Meet the Mentor // Tiffany Stokley

Welcome to the tenth episode in our “Meet the Mentor” series where we get to know Flatiron School mentors in an interview-style conversation. Whether you’re just starting out or looking to level up, these stories are packed with practical advice, encouragement, and insights to help you navigate your own path in tech. Each article includes a mentor snapshot + links to follow their work, their video interview, and their Q&A transcript with links to any references.

Follow along and discover the people shaping the future of tech, one student at a time!

Meet Tiffany Stokley

Tiffany’s path through tech has been shaped by curiosity and a desire to increase women’s representation in tech. From engineering roles to her current position as a manager at Leidos, she now leads projects and manages teams.

In her Meet the Mentor interview, she shares the importance of finding your voice and bringing versatility, critical thinking, and a curious mindset to the workplace. She emphasizes that mistakes are part of the process, rest is essential, and advocating for yourself can change the entire trajectory of a career. Her experience shows that you don’t need a perfect path to succeed; you just need persistence and the willingness to try.

Snapshot

Current Job Title: Software Engineering Manager and Flatiron School Facilitator

Current Employer: Leidos

Past Employers: ManTech, Antech Systems

Experience: 13+ years in Software Engineering

LinkedIn: https://www.linkedin.com/in/tiffany-stokley/

Technical/Professional Skills: Amazon Web Services (AWS), Java, Python, Continuous Integration and Continuous Delivery (CI/CD), C#, CSS

Teaching/Mentoring Experience: “I’ve always mentored and tutored in some capacity. A few years ago, I worked at Springboard.”

Words of Wisdom: “Don’t be discouraged because things seem like they don’t make sense or you’re having those imposter syndrome moments and you’re having those second thoughts. Don’t listen to all the noise. If it’s something you really want to do, stick with it.”

Favorite Part of Your Job: “When they come back years later and they’re software engineers or they’re moving up in their career and they tell me how much of an impact I’ve made.”

Meet the Mentor Interview with Tiffany Stokley

Q&A Transcript

Introduction: Who are you and what do you do now?

• Can you tell us a bit about yourself and what you’re working on these days?
  • I actually recently just became a manager, maybe about a month ago. I came on to Leidos after starting here in August, but I’ve been working on this contract under another contractor for about 2 years. So I’m actually new to the manager part of the role. A lot of other things changed, but as far as my day to day, I come in and work remotely. So as you can see, I got four screens over here and then I got two right here. Day to day, I meet with my team, then we all go on to our separate tasks, attend any meetings on the calendar, things like that. It’s pretty straightforward, other than when I have to speak to my direct reports, which is a whole other area I am still learning.
• How has your role been shaped by AI and what excites you about this?
  • Yeah, so actually we were just doing performance reviews. Right when I started, it was like, okay, next week we are doing performance reviews, so I had to learn all of that. Leidos tries to follow the SMART framework when they are talking about their goals. I don’t know if you’re familiar with that. It’s an acronym. I don’t know the acronym off the top of my head, but they try to follow that framework when you’re writing your goals. And a lot of people, especially engineers, you have probably heard about us, we just want to code, we just want to do our work. So when it comes to writing goals and doing all that administrative stuff, we are probably not the best at it. So as my direct reports, as I was reviewing their goals, I’m like, these really don’t follow the SMART framework. And it kind of made it difficult for me because when we talk about being SMART, one of the big things was being measurable. So how is the goal measurable? So I was thinking of ways that I could help my direct reports write these goals without just doing it for them. I came up with a prompt, and Leidos does have their own chatbot. I came up with a prompt for everyone to use, where you put in what you are starting with for your goal and what you do on a day to day basis, and then enter it into the chatbot. And I said, make these goals adhere to the SMART framework. And so it kind of made that process a lot more seamless for my direct reports, and my manager loved it. I gave it to everybody to use. Those goals have definitely improved since I gave them those. As far as how my position has changed, like I said, I did just start at Leidos, but previously I was with ManTech, but it was all on the same FBI contract. So individually, my role has changed from just being a software engineer to being a people manager. And as far as the role in AI in that, I think it definitely makes my job a lot more efficient on the manager side and the software engineer side. If you know anything about software engineering, sometimes we are called professional Googlers. We are always looking things up and things are always changing. It is nice to have a chatbot so when we have a simple question, we can get an answer just like that instead of reading a lot of documentation. Even in my role as a facilitator, when students ask questions, sometimes I do not know the answer off the top of my head. They do not see what I am typing, but on the side I am searching things like, why is this happening or what could be the issue. AI has definitely made my job and my life much more efficient. And Leidos, they have what they call the trusted AI mission. So they’re real big on trust and eliminating biases when we talk about artificial intelligence. So I’m happy to be a part of that mission with Leidos.
• What are the key skills crucial to the workplace now?
  • Yes, definitely versatility. That is a big thing. And like I said, I’ve been doing this for 13 years. I’ve worked with many different languages that I didn’t know. In college, I learned Java and I feel like in my 13 years, I’ve done everything but Java. So being versatile is definitely a big thing. When I started, cloud wasn’t a big thing, so being in a more senior role, I’m not in school, , and I’m not required to learn these things. I took it upon myself. Let me go get these AWS certs. Let me learn these different avenues so I can apply them to my job. And that’s the same thing with AI now. AI is blowing up. So I take time for myself to learn different things about AI, how that’s used in software engineering and things like that. So versatility is definitely a big one. Critical thinking is another. I tell my students all the time, it’s not really about what you know. It’s about how you think and how you use your resources and what you can come up with. I don’t know all this stuff off the top of my head, and I try to really instill that in them because I had one student ask me the other week, saying they felt like they did not know anything. And I’m like, relax. You’ve been here 4 weeks. And I came out of a 4-year degree out of 4 years, and I walked out feeling like I didn’t know anything. So it’s normal. And the last thing I would say is a curious mindset. I feel like I learned a lot from just being curious about things, even looking at a code base. And it can be something that’s not directly related to what I’m doing. But because I have a need to know how things work, when I get off, I’m googling or researching and asking why something works the way it does. So yes, I think those three things are big, and they are crucial skills in the workforce right now.

