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Mastering the Art of Managing Up: Essential Communication Strategies

Summary Keywords

communicate, communication, cybersecurity, empathy, gen z, generations, good, individuals, jax, leader, leadership, learn, love, manager, managing, organization, promotion, senior consultants, talk, work


Melissa Aarskaug, Jax Scott, Narrator

Show Notes

In today’s episode of the Executive Connect Podcast, Melissa Aarskaug welcomed Jaclyn “Jax” Scott, a decorated Special Veterans Warrant Officer with expertise in cybersecurity and electronic warfare. Jax shared invaluable insights on managing up and effective communication in the workplace.

Topics included:

  • Understanding the Importance of Effective Communication in Managing Up: Jax emphasized the significance of managing not only oneself and subordinates but also one’s superiors. Effective communication entails understanding the leader’s effectiveness and supporting them in improving areas like time management and organization.
  • Improving Ability to Manage Up: Melissa and Jax spoke about the need for clear, concise communication and radical candor when managing up. Seeking feedback and addressing pain points constructively fosters mutual understanding and credibility.
  • Addressing and Sharing Feelings in Professional Communication: Authenticity and empathy are essential traits of effective leadership. Active listening and acknowledging feelings create rapport and trust, enhancing communication effectiveness.
  • Engaging Generation Z in the Workplace: Recognizing the unique needs of Gen Z employees, Jax highlights the importance of genuine connection, mentorship, and providing opportunities for growth and leadership roles.
  • Bridging Communication Gaps Across Generations: Melissa and Jax discussed strategies for organizations to bridge generational communication gaps, including involving younger employees in leadership initiatives and fostering dialogue and mentorship between different generations.

Don’t underestimate the value of confidence and open communication in managing up and fostering effective workplace relationships. They emphasize the importance of mutual understanding, empathy, and continuous learning in bridging generational differences and driving organizational success.

Thank you for joining us on the Executive Connect Podcast, where powerful stories shape meaningful connections!

If you have any questions about today’s show or have a topic you’d like us to cover, reach out to me at executiveconnectpodcast@gmail.com.

Please subscribe so you can catch all our future episodes.

About today’s guest:

Jaclyn “Jax” Scott brings 16 years of invaluable experience from both military and civilian cybersecurity realms. Her strategic contributions have fortified national security via operations with NATO and various defense agencies as well as civilian firms such as Capital One and Mandiant. As an Army Cyber and Electronic Warfare Special Operations Warrant Officer, she mastered cybersecurity frameworks and policies, significantly enhancing cyber defenses. Jax is also dedicated to philanthropy, initiating the “Jax Act” with the Special Operations Association of America to support female special operators. Her role as a cybersecurity educator is amplified through her YouTube channel, Outpost Gray, and her award-winning podcast, 2 Cyber Chicks. Jax is a published author of the “Cybersecurity Career Master Plan,” offering insights into navigating the cybersecurity field. An avid hiker and outdoor enthusiast, she combines professional dedication with a commitment to service and personal passions, witnessed by achieving a Master’s degree in Cybersecurity Risk Management from Georgetown University.


About me:

I’m an energetic executive with 15+ years of experience steering companies to new heights of growth and scale. An engineer at heart (I started my career as an engineering manager on one of the world’s largest concrete bridges), I’ve become a trusted leader and business builder in the technology and cybersecurity space.



Narrator 00:08
Welcome to the Executive Connect Podcast, a show for the new generation of leaders. Join Melissa Aarskaug as she speaks to a wide variety of guests that bring new insights into leadership, prosperity, and personal growth. While no one has all the answers, by building a community of open minded and engaged leaders, we hope to give you the tools you need to help you find your own path to success.

Melissa Aarskaug 00:38
I’m so excited to have my friend Jaclyn “Jax” Scott  here with me today. She’s a highly decorated Special Veterans Warrant Officer with 18 plus years of military service, specializing in cybersecurity and electronic warfare. She is a renowned author, blogger YouTuber, and podcast host advocating for cybersecurity policies. Jax founded Outpost Gray, authored “Cybersecurity Career Master Plan” and is a board member of the Special Operations Association of America. She’s committed to empowering female combat veterans working on the “Jax Act”, and holds a Master’s in cybersecurity risk management from Georgetown University. Jax has also spoke at Harvard on successful military to executive leadership transitions in the civilian world. Welcome, Jax. And thank you so much for being here today. I’m so excited to have you. And talking about a much needed topic, managing up and proper communications. I think it’s such a timely thing to talk about in our world today. And so just simplistically, what is the importance of effective communication in the workplace when it comes to managing up?

