Barbara Doyle.

00:03:26:08 - 00:03:45:18
Jennifer
I'll never forget it. I'll never. I am so thankful that she was put in my path and a part of my journey. And she talked me into taking one computer class that semester. And after that I was hooked. So that's how I ended up into software. No one in my family, my. I have come from a, you know, I am a coal miner's daughter.

00:03:45:18 - 00:04:07:11
Jennifer
My dad ran a warehouse that supported coal mines. My mom was, you know, a community leader and and servant in that way. And so I computers were not even in my purview at that point, but that's how I ended up in the field 100%. Now.

00:04:07:13 - 00:04:32:00
Ashley
I did, based off of who introduced you, the timing of everything. I'd imagine you were, if not the only woman, maybe close to the only woman at that point and that type of role. I'm curious, what challenges did you face? How did those experiences influence how you approach leadership?

00:04:32:02 - 00:05:01:14
Jennifer
Yes, even in school, I was often the only girl in the class in the computer science classes. And so, you know, for me, I quickly I was I so enjoyed the classes and the experience and I, I just, I think had to learn and adapt to be able to be taken seriously and to sort of get past them, seeing me as a girl.

00:05:01:14 - 00:05:25:00
Jennifer
And that started in those classes when we had to work on group projects. And, and I, I don't I don't really know why. I never felt that I needed to be assertive or I guess I didn't. I didn't consciously think I'm the only girl I have to do something. I think I just naturally navigated that. And I had so many male cousins.

00:05:25:01 - 00:05:43:03
Jennifer
I grew up in such a crowd of boys that were my age that I. I was pretty rough and tumble in school, you know, I was not afraid to get in a fight. And my mom says I was the bully of bullies, so I was I didn't I wasn't intimidated, I guess is my point. And so that really served me well.

00:05:43:04 - 00:06:15:16
Jennifer
Having had all that experience, when I went into the workforce again, I was it was many years before I worked with female developers and I did hit some. It was sometimes it was challenging. There was sometimes I felt a double standard and I, I just faced it head on. I remember I went to this company that was very traditional company and they had a dress code and at 21 years old, day two, I went into HR and said, can you help me understand why women have a heel requirement and men don't?

00:06:15:17 - 00:06:36:04
Jennifer
And so it took me about 90 days in. The dress code was changed. So I was I don't know, I look back on that and think, I think because I was so naive and young, I didn't even think about how going to HR and voicing that opinion might impact my career. You know what I mean? I didn't give that any.

00:06:36:05 - 00:07:03:23
Jennifer
I just I was just like a bulldog, just a and it caused a lot of issues as well because, you know, I had to learn over time when to, when to take that approach and when to take a softer approach. But back then I really did. I feel like in some cases, that lack of experience and awareness of how that might be perceived was a good thing, because it I was fearless because I didn't know what I didn't know.

00:07:04:00 - 00:07:04:10
Ashley
Yeah.

00:07:04:11 - 00:07:08:21
Jennifer
Yeah, I knew I wasn't wearing three inch heels to work. I knew that.

00:07:08:23 - 00:07:11:06
Ashley
Thank you on behalf. I'm on the list.

00:07:11:07 - 00:07:26:06
Jennifer
Thank you. Yeah. It was. I remember three pieces you had to have three pieces on. You had to wear pantyhose. If you were wearing a skirt, you had to wear pantyhose. And you had to have a it was a two inch heel minimum. Yes. It was that specific.

00:07:26:08 - 00:07:37:05
Ashley
So ladies, now sitting here potentially in our virtual environments wearing sweats. Thank you. Jennifer. Yes you're welcome advocate.

00:07:37:07 - 00:07:49:10
Ashley
I'm curious at current company how do you approach building culture in alignment, particularly with with an international team as I believe you have?

00:07:49:16 - 00:08:22:19
Jennifer
You know, I think culture is built with trust and with empathy and caring. I think for without that you don't really have a culture, not a good one anyway. And so I think that whether it's international, whether it's shoulder to shoulder, you have to truly lead with kindness and with care and empathy and, and a real desire to serve the person you're leading and want to help them be successful.