Career Journey: How did you get here?

• Can you walk us through your career journey? What were some of the pivotal moments that shaped your path?
  • Like I said, I had a degree in computer science. When I graduated, I didn’t have a chance to do any internships, so finding that first job was proven to be very difficult. I had just gotten to a point where I thought, I have always been good at school, so I guess I’ll just go back to school because I can’t seem to find a job. And I feel like right when I had that thought, I was looking on Indeed and they were hiring for internships, a paid internship. It was in Charlottesville, Virginia, with a CACI. Some people refer to it as Khaki. I applied for it, and they called me. It might have been the same day. It was pretty quick. They called me like the next day. I drove in for the interview and they said, “Okay, you’re hired.” So I started there as an intern and they hired me on full time. So I believe I worked there for maybe about a year or a year and a half. I don’t know if you had a chance to look at my LinkedIn, but I’ve had quite a few jobs over the last ten years. One thing Khaki did give me that, I’ve used since then, I was able to get a security clearance. In all my roles I have been able to work on cleared work and government projects. I have mostly been in contractor roles. So I’ve worked for different contractors, including Northrop Grumman, Khaki, Leidos, Mantec, Indrasoft. So I’ve kind of been all over the place. As far as pivotal points in my career, I believe I struggled a lot in the beginning with what they call imposter syndrome. That is basically feeling like you are there by luck rather than deserving to be there. At the start of my career I kept my head down and just tried to get my work done. But over the years, as I’ve gotten more senior in my role, I’ve become more confident. If you would have asked me even 5 years ago, I would have never thought I would be a manager. I would have said, no, I don’t want to do this. I just want to code. So kind of finding my voice. And there wasn’t anything, any one pivotal moment in particular that happened that made me do that. I was holding myself back. Nobody told me I was not good enough. In fact, I received a lot of accolades. People always told me how good I was, and I would think they probably tell that to everyone. Leaning into my natural leadership abilities and being more confident and advocating for myself. Self advocacy is something I try to instill in my direct reports. A lot of times you can be overlooked when you’re working for a huge company and you’re just another number. And sometimes it’s not on purpose. A lot of times people take things personally. And I’ve realized, a lot of times it’s not on purpose, but you have to advocate for yourself. You have to be your own voice and you have to use your voice, get over that imposter syndrome, and realize that you’re not here by luck. You deserve to be there just as much as everybody else.
• What inspired you to pursue a career in tech, and how did you land in your current role?
  • So I had an uncle, and I didn’t know anything. I went to I.C. Norcom High School, and I was in the magnet program, but we really didn’t have a lot of resources. I didn’t know anything about programming or anything about that, but I had who always told me and my sister, STEM fields, STEM fields, and I didn’t know what it was, but I was like, “Okay, well, what am I going to do in this STEM field that you kept talking about?” But he always put it in our head. I had my sister, she’s one year older than me. So I kind of could watch her, what she did first and kind of follow in her footsteps. When she went to school, she got a full scholarship at the University of Virginia and their mechanical engineering programs. I was like, “Okay, I guess that’s what I’m going to do because I really don’t know what I want to do. That sounds right. It’s STEM. She did that.” Like I said, she’s a year ahead of me. When