Jax Scott 02:07
Well, first off, Melissa, super excited to be here. Thank you so much. And I love like we connected Gosh, it’s been like a couple of years. And I love how just like this community is so small, and I love that you’ve started a podcast too. So go, you really is awesome. Oh, this topic is so needed. It’s such a topic that I don’t feel gets talked about enough managing up in that communication piece is like foundational for it. So some of the most important things about managing up and communication is you don’t want to when you’re managing up, one of the key things is you’re not just managing yourself and the people below you, but you are managing your management. And I think one of the things when you’re getting into this space and trying to negotiate, well, how do I manage my manager? Well, the first thing you need to do is see how effective of a leader they are. And what I mean by that is what I’ve noticed and what I’m working with right now, because I’m in consulting, so it’s always different clients all the time. And if they are not effective leaders, you will be able to tell some of the things that you will see is cancelled meetings last minute, being very like disheveled when they’re on calls, that right there would tell me they’re probably not good at time management, they’re probably not good at like organizing their overall schedules. And they’re probably always having fire drills. So one of the most important things is understanding where they’re at, and then communicating to them in a way that will help them with their day to day work while still being effective within your current job, like what the tasks that they give you, but also helping support them to become, for example, like more organized within their space.

Melissa Aarskaug 03:46
I love that I think a lot of times people say oh, you’re if you have a title, and you manage people, you’re a leader. And I think that’s an often miss big misconception is because you have a title, you’re also a leader. So from an from, like an employee perspective, how can employees improve their ability to manage up effectively? What could they do to be better at that?

Jax Scott 04:13
So one of the things that, like popped into my mind is that there’s a book called Radical Candor. So I love that book. I think it’s awesome. There’s a million other books that you could probably pick. But I think one of the things is having clear, concise communication with your leadership and outlining exactly understanding exactly from the start. So when I get into a new environment with a client, what I will typically do is I will try to develop a relationship as quickly as possible with them. Try to understand kind of where they are, if they’re, if they’re good at managing their own time, have radical candor, communicate with them, kind of where the team is where they are, and then depending kind of on that relationship, maybe even possibly asking for feedback. That would be something maybe later on that and employee could do is asking for feedback and that feedback is more and not just saying, will you provide me feedback, but what they could do is they could ask for feedback as far as in this again, I would say do this in 60 to 90 days, it’s hard to do it within the first 30 days, depending on the OT tempo. Like, I’m right now in a contract I’m on, it is extremely busy. So I think I could probably do it. We’ve been there for six weeks. And I would say, we’ve been working with you for six weeks, I would love for you to provide feedback as far as the impact that we’ve been having. And she’s been like overly communicating that we’re doing really well. But what is really well, mean, right, can you define to me what that means and what we’re doing? Well, but can you also provide me some areas that we could improve, and what you will be telling, or he will be telling from their point of view is a pain point, you don’t even have to ask them what a pain point is, they will naturally tell you that, and then you as a manager, or a leader in that space, can then learn like creative ways on how to best fix that problem for them, in a way is the easiest way of explaining that. And that again, you’re going back into you’re helping manage up and manage them. And then what internally will happen for employees is the leaders of the managers they back off because that you built credibility, also, you’re making your life their life a lot easier. So they’re just like, they started to give you task, and then they just trust you to go and execute it. And that’s ideally what everybody wants to feel like in an environment. But it’s like, it’s learning how to manage up to be able to, like create that environment for you and your team.

Melissa Aarskaug 06:34
Yeah, I love that. I was just thinking when you were you were messaging like, a lot of times people say I’m so busy, or I’ve taken so many calls today, I can’t get with can’t get through my desk, or I can’t get through my emails, or I can’t do these things. But quantifying what I’m hearing you say is quantifying how much it’s being very specific. So it’s clear as to Oh, today I had how many calls two calls, 10 calls 15 calls, two calls, properly managed is very different than 10 calls mismanaged right. And so I love that you mentioned quantifying, and getting clear with the communication. And then we talked about like communication is kind of a touchy feely thing, right? So we’re being very specific. But when you’re communicating how does addressing and sharing your feelings fit into the context of professional communications and managing up.

