Kyle Elliott, the Founder and Career Coach behind CaffeinatedKyle.com, joins the pod on his quest to transform boring job searches into something fabulous. Kyle specializes in helping job seekers, especially those in technology and cybersecurity, find jobs they love and express the value they bring to potential employers. Need to know the secret to acing your next tech job interview? Look no further than Caffeinated Kyle.
[00:00] Finding your own definition of fabulous
[06:06] Standing out in a tech job interview
[12:19] Dealing with and learning from job rejection
[16:41] Targeting your dream tech job & telling your career story
[21:33] Breaking into technology the easy way and the hard way
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From your perspective, what makes someone fabulous?
Being “fabulous” can sound grandiose to most tech practitioners, but Kyle believes that everyone has the potential to be fabulous, especially when they’re forging their career path. There’s a lot of competition amongst large tech companies to find the employees that close skill gaps and stand out from the massive group of hungry job seekers. To be fabulous, one has to know how to stand out and what sets them apart.
“When I think of fabulousness, I think: What sets you apart from other people? I work with job seekers, so I think: What sets you apart from other job seekers or other applicants?”
When you look at standing out in a job interview, what are some of the key components that go into that?
Many job seekers that Kyle works with have the skills, meet the position requirements, show up for the interview, and still struggle with getting a job in tech. While this can happen for a variety of reasons, Kyle explains that a simple mistake job hunters are making is regurgitating their resume without backing up their experience. A strong story about the experiences you had and the value you delivered makes you memorable and explains what you can provide.
“When you're doing this, you want to think in the mind of a hiring manager. How have you added value to the organization? What sets you apart? I didn't just code, I didn't just have cross functional collaboration, here's the value to the organization and what sets me apart.”
How do you coach someone through being able to tell their story in an interview?
Career storytelling skills separate a potential employee from a pack of qualified applicants. However, a lot of technical people aren’t known for their storytelling skills or knack for creativity. Instead, Kyle recommends his clients in tech and cyber practice their storytelling through a more familiar world of spreadsheets. Each spreadsheet helps job seekers break down the value they bring with their skills, so they can tell a story that connects their past experiences to their future position.
“A lot of the people I work with in tech, they're amazing at their job, but they're just not used to practicing storytelling…It feels awkward. It feels different. It feels weird, because that's not something they’re used to.”
From your experience, what have been the easiest and hardest fields in technology to break into?
In Kyle’s opinion, there isn’t one field of the tech industry that’s easier or harder to break into. Instead, breaking into the tech industry relies more on professional experiences, background, and skillset. If the leap to tech feels like too many transitions at once, Kyle recommends slowing down to one transition at a time and building each experience off of one another. Instead of hiding that this may be a new path for you, embrace your past when job searching and explain why a potential employer should hire someone transitioning into the tech world.
“Everyone's like, ‘Kyle, how do I get a job in tech?’ I would start with your background, and I think that's gonna determine what's easiest or hardest for the person. What I always recommend is, try to make the least amount of transitions possible.”
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Who says tech can't be human?
Everyone's like, "Kyle, how do I get a job in tech?" I would start with your background and I think that's gonna determine what's easiest or hardest for the person. I don't think there's kind of one easiest or hardest role or vertical to go into. I think it depends on your background and trying to connect the dots.
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What's going on, everybody? You're in the Hacker Valley Studio with your hosts, Ron and Chris.
Welcome back to the show.
Glad to be back again, always with a great guest. Our guest this episode is Kyle Elliot. Kyle is the Founder and Career Coach behind CaffeinatedKyle.com. He helps people become their best and also show up to work fabulous, which is a topic that I would really love to jump and dive into more. But Kyle, most importantly, thank you for joining us and welcome to the podcast.
Yes. Good morning, thank you so much for having me. I'm excited to be here and to be talking about how we can help people show up fabulously at work.
Exactly. I can't wait to jump into this conversation, but first, let's get to you a little bit. If you could tell us a little bit about your background and what you're doing today, that'd be great.
