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Delegating is a Leadership Superpower with Jess Carter

Delegating is hard when you’ve developed extreme ownership about your role in the company. But it’s one of the essential lessons every leader needs to learn to elevate the team and truly win together.

In this episode, Jess Carter, Vice President of Client Experience & Delivery Options at Resultant, talks about the whirlwind of change her life went through during COVID that made her flip her leadership style around. Listen in to learn how the path of sustainable leadership is about meeting people where they are and respecting the period they’re in their own process.

After You Listen:

Key Takeaways:

  • Be determined in asking for feedback and advice from other executives to help you overcome your weaknesses
  • Winning in leadership isn’t about being in the spotlight and getting praise for hard work, it’s everyone going further together
  • Being aligned with the work that you do is crucial to being the CEO

Things to listen for:

  • [3:28] Lightning round with Jess
  • [9:45] Understanding that your decisions are hypotheses
  • [11:32] Cheating growth as a leader by asking for feedback
  • [13:29] Learning how to delegate in a rapid growth company
  • [20:34] Jess‘s advice for her younger self
  • [11:32] Cheating growth as a leader by asking for feedback

Jess’s Transcript:

[00:00:00] Craig: As I was getting ready for the last day of my vacation, my phone rang. I stepped away from the kids. It was my boss. She informed me that two of my teammates had resigned that day.

[00:00:14] Craig P: Welcome to Executive Evolution. I’m Craig Anderson. After spending 25 plus years in corporate America, I learned a lot of leadership lessons the hard way. I created this podcast so you don’t have to.

[00:00:29] Craig: One of the things that’s tough for new leaders is everything feels very immediate and a lot of things happen to you for the first time ever, and because of that, you don’t really have a sense of perspective because it all just can collapse in on you.

And that’s what happened to me that morning. It ruined the last day of my vacation. I was completely preoccupied. Later in my career, I would’ve realized that. These things happen, I would’ve been disappointed, but I also know that these things will ultimately work out and you don’t have to ruin the last day of your vacation because of every work crisis that pops up.

Today we’re going to interview Jess Carter,

Jess is the Vice President of client experience and delivery operations for Resultant, and she’s going to share her executive evolution with us today.

[00:01:16] Craig P: let’s jump right into this week’s podcast.

[00:01:20] Craig: Jess, welcome to Executive Evolution. I’m glad you’re here today.

[00:01:23] Jess: Thank you so much, Craig. I’m really glad to be here.

[00:01:25] Craig: Before we jump into the lightning round, which is everybody’s favorite part, or at least my part, can you tell us a bit about what you do with resultant, just so we get a sense of what you’re up to these days?

[00:01:36] Jess: Yeah, for sure. Thanks for asking. So at resultant, I am the VP of client experience and delivery Operations. And so what that means today, cause it may change over time, right. When I joined. Nine and a half years ago, we were 38 people. Now we have 500. And while I was a consultant, my job is now to kind of be the high tide that raises all boats.

So most of what I do is about scalability. So I work on client experience. How do we scale client experience? How do we make sure there’s a consistent client experience aligned to our brand delivery operations? How do we make sure we run the business well for our consultants so they have a consistent experience too? And then there’s some fun stuff in the middle. So I do some quality auditing of our delivery and our deals to make sure that we’re selling great deals that we can do well, not just to win work. And then I work with our teams. When I audit, you know, how the work is going, so is it going well and is there anything that we need to do better or differently? then our resource management team. my team also helps assign resources on client projects. So

it’s a few things that we kind of bundled together and gave me a title, but I’ve just been a consultant for 10 years and I’ve grown into now helping us scale the business.

[00:02:46] Craig: And what a ride in a company go from employee 38 to 500 employees. That must have been a journey

[00:02:53] Jess: It is a ride. It’s been a ride. You can call it a journey too, Craig. You can call it whatever you want to but yeah, I mean, we went from, we were owned by the, you know, the oldest c p a firm in Indiana, and then we’ve gone through two PE or private equity purchases. that’s been interesting and exciting to learn about too.

I didn’t know anything about private equity when I started, and so we’ve had kinda this exposure to what does that look like? And, it’s been fun, but it has certainly not been boring.

[00:03:17] Craig: I am sure. Alright, well, are you ready to jump into the lightning round?

[00:03:22] Jess: We’ll find out

[00:03:23] Craig: All right. Let’s go in with both feet. What is your favorite book on leadership?