Jax Scott 07:36
So in my opinion, a good leader, bottom line is going to have empathy and who’s going to be an active listener like period, you need to have those skills to be an effective leader. I just that’s because I’ve come from a military background, I had to learn empathy. It wasn’t taught that was not a key thing as a woman in the Special Ops to be empathetic. And then I wasn’t really taught active listening. Hence, you know, in the military, it’s do what I say don’t ask questions. So you didn’t have that dialogue back and forth, right. So I think for effective communication, regardless, if you’re managing up or anything, I would say this is across the board. You need to be able to sit and listen to your people sit and understand and have empathy. One of the things that I have done with my current client that I’m working with right now is when we’ve hopped on calls, and it’s just been one on ones. I have tried to get to know her more where and she’s remote. So we all work in the office, but she’s in another area in Georgia. So I just asked her like, why did you decide to move there? Her wife lives in another location, I asked her why. So I take all of these things into like consideration. She has an elderly cat, her vehicle, like broke down recently. So she has all these stressors. And then I’ve asked her about you know, you’re in an acting role right now, how is that going? And she volunteers, it’s very stressful. So these are all good things for me to understand and having empathy for because, you know, this will so when you’re talking about something, I know for me, if I’m sharing my feelings, you I might have just met you. But if you simply just go and I’m sharing how frustrating it is to live separate from my wife, or you know, the challenges of being in this, this acting role for me to simply just say to you, Wow, that must be really, really challenging. I can only imagine how much you have on your plate right now. That right there is just like, oh my god, I’m seen and heard like she gets it and it not could be like it not in a lot of plate like a lot of situations. That’s in a way instant credibility and it also allows them to feel like oh, she understands and so I am building that credibility as we’re building out this new program together and she has just met me but it’s also telling her like, I’ve got your back like I understand what you’re going through. So I am going to do the best I can to help make your life as easy as possible without saying all of those things to them because people, that’s how people communicate. So I’ve gotten I think empathy. And I think active listening, I think listening more than talking is so critical when you’re trying to understand your manager as a manager.

Melissa Aarskaug 10:16
Yeah, for sure, I think to getting clarity when you don’t understand too. So listen, make sure you’re hearing people. Yes. And so what I hear you saying is this, this, this and this, and getting that feedback and re saying it back to someone helps you really understand. So a lot of times, I feel like in the world today, we don’t have attention span, like we used to, we’re immediate gratification, to the point, get through the day, get through our meetings, but I think re saying what your expectation is, and what you hear helps people because people have different learning styles talking so many times people don’t listen, right, they have to see it written or they have to write it out and being able to understand and having empathy and and and truly listening to understand what’s that saying two ears and one mouth, use them proportionally or whatever, whatever that thing is, and I couldn’t agree with you more.

Jax Scott 11:17
I want to add to that, too. As far as sharing the feelings, I want to add another side to that. So we were just talking about like somebody who’s really receptive of that, and having like that nice little dialogue. But there are times and I just witnessed it, and I for anybody that’s listening to this, that like you’re wanting to share your feelings, there will be times, unfortunately, and it just happened where and like you were saying an individual spoke to me in a certain way was we were talking about promotion. And all I kept hearing him say, and he’s my above me is my manager. All I heard him say is all the ways why he could not support me and getting promoted. Now I understood he was trying, I’m giving them the benefit of the doubt that he was trying to prepare me in case I don’t get promoted again. However, I know I’m a high achiever, I know I deserve a promotion. And so when he got done explaining every single reason, and not one reason why he would support me, at the end of that I told him, because I have learned to be a very good communicator, I said, individuals name, I do not feel like I am being like seen and heard right now. And I feel like you are not supporting me. And this is the reason why I am feeling that way based on what you’re telling me. And then I actually told him, I said, what I would like to hear from you is that considering the situation that you as my leader will do the best that you can to support me because I truly think you will support me with this promotion, considering everything that’s going on. And you would think an individual would be like, Yes, like that. I have your back. But for some reason, and I have my I have my own assessment of why this happened. He he lost it, he started raising his voice at me, he started being very condescending, he then told me that my feelings don’t matter. So that happens too and that’s where you still have to stand your ground and your your feelings do matter. And it goes back to like, find leadership that cares. Sometimes you’re not going to be able to manage up. It’s just not it’s not I’ve had issues with him for months, and now I’m leaving his team. So don’t be afraid that it’s your first time to try to manage up and it blows up in your face. That is not you. It could be the other person’s going back to what you said, he’s a manager, she’s a manager, they’re not a leader. And they don’t have the proper tools in the toolkit. It has nothing to do with you and your feelings do matter.

Melissa Aarskaug 13:45
I love that you just said that. It made me think I had a similar situation years ago where I was managed by someone that talked down to me. And you know, I’ve an engineering degree, I have a minor in math, I know how to count very well and do math. And he kept telling me, you know, oh, are you sure you counted that? Right? And I remember I took a step back because he kept it was only me that he just in a room talk down to in a room. I just there’s something I about me that he just didn’t like and I can tell and so I pulled him aside and I said hey, like and I just hit him head on. And I said I’ve clearly upset you and I continue to upset you. Is there something I can do better as your direct report that I’m not doing and come to find out from this person. His most of his life has been around high, alpha powered women and he’s always been told what to do as a man. And so anybody that was direct and alpha so like his childhood, his wife, his family Any woman that, you know, had an opinion that it just didn’t just do what he said, it triggered him. And it took me a year to figure it out. And I figured it out. And this person came back around to me years and years later and apologized and said, Yep, I was wrong. I engaged you wrong. And I just said, Hey, you know what, you taught me something that I, myself, I learned how to stand up for myself, how to champion what I believed and because you think I’m this way, doesn’t necessarily it means it’s correct, right? I think no, people make an opinion about you or me because I’m a blonde that I’m a bimbo, right? Or whatever. And I’m just picking a random thing, right. And I think it’s up to me to decide if that is a valid assessment of whatever the trait is, or whatever the comment is. And sometimes I think people just having bad days, too, right? Like, I have bad days. And, you know, I was just mentioning, you know, I got presenting on something. And I forgot to introduce the person that was presenting, and I just jumped right into what I was doing. And so I think we’re human. And you know, you nailed it earlier talking about being genuine. And I think people can sense when people are phony, like I, I know, I can sense when people are saying, you know, the same how’s your day, or how’s the weather, and you can tell that they’re going through? Well, the weather’s great outside, right. And you can tell they’re just, they’re not comfortable. And so sometimes I try to help and soften that I’m like, the weather’s great, but it’d be better if I was, you know, in Florida, on the beach, or something. And so I think it also is generational to right how people communicate. So, you know, from your perspective, are there any trends or tools or skills that is effective for maybe the Gen Z group?

