Meeting summary for SIP Study Group - 14th May 2025

Quick recap

Winton led a session on preparing for interview questions, emphasizing the importance of formatting and structuring answers, incorporating past experiences, and bridging the gap between current and future job states. He also discussed the importance of creating a well-structured resume, using the STAR format for effective storytelling in interviews, and the value of active listening and genuine interest in the conversation. Winton also highlighted the importance of networking, leveraging one's network, and providing sufficient information in response to security questions without going too deep.

Next steps

• Attendees to prepare for interview questions using the STAR method (Situation, Task, Action, Result) for structuring answers.
• Attendees to create a "story toolbox" of work experiences to draw from during interviews.
• Attendees to practice answering both defensive and offensive security interview questions.
• Attendees to research and stay updated on emerging cybersecurity threats.
• Attendees to consider booking a discovery call with Winton through the Safer Internet Project platform for personalized guidance.
• Attendees to review and potentially use the resume template provided by Winton.
• Attendees to maintain a work diary or log of daily activities to use for future interview preparation.
• Attendees to prepare strategies for answering questions they don't know during interviews.
• Attendees to research and understand the differences between blue team and red team roles in cybersecurity.

Summary

Preparing for Interview Questions and Certifications

Winton led a session on preparing for interview questions, focusing on deconstructing questions and understanding their core. The discussion also covered the importance of formatting and structuring answers, incorporating past experiences, and bridging the gap between current and future job states. Winton emphasized the need for both hard and soft skills, including technical skills and certifications like CompTIA Security Plus and OSAP. The session aimed to help participants understand how to study for certifications, assess their readiness, and pass exams on the first attempt.

Resume Structure and STAR Format

Winton discussed the importance of creating a well-structured resume to effectively represent one's work, projects, education, and skills. He emphasized the need to avoid any doubts about one's capabilities and to make the resume stand out. Winton also introduced the STAR format as a tool for effective storytelling in interviews, highlighting the need for a balance between showcasing achievements and not exaggerating them. He concluded by mentioning the topic for the next meeting, which will focus on job regression, career paths, and opportunity costs.

Winton's Advice on Personal Growth

Winton emphasized the importance of setting clear goals and focusing on personal growth, including learning new skills and building deeper relationships. He shared his own journey of learning technical skills and networking, and encouraged others to do the same. Winton also offered his assistance to anyone seeking help with certifications, resume crafting, job preparation, or building a professional network. He invited viewers to connect with him on LinkedIn for further discussions.

Tailoring Interview Questions for Success

Winton discussed the importance of asking relevant questions during an interview. He suggested that these questions should be tailored to the interviewer's experience, a security initiative or project, and the team's decision-making process. Winton also emphasized the value of active listening and genuine interest in the conversation. He provided examples of questions that could be asked about the role, such as what success looks like after the probationary period and how others have adapted to the position.

Understanding Role and Team Dynamics

Winton discussed the importance of understanding the role and its impact on various teams, including operations, managers, customers, and engineers. He emphasized the need to ask specific technical questions about tools like Splunk and its challenges. Winton also encouraged learning about the company's products, platforms, and software tools, and understanding the company's core values and missions. He suggested asking about recent strategies, shifts in management or leadership, and how these changes affect the company. Lastly, he stressed the importance of learning about the team structure, its challenges, and the true culture of the team.

Networking in Job Interviews

Winton discussed the importance of networking in job interviews, emphasizing the need to build relationships and learn from others. He suggested that a solid resume, a portfolio of projects, and an optimized LinkedIn profile are essential for maximizing chances of getting hired. Winton also highlighted the importance of asking for help and not overlooking networking opportunities. He shared his personal experience of having interviews where he didn't get the job but still maintained connections that led to other interview opportunities.

Leveraging Network and STAR Method

Winton discussed the importance of leveraging one's network and offered a discovery call service. He also emphasized the value of the mentorship and live sessions on the platform. Winton then introduced the STAR method for framing answers in interviews, which involves setting the situation, describing the task, outlining the actions taken, and highlighting the results. He also stressed the importance of being concise and technical in answering interview questions.

Overcoming Imposter Syndrome in Interviews

Winton discussed strategies to overcome imposter syndrome and prepare for future interviews. He emphasized the importance of addressing gaps in skills and experience, using transferable skills and the ability to learn tools quickly. Winton also advised being upfront about not knowing something, but also highlighting past successes and experiences. He suggested structuring work log notes and activities to make it easier to recall and present them confidently in interviews.

Security Questions and Network Segmentation

Winton discussed the importance of providing sufficient information in response to security questions without going too deep. He emphasized the value of storytelling in explaining processes and experiences, and suggested that one story could be used to answer multiple questions. Winton also highlighted the need to understand network segmentation, threat intelligence, and cloud environments, particularly AWS, GCP, and Azure. He recommended taking certification courses to gain a better understanding of these topics.

Blue vs Red Team Roles

Winton discussed the balance between blue and red team roles in cybersecurity, noting that there are more blue team roles available but also the potential for increased competition. He suggested that blue team knowledge could serve as a better foundation for a career in red team, as it provides a deeper understanding of what needs to be defended. Winton also emphasized the importance of staying updated on emerging threats, as the industry is constantly evolving with new attackers and defenders needed to protect against them.

Pen Testing Methodology and Salary Ranges

Winton discussed the ongoing game of cat and mouse in the industry, hinting at the potential for a new pen testing methodology. He emphasized the importance of understanding the tools and methodology involved in pen testing, including different frameworks and tools. Winton also highlighted the varying salary ranges and examples of roles in the blue team, noting that red team roles generally have higher salary ranges. He concluded by sharing key takeaways, including the challenges of entering the blue team and the interview process, which typically involves behavioral questions, foundational knowledge, and practical assessments.

Interview Preparation and Red Team Focus

Winton discussed the importance of preparation and staying calm during interviews, emphasizing the need to be honest and not bluff. He highlighted the differences between blue and red teams, with blue teams focusing on tools and work activities, and red teams on red team questions. Winton also stressed the importance of career growth and job stability, and advised on how to handle questions one doesn't know the answer to. He concluded by encouraging the team to stay calm and not panic, even if they fail an interview, as life continues and they will have other chances.