[00:03:29] Jess: spoiler alert, I listened to some of your other episodes, so I’m trying to come up with something unique here, although they all have good ideas, so love this book. I’m not a nonfiction person unless it’s an audiobook, so that’s fine. love tactile learning, so what I’m gonna tell you is anything by Patrick Lencho or some people say Patrick Lencioni.

Anything that he does for me as a consultant was like I could borrow his experience

So I was really valuable to me when I was starting out as a consultant. But then also endurance. There’s this book called Endurance, it’s a nonfiction story about this captain of a boat named Shackleton this incredible expedition to the Arctic in like the 1920s or thirties maybe. the feats they went through, I mean, did I need a 1 0 1 on like ships? But it was to watch a leader through their journals telling the stories of. Unbelievable difficulty and realize what they had to do to survive it. It’s just an amazing story about leadership.

[00:04:29] Craig: Wow. And I wonder when you read through that, especially that first person account of something that’s such an ordeal, I always think about how leadership can feel like the weight is just sitting on your shoulders. And if you’re in the middle of like, Nowhere and everyone’s looking to you. Was that a big part of the discussion in the book?

[00:04:46] Jess: there’s a lot that you can take from it. So it’s essentially a book that is compiled based off of all of their journals. So the guys that were on this

kept their journals and so he, they, he kind of tries to tell this story throughout the journals and the day-to-day and what they experienced and pieces it all together. kinda reminds me of like Matthew, mark, Luke, and John in the Bible. Like they’re kinda

points and you’re trying to piece together what happened. it’s an amazing story about yeah, like how lonely he had to be as a captain, how scary that leadership had to be.

People’s lives are really on your hands. Most leaders on their worst day, that’s not the case.

It’s just an unbelievable story. I don’t think there’s anyone who can read it and not take something away from it.

[00:05:26] Craig: All right. Next question. Who is your leadership crush?

[00:05:30] Jess: I would say, I hope I’m saying her name right, Cy Wakeman, I think is doing some really interesting things right now around leadership, emotional intelligence, how you show up for your team. I’m also not someone who idolizes people. I don’t know. I just think that can be dangerous. So I would also tell you. The people around me, I have had a unique experience where there are some leaders that I’ve had the privilege of following that are incredible. So I think like Charlie Brant was our founder, you know, Josh Wakefield is somebody that managed me for eight years. Andrea Heiner has been a mentor, and then I was raised by like JR.

Samples like dad, right? Like he’s just a great leader. And I had the privilege of being around, like, some of it rubbed off, I hope. So I just, I think I’ve had some great leaders in my life too that You know, have been pretty important to me. I dunno if I’d call my dad a crush, but you know,

[00:06:19] Craig: Yeah in a different sense. So, yeah, no, but that’s true. Be, you know, a lot of times we think about it as these kind of far flung people who we see from afar.

But then you think about the people who you see kind of all the warts and awe of leadership, cuz you’re just close to them and see them go through things because you know, you can write a great book about how awesome you are as a leader and keep out all the ugly parts.

But when you see it and you see how people deal with that, it really gives you a different view into leadership.

[00:06:46] Jess: Oh yeah. I will probably say this again in our conversation, but I think a critical component of leadership is that it’s. Temporal. Some part of that matters, like in the place and time you’re so I think some of the people that have been great leaders for me aren’t just constantly or something. They’re a great leader for a specific point in time in my life that really has been meaningful, right.

[00:07:07] Craig: Yeah, that it’s all this kinda relative piece. Yeah, no, I love that idea. Alright, well within that then, can you define for me your view of leadership in 10 words or less?

[00:07:17] Jess: I think leadership is having sense or a vision of something about what the world should be or where it should be. An awareness of something we could do to get closer to that, reality and pulling people along with you to as much of that realization as you can.

[00:07:37] Craig: Love it. seeing the world as you see it should be bringing people together and getting there and making the change.

Jess, let’s go back. What we like to do is start out with your very first leadership role. Tell us what that was, and you can pick any of it. You know, I’ve picked band president, which was a whole different story, but what was your first real leadership role?

[00:07:55] Jess: probably when I was running my first independent project as a consultant and I had my first employee, I had kinda a sense for where. The project needed to go and what the client wanted out of it but not five years or more of experience to do that again. So I was sort of trying to

[00:08:11] Craig: Yeah.

[00:08:11] Jess: but bring everybody else along for the ride.

[00:08:13] Craig: as, you think about that time, what did you find so challenging or interesting about leading that you didn’t expect?

