Short Story Long: Life Lessons from Leaders, Coaches, and Entrepreneurs
Short Story Long shares life-changing stories of growth, resilience, and reinvention from leaders, coaches, and everyday people navigating pivotal turning points. Hosted by leadership coach Beki Fraser, each episode explores the moments that shaped someone's path and the lessons we can all learn.
Every other week, Beki follows up with a Skill Builder episode that breaks down insights from the previous story into practical tools, reflection prompts, and leadership actions.
Whether you're building a business, transitioning into a new career, or learning to lead with greater purpose, this podcast offers real stories and practical strategies to help you grow. New episodes every other week.
Short Story Long: Life Lessons from Leaders, Coaches, and Entrepreneurs
Aaron Wilkerson's Story: The Mindset Shift That Fueled His Promotion
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In this episode, I reconnect with Aaron Wilkerson, a former client and thoughtful leader whose growth journey offers real insight into what it takes to move from technical expert to strategic leader.
Together, we explore how leadership evolves beyond having the right answers — into building team capacity, developing others, and aligning your work with broader business strategy. Aaron shares what shifted for him during our coaching, how he built the confidence and skills to lead at a higher level, and why he's now focused on multiplying impact rather than going it alone.
His story is an honest look at what leadership growth actually requires — and what it makes possible.
Connect with Aaron on LinkedIn: Linkedin.com/in/aaron-wilkerson-81bb21a/
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Learn more about her coaching: TheIntrovertedSkeptic.com
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Short Story Long is produced by Crowned Culture Media LLC
The Cookie Analogy for Leadership
Speaker 1Are you the person that automatically goes into the oven , like goes into the kitchen and like , start baking cookies . Or do you start calling every single bakery in the area and say , hey , like I need , you know , I need 10,000 cookies , I need 20,000 cookies . So I think that's the big difference between the person who automatically goes to I need to bring in more people , or is it like , well , I'm going to be up all night baking cookies , 30 at a time , so I think I'd switch to the I need to go and grab and create the group that can deliver the outcome , because no one cares about how the sausage gets made at the executive level . They just want the outcome and they want the deliverable .
Introduction to Strategic Leadership
Speaker 2Hi , I'm Becky . Welcome to Short Story Long . In this podcast , we discuss ways you can integrate who you are into how you lead . The shift from technical manager to a strategic leader is greater than it appears . Many believe they are ready for promotion , and fewer who understand the deeper skills required for senior leadership . Today I'm talking with a former coaching client who learned to focus on team development , business strategy and understanding stakeholder needs , rather than just being the technical expert who could answer every question . The coaching helped him recognize that leadership is about building capabilities , setting expectations and driving organizational value , not just individual technical prowess . He likes giving me some credit , and I know he always had it in him .
Speaker 2Today's guest is Aaron Wilkerson , a lifelong learner whose curiosity began with dismantling toys and evolved into a career in data and strategy .
Aaron's Leadership Journey
Speaker 2From a young age , aaron was captivated by how things work , a mindset that now fuels his passion for solving complex business challenges Professionally . He thrives at the intersection of strategy , leadership and execution , three elements he believes are essential to meaningful transformation . As a specialist in data and analytics , aaron understands the economic power of data and how to translate insights into business outcomes . Throughout his career , he's built data products that not only inform but drive real value . Hi , aaron , welcome to the podcast . Hello .
Speaker 1Becky .
Speaker 2I'm excited for you to be here with me today . It's been a long time since we've chatted , so I'm excited .
Speaker 1I know right . Thanks so much for having me , becky . I'm definitely a long-time listener , so very fortunate to have the opportunity to be on this podcast .
Speaker 2Yeah , well , thanks , thanks . And , as you know , I warned you that we would be talking about a meaningful change in your life at some point in time , and why don't we just jump right into that ? Tell me a little bit about what was the inflection point that you wanted to discuss today .
Speaker 1Yeah , I think it's good to go back to the beginning of how you and I first met and started working together . So I'll say for me , I've been on this leadership journey for about 10 years now and I think there's a couple of inflection points around the initial jump to leadership , like the initial manager role , and then jumping from manager to like senior leadership , Like so going from a manager to senior manager and like senior manager to director . And I feel that when we first started working together I was kind of in that struggle to kind of get from manager to the next level , senior manager .
Speaker 2Absolutely .
Speaker 1I remember that was the last company where I believe our CFO kind of identified me as like someone with high potential . So they had a number of us working with you as a kind of a career coach to kind of at the time I didn't know . I mean , I didn't really have any idea about what coaching entails . So I thought it was just well I just go to you and you give me all the answers and I just leave and go away .
Speaker 2Yeah , I quickly dispelled that belief , I think .