it was my turn to start applying for scholarships and schools and things like that, I just applied to Virginia. I didn’t really know where I want to go, what I wanted to do. I didn’t have any money. So the school that gave me a full scholarship was the University of Richmond. Fortunately, they didn’t have an engineering program. They had a physics program where you attend their school for 2 years and then transfer to UVA the next 2 years. And I took that business class, and I thought, if this is engineering or if this is STEM, this is not what I want to do. They also had a computer science program. I was like, “Okay, well, that’s STEM. That’s really where my head is. I’m like, that’s STEM. I guess I’ll try that.” So I took my first class and I liked it. And that’s really how I got here. I really enjoyed it. I enjoyed the critical thinking aspect of it and I just stuck with it.
• What’s your perspective on tech education today? What is the value of a bootcamp compared to other options like teaching yourself or getting a masters, associates, or 4-year degree?
  • I do think my education was very valuable. My father, he was very big on his daughters going to school, going to college, and getting their degrees. He didn’t have a degree or any formal education. He was an immigrant from Jamaica and he couldn’t even read. My mother didn’t finish high school either so it was always a big thing they want their daughters to go to school and be all they can be so college was really like a natural next step after high school. It was kind of like an extension of school just something we were always taught we’re supposed to do. And when we talk about the value of it, I think we still live in a world where a lot of these positions do still require some type of formal education, like a bachelor’s degree. And I think every position I’ve been in, they’re looking for that bachelor’s degree. So I do think it was very valuable. As I got into before, I really didn’t know what I wanted to do. So it gave me that opportunity. I went to a liberal arts school, University of Richmond. It gave me that opportunity to kind of explore different things without having to feel like, “Oh, I got to work and get a full time job, be a part of the hustle and bustle of the world.” It kind of allowed me to find my place in this world in my own time. So I do think a degree in my education was very valuable. So when we talk about the different avenues of learning, like a 4-year degree versus bootcamps versus being self-taught, I will say I’ve always admired self-taught people because I don’t see how you just, like I’ve worked with them, they’ve sat side by side with them. I’m like, “Wow, you really taught yourself all this stuff.” But I think it’s a very individual choice. You have to know what type of learner you are. And maybe because these bootcamps and things weren’t that popular when I started school, I think on it. I’m like, I don’t think I could have been self-taught. I appreciate the 4-year degree and sitting in the classroom and things like that. But we live in a much different world now where we have these bootcamps and you can even get on YouTube and there’s good videos to teach yourself. And I think the bootcamp gives you the best of both worlds because you get the autonomy to be able to learn on your own time. And especially with programs like Flatiron that give you a facilitator. So it’s not like you’re just on your own and just trying to learn all these things. You have somebody you can talk to, somebody you can bounce ideas off of. Without having a strict schedule, you have to be in this class at this time every Tuesday and Thursday. So I think there’s a lot of ways to get to the same goal. There’s a lot of ways to achieve the same goal. And I think bootcamps, especially with older professionals or people who just don’t want to go to college, I definitely think this is a great option for those individuals.

Lessons Learned: What have you learned along the way?