00:08:22:21 - 00:08:54:00
Jennifer
I think when teams feel that about their leadership, the culture is a piece of cake. And then they will they will model, they'll take what you give them and that becomes the norm. So then you see them giving empathy and caring about each other and accepting of one another and valuing. Right. And so I that's how I've approached it is I, it seems so simple, but it's not always easy to have empathy for people who are annoying you.

00:08:54:00 - 00:09:17:12
Jennifer
Or there's biases that we have, whether we want to admit it or not, about personalities or even I don't know if you've done this, but I've had people with names. There's names that can trigger you because you had that horrible person that was named that certain name. There's things like that, that, that precede and you into these relationships.

00:09:17:12 - 00:09:38:21
Jennifer
And so you have to really be aware and be willing to push past that and really care deeply about about the person, the success of the person and, and try to, to get to know them in order for to me, in order for a culture to be built, at least one that I would want to work in.

00:09:38:22 - 00:09:46:01
Ashley
What an interesting call. I never thought that in terms of names. Literally, when you said that the name Coptic Brain. Yes.

00:09:46:02 - 00:10:10:23
Jennifer
And we forget that. And it's not I don't think biases, everybody thinks biases are all negative. I think that they're just a part of who we are. I think that's we were built to have those in order to survive, and it's how we let them impact us that matters. I think, triggers fear. Any of those things, they're in our DNA for a reason.

00:10:11:00 - 00:10:22:16
Jennifer
You know, we don't step in front of trains. We don't walk off a cliff. But when it, you know, so it's not a bad thing. There's not a bad thing unless you let it control you in ways that it shouldn't.

00:10:22:21 - 00:10:35:17
Ashley
Speaking of choice and environments. How do you go about fostering that genuine connection and care then across people who may not always agree?

00:10:35:22 - 00:11:22:22
Jennifer
Yeah, I think again, the leader sets the tone for me. I don't want people to agree. I want people to come. And the more divergent opinions and solutions we have, the better one we're going to end up with. And so when you actually reward and welcome dissent and challenge, and you do it authentically when you can take it, then you get such a better rich environment and people don't feel like to care about each other deeply and, and cheer for each other and support each other does not mean you have to be the same and have all the same ideas and beliefs, right?

00:11:22:23 - 00:11:44:18
Jennifer
That allows people who believe very different things to still be connected in a very deep way and care about one another. We are so missing that today in this world, you know, and I it does take work because naturally we are we naturally lend to go towards people that are like us, right, that are comfortable. And, and there's a place for that.

00:11:44:18 - 00:12:11:00
Jennifer
There are times that I seek out people that are just going to let me wallow a little bit, like, I don't I don't need any more challenges. I'm tired. I just want to I just want to be wallowed with, you know? But for the most part, I think and seek out people that will challenge me. And I make sure that I reward people when they do that instead of reacting negatively to it, because it's best for me and it's best for them.

00:12:11:00 - 00:12:28:05
Jennifer
It's best for the company. And when did we start thinking that the only people that were worthy of our time and care and support were people that believed exactly like we did, you know, how did we get that far off the rails.

00:12:28:09 - 00:12:46:20
Ashley
You know, gosh, if, as you said, imagine if the world's the work like this, right? What case would we be in? I am curious, how do you encourage this type of healthy debate while keeping the organization moving forward?

00:12:46:22 - 00:13:17:00
Jennifer
Yeah, so I've got a little I tell people, my teams, when I joined this company, I, I told them because I was working with, you know, a Latin American culture and they're extremely kind. And it's such a rich culture. I love working with them. And I told them in the absence of conflict, I'm going to create it because through conflict and through disagreement come the greatest ideas and growth.

00:13:17:04 - 00:13:43:17
Jennifer
And so you can either bring it or I'm going to, but we're going to get real comfortable with disagreeing with one another in a real great way. And so then I did some of the little activities like ritual descent where the the script is switched, where you are encouraged to say why an idea would never work. So everybody is, instead of it being seen as a negative.

00:13:43:18 - 00:14:19:04
Jennifer
Right now, dissenting views are seen as a positive, and they're welcomed and they're encouraged and it becomes fun. And so once people realize that, you know what? Nobody died. Nobody got angry. Like my idea wasn't shot down or ridiculed or, you know, I wasn't the hammer wasn't brought down. When they feel safe, when they when they can trust your reaction, then they bring it.