Speaker 1Yeah , it was interesting because I feel like I think we had like three or six conversations but I remember just you kind of peppering me with questions , right . So I think your approach was you always had like a question ready to go , where you were
The Coaching Experience
Speaker 1kind of asking me and kind of leading me kind of with these different questions and things to consider . And I remember at the end of it , I think one of the sessions , you said like aaron , like you already had , like you have all the answers , like you , that there's nothing you really need to to figure out , like you already like know how to process these things , you know how to talk about things . So I think that was a huge kind of in the like for me confidence in terms of I had the tools , I had everything I need .
Speaker 1I just need to go and kind of take that kind of out into the world yeah so I think after that it was kind of a , it very much helped me in terms of , you know , believing in myself a lot more . I know , even after I worked with you through the company and like even separately , you know you and I worked together for a little longer just to kind of talk through those things . I think that was a huge point because I think going from like a manager to like a director is a huge job and it's a different skill set .
Speaker 1Like getting to a manager role . I won't say it's easy , but it's very straightforward in terms of taking on more responsibilities . But that's a huge jump , kind of going into that senior leadership and having the tools to know , like , how to talk about strategy , how to lead projects , how to have executive presence , how to present to a large amount of people . So I think those were the things that weren't I was not as skilled at . I didn't like necessarily have the confidence .
Speaker 1So I think working with you kind of built out like the how do I think about my involvement , what do they need to know about me , like how am I presenting myself ? So I would say you know that was a huge inflection point for me because I know I struggled for a bit just trying to make that leap . But I think working with you kind of helped me gain the skills I needed to kind of jump and kind of doing more and taking more ownership of my career .
Speaker 2Yeah , making that transition right Because it's like you say , it's different . Even going from team lead to manager is different than manager to director and arguably , again , director to vp is another dramatic shift as well that can take place because they become larger jumps at that stage of the game , and so there are additional skills that need to be learned . But then there's also also like who am I in this role ?
Speaker 2And so I'm kind of excited to talk to you about those things . And yet , before we go there because you know I'm always excited to learn about those kinds of things I'd love to go back to that moment where you were sort of being told hey , you know , here's this opportunity for you to be able to expand your skills . You get to work with this coach and things . What was your experience at that point in terms of being a manager and being in that role at that point in time ?
Speaker 1Me going to that company I was at when we met . I had before then I had taken a step back because I was a manager at a previous company uh , it was more of an international company . I was very busy , I was making good money but wasn't very present with my family . Just the hours were crazy . I had a very young family . So I ended up having to take a step back to a different company .
Speaker 1So when I joined the company where I met you at , I got kind of back into leadership . At that point my version of leadership was kind of I was the guy who knows things . People have questions . They go to me . I can answer every question . I worked on the technical side , so I was the one kind of leading a team and writing code . So to me I felt that I didn't know that there was a different skill set . So I thought it was more like an entitlement where I've been doing this for a while . People go to me for answers . I'm the guy who they come to for things .
Speaker 1So why am I not getting promoted , or why is this taking so long and why is this so difficult ? So I think I approach it as kind of like the I've already arrived and I already have what I need . So this is just more formality . They need to promote me and move on , um . So I think I approached it . I definitely was excited to work with you and kind of figure out those gaps and what I didn't know , um , but I think I had started with you working . I won't say a frustration , but an eagerness of you know why is this not happening ? I'm ready , I'm the go-to guy . That should be enough to move on . But not knowing what I know now in terms of just all the different things I hadn't considered or the what else it took to kind of make that jump to the next level .
Speaker 2Yeah , and it's that opportunity to see yourself in a different way , right , because you're even now , as you're talking to me about it , talking about it in terms of before and after , and when you think about , even
Building Teams vs Being the Expert
Speaker 2while you were still at that organization and you were growing more and more into that director mindset , even without the promotion , right , like going forward and developing those skills and those capabilities , what were some of the things that you were recognizing at that stage , that were changing for you .
Speaker 1I would say building a team and building a capability , that I didn't have to necessarily be in the weeds . I think I took a lot of pride in knowing that when someone asks a question , I can explain to them in detail all the nuances of it and I was , and other people my team could but I was kind of took solace and like , well , I'm the guy who can answer all those things . So I think , realizing that I needed to build out the team itself , not just me , like I need to also build up , like who are the next leaders in the company under me ? Like who can I build up as as leaders and technical leaders and working with different stakeholders I think that's something I didn't think about . And I had some , you know , very frank conversations with my executive at the time and I remember showing him org chart where it showed me as like a director and I showed as like needing to hire in all like these different other managers . But it kind of showed and he kind of even pointed out , that I had not really built up any of the like the people under me . So I was like , well , I need they were like I need to bring in all these other leaders and what do I do with the team that's still there . So it kind of showed me , like from a development perspective , how I was lacking to recognize that , like who was the next person up on my team or who was I developing . So that was kind of a big eye-opener in terms of like talent development and things like that that I hadn't thought of at that time .
Speaker 1And also thinking about business strategy . I think when I first , when I was we first started working together , I wasn't thinking about like business strategy enough and how do I help the business make money ? How , how do we think about how the business can thrive and grow ? I would just think about like my corner of the world , but not really tying it to the business as a whole . So I think so that that's those kind of different changes that I start to consider and make as we started to work in together is starting to think about , well , if I'm working so I was talking with the COO like what does he care about ? What's on his mind ? What does that ? What do I want him to know about my involvement ? Those are kind of those questions that you had asked me . That was like oh , that's a yeah , I should think about what's important to him .
Speaker 2What's important to him making money .
Speaker 1I could ask him that yes , exactly , yeah , yeah , but yeah , so that those are those types of things that I just had to . Those are the mindset shifts that I had to make to get to the next level .
Speaker 2Yeah , and there's such common leadership transitions that we need to make right . It's that idea of I can't stop doing this job until there's someone else who at least has a certain degree of that capability , who can pick up some of the things , so that when I'm taking on responsibilities of this larger role , I can't do all the things below . That's not how capacity works . And so that opportunity to really see , wow , as I develop these other people , it actually creates room and creates space for you to be able to move on to that next level . And then my recollection was that you had so many capabilities that contributed to seeing these things from a strategic perspective .
Speaker 2And that's one of the things , too , that I think is really powerful is that we don't always realize what it is that we're bringing to the table that makes us have that potential for that leadership , because we're not quite sure what we're supposed to do . So it's hard to reassign those skill sets that we already have to just a different task and a different responsibility . As you build your team up , what are some of the risks that might be felt by someone right , like if you were giving advice to one of our listeners right now , and one of the fears can be , you know , but if I build other people up , then what am I supposed to do ? Do they just find me redundant and get rid of me ?
Speaker 1right .
Speaker 2Like what's the reason that you would give people to do that ?
Speaker 1I think one is capacity . So it's easy for you to think that you can jump in and do everything , but if you do that , you're not giving the organization as much bandwidth as you're capable of . So if I go and do task A and then I let my team do task b and c , like you're getting much more done , versus me doing all the work of my team and doing like lower level , like them doing like lower things . Like so , as I grow and do more things and I bring them involved , like the organization gets a lot more capacity and throughput and more things can get done . And also , to your point , it's can get done . And also to your point , it's leveraging our , our skill sets and leveraging using our talents most effectively .
Speaker 1So , while I could code , am I a better communicator , strategist and all these things and leader than a coder ? The answer is probably yes , right . So I think it's like like let the really smart coders who do this day and now , like , put them in a position to code and leadership should be going to . Like talk to stakeholders , figure out how our work contributes to the organization . Like do the things that are much more value added for you versus like doing like the bare bones kind of coding thing that you used to do in your previous role . So I think the capacity thing is always kind of the big one , like I mentioned earlier . It's just I think you and I talked about that , like with bringing up other folks , you can get more done which benefits the organization , versus you taking everything and just giving them scraps .
Speaker 2Yeah , it actually makes me think about . You know , there's never a lack of work to get done these days , and so what I hear you describing there is you create more capacity . By creating more capability and really having that ability to , then your team is able to deliver more and people start to notice and start to recognize that and then they go oh hey , aaron is at the helm on that . What's he been doing over there ? Building all those quality people up ,
Finding the Right Resources
Speaker 2and we need to pay attention to what's going on in that quarter of the organization . So I know that you're in a more senior role with a different organization right now . What are some of the things that , now that you're in that , that higher level role that before or during the time that we were talking , you were not in that . Yet what are you noticing now with hindsight , as you've made that change ?
Speaker 1I think the top thing is , when I understand work , projects and work streams , I don't assume that I'm the person to do it . Right ? It's like always the first question is who are we going to bring into the room to get the actual work done ? I don't assume it's me . Or , if we're limited , right , if my team is fully full , who else can I bring in out from outside ? Right , so consultants , contractors , like who else can we bring in ? So I don't assume contractors , like who else can we bring in ? So I don't assume , like my default is usually who do I need to get involved to work on this task ? I'm not assuming that it's only me that's going to be doing that , so that's , it'll been a huge shift , right ? So it's like okay , we have budget , like let's bring in more people , more people like my uh , a leader of previous company kind of uses analogy where you know , imagine like you were working at some event and someone says , hey , by tomorrow morning you need to have 20 000 cookies .
Speaker 1Like , are you the person that automatically goes into the the oven , like , goes into the kitchen , like start baking cookies ? Or do you start calling every single bakery in the area and say , hey , like I need . You know , I need 10 000 cookies . I need 20 000 cookies . So I think that's the big difference between the person who automatically goes to . I need to bring in more people , or is it like well , I'm going to be up all night baking cookies , 30 at a time .
Speaker 2So right , I think right , so I think I've switched to the .
Speaker 1I need to go and grab and create the group that can deliver the outcome , because no one cares about how the sausage gets made at the executive level , they just want the outcome and they want the deliverable . So if you had to bring in all these different people , like that's , like no , they don't ask me . Of course , if it's too expensive they'll care , but if you can do it like within budget , how you do it like that's up to you , so the less stress you can make it .
