FutureWorks 2022: A Conversation With Issa Rae

Known for her critically acclaimed web series and NYT best-seller “The Misadventures of Awkward Black Girl” and the hit HBO show “Insecure,” Rae offers unique insight into some of the most pressing issues impacting the world of work today, including women in the workplace and the benefits of equity and diversity, as well as the journey to find her voice and stay true to her values during her rise to success.

Held both in person in New York City and virtually on October 12-13, FutureWorks featured celebrity speakers, C-suite leaders and talent industry experts discussing the future of work and hiring. Enjoy this exclusive excerpt from the virtual-only session, “Creating a Career That’s True to You: A Moderated Conversation with HBO ‘Insecure’ creator Issa Rae.” (Note: This conversation has been edited for clarity.)

Enjoy this exclusive excerpt from her FutureWorks session, “Creating a Career That’s True to You: A Moderated Conversation with HBO ‘Insecure’ creator Issa Rae.” (Note: This conversation has been edited for clarity.)

Lauren Kort: As CEO of your own production company, HOORAE Media, what are you looking for when hiring for your team?

Issa Rae: I’m looking for someone who understands what we are trying to do at this company fundamentally and has ideas about what we can do better. I love when, in interviews, prospective employees will point out missed opportunities — to me that is essential, especially as a start-up. 

I also look for someone who wants to grow with me, who is looking for longevity and who has a plan. Nothing brings me greater joy and creative fulfillment than being able to usher someone along that path and take part in their potential, so I consider the hiring process pivotal for both the success of my company and brand, as well as in growing other future leaders. 

What kind of leader and manager are you?

I’m very hands-on, but also extremely trusting. I’m the type of manager who trusts you to do your job well, but I also want you to come to me with questions. I get a lot of “I thought you were busy and that’s why I didn’t want to bring this to you,” but I’m communicative when I feel overwhelmed or when I need to delegate. Generally, I want you to feel comfortable bringing something my way because I want you to do the best job possible.

What are your favorite questions to ask of a candidate to help you find good people to work with?

First, I always ask why they want to be at my company. I think it’s one thing to apply for a particular position you think you’d excel at, but diving into the “why us?” really helps us determine a candidate’s commitment. 

Second, I love to ask what scares people about joining us! We may not have the same resources that another company has, so I want to get a sense of how we can make you feel the most comfortable working here. Personalizing the hiring process in this way allows us to better connect with candidates — to delve into their true hopes and desires for their career. 

Third, I ask, “What can we do to help you be the best employee?” For me, it is so important to understand that hiring is a two-way street. You are coming to work here and you’re providing a service to us, but how can we help you be your best self here?

How can hiring impact a business? Can you tell us about a time where you or your team has been impacted by not having the right fit to meet goals?

I truly believe in teamwork and operating on an even playing field. I personally have felt the impact of how an employee can affect a team’s dynamic and efforts, which is why I place extra emphasis on the hiring process. For example, I worked with an individual that stifled the progress I wanted to see in the workplace. At the time, I loved my job — really loved the work I was doing and saw the impact their role had on the business, which included quickly shutting down ideas and questioning creative thinking or new approaches, especially when others would proactively point out missed opportunities. They were such a blocker for ingenuity that I vowed I’d never want to be this kind of leader, nor would I ever want to hire someone who possessed similar qualities. 

With the experiences you’ve had, what is some advice you’d provide employers and hiring managers? 

I’m big on company culture. I’ve been in enough writers’ rooms to know when the vibe is off,  your work and output is off! To me, this all starts with building the right teams. In staffing a writers’ room, I always want to ensure we have different voices and obviously the best people. Candidates come from all walks of life, all types of backgrounds and experiences, so casting a wide net when hiring is important to capture the level of diversity we seek. If you know anything about a writers’ room, you know you’re spending eight hours a day with people, every single day. So, to me, it is important for employers and hiring managers to think about how each employee or candidate fits into the overall equation to find that successful synergy. 

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