So, I'm a career coach. In a nutshell, I help people find jobs they love. My expertise is Silicon Valley and high tech. I always like sharing how I got into this because it's very unconventional. My background is not in recruiting, it's not in tech, even though most of my clients are in tech. It's not in HR. But instead, I literally started on Fiver, the online marketplace. I charged $5 for resume reviews, for LinkedIn profile summaries. I edited people's college essays and personal statements, and it was supposed to just be a side hustle through college. If I made 100 bucks a week, I was happy because I paid for pizza and Subway and Starbucks. And then, this blew up, almost all of my business came through word of mouth and still does. So, people would say, "Hey, Kyle can help you get a job. He helped me get a job," then it was Facebook and Google and LinkedIn and Apple, and I kept growing and growing and growing. Almost five years ago exactly, as of next month, I left that full-time job I had while I was doing the Fiver side hustling and began my business full-time. I absolutely love helping people find jobs, and my secret sauce is helping people identify what makes them fabulous.
Love that. So, let's jump right into it because I'm sure there's a lot that goes into making someone fabulous at work, and even getting that opportunity to show your worth and show the things that you're great at. When you started working with people, I'm sure you had to first make yourself fabulous. What all went into giving you the confidence to step out of just reviewing resumes, but to then go into fullblown coaching?
What's helped for me is taking little bite-sized pieces. So, saying, "Okay, I'm gonna start with just resume reviews." And then someone's like, "Can you write my resume?" Oh my gosh, that sounds scary, and I charged them $20, which was a lot when I was in college, and I wrote it. My dad's advice was every time that I had a weight list was to double my prices. So, I went from 5 to 10, 10 to 20, 20 to 40, and each of those was scary, but it was kind of like a bite-sized piece. And then, I remember when I was still doing it part-time, a really big fortune-100 tech executive came to me and said, "Hey, do you have experience writing tech executive resumes?" I remembered back in grad school, this improv technique, we were taught in one of our classes saying, "Yes, and." So, instead of saying no, I don't have experience writing tech executive resumes, I said, "Sure, I can help you I can write an executive resume," and I supported her and that kept happening over and over. I would take these bite-sized pieces, I would say yes and do things, and it would feel uncomfortable, but then the rewards were worth it. I kept doing these little bite-sized pieces every day and they really added up into this huge business that I have now helping some of Silicon Valley and tech's biggest executives. I encourage my clients to do the same thing. "Hey, let me update my resume a little and share my fabulousness there," or LinkedIn or an interview, and just take those little bites that will add up.
Let's dive into this definition of fabulous. I absolutely love the word. But from your perspective, what makes something, or someone, fabulous?
Oh, I love that. So, I use the word fabulous. Other people, sometimes clients are like, "I don't resonate, maybe for me, it's terrific or special." When I think of fabulousness, I think: What sets you apart from other people? I work with job seekers, so what sets you apart from other job seekers or other applicants? If you're applying to Meta or Google, or any other big tech company, or even hypergrowth startups, or most companies right now, it's a lot of competition. What sets you apart from the other hundreds or thousands of people applying? That's what makes you fabulous. However, rarely do people know that. We're not taught in school or at work to figure out what makes us fabulous, so it's really tricky for people to figure out what sets them apart from everyone else.
That's a really good point because sometimes, when I would interview, especially early in my career, I almost felt like I didn't have the opportunity to show myself completely. I didn't really get the opportunity to explain what I was best at. I was really bombarded with questions and trying to get my resume to follow a certain format. I think, at times, that was helpful to follow a specific format, to try to show up at the top of job search platforms, but I think there's much more that goes into it for standing out. I mean, a lot of people in cybersecurity, they reach out to us and our colleagues to see, "Hey, what can I do to stand out in this world of technology and cybersecurity?" And it's almost a daunting process for me, because I don't help people in the same way that you do. So, when you look at standing out, but also
explaining your value and showing that you're fabulous, what are some of the key components ortenants that go into that?
A lot of people reach out to me, and a good number of them in cybersecurity, and what they struggle with is they're like, "Kyle, I meet every item in this job posting, and I'm getting some interviews, but just not sealing the deal." I just talked to a client, he had 10 places where he had final interviews, and no offer. And I say, "Yeah, you're probably checking everything on the job posting, but what else?" Every one they're interviewing is hitting everything on the job posting, so what sets you apart? I often encourage clients to get the job posting, and then, we dissect it into three columns. The first column is here's the job posting, and each of them kind of gets their own line. A lot of my clients are in tech, so they love a good spreadsheet, so each one gets its own little box. And the second column is: here's where I've done all this before, my responsibilities. So, if it says you need experience coding, here's where I've coded. You need experience in cross functional collaboration, here's where I've done that. And then, in the third column, I want accomplishments. How have you added value, or impact? What results do you have to back up these responsibilities? When you're doing this, you really want to think in the mind of a hiring manager. How have you added value to the organization? What sets you apart? I didn't just code, or I didn't just have cross functional collaboration, but here's the value to the organization and what sets me apart, and then, take that third column and bring those examples and stories to your interviews, and put them on your resume as well. I find that helps clients kind of say, "Oh, it's not just that I check off everything on the job posting, but here were the results and here's how I did it maybe a little differently than my colleagues or my peers."