Speaker 1So I think that's one of those big shifts to me is going from I have to be the guy that does it to I have to build a team that can deliver that . Then also it's the the business strategy of okay , not only is like do I need to make 330,000 cookies ? Like , why do I need to deliver 30,000 cookies ? Well , it's for a nonprofit and we're trying to make a good impression , so we're trying to raise money for fundraisers . So that's also the next level of thinking of not only do you have the task , but like why do you have the task and what's it going to deliver and why do you need to do that ? So , because before it'd be like someone comes across with a request , I say , oh , I can do that , I'll get it done in two hours , I'll give it to them and they just go on their way . But now it's like , like why are they asking for this ? Like , what do they need from this ? Why is it important ? How does it make , how does it help the organization make money ?
Speaker 2so that's also kind of the evolution of , kind of how I've kind of changed over the past couple years yeah so my development well , and that sounds fabulous , right in terms of really that automatic , like I can make cookies , right , but I don't think that 30 000 cookies in they're probably going to be as tasty as the first , maybe 60 .
Speaker 1Right , right .
Speaker 2And right , because there's a diminishing return , because we're like baking all night and all of a sudden you're exhausted and you switched out the sugar for the salt , and now they're nasty , you know , and so there needs to be that recognition of where is my limit , that recognition of where is my limit , and because something that you can do in two hours you may reassign to someone else , or if it's really urgent and everybody else has gone home and you're like , yeah , okay , I'll spend two hours doing this , but it's a conscious choice then to do it , versus what you're describing as that automatic of who is it that I can rally , who has the capacity and the competency to be able to do this task ? Because you're not calling the woodshop to make cookies , right .
Speaker 2And so it's also identifying the right resources for the right task in that way .
Speaker 1And specialization is something I've learned that is very important . So I always say , like , if you have someone working on something part-time , you get a part-time result . So if I'm doing this like player coach thing , where I'm like sometimes leading , sometimes doing code , I'm only going to give it a part-time effort . But if I have a team of people who do this full-time , they specialize in this like I should be leveraging the people who are very good at this , much better than I am . Much like the cookie reference where , yeah , I can make some , but I have to go out and find a recipe . I got to figure out what works .
Speaker 1But if there's a bakery that already makes $10,000 per day and they're making money and they're good at this , I should be leveraging the people who specialize and are very good at this , who can deliver high-quality product , versus me , who can kind of throw something together but it won't be as good . So I think leaning in on specialization is something I've kind of realized , uh , lately . Just as important to talk to the experts , find that people are really good at this and let them like lead the charge I kind of throw . Another example , too is um , I have a growing up like in this local data community in the metro Detroit . So we're thinking about , we're looking at doing a doing a conference . So fabulous .
Speaker 1So in November we're planning on doing one . So I end up bringing in like an event planner because I realize , if it's just on me , like I could do a part time , but I don't have the time to like do a full calendar and planning . So I talked to someone I knew and say , like you're good at event planning , let's bring you in to help us out with that . So it's like that's a huge change from like okay , I'll do this and I'll do this after hours and a nighttime , I'll put together the schedule , but they want you to like find someone who's really good at this who does this for a living and have them do it because it could be a much higher quality product , right , and it's also one of those things where , if you do it , you make all the first timer mistakes .
Speaker 2Right , and so it does . That's what really contributes to . The better product is that they've had all of this experience , they have all this knowledge . And it makes me think about the reverse , where the leader thinks that you know , well , I'll just go in and I'll change this code , but maybe they don't tell people about where they did that right and so , or they meant to but they didn't , and things happen right .
Speaker 2Our brains don't always do the things that we planned for them to do and all of a sudden people are like I can't believe that he was in there and changed that code , but they don't want to go to the boss to say anything about that . But it kind of creates a bit of a culture dynamic in that . What would you say
Team Culture and Setting Expectations
Speaker 2you've learned about leading from a cultural perspective when you have this different focus and these different priorities now in your role ?
Speaker 1have this different focus and these different priorities now in your role yeah , that's something I've learned too from a previous leader is like the cultural aspects of not only especially if you have multiple teams it's not only do you have the teams , but understanding how they interact with each other . So learning those because easy to expect that we're all professionals , we all are full time-time , we make a good salary . We should just want to work together , but we're humans like that doesn't happen .
Speaker 1So right anytime you have groups of people within a team or different teams , there's a key aspect of how do they interact with each other . So , do they talk ad hoc ? Do they have recurring meetings ? Um , who owns that relationship ? Like , is it me ? That's a schedule , did they schedule that ? So those are those cultural things . I've had to learn how to ask and kind of draw to people , because when you make assumptions and things fall apart and you're like , well , what happens ? Like well , they didn't do that or they didn't schedule that , or it's like , well , do you have like standard operating procedures ? Do you have like a racy to talk about roles and responsibilities ? So that's the the real work of a leader that to find , like you have to go into the weeds and figure out like you need to know each and every individual on your team like what's their trigger ?