• What’s one lesson or insight from your career that’s stuck with you and continues to guide you?
  • A lesson that stuck with me is it’s okay to rest. I’m the type of person, like if I have a problem, it’s like I have to solve it now. And I’ll be on the computer all day until I solve the problem. And it’s funny, because a lot of the times, as soon as I say, “Okay, I’m gonna give it a break,” and the moment I walk away and go take a shower, I have the answer. So I will say, take that time. Take the time to yourself to rest. Everything doesn’t have to be perfect. I will say, when other people are looking at my work, I can be a bit of a perfectionist. I want to be right. I don’t want to feel like I’m not smart. So I want to get it right the first time. Sometimes you don’t have it right, and that’s okay. A lot of people don’t have it right. As long as you’re willing to learn from it and correct the mistakes and whatnot, feel free to make mistakes. That’s really how you learn. And I spoke about it a little bit before, that self-advocacy in your career. Like I said, I really didn’t do that a lot earlier in my career. And when I found my voice and when I really started to speak up, I saw the trajectory of my career change. Like I said, now I’m a manager. Now I’m managing other people. People are coming to me, asking for advice, even working on a project, you have your functional manager, where it’s kind of the HR side, and then you have lead projects type thing. So I wasn’t officially a manager, but I kind of stepped into the role because nobody else will, honestly. So that’s another thing I thought I would never do. So don’t be afraid of the unknown. That’s one, really lean into your talents. It’s funny because even at my first job, my first boss, he was like, “You need to work your communication, Tiffany, but I really see you being a manager one day.” And I was like, “No, not me.” And now here I am.
• Was there a moment where you faced a major challenge or failure, and how did you grow from it?
  • I won’t say where this happened, but I came onto a project and I had to kind of, it was somebody else’s project. And when an engineer has a project, it’s like their baby. They don’t want anybody to touch it. Nobody can do it right like them. But I was tasked, and a couple other people were tasked with taking that project away from them and doing different things to it. I won’t get into it. And they didn’t really like it. I didn’t understand what their issue with it was and why they didn’t want to do it. I didn’t understand all the politics behind it. I just came to do the job. But like I said, I had to step up in that role because nobody else was taking the reins and doing it. And I’m a person. I have to be doing stuff. I can’t just sit here. So I’m like, “Okay, this is what we need to do.” And they didn’t make it easy for me. They definitely didn’t play nice. There was a ringleader and his minions were following behind him every time he did that. So while I had people telling me, “Tiffany, we see what’s going on. We see what he’s doing.” I felt like nobody was really doing anything about it. So yes, you see it, but is anybody going to do anything about it? And working on remote teams kind of makes it difficult too, because I’m like, I know if I was there, he wouldn’t be saying this stuff. Like, he wouldn’t say it to my face type thing. But it’s easy to say these things when we’re behind a Teams chat. So progress wasn’t being made and it was making our team look like we couldn’t get things done. But upper management didn’t see everything that was going on at this level of things. So it was very discouraging, especially being new to the company, coming onto the project. And it was like, I didn’t do anything to these people. I don’t know why they’re treating me like this. I kind of felt like I’ve never had to deal with that in a professional lane. I was like my in high school, I just I really just wasn’t used to it. But after working through it, eventually people saw when things weren’t getting done. And, I keep very good notes. So I had a note on everything. This is what I asked for, this is what happened. They weren’t doing these things. I couldn’t really move forward with the project without their assistance. And they kind of shooed one guy away, the ringleader, and everybody else fell in place when he was gone. We were able to move the project forward. So it was definitely a learning experience. I had never dealt with anything like that before in my career. What I do recommend is making sure you’re keeping a paper trail of things that you do. Keep your calm, keep your composure. There were quite a few times where I wanted to say things that you’re not supposed to say at work, but I kept my composure, so I didn’t look like the one that was the aggressive one or the one that was causing problems. And eventually they kind of saw where the problem was coming from. And like I said, they went to another team or something. So, I would say definitely keep a paper trail. Definitely make sure your people know what’s going on. Like I said, everybody saw it. I had conversations with my manager and things about it, so everybody kind of knew. So just make sure that people know and you’re not just getting bullied, I would say. Nobody knows what’s going on, because when it comes down to it, they’re looking at you to do this project. They’re not looking at those people and they’re not looking for excuses. So you have to come and say, this is what happened and this is my proof of what happened.