Jax Scott 17:01
I love this group, because a lot of people struggle with the Gen z’s. But I have so many employees that are Gen z’s, that I am very close to some have even left the organization. And they have I have countless stories that on my birthday, or at something they’ve seen I post on LinkedIn, I’ve gotten like a, a Starbucks gift card, and then one reached out to me and we just caught dinner the other night, she was like, I really want to connect with you. I haven’t I really miss like seeing you in the office. And you know, she’s like, I don’t know, 23 or 24. So what. So I don’t have it figured out. I want to start by saying that. I don’t have it figured out. But I’m just going to tell you what I have done that seems to have worked. I think authenticity is key. I’m very authentic with my, with my gen Zers. I’m not authentic with everybody. I don’t BS. I am very much a like I over communicate. So I have high expectations for my team. I have realistic expectations, too. I know some leaders have, they say that and they’re a lot of times not realistic. I communicate at their level. But I also challenge my people. And so with Gen Z is what I have identified, and this is sometimes hard for leaders because they’re like, Well, I’m so busy, blah, blah, blah, blah, blah. But with Gen Z’s they need time, they need time with you, they need to know that you care. Now, we always have to develop the like devote that time to them on a weekly basis, 30 minutes, a week, every single week, maybe for a couple but a lot of times after they’ve established that rapport with you and you’ve set those meetings aside. They just want to be seen and heard. They live in a very overly stimulated environment. And so a lot of these Gen Z’s and I work in cybersecurity and a lot of them work remote. And they are at their like at their desk and they just type in their on their phones. And so that first initial interaction is a little awkward that from what I’ve seen, but what I do is I just try to I ask them like, how are you doing? I still to this day, if we have team meetings and I haven’t talked to one of my people in a while. I’ll be like, Hey, can you stay back? And I’ll just ask, How have you been? Have you done anything on the weekend? Have you done any weddings? I have one from Africa I was like oh what did you. What was the like outfit that you wore share with me? What? Like what do you do? She always goes in parties. So I’m like what did you dress as is Halloween what it because I know she’s a social person. So it’s getting to know them and this is like, to be honest, Melissa it’s common sense. But I think because we have neglected this like connection piece because let’s be honest, I’m a millennial. I don’t need the whole connection thing as much. There’s like all these generations but what I have felt is that connection piece is critical for Gen z’s. You are not going to be able to have influence and they are not going to want to follow you and stay with you and give you the highest quality of work if they don’t feel like you have invested in them and you care about them. And I think we should take that I think the Gen Z’s are actually teaching me how to be more of a human again, and take more time for all of my employees. And I really, I get caught up and I’m busy. And there’s times where I’m like, I don’t really want to talk to them. But then I stop and take a moment and and I put myself empathy. I put myself in their shoes, I reflect and I’m like, How many times have I reached out to leadership? And they haven’t made time for me? Or when they do, how does that make me feel? Yeah, so it was just taking those moments to remember where they’re coming from. And a lot of these kids and I’ll end with this is because I could go on forever. For Gen Z’s, I feel like they don’t have a lot of mentorship in their life, their mentorship is their social media. And I don’t know what their family life is. Some of them come from really good backgrounds. But what I’ve noticed is they just want that quality, friendship, quality, mentorship, they, they from my lens and being in consulting, they want to grow, they want to learn, they just need some guidance they need to get you need to help pull them out of their shell a little bit. And you can only do that by being authentic, having one on ones really connecting and really desiring to learn about them.