Speaker 1like you know , everyone has trigger words . Where their trigger words ? What sets them off ? Are there any baggage ? Like you know , they don't work well with a certain person because of these historical issues . So that's another one of those like team building thing that has nothing to do with , like , if you're technology , writing code , deploying software , implementing things . It's all about interpersonal dynamics that you have to learn to build out a good team culture to get things done , or else you have a lot of smart people who just can't work together to get things done or else you have a lot of smart people who just can't work together .
Speaker 1So that's another kind of learning experiences figuring out those dynamics , because you have to know how these people interact with each other and what works and doesn't work and where there are gaps that you have to fill in .
Speaker 2Well , and I've found because , as you know , I work with a lot of folks who are in technical spaces , right , and I think there's also that element of just give me the rules of engagement , just like , what am I supposed to do ? What do you expect of me ? And , you know , if they don't like them , hopefully they say something about those rules of engagement . And really , I was talking to someone even recently who was saying look , if there are more than six people in a room , someone needs to be facilitating that conversation , because otherwise it's just a circular kind of conversation that tends not to go anywhere .
Speaker 2I'm designating a person on my team , as you own this meeting , and I expect that you handle whatever comes up when there's a bit of you know , of a kerfuffle , if you will , around what's going on between and among people .
Speaker 1Well , I would say setting expectations is one of the top things I think leaders have to do and I think a lot of the even with pre-epidemic performance challenges , I usually find that expectations were not set , Even like I've dealt with that with even people on my team where I'm like , well , why aren't they doing this ? And I hope they were doing that I was like , well , did you set the expectation ? Did you tell them I'm expecting you to do these things ?
Speaker 2Well , they should have known . Yeah , exactly , exactly . They should know , or they ?
Speaker 1should magically read my mind . Yeah , so that's been a hard lesson too is just , even when I'm in meetings , setting agendas , setting timelines , like setting expectations and saying out loud , even in writing is I expect you , this is what I expect of you , I expect you to do these things , these things , these things that they pick up on , and that's great . But sometimes you do have to kind of set expectations of your team , of individuals , of stakeholders , and I think that's also like those kind of more advanced kind of things I've kind of picked up on is in order to kind of get away from just argument to like resentment , like if did you set that , I would tell my team , like , okay , did you tell the person you expect that ? Did you set the , the lead for what you expect them to do ? Did you lay out what that means ? Yeah , of course you can't micromanage them , but at least you can give them a framework of .
Speaker 1Here's the bare bones of what I expect from you in this role , this project , this task , this meeting . To your point , the six people there are you . Who are you expecting to talk like ? Is there an agenda whose names on ? Are they supposed to prepare something ? So those are those things that you don't think about until you kind of get into more conversations about kind of career development and growth .
Speaker 2Absolutely , and it makes me think about , too , that whole component of they might also be looking for that next step forward , might also be looking for that next step forward . So you preparing them for being able to lead the team and being able to ask those questions not only keeps them sharp where they are but also continuously helps them step up to a higher level , gives you room to be able to move forward with that as well . So I know you're in this senior level role now and you have these responsibilities . You have the larger team . You're exercising these strategic things , building the team . When you think about what you expected that role to be back when you were kind of seeking that promotion to be at that level , how much is it the same and how much is it different from what you expected it to be now that you're there ?
Speaker 1I realized in retrospect that I wasn't ready . Now and I think that was kind of through working with you , I think I got more of a glimpse of why I wasn't ready yet . But I'm very happy that I didn't kind of get what I thought I wanted at the time at the time because I realized that I would have been of get what I thought I wanted at the time at the time because I realized that I
Growing Through Community Building
Speaker 1would have been not prepared and I would have like struggled in the early days kind of getting ready .
Speaker 2So I mean , I think I didn't really .
Speaker 1I think I think one of the best questions you asked me was when I was talking about like my next , like my next leader in a skip level . You asked questions around okay , like what's important to that person ? Like what do they need to know about what you're working on ? Like what's important to them , how are they successful . So it's kind of like that empathy around thinking about okay , my leader , he wants , he's thinking about the entire group , he thinks this is a measure of success . So it was kind of a way of me thinking about okay , that's where I need to think about . So , if I'm trying to get to the next level , okay , what does the next level entail ? What do I need to consider ? What's the measurement of success ?
Speaker 1So I would say that kind of prepared me to kind of think about well , my thinking needs to be different , I need to have different expectations , the way I work needs to be different . So I think I was better prepared for the role , like after some time and kind of doing some soul searching , versus kind of when I thought I was ready at the time . Um , I mean , I think I mean to answer your question about just what is it ? What I thought it was , and I I think it's . I think it is because I was more prepared for it in terms of knowing what to think about , and I think one of the biggest questions I got was about strategy . So that was one of the other kind of some other pivot points was me being told that I wasn't going to get promoted because I need to create and execute a strategy , and at the time , I had no clue what that means . Like . If you ask people what strategy means , you're like can get different definitions .