You just mentioned a hot button topic for Ron and myself, stories are everything. It seems like stories are almost becoming this forgotten aspect of humanity. Sure, there are people that really tell good stories, but there are some folks that have an issue of being able to tell stories, even their own story. How do you coach somebody through being able to tell their story about whether they have this skill or made this impact? How does that ultimately come together?
So, a lot of the people I work with in tech, they're amazing at their job, but they're just not used to practicing storytelling. What I encourage people to do, during my sessions, and for everyone listening, you can do this, is to write your name with a pen and a piece of paper, and then see how that feels. When I ask people how it feels for me, I'll write it now: Kyle, it feels normal. It feels good. It feels like I'm not thinking. And now, if I switch the pen to my other hand and write my name again, Kyle, it's gonna take a little longer now. It feels awkward. It feels different. It feels weird, because that's not something I'm used to, and that's how storytelling is for a lot of people, especially people in tech. They're like, "Oh, this is weird. I'm not used to telling my story," and that's what I think of when it comes to storytelling. If I had you right with that opposite hand 10 or 20 or 50 times, you would start getting better at it and that's how you get better at telling stories. and really sharing your fabulousness, is just practicing, practicing, practicing.
That's pretty interesting to do that exercise, I'm definitely gonna try that, I was just kind of scribbling with my right hand, I'm a lefty, and seeing how that felt. But you know what? It's almost like, I would imagine that you had to go through these lessons yourself. Storytelling, it sounds like you're already maybe a natural-born storyteller, or someone that has focused on increasing that skill. Where does storytelling fit into your life, and how have you progressed it over time?
I am definitely not a natural storyteller. When people are like, "Oh, my gosh, it comes so natural to you." I actually remember a college professor. She was like, "Kyle, you're really good at technical writing papers, but when it comes to the personal part," my undergrad was health education. She was like, "You struggle with saying things really simply." So, what I did is I created a blog, it was just a health blog for myself, and I would post it for friends on Facebook. I would just practice writing simple stories, like, "Here's why there's curb cuts on the sidewalk, or here's why water fountains are important," or different random stories to practice. It was me practicing, essentially writing with that opposite hand and getting used to it. And now, it comes a lot more naturally, because I practice, but every time I started exploring, telling a new topic. A few years ago, I started sharing more about my mental health, and now my dissertations on student mental health in college, it's always kind of at first feels a little awkward, like riding with that opposite hand. And then, as I do it more and more and more, it becomes more natural. So, I encourage people to just recognize that first few times you do it, it's gonna feel awkward and it just takes practice.
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One of the things that really stood out to me because I've been on a ton of interviews and work with a bunch of different companies. And sometimes, things just don't work out, right? Sometimes, you have all the skills, you might even have the impact that they're looking for, but there might be just something about your personality or way of thinking that just isn't a good match. Maybe you're too homogenous to the folks that are already there. Maybe you think too much like them, and they're looking for something different. What do you often tell candidates when they don't get the job, and they're like, "Aw, I really wanted to work at X, Y, and Z, and they didn't see the value in me?" Because it seems like a situation where it might be better that they kind of freed you up to find the place that you deserve to be at. But how do you walk through this with candidates when that happens?
A lot of candidates, when that happens, what they'll say is, "Oh, this is personal. They don't like me." And I think it's important to recognize it's rarely, rarely personal. It could be so many other reasons. It could be there was some other skill they were looking for that maybe wasn't even in the job posting, but through interviews, they were like, "Ooh, this person has that skill and we really want someone who has experience working with people in Southeast Asia. Someone brought that up, and we didn't even realize we needed that skill." Or, it could be someone had an internal referral, and they're cousins with someone, or it could be they decided to hire someone internally. So, when clients get rejected, or redirected to maybe another opportunity or another role, I like going through with them and saying, "Let's map out all the reasons, besides it being personal, that you could have been rejected or redirected and look through that." And people realize, "Oh, my gosh, there's a lot of reasons." It could have just been they ran out of budget. There's so many reasons and rarely is it personal. However, I
also like people to look back at that interview and not say, "What did you do wrong?" But let's look at all the things you did right, to have clients write out at least 10 or 20 thing, and then say, "How can you throw fuel on those things that you did well? Make them really flame out in your next interview and say, "Oh my god, I'm gonna keep doing these even more moving forward."
