Whether you’re already a member of Cyberspace Innovations or just exploring what our mentorship program has to offer, you might be wondering what kinds of questions you can ask. That’s a perfectly reasonable question, especially if you’ve never worked with a mentor before. The good news is that you don’t need some enormous career crisis or complicated problem to benefit from mentorship. Sometimes the simplest questions lead to the most interesting conversations!
I’ve spent nearly four decades working in technology, cybersecurity, leadership, and business, and I’ve mentored thousands of people along the way. One thing I’ve learned is that people often hesitate to ask questions because they think they should already know the answers. Believe me, I’ve asked plenty of questions myself over the years, and I’m still learning new things all the time. Nobody has this entire industry figured out, especially with how quickly things are changing. Ha!
So, What Kinds of Questions Can You Ask? #
Maybe you’re trying to figure out how to get started in IT or cybersecurity. Perhaps you’ve been working in technology for years and feel stuck in your current position. You might be considering a move into management, wondering how artificial intelligence will affect your career, or thinking about starting a business of your own. These are all perfectly reasonable things to discuss with a mentor.
You can also ask about professional relationships, workplace challenges, certifications, education, interviews, career transitions, or decisions that have you scratching your head. I’ve experienced quite a few twists and turns throughout my own career, including some that I certainly didn’t see coming. Sometimes an outside perspective from someone who’s been through similar situations can help you recognize opportunities or avoid mistakes.
And mentorship isn’t just for beginners! I’ve worked with people who were just getting started and others who already had successful careers but wanted a different perspective. Experience doesn’t magically eliminate uncertainty. If anything, the decisions tend to get more complicated as your responsibilities grow.
I also enjoy challenging people to think beyond the obvious. Maybe you’re chasing a particular career because everyone says that’s where the money is. Or perhaps you’re collecting certifications because you think the next one will finally open some magical door. Hahaha! Sometimes the best advice I can give you is to question whether you’re heading in the right direction in the first place.
How Should You Ask Your Question? #
Start by telling me a little about yourself, what you’re trying to accomplish, and what’s making the decision difficult. A few paragraphs are usually plenty. You don’t need to write a novel, upload your entire professional history, or explain every technical detail of a project.
For example, rather than simply asking, “How do I get into cybersecurity?” you might explain what you’re doing today, what experience you already have, and what interests you about cybersecurity. Maybe you’re working in customer service, studying for a certification, or already supporting computers at your workplace. Those details help me understand your starting point and offer guidance that’s more relevant to your situation.
Another example might be, “I’ve been working as a systems administrator for five years, and I’m considering moving into management. I enjoy technical work, but I’m not sure whether I’d enjoy managing people. What should I be thinking about before making that decision?” Now that’s a conversation we can work with! You’re giving me enough background to understand the situation without writing your entire life story.
You don’t need to have the perfect question, either. If you’re struggling to explain your situation, start with what you know. We can work through the rest as the conversation develops. That’s part of the mentoring experience, my friend!
What Does the Mentorship Program Actually Include? #
Cyberspace Innovations offers private, asynchronous mentorship through our online Mentorship Tickets system. That means you can submit questions when it’s convenient for you without scheduling an appointment or rearranging your day around somebody else’s calendar.
I review each question and respond personally, typically within 2 to 5 business days. Members can submit additional questions, but we work through one active question at a time, with other questions queued. This helps me give each conversation the attention it deserves while keeping membership affordable.
My role is to share experience, offer perspective, challenge your thinking when appropriate, and help you make better decisions. Sometimes that means discussing career options. Sometimes it means helping you evaluate whether a certification, degree, job opportunity, or business idea makes sense for your goals.
And occasionally, it means telling you that your idea might need a little more thought before you charge ahead with it. Ha! I’ve led hundreds of people throughout my career, and I’ve learned that being a good mentor isn’t about telling everyone what they want to hear. Sometimes a little tough love and a different perspective are exactly what someone needs. I want you to succeed, and that means I’ll be real with you!
What Isn’t Included? #
Mentorship is not the same thing as technical training, employment assistance, or consulting. