Hacking your Cyber Career

Episode 11: What's Your Biggest Weakness? And Other Interview Questions Nobody Likes

"What's your biggest weakness?"

"Chocolate."

Yes, chocolate.

That was Steve's actual answer during a job interview. Not a carefully prepared response about professional development. Not a thoughtful explanation of something he was working to improve. Just chocolate.

And the strangest part? He doesn't even eat that much of it.

Fortunately, everyone laughed, he recovered, and somehow, he got the job.

But it could have gone very differently.

In this episode of Hacking Your Cyber Career, Steve tackles those predictable, awkward, and occasionally ridiculous HR interview questions that have been around for decades and apparently aren't going anywhere.

Drawing on more than 30 years of IT experience and decades of interviewing and hiring candidates, Steve explains what interviewers are really looking for, how to prepare meaningful answers, and why being genuine is far more effective than memorizing the perfect response.

In this episode, you'll discover:

• "Tell Me About Yourself": How to introduce yourself without reciting your entire résumé or providing your complete life history.
• "What's Your Biggest Weakness?": How to demonstrate self-awareness and personal growth without falling back on clichés like "I'm a perfectionist."
• "What's Your Greatest Strength?": Why specific examples are more convincing than describing yourself as hardworking, passionate, or a team player.
• "Tell Me About a Time You Failed": How to discuss mistakes, conflict, and difficult situations while demonstrating accountability and what you've learned.
• "Where Do You See Yourself in Five Years?": How to explain your career ambitions without pretending you can predict the future.
• From the Hiring Desk: What actually impresses an experienced hiring manager, and why honesty, curiosity, and genuine conversation matter more than polished answers.
• The Questions You Ask Matter Too: How to demonstrate genuine interest in the role and why opening with questions about holiday allowances might not create the best first impression.
• Prepare, Don't Memorize: Five practical steps to get ready for your next cybersecurity interview without sounding rehearsed.

Steve also shares his perspective on why many traditional HR interview questions aren't particularly useful, why he prefers conversational interviews, and what happens when candidates exaggerate their experience or can't explain what's written on their own résumés.

The biggest lesson?

You don't need perfect answers. You need honest answers that demonstrate your experience, judgement, and ability to learn.

And while a little humor can sometimes break the ice, relying on chocolate to save your interview probably isn't the best career strategy.

Your Next Move: Learn how to prepare for common interview questions, develop examples from your own experience, research the employer, and approach your next interview with confidence.

Whether you're trying to land your first cybersecurity job, preparing for a promotion, or looking to advance your IT career, this episode offers practical advice to help you stand out for the right reasons.

Because the best interview answer isn't the one you've memorized. It's the one that genuinely sounds like you.

🎧 Hacking Your Cyber Career | Real advice. Real experience. Your next move.

#CybersecurityCareers #CybersecurityInterview #InterviewTips #CareerAdvice #CybersecurityJobs #JobInterview #ITCareers

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Episode 10: Why You're Not Getting Hired in Cybersecurity (And What to Do About It)

You've earned the certifications. You've polished your résumé. You've applied for cybersecurity jobs, and maybe you've even landed a few interviews.

But the job offers aren't coming.

So what are you doing wrong? And is it really all your fault?

In this episode of Hacking Your Cyber Career, Steve takes you behind the hiring desk to reveal what cybersecurity hiring managers actually look for, why qualified candidates sometimes get rejected, and what you can do to improve your chances of landing the right role.

Drawing on more than 30 years of IT experience and decades of hiring and leading cybersecurity teams, Steve shares his perspective on what separates successful candidates from unsuccessful ones.

And surprisingly, it's not always technical knowledge, certifications, or experience.

In this episode, you'll discover:

• Why Your Résumé Isn't Enough: How to tailor your experience to the position and why a great résumé only gets you through the door.
• Communication Matters: Why the ability to explain yourself, engage in conversation, and demonstrate how you think can be just as important as technical skills.
• The Dangers of Bluffing: How hiring managers spot exaggerated experience and why admitting what you don't know can actually work in your favour.
• Breaking Into Cybersecurity Without Experience: How skills from IT, audit, finance, risk management, and other disciplines can open doors.
• Interview Preparation: The research you should do before every interview, including a personal story about the one job interview Steve didn't get through.
• Understanding Cultural Fit: Why collaboration, attitude, and the ability to work with others matter, without expecting everyone to think or behave alike.
• From the Hiring Desk: What actually makes an experienced cybersecurity leader say yes to a candidate.
• The Interview Is a Two-Way Street: Why you should be evaluating the employer just as carefully as they're evaluating you.

