The Art of Saying Yes: Jennifer Ryan on Career Growth and Adaptability

December 21, 2023
Content Marketing | Marketing Strategy | Taking the Lead

Episode Summary

In this episode of Taking The Lead, host Christina Brady engages in a conversation with Jennifer Ryan, the Director of Global Sales and Pre Sales Enablement at BlackLine. Jennifer shares her unique professional journey, which demonstrates adaptability and seizing opportunities. Her career transition from procurement to IT, training, and eventually to sales enablement exemplifies her willingness to embrace change and diverse experiences.

Jennifer discusses her approach to challenges and opportunities, underscoring the importance of saying “yes” and learning from failure. Her stories, including spontaneous moves into IT and sales enablement, showcase a career built on adaptability and a positive mindset. Her journey is a testament to the value of being open to new experiences and finding learning opportunities in every situation.

The conversation also covers Jennifer’s philosophy on personal growth and professional development. She advocates for having a personal “board of directors” – a support network for navigating career and life challenges. Jennifer’s insights provide listeners with valuable lessons on career evolution, embracing change, and the significance of a proactive and positive approach in professional and personal realms.

Featured Guest

Name: Jennifer Ryan

What she does: Director of Global Sales and Pre Sales Enablement

Company: BlackLine

Noteworthy: Jennifer has had a remarkable career path, including roles at LexisNexis and speaking engagements at ATD Cell, known for her extensive knowledge and engaging personality​.

Key Insights

Confronting and Overcoming Fear

Jennifer discusses her reflective approach to life, emphasizing her efforts to avoid repeating past mistakes. She identifies a binary mindset rooted in various fears, including the fear of failure, success, and the opinions of others. This mindset, she notes, is often driven by irrational fears. She references a quote that encapsulates her perspective on fear: “Forget everything and run, or face everything and rise,” highlighting her approach to confronting and overcoming fears​​.

The Concept of a Personal Board of Directors

Jennifer introduces the concept of a personal “board of directors,” a support network to identify and address personal and professional gaps. This board consists of people who complement your strengths and weaknesses, fostering a partnership that enhances overall growth and development. She emphasizes the importance of being aware of one’s gaps and working collaboratively with others to leverage mutual strengths, creating a “professional village” of sorts that aids in continuous self-improvement​​.

Finding the Right ‘Yes’ in Challenges

Jennifer shares a pivotal moment in her career when she learned to reframe the concept of saying “no.” When faced with a challenging request from her boss, Keith James, she initially refused. However, Keith advised her to find a different “yes” — a way to agree while also meeting her needs and boundaries. This advice shifted Jennifer’s perspective, leading her to see every situation as an opportunity for a win-win outcome. This approach transformed her attitude towards challenges, focusing on finding agreeable solutions that benefit all parties involved.

Episode Highlights

Empowering Team Creativity Through ‘Game Jam Day’

Jennifer discusses her approach to team empowerment and innovation. She describes the implementation of ‘Game Jam Day’, a concept introduced by one of her team members. On this day, each month, the team is encouraged to block out their calendars and engage in creative, unconventional activities. This initiative reflects Jennifer’s leadership style, which prioritizes creativity and employee autonomy, fostering a more dynamic and innovative work environment.

“I created what we called […] Game Jam Day […] And on that day, I want you to just do something wacky. Do something cool.”

Transition from Music to Training and Solutions Consulting

Jennifer shares her career transition from music to corporate training and solutions consulting. Her background in music education and therapy led to a unique opportunity in training, showcasing the versatility of her skills. This part of the conversation reveals how diverse experiences can lead to unexpected yet fulfilling career paths.

“I got a job as […] a customer trainer and then, from there, I became a solutions consultant.”

Artistic Expression and Taking Professional Lifelines

In this segment, the discussion revolves around the impact of artistic expression on professional life. Jennifer and the host explore the concept of being open to taking ‘lifelines’ in one’s career, such as unexpected job opportunities. They discuss how an artistic background can lead to a unique perspective on career development, emphasizing the importance of being open to new opportunities.

“You have that yes mentality first […] Taking the lifeline […] so many of us so often just need the lifeline.”

Career Aspirations and Humorous Insights

Jennifer humorously reflects on her initial career aspirations to become an astronomer, sharing a personal anecdote about her experience stargazing. This part of the conversation provides a lighter moment in the podcast, showcasing Jennifer’s personality and the humorous side of re-evaluating childhood dreams.

“I wanted to be an astronomer […] And then we sat there for four hours freezing with hot chocolate looking at stars. And I’m like, ‘I don’t want this.’ This is boring.”

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