How CHA Senior Career Coach Helps Residents Find Good Jobs
DEIDRA WINSTON
Senior Career Coach, EPS Program
Deidra Winston, is a Senior Career Coach with Employment
Placement Services (EPS) through the E&ES CHA program. She is an incredible four-time winner of the prestigious Hustle Award in 2023 and has been a devoted member of the company for 15 years, during
which she has accumulated a wealth of knowledge and experience.
APPROACH TO CAREER COACHING: ACTIVE LISTENING AND RESPECTFUL ENGAGEMENT
During our conversation, Deidra shed light on her approach to Career Coaching, which is the source of her success. She says, “This is more than just a job for me.” Deidra’s main focus is on active listening. She believes it’s crucial to understand her client’s overall needs and recognizes that they often face multiple challenges that go beyond just finding a job.
“When clients come to E&ES, they bring more problems than just needing a job,” she notes. “I let them talk through their needs to get a better idea of how to serve them.”
Deidra doesn’t exaggerate. She evaluates her clients without them knowing. She talks to them and asks about their background and important questions to make detailed notes. Deidra remembers a time when she felt ignored and unimportant by a case manager.
She told the case manager about her degree in special education, but the case manager, without ever looking up from her keyboard, suggested she apply for a job at the Taste of Chicago. “That was improper coaching to me,” she reflects. “I would never downplay my customers and the knowledge and experience they bring.” She believes in treating customers with respect, just like she would want for herself. That experience is a constant reminder of her commitment to advocating for her client’s goals. She believes in uplifting them and empowering them to pursue their desired career path.
CLIENT-CENTERED COACHING PHILOSOPHY
Still, Deidra’s true source of success with job placements is in the quality of service she provides.
“Quality service brings the quantity of placements” is her motto.
And it works! Deidra helped 95 people find permanent jobs in 2023, accounting for 43% of her team’s overall placements!
Deidra is a critical part of her team’s successes.
She focuses on building strong relationships with her clients and creating a welcoming atmosphere where they feel important and in control. She believes that being a bad coach means not being available for your clients and treating them like a statistic instead of an individual. Deidra has a big influence beyond just one-on-one conversations. Thanks to her personable attitude and ability to connect, she serves as a conduit for valuable information and resources. She talks about how she gets job leads from the clients she serves which she then passes on to others – even if they aren’t on her caseload.
PROACTIVE GOAL SETTING AND INSPIRATIONS FOR SUCCESS
When asked how she sets personal goals for helping clients. She said she likes to be proactive. She strategically sets goals for the number of people she aims to assist each quarter, taking the initiative to share these goals with her supervisor.
This proactive approach helps her stay on track and ensures that keeps her focused on making a positive impact within the program. Upon reflecting on her habits and the mindset that led
her to win the Hustle Award in all four quarters of 2023, the only question left to ask was, what inspires all of this?
Deidra at the start of the 2023 LDP Cohort
Upon reflecting on her habits and the mindset that led her to win the Hustle Award in all four quarters of 2023, the only question left to ask was, what inspires all of this? Deidra attributes her success to her leaders’ constant support and belief in her abilities, in addition to her own compassionate nature. “Larry and Anissa have given me some opportunities, which showed me that they respect me and value me at this company,” she shares warmly. She is also motivated by their public recognition of her work, both within the company and among funders. This drives her to strive for continual excellence.
Deidra Winston is a career coach who stands out for her exceptional skills and her ability to help people succeed. She understands the importance of empathy, dedication, and commitment in guiding individuals toward reaching their goals and finding fulfillment in life.