Melissa Aarskaug 21:09
Yeah, I love that. I just spoke at the Texas Cyber Summit a few weeks ago, and I had several Gen Z’s coming up to me and asked me like, What do you think and you know, I would I tell a lot of them I’m like, shadow people learn what, what, how people have failed, how people have succeeded. Try all the things I always say, you know, try to shoe on if it doesn’t fit, try another one on. And I love that you mentioned connection, because I do agree. I think COVID brought us all indoors in front of a TV. We weren’t as social we’re a lot of online, it you know, we want everything now delayed. You know, we used to go places and stand in line and talk to people. And now it’s like Amazon and other other eats. Uber Eats has made it so easy to not talk to people or communicate with people and I, I even see this in the food and beverage industry hospitality how, you know, before when people used to wait on you, they talk about, you know, with you and what you like and what you don’t like now they say, Oh, do you have any allergies? No. Okay, what do you want to order, right. And I think that’s always true. We’ve come to a point where we’re transactional in the world. And I think, to your point Gen Z’s they want to be touched and felt and know you have their back and know you’re gonna help them and know that, you know, they’re gonna make mistakes. And I always tell people I’ve managed, the more mistakes you make young, the better, make a ton of mistakes, don’t do them when you get like in your 40s 50s and 60s, because it’s harder to recover. So how you’re living in your 20s 30s and 40s, is how your 50s 60s and beyond are going to happen. flourish. Right? If you’re not communicating with people, you’re going to be more lonely, right? You’re not talking to people. And so I love that you said that because I absolutely echo they want to be touched. They want some of that balance in their life. I hate that word. But I’m going to use the word balance they want to be done. So they can go out with their friends, like you said, and get you know, get dinner, get whatever they’re doing go into an event. So I absolutely agree. So from like a company perspective, how can organizations bridge that communication gap between different generations from Baby Boomers who do things very different than Gen X, Gen Z, millennials? Like how do you bridge those gaps across all different generations?

Jax Scott 23:51
Woo yeah, it’s such a challenging question. And the first thing I think of when that question, the first thing I thought of when you said that question that popped into my head was that I was trying to coordinate getting individuals to come into the office. And one of the things I was tasked with, Okay, put together a like a program or something to get individuals in. So one of the first things that I did is I brought they’re, like C2. So it’s like a junior Junior, not a senior consultant, but a pretty junior person. And she’s like, I don’t know, maybe 24/25 in the org. And so I’m like, Well, we’re trying to bridge this gap. But we’ve got the majority of the organization is like senior consultants and below, let me pull her in to this project. So she can not only work with me, and we can and we’re working on a project together. But I also am going to have her brief executives and like start getting around like associate directors and directors. So one thing that I think we can do is let’s start tapping the younger generation and giving them more responsibility because again, they want to feel like they’re part of something versus just being a worker bee, so I think that’s one of the first things that we can start doing. She crushed it on the brief, like, she flourished, she did so well. And I gave her tasks and she, and I even told her, I was like, You’re gonna own this slide, I’m not touching it. And that meant, like, you’re gonna, and I told her, I said, you’re gonna be briefing leadership, we’ll do a dry run, you are owning this. So they need to feel like I own something like I’m having an impact. So that’s a key. And the other thing is this is for higher leadership at any organization is they I think we get so disconnected when we get into those executive roles. And we forget the impact it has on the lower leadership, even managers, but especially those like senior consultants and lowers the impact that we they have when they decide to have breakfast. And they set aside time to have a mentoring session for breakfast with like a partner, because our highest individuals are partners. So those are the executives. And just setting that time aside, where these lower like Gen z’s, these, like individuals that are new within the organization can come and just in an intimate environment, 10 people, 20 people, and they get to actually ask these partners questions. And these partners ask these individual questions. Now you’re starting to bridge that gap. In my opinion, I think events are great, but events are so just like skin deep. That’s why those engagements, pulling them in and getting them involved, because they’re not going to volunteer there, they’re going to be quiet, they’re going to be in the corner, most of them and they’re just going to work. And other thing I’ve seen is if they don’t feel like they’re being accepted, or part of something, they’re going to, they’re going to jump every year and a half and move organization. So it’s like, we’ve got to figure out how to bridge this gap. Because then we can keep them longer and breathe, bring them in. But it’s really all about like, again, it goes back to communication, though. It’s it’s being creative on ways that we just can connect and, and learn more about these individuals.