[00:08:20] Jess: There’s this dilemma for that period of time, your first leadership your first leadership experience where you don’t have the aged experience, you don’t have the proven, demonstrated confidence in your yourself to handle anything. Well, that. I think people handle that stress differently. I was somebody who was high anxiety, checked every box three times, wanted to, I mean, I worked all day and all night. I wanted to make sure I did a good job. I think some people will also hold that more loosely. Like, it’s like I don’t want to be completely puddle on the floor if it goes poorly. And so I’m just gonna hold it more loosely.

So I think for me, what was hard was. Trying to be confident in what needed to happen when I didn’t have assurance that was what needed to happen. It was

[00:09:09] Craig: Yeah.

[00:09:09] Jess: A hypothesis at all times, and I was nervous about that.

[00:09:12] Craig: And you said appear confident. Did you feel confident?

[00:09:15] Jess: I live in Indiana now in Hoosier hospitality. Right. So I probably always sound a little more brash than anyone around me because I’m Chicago and at heart and I just play it straight.

I think my marriage counselor, I remember this specifically told my husband when in marriage counseling, The more confident Jess sounds, the less confident she probably is

[00:09:33] Craig: So when you think about that experience and that opportunity for leadership, were your big takeaways that have kind of influenced you over time?

[00:09:43] Jess: I think this concept of everything’s a hypothesis was really freeing for me. I wanted to know with certainty that in nine months the project would be done and it would be successful, and I was trying to keep track of every little minute to hour to week of all the data I could to make sure we were headed there.

I think if I step back and look at it differently now think there’s a breezier way to go about that where there’s just some hypotheses I’m making this month on what I think matters. And the reality is we might find out next month that it didn’t matter or that I was wrong about my hypothesis of the direction we should take. But I was very rigid back then because I wanted it to be perfect. I wanted it to be enough. And so I was really trying to be. Faithful with what I’d been given honor it and make sure that good things happen. So it’s all well-intentioned, but I look back and think if I had just been a little bit more reasonable about what we were doing and how big a risk might be, If it is actualized and it’s actually a problem. Again, nobody’s largely dying because of the project I was working on. And so there’s just this reality of how big is that risk really? And what happens, I think I just listened to your episode with Kyle Lacey, where it talks about getting all the way through that risk.

And I think that’s, really powerful stuff to get there and be like, okay, if this happens, does the project end? And I get walked out. Like

[00:11:06] Craig: Yeah.

[00:11:07] Jess: I sort of behaved like anything that went wrong could have lent itself to that kind of an outcome, and that just wasn’t true.

[00:11:12] Craig: And I loved what Kyle said about that. Of course, my head was always like, yeah, true, but just not yet.

But early on, what kind of timeline was it for you before you started getting that perspective to say, okay, I can see a bigger picture here cuz it feels like a lot. It’s weight when you’re a young leader.

[00:11:27] Jess: Yeah. Well I cheated. So for anyone else out there who wants to cheat one of the things that was really important to me was executives in my life who would kinda speak into it. So I have this incredible moment in my memory that’s like blazed in it, where my. boss at the time running the project was on vacation, instead of canceling the meeting with the executives, our founder was like, Hey, why don’t I just come with you? You’ll do it, but I’ll be there. Make sure it goes okay. And So I’m showing up with the founder of my company and the executives on my client account, and I ran the meeting, but I was so nervous, so scared. I wanted it to be good. I didn’t know how to come off. I wanted them to not have any questions because everything I said was so well said and so concise.

But at the right time and the right way, was just so hard on myself. So I got through the meeting, I’m walking all the way back to where my laptop was, in our project office, and my founder says, Hey, biggest piece of feedback. They’re already sold, You didn’t have to try so hard in that meeting.

It almost came off like the wrong tone. Like, you’re in the room, this wasn’t an interview. Be in the room. there’re our partners. You don’t have to treat it like, it’s this really hefty test of Jess. It’s really just like, you should have come in

represented the boss that was on PTO and try to be like, calm, cool about it. I, valued that so deeply. That for the first three or so years, I kind of demanded managing up that feedback from my superiors. Like, Hey, what do I need to do differently? Will you come to this meeting and watch me? Hey, I’m nervous about how to articulate this to a client.

Can I try it out on you? Give me some

feedback So I kind of demanded that support and they were gracious enough to provide it every time.

[00:13:02] Craig: Yeah. And it, it’s so interesting when you talked about kind of leadership crushes, being those mentors and, things that makes a lot of sense because you really leaned into them for experience, guidance, insight. As you were coming up through,

and now here we are in your current role, seasoned, you’re the one mentoring other people.