So important to double down on your strengths and really work on your weaknesses as you go, but really highlighting the things that are most special about you because that's what's going to get people excited ultimately. What about those maybe weaknesses to avoid? I'm sure that there's common themes that come up for technologists, practitioners, maybe even executives, that they should just really avoid going into some areas. Maybe it's areas of conversation, or too many specifics about your personal life.
Something I see a lot that people don't recognize is reading from a script, especially now, with more interviews being via video and via phone call, a lot of people read from a script when I do mock interviews or interview coaching with them. And I say, "Okay, it's great to have a few notes on your screen, but you don't want to be reading from a script," because they're gonna be able to tell that, one, you're reading from a script, and then two, if they ask you something that's not on that script, all of a sudden, you're not going to come off as polished. So, it's really important to not be reading from a script, or look like you're reading from a script. And then, the second thing I see a lot of interviewers do that's a huge mistake is not connecting those stories or their examples or their results back to the company. So, a lot of job-seeking experts out there will recommend the star storytelling method. Here's the situation, here's the task, here's the action, here's the result of this story. What I like instead doing is a START, so I added a T to the end and I like every answer to have one or two or three sentences that say, "Here's how my answer ties back to your company in this position." So, if I'm coming from finance, and I'm interviewing at Meta, you need a sentence or two to say, "Here's how an example from finance relates to Meta." Or, if I'm switching to program management, you need to explain how your skills are relevant to program management. I think of it kind of like putting the wrapping paper on a gift. If I handed you a cheese board, you'd be like, "Kyle, why are you giving me a cheese board? It's the middle of June." But if I said, "Hey, here's a cheese board as a gift for allowing me to be a guest on your podcast," you'd be like, "Oh, now I understand why you're handing me this." It's just giving that context for that interviewer so they can connect the dots and envision you working at their company in this role.
When someone is getting ready for their dream role, whether it's to go to that company in Silicon Valley or do that job they've been trying to get to since they were a kid, what is some of the advice that you give to them when they're putting so much on this particular interview? How do you get them to relax or be themselves, or ultimately just crush it and let themselves be fabulous?
So, there's two things. One, is to really identify what sets you apart from everyone else. If you don't have a clear idea of what sets you apart from everyone else, the recruiter or hiring manager, they're not going to be able to articulate that. So, I encourage people to start there, and if you're not sure, we can kind of talk about the formula I like doing to help people identify what makes them fabulous. And then, the second is, I like people having a number of companies they're targeting during their job search. A lot of people want to go work at Meta, Apple, Amazon, Salesforce, these big ones, and I suggest having kind of three levels of companies you target. One is your kind of dream companies, the second is here's the companies where I think I have a good chance of landing, and then, here's kind of my safety
companies if the first two categories don't work out. I remember back in 10th or 11th grade, my English teacher was like, "This is how we apply to colleges, you have your dream colleges, you're here's where I think I'll get in, and then, my safety of oh my gosh, nothing works out," and I would approach the job search the same. So, you're not going in with an all or nothing mentality, if you go for this huge company where you're like, "Oh, my gosh, I need just this job and nothing else will satisfy me."
I would love to hear a bit more about your personal story of gathering clients. I think one piece of advice that your dad gave you of doubling your price was excellent, just because it's so hard as an entrepreneur, solopreneur, whatever the case may be, to accurately price your services and your value. So, how did that work out, being on the other side where you're almost the one interviewing to get the work for executives and technologists?
Yeah, so, most of my clients back when I started where Fiver or even Craigslist, I got a bunch from Craigslist, I would get people from LinkedIn, and then through that, most of my clients now come through word of mouth. One person would then refer me to another person, another person, another person. I actually had someone the other day, who purchased a package and they came from someone from Fiver. I was able to trace it back and realize this person came from someone who originally worked with me on Fiver. And I was like, "This is the power of word of mouth and having all these cheerleaders out there who are sharing my name and saying hey, work with Kyle," and I'm really mindful of: How can I remind people I exist? So, with my clients, when we're done working together, I send them a coaster because my brand is Caffeinated Kyle that says, "You are fabulous." And I send people holiday cards and a newsletter to just remind them I'm there, if they need a coach or someone else they know needs a coach. With job seekers, I suggest the same. How are you reminding people
you're looking for a job? So, that it's not just you are looking for your job, but then your cousins, your aunts, your friends, your alumni, all these other people you can really notify them, "Hey, I'm looking for these types of jobs and tech. If you know anyone that is looking for this kind of person, can you let them know?" Then, you have all these people supporting you with your job search, just like I've had with my business and how it's helped me grow.