Steve also challenges some of the industry's hiring practices, including unrealistic job requirements, excessive expectations for junior positions, and recruitment processes that overlook potential in favor of keywords.

Your Next Move: Five practical things you can do before your next cybersecurity interview to improve your résumé, demonstrate your capabilities, prepare effectively, and find an organization that's genuinely right for you.

Whether you're trying to land your first cybersecurity job, transitioning from another career, or struggling to progress despite having the right qualifications, this episode offers practical advice from someone who's spent years making hiring decisions.

Because getting hired isn't about convincing everyone you're the perfect candidate. It's about finding the right opportunity where your skills, potential, and personality can make a difference.

🎧 Hacking Your Cyber Career — Real advice. Real experience. Your next move.

#CybersecurityCareers #CybersecurityJobs #CybersecurityInterview #BreakingIntoCyber #CareerAdvice #CybersecurityHiring

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Episode 9: Stop Collecting Certifications. Start Building a Cybersecurity Career

CompTIA Security+, CISSP, CISM, CEH, OSCP, CCSP... With so many cybersecurity certifications available, how do you know which ones are actually worth your time and money?

And more importantly, which certifications will genuinely help advance your career?

In this episode of Hacking Your Cyber Career, Steve draws on more than 30 years of IT experience, including decades leading cybersecurity teams, to help you navigate the often-confusing world of professional certifications.

From entry-level qualifications to advanced security management credentials, Steve explores which certifications make sense for different cybersecurity career paths and stages, why practical experience matters just as much as qualifications, and how to avoid collecting credentials without developing the skills to back them up.

In this episode, you'll discover:

• Starting Your Cybersecurity Career: Where CompTIA Security+, ISC2 Certified in Cybersecurity (CC), and foundational IT certifications fit into your learning journey.
• SOC and Incident Response: Certifications worth considering for security analysts, threat investigators, and incident responders.
• Ethical Hacking and Penetration Testing: Understanding the differences between eJPT, PenTest+, PNPT, and OSCP.
• Security Engineering, Cloud, and Identity: When vendor-specific certifications from Microsoft, AWS, and Cisco make more sense than general cybersecurity qualifications.
• Governance, Risk, and Compliance: Why ISO 27001 training, CRISC, and CISM can be valuable for professionals interested in risk management and security governance.
• From the Hiring Desk: How Steve evaluates certifications alongside experience, personality, initiative, and practical capability when hiring cybersecurity professionals.
• Cybersecurity Leadership: Why CISSP and CISM become increasingly valuable as you progress toward senior management and CISO roles.
• Learning vs. Collecting Credentials: Why Steve pursued his recent ISACA AAISM qualification to deepen his understanding of AI security rather than simply add another certification to his résumé.

Steve also shares why his CISSP, earned nearly 20 years ago, remains one of the most valuable qualifications of his career, and explains why passing an examination doesn't always mean you've met the requirements to hold the full certification.

Your Next Move: Build a practical six-month certification roadmap based on your career goals, current experience, skills gaps, and budget.

Whether you're just entering cybersecurity, transitioning from another profession, developing a technical specialization, or preparing for a leadership role, this episode will help you make smarter decisions about your professional development.

Because your cybersecurity career isn't a game of Scrabble. You don't win by collecting the most letters after your name.

#HackingYourCyberCareer #CybersecurityCareers #CybersecurityCertifications #CompTIASecurityPlus #CISSP #CISM #CybersecurityJobs #BreakingIntoCyber

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Episode 8: SOC Analyst, Hacker, or GRC? Finding Your Place in Cybersecurity

When people hear the word cybersecurity, they often imagine hackers, dark rooms filled with flashing monitors, and dramatic battles against cybercriminals.

But here's the reality: cybersecurity is about far more than stopping hackers. And you don't have to be a technical genius to build a successful career in it.

In this episode of Hacking Your Cyber Career, Steve draws on more than 30 years in IT and his experience building and leading cybersecurity teams to explore the many different career paths available in the profession.

From investigating security incidents and ethical hacking to engineering, architecture, governance, risk management, and security awareness, Steve explains what these roles actually involve, the skills they require, and how to discover which might be right for you.