Speaker 1So that one really threw me off because I couldn't really answer it . So I think , going through yet another kind of process of understanding strategy , how to deliver it , how to communicate it , that did prepare me for , you know , eventually kind of getting into that senior leadership role . So I would say and when I first started is so , I think , when I first thought I was prepared the role is definitely different than what I thought .
Speaker 2So I think at the time I thought it was just going to be .
Speaker 1Well , you do what you were doing already because you're so smart and talented . You just keep doing that . But you get a new title , and you get a title and you get more pay , which I was definitely not prepared for . But I think now , on the other side of it , I realized that I had some work in soul searching to do , which I've kind of gone through the process , and then I did get the promotion . So I did feel prepared once it did happen , because I had done more work than just trying to get better at the job I was at the time . I started to get myself ready for the next level .
Speaker 2Yeah , that's really insightful . It was a classic example of what got you here won't get you there , right ?
Speaker 1Yes .
Speaker 2Kind of mentality and it's hard to see what you have not yet experienced , right , and I think that there's a really powerful thing in there has been very diverse , right , because sure , you did the work with me and you've done some growth things within your employer , but then you took that outside of your employer as well . Talk to me a little bit about what you've learned from some of these other , what I kind of want to call extracurricular , but they're still related to work for you it is , uh so .
Speaker 1So that was like so I think you and I were you and I first started working together and I think 2020 or 2021 so 2022 is when I had that first kind of had another challenge where I was told I need to be more strategic .
Speaker 1I didn't know what that meant , so I kind of went on like a personal learning goal so I kind of jumped in on LinkedIn and started just reading , like learning from the community , so I kind of started following people and I really kind of got a real crash course in what I thought was strategy versus what these people who are experts in the field saying that .
Speaker 1So that was a huge undertaking to kind of grow in terms of what I understood strategy to be from LinkedIn and I started building up these goals right . So my first goal in 2022 was I want to be on a podcast , I wanted to present at a conference . So I started posting a little bit on LinkedIn and those opportunities came to me . So I was invited to present at a conference locally and I was on a podcast and I think those were kind of those ways to grow in terms of authenticity , finding my voice , finding my authentic voice , building my brand . So that was kind of 2022 , just kind of playing around , and 2023 was I think I talked to you actually , I think right before I did it , so I did this year challenge .
Speaker 1So in 2023 , I said I'm going to post every day on LinkedIn Because I found success in 2022 . So I said , if I going to post every day on LinkedIn , like that was because I found success in 2022 . So I say , you know , if I just posted every day , what would change ? I think I remember I talked to you like right before then . I was like I don't know if this is going to happen . I'm kind of afraid . How am I going to do this every single day , every single day ? So it kind of went all in with that . So I said every day I'm going to post and I did value .
Speaker 1So it's one of those things where you make small investments , you see , you know you bear fruit and you do kind of bigger investments and you see more fruit . So it's one of those things where the flywheel it just kind of snowballed because I saw some small successes , I did more , I saw more successes . So I found that you know , if I invest more and more into like personal development , I'll see more and more come out of it . So yeah , I just kind of went all in on linkedin in 2022 , um . 2023 went all in um .
Speaker 1Last year I started building communities , so I started like the , the meetups , uh , every single month at different bars and restaurants within data folks so kind of continue to invest in the community and you know , it's kind of like planting seeds where you don't know what's going to happen , but you just kind of throw a bunch of seeds in the ground and you hope that it one day bear fruit . So I would say , yeah , that's been another part of my career is just kind of doubling down on professional networking , brand authenticity and building community , and that's also helped me in terms of growing like learning about strategy , learning about leadership , learning from my peers People are older than me who kind of have been doing this for a while , opportunities to speak and kind of share my thoughts on things , but I'll say that was another huge shift for me was kind of digging into the LinkedIn , yes , and one of the things that , even as you describe that sequence of events , it shows that you developed the skills that you needed to that first year .
Speaker 2The second time , you're like I'm going to wade a little bit deeper into this and I'm going to develop even more capabilities and make this commitment to myself , which is so impressive , that you posted every single day . I remember talking to you about that at one point in time and you're like , some mornings I woke up thinking I have no idea what to say , but you know , eventually right , Like something comes to you and you post and sometimes it might be up thinking I have no idea what to say .
Speaker 2But you know , eventually right like something comes to you and you post , and sometimes it might be hi , I posted .
Speaker 1I don't think you ever did that , but I might have if .
Speaker 2I were in that shoes , close to it . Pull together and get some excitement around where you were talking even about the opportunity to do a conference this fall and really be able to do that . That's an exciting adventure that is outside the day to day that taps those same skills and grows you in a different way , on the same path , it seems .
Speaker 1Yeah , well , and also it's a like in 2022 was when I made a shift . I kind of I switched jobs so I went from my last company to my current company , and that was also through LinkedIn . So that was I was on a summer vacation in North Carolina with my family . Someone reached out to me on LinkedIn and said I had this opportunity and I was on vacation , so I updated my resume and I submitted it and then things happen and I have the job that I currently have .