So talk to me about leadership today in a company that has grown dramatically since you joined.

[00:13:26] Jess: you know, there were moments where our company was growing fast, Craig, that what was really difficult was we were hiring a hundred people in one year that I didn’t know. I was on the first account in public sector that we had. I mean, this was my baby. We, grew it, I sold our first contract outta state. helped write our first. public R f P. I had this really extreme ownership. We talked a lot in our company about cultivating extreme ownership over the business, thinking about every dollar as if it was your own. And that worked. But then we went to scale. It was really hard to share my toys, cuz they were mine. They were

And I wanted to know that you were good enough. I broke all the, rules that I know today that I would use today where I, you know, I kind of tested people. I, withheld some of the work.

I didn’t delegate in pieces. I just sink or swim, come in and keep up with me or not. And so there’s a whole bunch of that I would wildly wish I would’ve handled differently. And I got to a breaking point in. where in 2020 I had the privilege of helping Indiana’s governor’s response to Covid. so that was intense. That was 64

straight of 18 hour days from March to May in 2020. That was ongoing work. Every holiday, Christmas, new Year’s, we’re making sure the dashboards are up. it was a lot. And it was the first time in an IT consultant’s career where like lives were kind of on the line

[00:14:42] Jess: And so I was pretty burnt out. And then I had my second son, my child, and he was in the nicu. And then my mom passed away just two months later. And so there was just a lot in my life that got kind of turned upside down. I had this moment where the thing I’d been building for eight years, I took all this pride in for my career. for the first time in my life, didn’t matter. I was looking at a mom that passed away at 64 and a son that I thought was gonna have some major diagnoses in his life, and he didn’t thank God, but it was terrifying. I was terrified. I had real risk in front of me, My career took a backseat, had to, and I’d never been in that. What do you mean that’s, it doesn’t matter. It’s always mattered to Jess. It’s always very important to my identity. So I went through some major therapy and some major executive coaching and some other support I had, and of landed in a place where I am today where there’s more of this sense of everything I touch needs to be about scalability and empowering our consultants, not testing them until they prove themselves, but actually providing. Support to their agency, to their careers, to see them as people that are gonna be way more important than me in eight years faster than I became a great consultant. And my job is to make sure that happens. My job is to invest and empower those consultants around me. It’s a totally different paradigm than when I was hovering over my toys and terrified to share them.

It’s like a totally different mindset, right? And so that’s kind of where I sit today is I use a delegation technique and I process each person on my team differently based on their skill sets and abilities. And we talk through what they wanna try and test and, you know, we kind of manage things commiserate to their experience and capabilities.

[00:16:22] Craig: It’s so interesting on delegation. teach a leadership training program for my clients, and delegation is almost mind blowing to people. One, just giving away responsibility. Then when you talk about, and maybe this is where you’re at with your, the way you do it is kind of like the situational leadership model, right?

Where it’s like I treat everybody to where they are. I meet them where they are versus where I think they need to be, and then I get ’em there. A lot of times people are just like, that seems like a lot of work, but the dividends are

[00:16:50] Jess: Right,

[00:16:50] Craig: It’s an investment in freedom, effectiveness, efficiency, sustainability.

[00:16:56] Jess: right. I had two or three executives that were saying, Jess, your only job, we care if you bill, but just go make more Jess’s. that actually created a barrier in my mind of like, it was an ego problem of, well, who’s gonna be me? Instead of this empowering moment of you get to help people get there.

[00:17:14] Craig: Yeah.

[00:17:14] Jess: I think that it was well intentioned, but it didn’t land the right way. And now I look back at all these people who are not me, but they’re better in all these different ways. And so it’s been neat to find, yes, this. Delegation technique really matters. And I think I’ve found times where I’ve failed and I’m over here letting people just try stuff out that they have no business trying and I’m realizing they wanted very much authority, but I still have a job in leadership to guide them to be supported and succeed. But it’s also Craig like, As our company’s grown, it’s really difficult to, to your point, to share the ROI on this style, this approach. It’s difficult to show on a P&L Here’s what happens when I lead differently but I think you can, I think longitudinally over two or three years, Old Jess was burning people out around me, people who didn’t feel like they, I probably made people feel like they weren’t enough, cuz I never felt like I was like, there’s all that. But if you look now, I’m hoping that in the next few years what we start to see are a bunch of really empowered, unique consultants who find their voice and figure out how to be successful.