Mentorship: Why did you decide to become a mentor?

• How did you first get connected with Flatiron School, and what drew you to the school?
  • So my contract with my last company, like I said, they lost the contract. And I was looking for a job. So I’m on LinkedIn every day. And I started scrolling LinkedIn, like Facebook and Instagram, just scrolling and seeing what’s up there. And I came across Flatiron. I’ve always mentored and tutored in some capacity. A few years ago, I worked at Springboard. That’s another bootcamp. So when I saw Flatiron’s posting, I was like, it looks something kind of similar to what I’ve done. I don’t know if this new contractor is going to hire me. So maybe this will be something I can do in the meantime. I do enjoy teaching and sharing my experience with people. So it seemed like something good to do. Then I went and read about Flatiron. I read a little bit more about their program and their bootcamp and what they teach, and I decided to apply for it.
• What inspired you to become a mentor (cohort facilitator)?
  • So in the tech field, there’s definitely a disproportionate amount of women and people of color in the technology field. And I always felt like I wanted to, what they say, be a part of the change in that. I wish I would have had more early in my career, more representation, more people that looked like me. Instead, I’m always usually walking into a room of older white gentlemen, so it’s just like, I wish I would have had those things. And I started with myself, you can do it. Just because you don’t see yourself right now, you can change that trajectory of the field. It’s not there’s nothing stopping you. I always want it to be an example to other people who might not think they can do work in this field.
• Was there someone who influenced your career path and who (knowingly or unknowingly) mentored you?
  • I’ll say my advisor in college. It’s funny because I was reading the questions, and I’m like, what is Kelly Shaw doing? I added her on LinkedIn right before this meeting. But yeah, she definitely, my advisor, served as my mentor. She was also a professor at the University of Richmond. I think she was the only woman computer science professor. She dealt with all the things coming from that. So in our talks, we talked about those issues. She always said so many women drop out of the program after the first class because they’re like, this isn’t for me. So she always encouraged me to stay in the program. She made me read books at the time. I’m like I’m not a big reader. And I’m like, “Oh my God, I got to read this book.” Then she wants me to discuss it. Like I have other things to do Kelly, but I actually enjoyed the book. It was a book called Woman Don’t Ask. And it was basically about how women don’t move up in careers because they simply don’t ask and how we’re conditioned and taught as women that we’re not supposed to do certain things. So through reading that book and through those discussions, there are a lot of things like just negotiating salaries that a lot of women don’t even think to say, “Hey, you know, can we negotiate this?” So definitely the things that we talked about and the things that she instilled in me during our talks, I definitely still use those things in my career today.
• What’s been the most rewarding part of mentoring students so far?
  • The most rewarding part is when I get, I keep wanting to say kids, but I feel like I’m dealing with adults now. When they come back years later and they’re software engineers or they’re moving up in their career and they tell me how much of an impact I’ve made. When I’m teaching and when I’m doing these things, I’m not sitting here on a pedestal like I’m some sort of inspirational leader or anything like that. I’m really just talking about my experiences. So to know that people are really listening and really taking heed and really using my advice, seeing where they are years later is definitely rewarding. I even had one of my current students just tell me a few weeks ago, “you’re very motivational and inspiring.” And it just makes me feel like the things I do aren’t in vain, I’m making a difference somewhere.
• How do you keep your students motivated?
  • I think personal experience, like just being real with them and talking about my personal experience on the job and my career and school, even just learning software engineering, because coming into it, it is a lot. It’s a different way of thinking. And if you just took one class and you’re like, some classes start with front end development. I tell my students, I’m not a front end developer. I can’t make anything look pretty. I know the language, I can work my way around it, but don’t ask me to design a website or nothing like that. So when they come in and they’re like, “Oh my God, CSS and HTML, I hate it.” And I’m like, “this is just the first part. You don’t have to be an expert at this. Back-end development is next. You might be better there. There’s so many different avenues that you can take. And just because you felt like something was so complex and you didn’t understand it, it doesn’t mean you won’t understand anything at all.” So just telling them my personal experience, like I mentioned earlier, I left, I was at a 4-year degree and I still left and I couldn’t put together anything. Like I didn’t understand. I had no real world application. So I think sharing those experiences with them and listening to what they have to say and giving constructive feedback. That’s how I keep them motivated.
• If you could give one piece of advice to someone just starting out in tech, what would it be?
  • It would be to stick with it. Don’t be discouraged because things seem like they don’t make sense or you’re having those imposter syndrome moments and you’re having those second thoughts. Don’t listen to all the noise. If it’s something you really want to do, stick with it. I can’t name any engineer I know that can just hop on the IDE and just create a whole program. Now with AI, you can type something and it probably can, but most of the time we’re referencing Google. I always say engineers are good researchers. We just don’t know all these things. That’s a lot of information. So when you’re going through these programs, these bootcamps and things, they are throwing a lot of information. And it’s not expected that you just immediately grasp it. So stick with it, and also internships and apprenticeships. Because like I said, I graduated college, and I didn’t do those things, difficult to find a job. I was getting interviews, but I wasn’t making it because more people had experience. People who did those internships and things were one-upping me. So I would say, while you can and when you have the time, definitely, do those internships or apprenticeships.

