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Professional highlights, Student Events

Black business leaders' best career advice

Watch experts share their guidance for the next generation of Black professionals.

While no two career experiences are completely alike, it's important to learn from people who've been there, done that.

During a recent Handshake Career Event, Black professionals came together to reflect on their journeys so far and provide guidance for the next generation. Terry Jones, Talent Development Trainer and TikTok career coach, fostered a lively and honest discussion between Jameel Bennett (Onboarding Manager at Duolingo), Tayvion Payton (Sr. Security Engineer at Ripple and TechTok advisor), and Sherry McCaskill (HR Talent Acquisition College Programs, Diversity & Employer Brand Manager at Toyota).

During the event, our panelists joined in conversation about the following topics and more:

  • Advice for young Black professionals starting their careers in business and tech
  • Red and green flags to watch out for when evaluating a potential employer
  • How to cope with imposter syndrome in the workplace

Read our key takeaways and watch the full session below:

What do you actually do at your job?

Sherry: I’ve been with Toyota for 23 years and worked in many different departments, including parts and service, marketing, and now HR. I now manage all the intern/co-op programs across the US and oversee employment branding initiatives for outreach and social media.

Tayvion: I’m a senior security engineer at Ripple, and the main thing I do is threat detection. To simplify that, I’m the guy who stops hackers from hacking the company.

Jameel: I’m an onboarding manager at Duolingo, and I’ve been there for four years. I basically ensure all new people joining the company are well taken care of, and I manage what their first 90 days at work will look like.

How did you get to where you are today in your career?

Jameel: After I got my undergraduate degree at Howard University, I thought I’d end up being a lawyer. Then life happened, and I pivoted and went to the University of Maryland for my master’s degree. I then worked in government for fourteen years before I moved back to my hometown of Pittsburgh, Pennsylvania, where Duolingo is headquartered. When my banking governance career track there failed to satisfy my desire to work with people, I landed a job at Duolingo, and it has been magic ever since!

Tayvion: I graduated from the University of North Texas with a bachelor’s degree in integrative studies—which was basically a degree just to say I have one. I also have an associate’s degree in cyber security. A lot of people ask me if you need a degree to get into the field I’m in, and honestly, you don’t. All you need is a demonstrated willingness to learn. While I initially thought I’d be an entrepreneur or a politician, I was always good with computers and taking stuff apart. After a few years of college where I wasn’t applying myself, I found myself very interested in engineering classes. I turned my experience around and graduated with a 3.3 GPA.

Sherry: I’m originally from Torrance, California, and I went to California State University Dominguez Hills, where I got my undergrad in business and leadership. I then went on to get my master’s degree in human resources. I relocated to Texas in 2017 along with Toyota, but I’m going to be very honest: when I first joined the company, I was coming from being a seasoned, non-traditional student and candidate. I had a child, and at that point, I just needed a job that could support us. I ended up loving Toyota and quickly found mentors who helped me gain new skills and interests, including development and mentoring for others. I’ve thus far had 13 different roles in 4 different divisions, but each one was a stepping stone to get to where I am today.

Do you have any advice for Black professionals who are starting their careers?

Sherry: When you get into an organization, have a plan. It doesn’t have to be a 5- to 10-year roadmap, but have a goal for your trajectory. Then get mentors and sponsors. These people don’t have to be C-Suite or senior executives—they can be people you work with or colleagues from different divisions you have an active interest in. They can ultimately become a “board of directors” who will advocate on your behalf in front of higher-up managers you may not have access to. Finally, join employee resources groups (ERGs). Not only can they help you find new opportunities, but they can help you build out a career journey map and give you practice in discussing it—a great skill for future interviews.

If you could go back and give your 18-year-old self career advice, what would it be?

Tayvion: I was an introvert in college. I kept to myself and took classes online as much as possible. Now, I’d tell people to get involved in groups, especially if you want to get into tech. It’s a small world once you get into the industry, and networking is everything. I actually used Handshake to get one of my internships—I reached out to a well-known Hacker in Dallas who was CSO of his company. He saw that I was passionate, and he offered me an internship on the spot. Every internship I got after that—along with my second job—was due to him. So, yes—to echo Sherry, find a good mentor or sponsor.

Have you ever questioned your career path, and if so, how did you overcome the uncertainty?

Jameel: As I alluded to earlier, I used to work in the banking industry, helping smaller banks push funding into their communities. I loved the people and the work, and I had a great mentor and sponsor. When she advocated for me to get into governance, I hit an unexpected snag: I didn’t enjoy the work despite the higher pay and profile. I was a single mom and couldn’t just quit, however, so I started looking for new options. That was when I found Duolingo. If you’re experiencing uncertainty, my advice is to follow your passions! The role at Duolingo truly excited me, and even after my banking colleagues did everything possible to get me to stay in governance (including trying to dissuade me from entering tech), I followed my heart and made the leap. Ultimately, the lesson was to be thoughtful and intentional with a career strategy.