00:14:19:06 - 00:14:45:05
Jennifer
And that's that's the key. People don't tell you the truth unless they can trust your reaction to the truth. And so for leaders, in order to have that and invite that in and make that part of a normal part of your culture, you have to be able to handle the truth in a way that people will continue to bring it to you.

00:14:45:05 - 00:15:12:15
Ashley
I love this on so many levels. It's one truly creating an environment, a trust. It's also creating environment of a bunch of yes people who aren't actually sharing your authentic, genuine perspectives. Right? And as you said, everyone comes from a different perspective or thought. And that's actually build into hell. Things even better. Wicker that's fascinating is step in this direction.

00:15:12:17 - 00:15:33:06
Ashley
In this current landscape, many companies are reexamining community or community groups or how they're engaging internally. Right. How do you balance the need for employee community with concerns about segmentation?

00:15:33:08 - 00:16:04:07
Jennifer
Yeah. And that's it's a tough one because I've always been fascinated by like I remember from and I'll speak from the only view I have as a female getting, you know, equal pay equal all these things equal, equal, equal. And then being confused when they call out the first all female this the first all female this I'm like okay, so how can you be equal and still separate right.

00:16:04:08 - 00:16:34:20
Jennifer
Like I look forward to the day when there's no need to call that out because it's just been normalized, right? And so when I'm building the culture, I really try to focus on how I want and desire everyone to treat each other and the value in that. If people understand the why behind what you're trying to do, then they can choose to align with it or not in the absence.

00:16:34:20 - 00:16:58:05
Jennifer
If I haven't done a great job to say, this is why I think these things are important, then they may do what I say because they want their job, but nothing really has changed. So I what I have done is I don't even really think about all of that as much as I think about collectively. If we can all show up in this way where we care deeply about each other, we respect one another.

00:16:58:06 - 00:17:26:02
Jennifer
We support in our a fan of helping each other be successful, seek positive intent, extend grace to each other. Then the rest of that stuff takes care of it, you know? And we have groups, we have folks that play guitar and they, you know, they like they have their little jam sessions and, and we have, you know, different pockets of like, we we really foster support for new moms.

00:17:26:04 - 00:17:51:21
Jennifer
Right. But it's, it's not the traditional what you would think of segmentations that we're looking at. It's it's more segmentations about who they are and their season of life, not what race, religion, gender, you know what I mean. And so I want people to to care about doing life with one another. Yeah. And and doing that unifying.

00:17:51:23 - 00:17:54:07
Ashley
It's really. Yeah.

00:17:54:08 - 00:18:21:16
Jennifer
Yeah. It's really I think it's changed me. You know, I didn't wake up like this. I wasn't born like this. And there's been a lot of work done on my own heart and thoughts and judgments and and I'm still I'm a constant work in progress. But I learned so much from the people I lead. That's what drew me to do this podcast when I met you.

00:18:21:16 - 00:18:42:22
Jennifer
I learned things from you during that call, things that inspired me to go dig into other things. You know, that's that's who I want around me is people that inspire me, that are I felt instantly that you were invested in me. Right? That's that's what I want to foster. I want people to feel like, you know what? I'm.

00:18:42:22 - 00:19:14:01
Jennifer
I'm willing to invest in you and do life with you. I think. I think if we could do more of that, our companies would be so much more successful. You know, when you talk about trust, leaders are leading in the blind. They're leading in the dark. If they are not promoting trust because your team members can save your bottom, if they know telling you the truth will not be a negative for them.

00:19:14:03 - 00:19:15:10
Jennifer
In the absence of.

00:19:15:11 - 00:19:16:02
Ashley
That.

00:19:16:07 - 00:19:36:20
Jennifer
They will let you walk right off a cliff. And so I don't understand. And we've seen it over and over. I know you've worked places where everybody knew the Emperor wasn't wearing any clothes, but no one was going to tell him. Right. And then it it finally comes out when there's no, no, there's no way but for it to come out.

00:19:36:22 - 00:19:44:15
Jennifer
And then it's a mess when people knew at the very beginning and they just were too afraid to say so.