Melissa Aarskaug 27:01
I love that. And I think the more you bring them, like you mentioned up the different set of goggles, senior leadership has they have, they have good ideas and faster ways to do things and things we never thought about, right. And I think, to your point, when you give people the ability to lead something they learn as well, right? They’re nervous, they’re out of their comfort zone, and they grow as people and that is the key. Key thing is they’re out of their comfort zone. They’re growing. And they’re bringing perspectives that maybe other senior leaders had never thought about. Right? And one of the tactics I love is to match my baby boomers up with other generations because like social media, they’re like, what, like, what are you posting? We go out to see the clients like we’re gonna sit down, we’re gonna have a coffee. And other generations are like, no, no, no, we’re just gonna get him on a zoom call. We save ourselves money traveling, we save our time. And I think there’s something to learn from all generations, because the baby boomers are right it we do need to get face to face in front of people, you learn more, you you, you know, we’ve gone away from that a lot these days, seeing your clients face to face, like we’re not doing that, like we used to, because we have zoom and other methods that communicate. But the baby boomers, they everything was built on that face to face handshakes where we get a contract, we’ll just shake hands. And and I think that’s something there’s something to take from that. Because, like you mentioned, there’s a communication factor, there’s a trust factor, that maybe other generations don’t have, that they help each other. And I think that I personally love hiring all generations, I think everybody has something, you know, all generations, all cultures, all races, I think everybody has different perspectives. And the more we can let people lead their own thing and come up with strategies, the better it is for the organization. So when all everybody’s thinking how to build things, and how to do a better, leadership is better. And the companies are better because they’re having ideas brought to them instead of paying, you know, for consultants, consultants, and other consultants are great. It’s just you have people that are in the business tap into that knowledge. And so just kind of some a couple of like, closing thoughts, just top takeaways for people that are looking to manage up or even get confidence to manage up or to have sometimes it’s a confidence thing, even talking to your manager and saying, Hey, I’m thinking about this promotion. Yeah. What do you think? Right? Sometimes managers don’t even get that right. don’t get what employees are thinking. So I think from both sides, like, whether it’s the person managing up, or the manager, managing the employee, any thoughts on that? Or any suggestions?

Jax Scott 30:12
Yeah, the promotion thing. So I just had a talk with one of my best friends I’ve known for, like 15 1516 years last weekend, and she’s a PA, and she deserves a raise, and she is terrified to talk to her boss about it. And this is very, very common, I see it more in women than I do men. I don’t have any problems with it at all. I’m like, I deserve a raise. I deserve a promotion. But I’m like, here are all the reasons why I obviously don’t like approach it that way. But I understand the fair. So what I told her and what I and obviously, this is, this is going to be situationally dependent. It’s also going to depend on the relationship you have with your boss and all of these other factors. But you have to believe in yourself. And I know, that is harder said than done. But you do have to believe that you are worth it. And you like you have to work on some way of like self love, because a lot of times that fear is based around for women is based around, I don’t feel like I’m good enough. Because I asked her, I said why are you afraid? She said, Well, because I want to go into this surgery thing. And I don’t think I have enough experience. And I’ve got only two years and blah, blah, blah, blah, blah, and she works all the time. And I was like stop that, like most people would not consider all of those factors, like you have to know where you’re at right now is enough to be able to deserve this. So I said, instead of just going in and saying, Hey, I need to I need a raise, why don’t you I always like to promote, like go in and approach it very positively. And so and I like to practice too like I tell people all the time, run through scripts with your friends, like maybe you have a friend that’s in a higher management spot, talk to them and run through like, hey, I want to pretend that you’re my boss, and walk through the script and how I approach it is just assume they’re already going to support you, like put yourself in that because a lot of times we’re like, they’re not gonna support us, we have to get rid of that negative energy. And we have to go in as if they’re going to support us because we rock and we deserve this not egotistical, but with confidence, right. So you just go in and you go, Hey, I wanted to talk to you about you know, it’s that time of year for end of year reviews. And I’d love to work with you, like talk to you about how I can like, position myself for promotion, I really believe that you would support me in this knowing that for the amount of time that we’ve worked together, and it’s been a great experience working with you, is there some feedback that you can provide me, I do believe that this is the period of time that I should be up for promotion, and bla bla bla bla bla, because you can really, like, finesse it in a way that you’re still firm. But you’re not just like I need, you need to promote me, like, Please promote me and all these things. So I would encourage somebody, if they’re afraid of approaching their leadership about any challenges or learning how to manage up. First off, you’ve got to believe that you’re worth it, you and you can do this. And then work with friends work with somebody that you can talk through these scenarios with, because I I still do it if I get into a challenging situation it hasn’t happened in a long time. But if I if I’m like, I don’t feel comfortable with this conversation I’m about to go into, I will either write it multiple times and read a script, or I will like phone a friend and be like, hey, I want to talk to you about the situation how I how I’m going to present it, will you give me your feedback, that’s like, I’ve never failed with that. And it’s always great, especially if you think it’s going to be a really challenging one to get that outside opinion.

Melissa Aarskaug 33:33
100% Having people mentor and I think one other kind of piece is having data, so why you deserve the raise, what have you done 100% So going to a manager and saying I deserve a raise is a whole different way than saying, you know on your review, this is what I’ve accomplished. This is what I want to accomplish for the company. I’m all in I like to be in this role. What do I have to do to get there and really being collaborative with your leadership and sometimes it’s timing and timing is not right. And I’ve asked for roles and and not got um and I think sometimes people don’t want to give you the role because maybe they just don’t like you or they’re intimidated by you or you they’re looking for a different they feel like it’s a male role and you’re too you know, aggressive as a female or too direct and they want less of that on the leadership team. So I think there’s two perspectives think about it from the company’s perspective like what have you done to to warrant this raise this raise and two be okay that timings not right but don’t stop asking and it is uncomfortable and you got to do it. You got to push yourself out of the boundaries. And like you said, having friends practicing on your friends before and fumbling with friends is a safe place to try and learn and your friends will make suggestions and in recording yourself and re listening to yourself, and, and thinking what I give myself a raise.