[00:18:17] Craig: And, I agree with you it’s something that I don’t think you can measure in the moment. But it’s over time. And when you were saying that, what popped in my head is like in N F L football, there’s these coaching trees, but not every coach created a coaching tree. And they were great coaches in and of themselves, but you don’t have eight coaches that they developed over time to be the next superb bowl coach.

And that’s the difference when you’re developing your coaching, your leadership tree underneath you. That’s what’s gonna help that next level grow and help your company grow. Cuz now those leaders are moving up because you’ve shown them how to do

[00:18:51] Jess: I think we create generational crisis and leadership in our organizations when we don’t take the time to do that.

I completely agree with you and I think some leaders around me who are Socratic, But I think there was this important moment to where I was talking to an executive coach two or three years back, I was kind of demonstrating how I’ve spent my years. Essentially mimicking or echoing the leadership around me. So I would put on, you know, Charlie hat when I wanna behave more like that leader or Andrea’s hat or my dad, got so good at studying them that I would replicate them.

And she said, do you want to just replicate leadership or do you want to define your own

And I think that’s another piece that’s really different for me is now when I’m seeing people around me, There’s a respect for their agency, there’s a respect for their style. And at before it was kind of like why I borrowed these three people’s styles.

So then you need to demonstrate mine before I trust you. And now it’s like What are your unique strengths and weaknesses? What are the real things that make you a great leader around us? How do I help catalyze where you’re already going. Like, I’m not the reason you’re gonna get there.

I just get to maybe have some influence over helping you do it faster if I can. And I just think that those. Frameworks are so different. It’s very interesting to look back at it. It served me well. I mean, those are still skills I’ll use, but in my own way,

and that did just take some time for me to figure out.

[00:20:12] Craig: Now, probably my favorite part is we’re gonna jump in a time machine. We’re gonna take you back to young Jess in that first leadership role. Given all the things you’ve talked about of how you’ve evolved over the last several years, what’s the one piece of advice you would give young Jess that would make her more effective as a leader?

[00:20:32] Jess: you’re not on by yourself trying to get across the Atlantic. You are on a team how you behave represents the people above and below you on your org, your brand. And so it’s not just about out outcomes. Stop just trying to become like a wild achiever and be in the limelight. Jess, you’re the, you’re so good. That’s not winning. Winning is everyone around you. Feels and knows their sense of how good they are and feels some of the success around them that you helped generate. that’s winning. Winning is not just, we got through the project and everyone’s like, Jess is so great. Winning is, we all got somewhere further together. Be, and maybe because I was there,

[00:21:15] Craig: Great. So yeah, that’s, and I love that kind of analogy of just, you know, in my head as you’re talking about that I just kinda see everybody, the rising tide kinda lifting everybody up and that’s where we really get there to success. So, fantastic. So Jess, if people wanna find you or follow you, what is the best place for them to go and do that?

[00:21:31] Jess: LinkedIn. So I don’t know how many Jess Carters there are on LinkedIn but it should be fairly easy to find me there. and then you can always email me at resultant too. So j carter

[00:21:41] Craig: Thanks so much for sharing your executive evolution with us, Jess.

[00:21:44] Jess: Thanks Craig.

[00:21:45] Craig: I really appreciated Jess’s insights on this episode of Executive Evolution. As always, I want to provide you with my key takeaways in the important leadership areas of confidence, competence and calm. When we think about confidence in Jess’s story, she talked about how at one point she took on the personas of the leaders that she respected and the way that she spoke and led people.

But over time, as her confidence grew, she was actually able to. Take all those learnings and integrate that into her own leadership style, and that is a sign of leadership competence in the area of competence. She realized at one point in her career she was taking everything on herself and it was no longer sustainable, so she not only took steps to do something about it, she actually sought out a solid framework for how to handle delegation called situational leadership.

And by doing that, she’s actually meeting her team where they are showing her own competence by respecting where they are in their own process. And then finally in the area of calm, she just talked about one time in her life where a lot of things came at her all at once from a personal life and and professional life.

And that’s when she realized that everything was just going to be too much. And the attitude that she brought to the table. Was no longer really gonna help her going forward. And it’s that self-awareness that we can develop as leaders and as people that allows us to build a sense of inner calm in our leadership style, in our day-to-day role.

That’s it for this week’s episode of Executive Evolution. If you enjoyed it, please like shared subscribe. If you would like to follow me, you can find me on LinkedIn under Craig p Anderson, or check out my slash blog. And remember, you can go from being an accidental leader to the greatest leader of all time.

All it takes is developing your confidence, competence, and comp. See you next time.