Speaker 1So it's another things where , if you try out these new , different things , like opportunities kind of come your way . So the same with the community we've been building , that was kind of identifying gaps . Right , so in your day to day job , your job is to kind of identify gaps and right so , in their , in your day-to-day job , your job is to kind of identify gaps and like come up with creative solutions to solve them . So I kind of took it a step further from like a one-on-one with my company to saying , like Metro Detroit . So I think a group of us said , hey , there's a gap here where we don't have opportunities for people to meet up in person , meet in the real world , talk about what you're working on , because COVID killed a lot of that , because a lot of them fell apart .
Speaker 1So that was one of those things where , like you know , part of my job is just finding problems and solving them . So it was a hey , like let's just take this medium called LinkedIn and like put out some flyers , find a place , get people together and see where it goes . Because also , like some people always ask me what's the plan ? It ? Some people always ask me what's the plan it's like there's no plan . The plan is you kind of go month to month and kind of see where it goes . You listen to what the people say . It's really just kind of those placing bets and just trying things out . Even with the newsletter . Right , I kind of have a loose newsletter . I kind of do it once a month . I need to do it more often .
Speaker 1It's one of those things where it's like another avenue which to kind of share , like the storytelling around what I'm working on , my thoughts about things , like what I see as challenges . So I mean I think I've seen so far is that as much you can put into the world , as much good energy , as much , um , you can help people , like that comes back to you at you tenfold . So I think now I'm looking at outside of my current job like what are other ways in which that are connected to that , that I can still help people problem solve , offer uh connections , uh community . So I think those have kind of expanded my career to kind of be something what it is now , which is definitely not what I expected like four years ago , like doing the newsletter , newsletter doing podcasts , building a community . So it's just kind of . They just kind of build upon each other . We started with just like just one of the posts on LinkedIn .
Speaker 2Yes , absolutely , and it all of what you're saying to highlight something that I remember noticing about you very early in our discussions too , that there's a generosity of spirit , like even when you were jumping in , I can do it , I can be the go-to guy .
Speaker 2You was from a place of I want to help people and I want them to get what they want , and you've shifted that and you can still like give a person a hand directly maybe not in coding , based on what you're talking about here maybe not in coding based on what you're talking about here , but at the same time , hey , if you have a need , I want to see what I can do to fill that gap and help you get to where you want to be , which is a beautiful thing , and it just makes me really excited that we had a chance to talk about this today , and I guess my question to you would really be is there anything that you would want to talk about that we didn't discuss or questions that you would have for me today ?
Speaker 1So I think the like , the evolution of career right so I think we were talking about that now where I see my career is growing into not just the day-to-day work but also like building a community and kind of so I think I think career is kind of building , kind of seeing these offshoots of like a traditional nine to five plus these additional things that can kind of create a career
Career Evolution and Taking Risks
Speaker 1. That's not like a like you're kind of cookie cutter and I know that . You know you've written a book . Like you know , and I've seen you've grown in that too , where you have you have this podcast . I know you've written a book . So I guess what are your thoughts on careers in 2025 and from your work and your coaching kind of , where you see the idea of careers going into the future ?
Speaker 2I think 2025 has been a rough year for careers and there's a lot of uncertainty that's out there right now . I mean we see in the news maybe a little bit less so now , but I mean we see in the news maybe a little bit less so now , but certainly especially in earlier months of the year there were a lot of changes and a lot of cuts to roles . There are still some of those that are happening and there's a lot of fear and what that does is it limits the willingness to take a risk and to do something . That's a little bit off script and I actually went to a coaching course . I was certified already but I just thought , hey , this is a really cool guy who's got really great ideas . So I went to his coach training and he was talking about when you're ready to leave a role or you think that they are ready to get rid of you . That's the best time to take a risk . I mean , what are they going to do ? Fire you , right , if they were going to do that anyway , like , go gangbusters .
Speaker 2Now my HR colleagues from history are like Becky , stop it . It's the people who take the risks that are the ones who get noticed and have that opportunity to move the needle in some place . So when we stay quiet , when we stay small , those are the moments where we're just suffering through our employment because you're seeing those things that need to change , but now you're timid about sharing it and , of course , nothing's going to change . Now I'm not encouraging loud mouth , be obnoxious , right , like , please understand , but it is verbalize , come with a solution . Look , I'm seeing this gap . I feel like this could be something that we could develop as a solution .
Speaker 2I don't have it all figured out , I don't know all the ins and outs . I just want to get started on figuring this out . I find so many people that I've worked with over the last couple of years have gotten very hesitant to say what they want and what they need . And I'm out there encouraging people . Find the right way to say it and yet deliver that message in a way that is meaningful to your employer , kind of like that question I was asking you right about the skip level . What is it that they're thinking about ? What is it that they're worrying about , and how can this thing be relevant to them in that world ?