Jax Scott 35:13
Exactly. Yeah.

Melissa Aarskaug 35:14
And just listening. And I’ve done that for myself, I recorded myself a few times. I’m like, Wow, that sounds terrible. I better try it this way. And I’ve had, you know, it’s funny enough, I’ve had people walk in when I’m recording myself, and they’re like, What are you doing? I’m like, I’m having a conversation with myself. Better myself, and you should really see people’s face.

Jax Scott 35:38
That’s awesome.

Melissa Aarskaug 35:40
Oh, no, I think you’re right, you got to push yourself out of your zone, you are worthy, you are worth it. Maybe you’re not at the right company. Right? If you’ve been asking for a promotion for a while, and they don’t listen to you and talk to you. Maybe you’re in a bad dating relationship with that company. And and you need to, you know, shop your talent. So, absolutely, really good perspectives. So two final thoughts for you any, like closing thoughts that you want to share? Before we finish up?

Jax Scott 36:15
Two of them, I have to do only two. Okay.

Melissa Aarskaug 36:18
How about five, whatever you are like.

Jax Scott 36:25
I would just wrap up, it could just be one big wrap up of, you know, it’s kind of the last thing we talked about. But anybody that’s listening to this, it’s all about effective communication. Everybody needs to learn. And I truly believe I’m really good communicator. But I used to be a terrible communicator. But I still need, like, I still need growth, because I’m really good with the people that are in my like, sphere of influence right now. But there might be an individual that comes in in the near term, that’s going to rock my world. So always be on your toes. And just remember that communication is more than just words. It’s about empathy. It’s about taking time in this busy world to truly care about your people. Yep. And just take the time to understand and have empathy and understand where they’re coming from. That’s really it.

Melissa Aarskaug 37:17
I love it. I love it. I’m so glad to I love riffing with you. I love I mean, I could just chat forever about all these things, cybersecurity, and veterans and women leaders, all these things we could talk about. So thank you so much for being here. Maybe you could do a quick plug about Outposts Gray or yourself or your writing or how can people follow you or give us the scoop.

Jax Scott 37:41
Heck yes. Thank you for the plug. Yeah. So Outposts Gray, that’s with a G R A Y not E Y, find me anywhere it’s on every handle. We are like really vesting in a podcast that we have under Outpost Gray that’s actually going to branch out on its own, we’re really excited about but it’s called two cyber chicks. So definitely check that out. But that’s where you can find all my information on YouTube, primarily Instagram, all the things and I’m huge in like giving back and cybersecurity. But Melissa, thank you for allowing me to come on the show. This was amazing.

Melissa Aarskaug 38:17
You’re welcome. Glad to have you here. And that’s Executive Connect. Have a great week.

Narrator 38:24
You’ve been listening to the Executive Connect Podcast. If you have questions or ideas on how to bring leadership to the next level, email us at executiveconnectpodcast@gmail.com And don’t forget to subscribe so you can catch every few episodes. Until next time.

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Bryan Hancock Headshot — Founder of Integrity Development

Bryan Hancock

Founder of Integrity Development

Integrity Development

Executive Biography

Bryan Hancock has been managing real estate investments—and overseeing development and construction projects—for nearly two decades. He has deep roots in Austin, Texas, and comprehensive knowledge of the opportunities and challenges in this fast-growing market.

Through his development and syndication companies, which he built from the ground up, Bryan has developed 50+ urban infill projects and managed $25M in real estate sales with approximately 35% return on investment at the project level. He also co-founded two private equity funds.

Bryan brings in-depth industry awareness, sharp business acumen, and extensive in-the-trenches experience to his work as co-founder and principal of Integrity Development. He partners with a team of professionals and industry experts (many have been involved in Austin real estate for 40+ years) to identify value-added and opportunistic investments that protect capital and reduce risk for lenders—while delivering outsized returns for investors.

Earlier, Bryan founded and directed Inner 10 Development, a residential development firm focused on Austin’s top zip codes and surrounding communities, and H2i, LLC, a real estate syndication company. He steered these organizations for 17+ years, overseeing the acquisition, buildout, and sale of single-family and multifamily properties, including a 350-unit urban infill joint-venture project.

Bryan was successful in delivering strong returns while minimizing risk for bankers and investors by taking a targeted, data-driven approach to opportunity analysis, due diligence, and strategic decision-making. He zeroed in on potential risks and developed proactive mitigation strategies to protect and grow investments.