I'm sure, along the way, you've met some incredible people and been in some incredible scenarios. What's a story that really stands out to you that has been impactful in your life? When you think about all the work that you've done, this is the story that really stands out for you.
What's most exciting about my work isn't that my clients work in tech, or that they have these big jobs, but really being able to change their lives and know that my work is changing life. So, there's kind of two stories that come to mind that have had a big impact. One is a client coming to me and saying, "Kyle, I have—" it was either 60 or 90 days to get a job, or they'd be deported. They needed a job, and they needed to be sponsored for them, their partner, and their young child to stay in the country. I was like, "Oh, my gosh, this is a lot of pressure, let's make it happen," and they landed that job. They got a higher title, a higher salary, but most of all, they were able to live this American dream that they really wanted and not get deported. Through my work, I was able to help this person and change their family's life, and that's why I do this work. And then, the second example that comes to mind is this other client, I helped them get a job at a large tech company. They worked on a diversity campaign that was impacting literally billions of social media users, and I said, "Wait, I helped them get this job, and now they're doing this diversity campaign that billions of users are going to be impacted by." Just that ripple effect or impact of my work is so exciting, and so rewarding for me.
Hmm. From your experience, and working with so many people, what has been the easiest field in technology to break into? And also, what was the hardest field?
I've never been asked this question. I think it really depends on your background. Everyone's like, "Kyle, how do I get a job in tech?" I would start with your background, and I think that's gonna determine what's easiest or hardest for the person. I don't think there's kind of one easiest or hardest role, or vertical to go into. I think it depends on your background and trying to connect the dots. What I always recommend is, if you're trying to break into tech, or trying to break into a specific vertical within tech or a specific company, try to make the least amount of transitions as possible. So, if you're trying to break into tech, and you're a finance executive, you don't want to be also trying to switch to maybe becoming a business operation executive, who's also trying to break into tech. You want to make one transition at a time, rather than trying to make multiple. I found that's when people are most successful, and that's going to make it easier if you make fewer transitions. And then, second, you're really clear on, "Here's what sets me apart from other people." And if you feel like, "Oh, but I'm trying to get into this new field," or industry or function, one way is to say, "This is how my background is actually a benefit." If you come from finance, as we said earlier, shine a light on that and say, "Here's why you should hire someone from finance," rather than trying to hide how you don't have industry experience.
I love that. Leverage your strengths, but also give yourself room to grow. I love being able to pivot, take on things that I haven't done before, but you can always fall back on the experiences that you do have. I'm sure there is someone listening to this podcast. They're biding their time, they're putting in the work to get to that ultimate goal of being at some of those companies that you recruit for. But what is that piece of advice that you would have for them as they put in the work? They're marching towards this goal that they have. What are the words of wisdom that you would have for them right now?
My biggest piece of advice would be: ask for help. Who are your mentors and who is supporting you? And if you don't have those, started seeking them out. I'm a huge proponent of reaching out to people who are where you want to be in a year, or 3 or 5 years. So, let's say you want to be a software developer at Meta, go reach out to software developers at Meta and say, "Hey, I want to be a software developer at Meta. I currently do X at this company. Do you have 20 minutes to chat?" Start developing friendships and relationships, mentor-mentee relationships and mentor relationships, with people who are where you want to be, because that's going to be such a great foundation or area of information that you can get from these people.
Outstanding, Kyle, great information for anyone out there that is in this world of technology, or really anyone that's looking for jobs out there. For the folks that want to stay up to date with you and all the incredible things that you do with Caffeinated Kyle, what are the best ways for people to do that?
Yes, my website is one of the best places, CaffeinatedKyle.com. I also spend lots of time on LinkedIn at Kyle Elliott, and on social media @CaffeinatedKyle.
Excellent. We will be sure to drop that into the show notes for everyone to stay up to date with you, Kyle, we much appreciate the conversation and hearing so many great tips and tricks on how to be fabulous in the workplace, while getting that job. And with that, we'll see everyone next time.
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