Mentorship and Leadership: Career Spotlight with Chakena Sims, Deputy Press Secretary at Chicago Public Schools

Chakena Sims is a rising leader. She serves as the Deputy Press Secretary for Chicago Public Schools and is also a Trustee at Connecticut College. When she isn’t busy working, Chakena may be found brunching or reading a good book.  During our time with Chakena we spoke to her about the public school system, leadership, and how to find a good mentor.

Tell me about the work you do with Chicago Public Schools (CPS)

I began on May 31, 2016 as a Press Assistant in the Communications Department. That was more of a support role for the director and chief strategist. It was a very comprehensive experience. For example, I had lots of hands-on experience drafting quotes and staffing the CEO and Chief Education Officer at their events. I was promoted after seven months to the Deputy Press Secretary role, where I now have more responsibilities and am actually able to implement a vision that I have for CPS. I am in charge of shedding light on the positive events that go on within our schools and pitching them to the media. Most of the positive things you see online or in the news that are related to CPS is a result of my work. I work directly with local television and newspapers outlets, and school communities to make sure their students are getting the attention that they deserve.

How did you come across this position and how did you solidify that this was the right job for you? I never envisioned myself working for CPS.

I was always very hesitant to work for CPS because I felt that people wouldn’t view me the same, or would see me as a part of an inefficient system. I really want our communities to hold us accountable and help shape a school system that all of us can be proud of. I know who I am and what my personal politics are, so whatever my position is, it’s done with love. I’m working towards the greater good.

In terms of actually getting the job, I graduated [college] early in December 2015 so during that time I was applying to lots of financial firms. I am very interested in business and real estate, but I applied to many firms and I was rejected because of my lack of finance background. I did have a couple job offers, but it just didn’t feel right. I didn’t see my vision for community building aligning with those jobs, and I felt that I would be stagnant. I went into 2016 jobless. Then I found out that Kim Foxx was running for Cook County State’s Attorney and jumped on her campaign, and also helped get students registered to vote and become first-time voters.

Someone randomly sent me the link for the Press Assistant position and I just let it sit in my inbox. Eventually I thought about it and figured, why not? I don’t have a background in communications but I also did not have a finance background and that didn’t stop me before. Throughout the interview process, I leveraged my past experiences, my skills and abilities, and my vision for CPS that other people may not have.

What do you feel is most effective in terms of motivating young students?

Motivation has a lot to do with exposure to opportunities. Reflecting on my own experience as a CPS student, I always got excited when opportunities were presented to me or stories of others’ achievements were shared with me because it motivated me to pursue them myself. When students are aware of someone who has done the work that they are themselves interested, in that organically creates passion and motivation. Lots of CPS students are low-income students of color. Many don’t see job opportunities, or resources in their own communities. Many are from families that have endured generational poverty, and it becomes very easy to believe that that is the end. When students actually know that opportunities exist, they have something to look forward to. It is important that CPS alumni, like myself, give back to the current students so we can help them craft a short- and long-term vision for success.

What does leadership mean to you?

I think we need to change our perception of leadership. I believe that anyone can be a leader, it just takes honest conversations with yourself and a very intentional attitude. Leadership comes in many different forms, and it doesn’t just have to be the person that is in the spotlight, it is also the people in the background that are getting their hands dirty. We have seen that throughout history, and sometimes those people get overshadowed, but that doesn’t reduce the effect that they have left on society.

What is the best way to find a mentor?

In college, I was always looking for a “polished” person–someone who is ten years into their career with advanced degrees. I realized that these people are extremely busy and although they seem complete from the outside looking in, they are still working on themselves. When they hear the term “mentor,” sometimes they cringe because mentorship is synonymous with time commitment and that scares people away sometimes. There aren’t many people who don’t want to help young professionals be great, but they just don’t have the time to invest into mentorship. When there is someone who I really admire, I don’t frame it as “I want you to be my mentor.” I make sure to do my research and pose different questions to them that they can answer on their own time. If I find their responses to be valuable, I simply ask whether I can use them as a resource down the road to get their insight. When you do that, people are more receptive to offering guidance.

What’s in the future for Chakena Sims?

I would ultimately like to become governor of Illinois. That’s my dream. I’ve spent some time in Springfield, my job has deepened knowledge about State budget and politics, and I enjoy reading about what’s happening at the State level. However, my dream is bittersweet because although I think I would do a good job, an even better job than some of our predecessors, sometimes politicians can become far-removed from the community. Sometimes it’s unintentional, but I’d imagine it’s a hard balance. I also see myself pursuing entrepreneurship. I envision myself running a corporation that’s so well-managed that I can hire the previously incarcerated, the homeless, immigrants–all individuals who have been left out of the work force. I am not sure exactly what the corporation would be, but I know who I would like to serve and I would like to hold on to that vision.

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