What are red flags and green flags that you look for when evaluating potential employers?

Tayvion: Red flag: if a company is trying to force you to take an offer without allowing you to consider all your choices. That’s bullying. Question it. A good company will give you a reasonable amount of time to consider an offer (usually between 1-2 weeks).

Green flag: if a recruiter is upfront about salary requirements and what they’re willing to pay. Often, they’ll try to play the numbers game and get you to agree to a lowball number when you have no insight into a particular position or how much it actually pays. Compensation transparency makes it so much easier, so always ask about the position’s salary range before sharing your own expectations.

Jameel: Red flag: when there aren’t many people at the company who look like you. Building your network—and feeling comfortable, seen, and accepted—is really important day-to-day. If you don’t see many people who look like you during the interview process, consider reevaluating. Ask about the company’s hiring practices and diversity goals so you can see where they stand on the issue of increasing representation. That said, if there’s no diversity in leadership positions, that can also be an opportunity for you to grow into them.

Green flag: a company that offers you a growth track. Ask about growth opportunities during the interview process, because everyone knows you’re not going to be at the same level the whole time you’re there. What does a company’s ladder look like, and where could you go from this first job?

Sherry: Red flag: no growth opportunities, to echo Jameel. If I’m looking for a position and I see that there are folks in HR who’ve been in the same job for 5-10 years, I might question how many growth opportunities there are—partially because I love developing my skill set.

Green flag: stability and culture. As an example, Toyota isn’t a company that considers layoffs. We really want to take care of our people, so even during the pandemic, we found ways to do that. Part of our culture and philosophy is to respect people and to respect diversity of thought. Being able to see and feel that during the interview is important. Feel out whether your voice will be heard and whether management actually listens to team members.

Have you ever dealt with imposter syndrome? If so, how did you overcome it?

Tayvion: I was 19 when I entered the workforce, and I was a senior consultant by age 21. The majority of my colleagues were 30 to 40 years older than me, and when I was leading projects, they were always second guessing my work. At first, I thought they were trying to help, but as it became more aggressive, I never quite noticed what was going on until I spoke with other people who looked like me. I learned that consulting is very, very political. I ultimately left the company to become a security engineer. To overcome the imposter syndrome, realize that if you were hired to do a job, you’re probably good at what you do. Otherwise your team wouldn’t have hired you or put you in a position to succeed. They don’t want you to fail, because if you do, then the company fails. Ultimately, my advice is not to think about it too much!

What do you recommend to new Black professionals and graduates looking to build a solid network?

Sherry: Use all the opportunities and resources you’re given. It’s never a waste of time—even if you “don’t have time”—because it’s not just about volunteering or spending time in groups. It’s about building a network of people who can help you grow and develop. This has been very key in my career. I still connect with people I’ve known for many years and turn to them for solid advice so I can keep doing a good job and knocking it out of the park.

What’s a common mistake you see people making in their job search or application process?

Tayvion: Blindly applying for positions. I see it so much. Applying for jobs these days is different than it used to be. Most of the time, Handshake or LinkedIn job postings will have a hiring manager or someone you can email directly. When you’re entry level or making a career transition, your resume often won’t paint an entire picture. So, reach out to make a connection to show your interest and passion. Tell them that you’ve seen the position open, why you’d be a great asset, and what you’re doing to make this transition. If you use Handshake and LinkedIn to connect with as many people as you can, you won’t be waiting weeks for a boilerplate rejection.

Jameel: Also use Glassdoor to research positions you’re interested in. Not all companies will be forthcoming with salary, so don’t be afraid to negotiate—it really isn’t taboo. Just be sure to do your research ahead of time so you know what a realistic salary range is. Also, use LinkedIn to find the team you’d possibly be working with. Do they have skills that you want to grow in? Do they post positively about the company? What is the culture and stability like? You can gain a lot of insight by doing this type of research!

What tips do you have for interview preparation?

Terry: Often, you’ll know who’s interviewing you. Look them up online, and see how they talk about themselves there. Analyze how they describe their own experience, notice what keywords they use, and try to incorporate this into your own responses. It’s also really important to prepare for basic interview questions: Why do you want to work at the company? What are your strengths and weaknesses? Finally, look up typical questions asked for the particular industry you’re looking to enter, and get ready to answer.

How do you identify someone at work and ask them to be a mentor or sponsor?

Sherry: There are a few ways it can happen. It can happen organically with people you meet, hang out with, and work with on projects. Some companies—including Toyota—have programs that match team members (including interns) with mentors. I also recently had someone approach me to ask if I would be a mentor. I hadn’t interacted with her much, but she knew me from my DEI speaking engagements and other HR work. She came to me and said, “I don’t know you very well, but I know your work ethic, and I’ve seen how you work with your team and integrate with others. Would you mind being a mentor to me?” This was wonderful, because it showed me that I have the ability to inspire others. Ultimately, notice how people lead, and approach the ones who resonate with you.

Photo by Christina @ on Unsplash

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