In this episode, you'll discover:

• Security Operations (SOC): What analysts really do, why curiosity and perseverance matter, and what life on the security front line looks like.
• Ethical Hacking and Penetration Testing: The reality behind the Hollywood image and why communication is just as important as technical expertise.
• Security Engineering and Architecture: How cybersecurity professionals design, implement, and maintain secure systems.
• Governance, Risk, and Compliance (GRC): Why this often-overlooked discipline is essential to cybersecurity and offers excellent opportunities for people with business, audit, and risk management skills.
• Cloud, Identity, and Security Awareness: Exploring specializations that need very different combinations of technical and interpersonal skills.
• From the Hiring Desk: Why Steve values curiosity, enthusiasm, initiative, and teamwork alongside technical knowledge.
• Career Transitions: How experience in IT, finance, internal audit, project management, or other business disciplines can provide a valuable foundation for cybersecurity.
• Cybersecurity Leadership: How Steve's own career evolved from infrastructure into leading cybersecurity organizations, without following a predetermined career plan.

Your Next Move: A practical 30-day exercise to identify your strengths, explore two cybersecurity disciplines, and discover which type of work genuinely interests you.

Whether you're considering your first cybersecurity job, transitioning from another profession, or wondering which direction to take your existing career, this episode will help you understand the opportunities available.

Because the best cybersecurity career isn't necessarily the one that sounds most exciting. It's the one where your strengths, interests, and contribution come together.

#CybersecurityCareers #BreakingIntoCyber #CybersecurityJobs #SOCAnalyst #EthicalHacking #GRC #CybersecurityTraining #HackingYourCyberCareer

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Episode 7: Your First 90 Days in Cybersecurity — Don't Blow It

You've landed your first cybersecurity job. Congratulations! But now comes the real challenge: proving they made the right decision.

Your first 90 days can set the tone for your entire cybersecurity career. And here's something that might surprise you: success isn't necessarily about how much technical knowledge you have. It's about your attitude, relationships, willingness to learn, and ability to contribute.

In this episode of Hacking Your Cyber Career, Steve draws on more than 30 years in IT and his experience hiring and leading cybersecurity teams to share what really separates new employees who thrive from those who struggle.

From enthusiastic newcomers who exceed expectations to overconfident hires who expect promotions before they've contributed anything, Steve shares lessons from the hiring manager's side of the desk.

In this episode, you'll discover:

• Days 1–30: Why understanding the organization, its culture, and the people around you matters more than immediately demonstrating technical expertise.
• Enthusiasm vs. impatience: How to maintain your motivation when your new employer doesn't move as quickly as you'd like.
• Understanding the business: Why great cybersecurity professionals understand business risks, not just security tools.
• Days 30–60: How to identify your most important skills gaps and create a practical learning plan.
• Mistakes and accountability: Why owning your mistakes can actually strengthen your manager's confidence in you.
• From the Hiring Desk: What Steve really looks for in new employees, and the behaviours that quickly undermine trust.
• Days 60–90: How to move from learning to delivering tangible value and taking ownership of your work.
• Finding your place: How to adapt to your team's culture without losing your personality or ambition.

Your Next Move: A practical 30/60/90-day action plan, followed by two pieces of advice Steve wishes he'd understood when starting his own career.

Whether you're beginning your first cybersecurity role, transitioning from another IT discipline, or preparing for your next career move, this episode will help you build credibility, earn trust, and establish the foundations of a successful career.

Remember: Getting the job opens the door. What you do next is what builds the career.

#CybersecurityCareers #CybersecurityJobs #BreakingIntoCyber #CareerDevelopment #First90Days #CybersecurityTraining #HackingYourCyberCareer

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Episode 6: What Happens Behind the Interview Door

You've landed a cybersecurity job interview. Congratulations! Now comes the tricky part: convincing the people across the table that you're someone they want on their team.

But here's the secret: cybersecurity interviews aren't just about how much technical knowledge you have. They're about how you think, communicate, solve problems, and respond when you don't know the answer.

In this episode of Hacking Your Cyber Career, Steve draws on his experience hiring and leading cybersecurity teams to explain what interviewers are really looking for and how you can stand out, even if you're just starting your career.

In this episode, you'll learn:

• How to prepare for a cybersecurity interview and research the employer.
• How to answer the dreaded "Tell me about yourself" question.
• What to do when you're asked a technical question you can't answer.
• How to demonstrate transferable skills without previous cybersecurity experience.
• How to handle behavioural questions and talk about mistakes.
• What hiring managers actually look for beyond certifications.
• Which questions you should ask before accepting a job.

From the Hiring Desk: Steve shares what separates memorable candidates from those who struggle, and why curiosity, honesty, and communication can matter more than an impressive list of qualifications.

Your Next Move: Four practical steps to help you prepare for your next interview with confidence.

Whether you're applying for your first cybersecurity position, transitioning from IT, or looking to take the next step in your career, this episode will help you approach interviews with a clearer understanding of what really matters.

Because getting hired isn't about knowing everything. It's about showing that you're someone worth investing in.