Future Focus: Where do you want to go next?

• What’s something new you’re learning or exploring right now, and why does it excite you?
  • I actually just started my master’s degree this month. I’m getting an MBA with a concentration in IT management. So that’s exciting because I always said I would never go back to school, but here I am. I’ve done a lot of things this year I said I never would do. So that’s taken quite a bit of my time these days.
• Are there any projects or goals you’re currently working on that you’re particularly passionate about?
  • No, not really any projects. Like I said, between work and school and everything else in the world, I don’t really have a lot of time to do personal projects. I am learning. I’m trying to learn more about AI and Retrieval-Augmented Generation (RAG) systems and things like that. Again, when you’re working full time, it’s kind of hard to find time to hone in on your skills or try to advance your skills, especially when you’re not really using particular technologies in your current position. But I’m interested in it and I wanted to learn more about it. So I took it upon myself to take some Udemy courses and things like that to learn more about it.
• Looking ahead, what’s a big dream or ambition you’re working toward in your career?
  • I would say maybe leaning into a project management position. I still always want to do software engineering because it’s something that I really enjoy doing, but now that I’ve kind of honed in on those other traits that I naturally have, like being a leader and managing projects and taking something from the beginning to the end. I would definitely like to, I feel like that would be the next progressive step in my career. Got to get through this manager part first. See how this goes.

Lightening Round Questions

• What’s something you’re listening to or reading right now? (It can be any genre and can be a book, audiobook, or podcast.)
  • I’m a big audible person. So I actually have two on my list that I want to start. They’re sitting in my cart right now. One is the little black book of success. It’s basically talking about black women in corporate America. And the other one is the subtle art of not giving, I don’t think I can say it up here. But one of those will be my next article.
• What’s one product or tool you’re into right now?
  • Claude code. I’m learning how to use it. Being that the stuff I work on at work is national security and sensitive in nature. I can’t really just pull AI tools and just use them how I want. So when I saw a lot of people using these tools to build and develop projects, I was like I want to learn how that’s done. So I’m working in the VS code and doing the cloud code. So yeah, I’m excited about learning that.
• When is your next cohort?
  • December. I think I got the email today asking that we want to do the December cohort. I skipped November. It’s my birthday month and I’ll be on a trip to Brazil. So I was like, I’ll come back in December.
• Where can listeners find you?
  • You can find me on LinkedIn. I’m very active up there.
• What made you smile this week?
  • My son got accepted and it’s a program in Richmond, Virginia. I didn’t know what it was because he just signs up for stuff and just tells me about it. He needs a ride. It’s called Youth Empowerment and I don’t know what the S stands for. He’s just like, “Mom, I have to get to this meeting.” So I’m like, “Okay.” It was the orientation meeting, so the parents were encouraged to stay. I sat in there and just seeing these kids, I think it was like a 100 something applications and they accepted maybe 20 students. And they did like a round of talking about issues with the government and things like that. I’m looking at my son thinking, what do you know about government? But when I take him to school, we do have those conversations every morning, so he knew a little bit. But just seeing the kids, young people, talk about these things. So very articulate, very involved in their community. That made me smile, just seeing how passionate these young people were.