00:19:44:17 - 00:20:17:06
Ashley
Everything you shared there, I my reaction from our initial conversations now is you lead with safe safety and trust. You encourage curiosity and flexibility. You leave with grace. I mean truly. And what's interesting, what I'm hearing here is where others can see grace as soft. You believe it? Safeguard to the bottom line. Yeah. You have to the people.

00:20:17:08 - 00:20:39:00
Jennifer
Everything I do, people get confused. And this has been since the beginning of my career. Everything I do is in service of the bottom line because ultimately, if you have people feeling highly creative, highly supported, highly inspired, your bottom line will get the benefit of that.

00:20:39:02 - 00:21:12:02
Jennifer
For me, extending grace and having empathy requires extreme amounts of strength and confidence. I see. I see that as the harder path. It requires way more courage and it requires way more of yourself. Right? Because you are giving, you know, you're not saying it's okay. It's not a lack of accountability. You're saying, you know what? This happened and it's not okay, but this is not going to this doesn't have to define you going forward.

00:21:12:04 - 00:21:47:17
Jennifer
Right. And so we're going to we're going to work on this. Right. That takes a lot more than just bringing the hammer down on someone. And it takes a lot more intention and confidence. So I it's fascinated me to to see people will see extending grace and mercy and empathizing as a lack of strength or power. But I think when you extend grace, you are giving up your power.

00:21:47:17 - 00:22:14:14
Jennifer
When you don't have to, right? You're choosing to let someone save face right and and leaving them as much intact as possible so that they can continue to be successful as quickly as possible. I don't see that as weakness. I see people who master that, the people that have mentored and coached me, that do that so well, I see that as such a deep example of strength and courage.

00:22:14:14 - 00:22:15:09
Jennifer
As a leader.

00:22:15:09 - 00:22:27:06
Ashley
I imagine, to just to ask that has to have a dramatic impact on retention, right? People want to be around that space, that energy, that thought.

00:22:27:08 - 00:23:03:21
Jennifer
Yes. Yeah. It doesn't. It's so sad how little it takes to for people to feel cared for and valued. And we've got people right now who have left and are waiting to come back for when we secure additional engagements. That is a constant for us and I. It really makes me feel so thankful for the groups that I work with and for how these people have been served by myself and the leaders that work with me, that they feel that way.

00:23:03:23 - 00:23:23:01
Jennifer
That's, you know, at the end of the day, actually, there's not a line of code that I ever wrote. There's not a session I've spoken at. You know, I wrote a couple chapters in a book that will not matter. The only thing that's really going to matter and have lasting impact is the investment I make in people, period.

00:23:23:01 - 00:23:51:07
Jennifer
When I am gone, the only thing that will matter is the investment I made in people. And, you know, I think that's why it really makes me so happy and brings me so much joy when we have these people come back. Right? I have at least 7 to 8 people who have left and have asked to continue to do one on ones with me, and I make time for them because it's an honor to continue in someone's journey and to help them.

00:23:51:09 - 00:24:24:15
Jennifer
You know, I and again, I try not to let that like I try not to bring my ego, but it does give me a boost and ego to know that, you know, they value me. So I, I really I just I wish more, I wish they taught this more. And when you're getting an MBA, when you're in your little leadership training classes, whatever, when people are investing in leaders, I wish they would call these things out more.

00:24:24:17 - 00:24:47:17
Ashley
You clearly give back to your fellow human right you you pour from your own cup. That is obvious. I'm curious and I'm sure those who are listening are curious. So how do you fill up your own? How do you stay in a position to be able to give? What are your self-care must do ritual things to put you in this position of strength?

00:24:47:19 - 00:25:12:10
Jennifer
So every morning I start out with I read my Bible and then I have prayer time and I journal my prayers. So I've done that for a very long time. And that I think is is PivotTable to to me, continuing to grow is the human I want to be based on my faith. I also have a coach, Bob Galen, who is amazing.

00:25:12:10 - 00:25:35:19
Jennifer
You should reach out to him. He is just one of the greatest human beings and he's awesome. He has. He has taught me and continues to teach me so much. And then I have a mentor named Alice McClellan, who is one of the strongest women I've ever known, and I meet with her regularly in the capacity of mentorship in areas that I grow in.