#CybersecurityCareers #CybersecurityJobs #CybersecurityInterview #CareerAdvice #BreakingIntoCyber #HackingYourCyberCareer

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No experience? No problem. Well, perhaps a small problem. Let's work on that.

You've completed your degree, earned a certification, or spent countless hours learning about cybersecurity. You're enthusiastic, motivated, and ready to start your career.

There's just one small problem.

Every entry-level cybersecurity job seems to require three years of experience.

Apparently, you were supposed to start your career before you'd even finished school.

In this episode of Hacking Your Cyber Career, Steve tackles one of the biggest challenges facing aspiring cybersecurity professionals: how do you convince an employer to hire you when you don't have direct cybersecurity experience?

Drawing on more than 30 years in IT and cybersecurity leadership, Steve takes you behind the hiring desk to explain what employers actually look for, why experience doesn't always equal competence, and how to demonstrate your potential without exaggerating your achievements.

You'll hear why Steve has hired candidates with little cybersecurity experience, including someone who previously worked in a company mailroom, and why enthusiasm, initiative, communication, and integrity can sometimes outweigh years of technical experience.

Steve also shares a rather embarrassing early-career interview experience that taught him an important lesson about researching an employer before walking through the door.

In this episode, you'll discover:

• Why hiring managers sometimes choose less experienced candidates over more qualified applicants.
• How to turn university projects, internships, help desk work, and everyday experiences into valuable evidence of your abilities.
• The biggest CV mistakes that can undermine your chances of getting an interview.
• Why honesty matters more than an impressive list of exaggerated achievements.
• How recruiters, HR screening, and automated application systems can influence your job search.
• Why personal referrals and professional relationships can help you get noticed.
• How internships and adjacent IT roles can provide alternative routes into cybersecurity.
• What to research before an interview and how to demonstrate genuine interest in an employer.

From the Hiring Desk: Steve explains why years of experience don't necessarily indicate competence, and why he often valued curiosity, initiative, communication, and a willingness to learn over an impressive CV.

Your Next Move: Take the seven-day job search challenge. Identify realistic opportunities, improve your CV, demonstrate your transferable skills, research employers, build a professional connection, and submit applications that actually stand a chance of getting noticed.

Whether you're a university student, a recent graduate, changing careers, or trying to move from IT into cybersecurity, this episode provides practical advice to help you turn your potential into your first opportunity.

Because getting hired isn't about pretending you know everything.

It's about giving someone a reason to believe you're worth investing in.

Expect real hiring experiences, practical career advice, and the usual healthy dose of British sarcasm.

Hacking Your Cyber Career

Real advice. Real experience. Your next move.

Because getting in is just the beginning.

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Finding your strengths, exploring career paths, and choosing a role you'll actually enjoy.

So, you want to work in cybersecurity. Brilliant!

But what exactly do you want to do?

When most people think about cybersecurity, they imagine hackers in hoodies, six monitors, and someone dramatically shouting, "We're in!" The reality is rather different.

Cybersecurity isn't one job. It's an enormous collection of careers, from security operations and engineering to risk management, architecture, awareness, and leadership. And finding the right fit can make all the difference between a rewarding career and a rather miserable Monday morning.

In this episode of Hacking Your Cyber Career, Steve draws on more than 30 years of IT experience and cybersecurity leadership to help you understand the different career paths available and how to identify the ones that suit your interests, strengths, and personality.

In From the Hiring Desk, Steve shares the story of an employee who struggled to manage complex cybersecurity technologies despite extensive training and coaching. Rather than giving up, they changed direction and went on to build an exceptional cybersecurity awareness program, delivering even greater value to the organization.

It's a powerful reminder that struggling in one cybersecurity role doesn't mean cybersecurity isn't for you. You might simply be in the wrong part of it.

In this episode, you'll discover:

• The differences between security operations, engineering, penetration testing, governance, risk, compliance, and other cybersecurity disciplines.
• Why cybersecurity needs great communicators and problem solvers, not just technical experts.
• How to recognize your strengths and find roles that match your interests.
• Why choosing a cybersecurity career based purely on salary can be a mistake.
• What Steve valued most in the people who made his cybersecurity teams successful.
• Why initiative, curiosity, and the ability to work independently can accelerate your career.
• How to explore different cybersecurity disciplines without starting your career over.
• Why your first cybersecurity job doesn't have to determine your entire future.

Your Next Move: Explore three dimensions of cybersecurity: technology, risk, and communication. Identify a role in each area, investigate what the work actually involves, and decide which direction best matches your interests and abilities.

Whether you're a student considering cybersecurity, a recent graduate trying to choose a specialization, or already working in IT and thinking about your next move, this episode will help you make a more informed career decision.

