Meeting with Anna Winskill
As someone considering a project management role in tech, I wanted to meet someone exactly like Anna Winskill, who graduated from Wesleyan with a degree in French and Government. She also completed a certificate in International Relations, which has since become a track within the Government major. I am also contemplating this major and track alongside my studies in Computer Science. After talking with Anna, I realized that, besides her current role as Innovation Manager at 11:59, she had extensive experience teaching in the public education system, which I found very admirable. It truly illustrates that conversing with people is like exploring a whole new world each time. Professional labels like Innovation Manager or Software Developer provide only a glimpse into the depth of experience and knowledge individuals accumulate over their careers.
My meeting with Anna lasted for half an hour, during which she warmly answered my questions. I asked about her experience working with individuals from highly technical backgrounds and how she navigates conversations with them in the workplace. Her insights were incredibly valuable. She emphasized the importance of developing a solid understanding of the technical aspects relevant to her projects, even if she didn’t have a technical background herself. This foundational knowledge, she explained, helps bridge communication gaps and fosters mutual respect between project managers and technical team members.
Anna also shared strategies for professionally communicating feedback and assigning responsibilities to team members. She advised using clear and concise language, focusing on the task rather than the individual, and always framing feedback constructively. I expressed my concerns about being perceived as “bossy” and asked for her advice on managing this perception. Anna reassured me that being assertive and clear is not synonymous with being bossy. She suggested using collaborative language, such as “we” and “our team,” to foster a sense of shared purpose and responsibility. Additionally, she highlighted the importance of active listening and showing appreciation for team members’ contributions, which helps build a positive and cooperative team environment.
Furthermore, Anna shared her journey from Wesleyan to her current role, emphasizing the value of diverse experiences. Her time teaching in the public system, she noted, honed her communication skills and her ability to adapt to various situations—skills that have been invaluable in her role as an Innovation Manager. This part of our conversation was particularly inspiring, as it underscored the importance of embracing a range of experiences and learning from each one.
Anna’s advice extended beyond communication and team management. She recommended continuous learning and professional development as critical components of a successful career in project management. She encouraged me to seek out opportunities for growth, such as attending workshops, pursuing certifications, and staying updated on industry trends. Her perspective on lifelong learning resonated with me, reinforcing the idea that adaptability and a willingness to learn are key to thriving in any field.
Meeting with Anna Winskill was enlightening and motivational. Her diverse background, combined with her practical advice and warm demeanor, left a lasting impression on me. I gained valuable insights into effectively communicating and managing teams, as well as the importance of embracing a variety of experiences. This meeting reinforced my interest in pursuing a career in project management within the tech industry, armed with a better understanding of the skills and mindset required to succeed.
The guidance and support from experienced professionals like Anna, along with the resources available at Wesleyan, have been instrumental in shaping my career aspirations. I feel more confident and prepared to navigate my future career path, equipped with practical strategies and a broader perspective on the importance of diverse experiences and continuous learning. I am grateful for the opportunity to connect with such an inspiring individual and look forward to applying the lessons learned in my own professional journey.