00:25:35:21 - 00:25:55:23
Jennifer
I also am constantly reading. I'm reading a book now that you should read Ashley. It's called Permission to Feel. It's awesome, and I'm always reading books to try to improve, and I try to read them with people. So I, I buddy up with people to read through these so that I don't just get my perspective, I get their perspective in it.

00:25:55:23 - 00:26:24:09
Jennifer
So I'm a big fan of that. And then I spend an amazing amount of time with my family, spending time with people that love you deeply and you can laugh with and just be with, I think is just so. Such a way to continue to keep my family keeps me grounded. Let me tell you that. That's if I start feeling a little too important.

00:26:24:09 - 00:26:29:23
Jennifer
I just need to spend an hour with my sister.

00:26:30:00 - 00:26:31:21
Ashley
So good to have those people.

00:26:32:00 - 00:26:32:09
Jennifer
Yes.

00:26:32:10 - 00:26:53:06
Ashley
On my my final question and my absolute favorite question, I'm very curious how you were going to answer this, knowing all you know now, all of the incredible experiences you've had along the way. If you can tell your younger self one thing, what would it be?

00:26:53:07 - 00:27:25:03
Jennifer
I think I would start with a verse and it's and I'm paraphrasing. Trust in the Lord with all your heart and lean not onto your own understanding. Submit to him all, and he will make your way your past straight. And then so, prioritizing your faith, I would tell her, prioritize your faith. It will take care of so much and then be bold and courageous.

00:27:25:07 - 00:27:49:16
Jennifer
Don't shrink back, right? Know who you are and who you belong to and be bold. That's what I, I would have told her. And that's that's what I tell myself when I feel imposter syndrome, when I feel, you know, discouraged or, you know, where I'm just there days I remind myself who I belong to. I remind myself who I am.

00:27:49:18 - 00:28:04:12
Jennifer
And. And that's what I would tell. I also would tell her that it 40. You're going to get to meet Scott Hamilton. So hold on.

00:28:04:14 - 00:28:10:23
Ashley
Oh that's wonderful. You Jennifer, are just a delight. I need.

00:28:11:00 - 00:28:12:12
Jennifer
You Ashley. Same.

00:28:12:14 - 00:28:38:21
Ashley
Oh thank you, thank you. It's. You bring such important light in a moment in time where things are moving so quickly. Right. And we can potentially prioritize speed and technology and the robotics of it all over this human touch, human experience. And you have highlighted the importance that we all have with each other. Right. So I just appreciate you in your perspective.

00:28:38:21 - 00:28:40:15
Ashley
And I thank you for being here today.

00:28:40:17 - 00:29:10:12
Jennifer
Absolutely. You know, Ashley, one last thing I thought about, and this is when did we start valuing maximizing the value that people bring over, valuing the people that bring it. When is enough going to be enough? You know what I mean? Like I thought about that. I was reading some things today, articles today and I more layoffs and more.

00:29:10:12 - 00:29:27:00
Jennifer
And I thought, gosh, when did we stop valuing the people that get us where we're at? You know, oh, like we're valuing the profit over the purpose.

00:29:27:01 - 00:29:46:12
Jennifer
It just it really hit me today. And I know, you know, you're in the financial sector. And so you see this playing out in real time. But man I don't you know, how do you undo that. And how do you change that mindset. So that we that we see the equal right where it's not a either or.

00:29:46:14 - 00:30:06:06
Ashley
Yes. And I think that you and I having this conversation right now is part of that. I truly believe that because there's many folks we get listeners at right in that with feel disconnected right now and these important reminders from leaders like yourself. I think that's a good start.

00:30:06:10 - 00:30:09:01
Jennifer
We do what we can, right?

00:30:09:03 - 00:30:09:16
Ashley
Amen.

00:30:09:20 - 00:30:15:17
Jennifer
Amen. Thank you so much. It's been a pleasure. And look up Bob, Galen.

00:30:15:19 - 00:30:22:00
Ashley
Don and folks to read. I've got we've all got a whole list here from Jennifer. So beautiful.

00:30:22:06 - 00:30:24:17
Jennifer
Well thank you so much, Ashley, I appreciate you.

00:30:24:19 - 00:30:25:09
Ashley
Yes.