Because the best cybersecurity career isn't necessarily the one with the most impressive title or the biggest salary.

It's the one where you can develop your strengths, enjoy the work, and become genuinely excellent at what you do.

Expect practical advice, real leadership experiences, and the usual healthy dose of British sarcasm.

Hacking Your Cyber Career

Real advice. Real experience. Your next move.

Because getting in is just the beginning.

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University, certifications, experience, and what really matters in cybersecurity.

Do you really need a university degree to build a successful cybersecurity career? Or can certifications, practical experience, and a willingness to learn get you just as far?

Ask ten people in cybersecurity and you'll probably get ten different answers. Some insist a degree is essential. Others claim it's a complete waste of money. And somewhere on the internet, somebody's promising you a six-figure salary after a six-week bootcamp.

So who's right?

In this episode of Hacking Your Cyber Career, Steve draws on more than 30 years of IT experience and cybersecurity leadership to explore the real value of education, qualifications, and continuous learning.

He shares what his Computer Engineering education in the UK actually taught him, why he's maintained a lifelong commitment to learning, and how his approach to professional development evolved as he progressed from fixing printers to becoming a Chief Information Security Officer.

And in From the Hiring Desk, Steve shares the story of hiring someone into cybersecurity directly from the company mailroom. No cybersecurity degree. No impressive collection of technical qualifications. Just the right attitude, dedication, and potential.

In this episode, you'll discover:

• What a university degree actually tells a cybersecurity hiring manager.
• Why learning how to learn may be more valuable than any individual qualification.
• How people without degrees can build successful cybersecurity careers.
• Why certifications can be valuable, but collecting them like trophies isn't a career strategy.
• How apprenticeships, internships, entry-level IT jobs, and affordable online training can open doors.
• Why your attitude, curiosity, and willingness to learn can matter more than your current job title.
• How your educational needs change as you progress into management and leadership.
• Why looking ahead to tomorrow's technology is essential for long-term career success.

Your Next Move: Choose a cybersecurity role that interests you, identify your knowledge and experience gaps, and compare three ways to close them: formal education, practical experience, and self-directed learning.

Whether you're deciding if university is worth the investment, looking for an affordable route into cybersecurity, or wondering which certification to pursue next, this episode will help you make a more informed decision.

No expensive promises. No magic shortcuts. And definitely no suggestion that collecting another dozen certifications automatically makes you an expert.

Just practical career advice, real hiring experiences, and a healthy dose of British sarcasm.

Hacking Your Cyber Career

Real advice. Real experience. Your next move.

Because getting in is just the beginning.

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How do you get experience when nobody will give you a job?

You've studied cybersecurity, earned qualifications, and you're ready to start your career. Then you find an entry-level job asking for three years of experience, five certifications, and expertise in just about every technology ever invented.

Sound familiar?

Welcome to the cybersecurity experience trap.

In this episode of Hacking Your Cyber Career, Steve takes you behind the hiring desk to explain why cybersecurity job descriptions often seem impossible, what employers actually look for, and how you can stand out even when you don't have years of experience.

Drawing on more than 30 years in IT and cybersecurity leadership, Steve shares real experiences of hiring people straight out of college, helping IT professionals transition into cybersecurity, and interviewing candidates whose impressive resumes didn't quite survive a few simple questions.

He also shares a rather embarrassing story about the one job interview he didn't get, and the important lesson it taught him about preparation.

In this episode, you'll discover:

• Why entry-level cybersecurity jobs often demand unrealistic experience.
• Why job descriptions are frequently wish lists rather than absolute requirements.
• What hiring managers really value in inexperienced candidates.
• How enthusiasm, curiosity, honesty, and fresh thinking can give you an advantage.
• How help desk, networking, infrastructure, and other IT experience can open doors into cybersecurity.
• Why exaggerating your qualifications can destroy your credibility.
• How to create opportunities before a cybersecurity position becomes available.
• Why researching an employer before an interview is just as important as knowing the technology.

Your Next Move: Choose a cybersecurity role that interests you, identify one skill you need to develop, and spend the next seven days building practical evidence of that skill. Then research an employer you'd genuinely like to work for.

Whether you're a student, recent graduate, career changer, or IT professional looking to move into cybersecurity, this episode offers practical advice from someone who's spent years on the other side of the interview table.

No unrealistic promises. No magic shortcuts. Just real-world advice, a few lessons learned the hard way, and a healthy dose of British sarcasm.

Hacking Your Cyber Career

Real advice. Real experience. Your next move.

Because getting in is just the beginning.

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