Concurrent with his work at Inner 10 Development and H2i, Bryan established Gentry Lending Group, a private-equity debt fund. He also served on the board of Bullseye Capital Real Property Opportunity Fund. These experiences provided Bryan with a grasp of both investor and banker viewpoints, including an understanding of risk and liability on the lending side. This aspect of his background continues to shape his real estate decisions to this day.

There is another unique aspect to Bryan’s career—a corporate history that differentiates him from other investors and developers in this field. Bryan has built organizations, controlled multimillion-dollar projects, and supported billion-dollar programs for some of the world’s largest companies: Lockheed Martin, Microsoft, Dell, CACI, and Charles Schwab. He managed teams and vendors in the US, China, France, and India, and often balanced up to 10 projects at a time. He was trusted with a Top Secret Security Clearance from the United States government.

A business-savvy leader and lifelong learner, Bryan holds an MBA in Finance and Entrepreneurship from Texas Christian University and a Bachelor of Science in Electrical Engineering from the University of Texas at Austin.

Bryan founded the Wealth Investment Network, co-founded RealStarter (a crowdfunding platform for real estate investors), and was a member of the Urban Land Institute and Central Texas Angel Network. He has been a guest speaker at 20+ national events, including conferences and meetups through the Information Management Network (IMN), SXSW, Rice University, Bay Area Real Estate Summit, Soho Loft Conference, Texas Entrepreneur Network, and many others.

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Melissa Aarskaug Headshot — Founder of Executive Connect

Melissa Aarskaug

Founder of Executive Connect

Senior Executive, Board Member & Advisor

Vice President of Business Development
Bulletproof, a GLI company

Executive Biography

Melissa Aarskaug is a global executive and business leader at the forefront of the technology/cybersecurity industry. She shapes strategy, leads teams, and partners with Fortune 500 companies and other enterprise clients to protect their organizations from risk and noncompliance—while improving operations and accelerating growth.

For 15+ years, Melissa has taken the reins to propel organizations to the next level of performance. By combining business acumen and revenue optimization with the sharp mind of an engineer, she uncovers and seizes opportunities for profitable growth in the US and around the world.

Melissa has established a distinguished career with Gaming Laboratories International (GLI), where she is a key member of the senior executive team. Throughout her tenure, she has assembled teams, developed new markets, and influenced P&L impact, ultimately positioning GLI as the #1 provider of testing, certification, and cybersecurity services to the global gaming and lottery space.

After achieving this feat—a big win for GLI and game-changer for clients worldwide—Melissa steered both GLI and Bulletproof (acquired by GLI in 2016) into untapped verticals: finance, government, healthcare, higher education, hospitality, and retail. An enthusiastic, knowledgeable growth driver who cultivates partnerships and rallies teams, she led GLI/Bulletproof to dominate these markets as well.

Before joining GLI, Melissa shaped and executed strategy as Vice President of Business Operations for LV Investments, where she built and optimized a portfolio of commercial and industrial properties. Earlier, in a very different role as Project Engineering Manager for Fisher Industries, she directed and mobilized a team of 550 employees and contractors to develop the world’s largest concrete bridge. Previously, she headed a major engineering project for Pacific Mechanical Corporation.

A curious, lifelong learner, Melissa holds dual Bachelor of Science degrees in Civil and Environmental Engineering with minors including Business and Mathematics. She is a Karrass Master Negotiator and C4 Executive Coach who actively pursues ongoing education and inspiration as a member of Chief, Austin Technology Council, Austin Women in Technology, and Toastmasters International. In addition to her own personal and professional development, Melissa is committed to helping other people thrive both inside and outside of the workplace. She actively mentors and empowers team members at GLI/Bulletproof, and is an executive leader and coach for Global Gaming Women. She founded Young Nonprofit Professionals Network (YNPN) Austin and is a current or past board member of many organizations, including Emerging Leaders in Gaming, Ballet Austin, Texas School for the Blind & Visually Impaired, the Society of Women Engineers, and the American Society of Civil Engineers. She has been a Junior League volunteer in Austin, Las Vegas, and Reno for 15+ years.

Throughout her career, Melissa has inspired individuals, teams, and entire organizations to think differently about innovation, cybersecurity, leadership, and business development. She was honored as one of the “Emerging Leaders in Gaming: 40 Under 40” and she continues to share her ideas and expertise through publications, podcasts, webinars, and presentations.

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This is the Executive Connect

A show for the new generation of leaders. Join us as we discover unconventional leadership strategies not traditionally associated with executive roles. Our guests include upper-level C-Suite executives charting new ways to grow their organizations, successful entrepreneurs changing the way the world does business, and experts and thought leaders from fields outside of Corporate America that can bring new insights into leadership, prosperity, and personal growth – all while connecting on a human level. No one has all the answers – but by building a community of open-minded and engaged leaders we hope to give you the tools you need to help you find your own path to success.