Speaker 1I would agree . One of the things I had to overcome was the fear of telling people what I wanted , and I think that was the huge one and say , hey , I would like a promotion , I would like I would like to move to a senior manager , I would like to move to a director level . So I think , as I think , being comfortable asking your employer , asking strangers I mean , it's the last year was hard for me even to say I want , like , I would like you , I don't know , to come to this restaurant and meet a bunch of people you don't know absolutely and talk to each other like but you have to ask .
Speaker 1I think the spirit of saying , hey , this is what I want to see happen . I would like you to be part of that , or I would like you to make this decision and say yes to this , like that's a huge change that I think people aren't used to , and even it was uncomfortable for me . I had to get accustomed to people saying well , what do you want to do your career ? You're like well , I don't know what you want . I know it's like I would like to get a promotion . I would like to do this , like you . But that's one of the things that even I had to evolve in is like saying out loud what is it that you want to see happen ?
Speaker 2It's one of the main things that I'm actually focusing on these days is know what you want . And if you don't know what you want , then you will never get it . Or if you do get it , you won't even know that you got it because you weren't planning to go that direction . And sometimes it can be as small as saying I want to learn more about X . It doesn't need to be yet I want that promotion because maybe you recognize kind of I've been in the role for three months and maybe I'm not ready for a promotion , but I feel like I've mastered A , b and C and I want to learn D , e and F . So teach me more , give me more challenge , and that's usually not shut down . You do have to be careful of volunteering for everything and then get dumped with all of the stuff right there has to be a balance there .
Speaker 2If you raise an issue , sometimes it becomes your assignment and recognizing the balance of that . But that's the other thing I talk about , which is how do you say no without saying no ?
Speaker 1Yeah , well , also , what happens if they say yes ?
Speaker 2Yes , that can be more terrifying . Yeah , well , also what happens if they say yes like yes ? What if they say yes ?
Speaker 1are you ? Are you ready for what happens like you ask for a project and say sure you can lead in like oh I don't , I don't know what to do now . I didn't expect that you're gonna say yes , so I didn't think about that um , yeah , no , it's the step beyond the ask right , yes , I love that . That's really insightful yeah , I mean , do you , you see , the saying yes , or this being afraid to ask for the yes , or the afraid to saying no ?
Speaker 2I actually think that both can be very challenging because it takes a fortitude .
Speaker 2One of the things that I talk to people about a lot and I use a lot just in my practice , is this is an invitation , it's not an obligation .
Speaker 2Everything is optional and if you go in with that mindset that I'm asking for this and I am inviting my employer to give me a promotion , if they decline , I may invite other people to give me that promotion or that education or you know that whatever that they might be wanting at that particular point in time , and they aren't obligated to give you what you want . But you have permission always to ask for what you want , and it's just making sure that you're asking it in a way that other people can accept it . And that's what I hear in your story about being out on LinkedIn and having that stronger presence which gets you noticed and an invitation to apply for a role that you are now in and feeling good about . And I still believe you have everything within you to do what you want to do , and I really have enjoyed our conversation here today , aaron . As always , a pleasure to talk with you and it's been great having this conversation .
Speaker 1Yeah , it's always a pleasure talking with you , Becky . I always appreciate our time together because I'm usually reminded of that time in which I wasn't as confident and you helped me . So it's always good to kind of go back and reflect on what was and kind of how the steps have been laid to kind of get me to where I am today .
Speaker 2Yeah , absolutely . I loved hearing Aaron's story and how his perspective has shifted since we partnered through coaching . Watching someone move from being the technical expert to becoming a strategic leader is one of the most rewarding parts of this work . He offers a powerful reminder Leadership is not about having all the answers . It's about creating the conditions for others to thrive . It's about building capacity in your team so they can do more than you ever could do alone .
Speaker 2When you invest in developing others , delegate with intention and let go of being the one who always needs to step in . Something important happens . You shift the center of gravity . Your team becomes stronger , more resilient and more capable , and you , as a leader , create the space to think more broadly , more creatively and more strategically . This is where strategic leadership truly begins . It's not just about stepping up , it's about stepping back . It's the moment you start thinking beyond tasks and timelines and begin considering the bigger picture . What actually matters to the organization ? What are our stakeholders concerned about ? How does this initiative connect to long-term goals ? In this way , you move from being the person executing the work to the person shaping how work gets done , why it matters and where it's going .
Speaker 2That shift from doing to directing , from
Closing Reflections on Leadership
Speaker 2knowing to empowering is incredibly valuable . It's what earns trust from senior leaders . It's what positions you for greater responsibility and impact . You start to be seen not just as someone who can deliver , but as someone who can lead others to deliver at scale , with purpose and in alignment with the organization's most important priorities . That's the real growth . It's not a title or a promotion . It's a mindset and , as Aaron's story shows , it's a transformation that benefits everyone your team , your company and you . If you'd like to learn more about Aaron and what he's been up to lately , be sure to find his LinkedIn in the show notes . Thanks for listening . If you found this episode helpful , share it with someone who could benefit from it . Until next time , I'm Becky Fraser , reminding you to integrate who you are with how you lead . Okay , bye .
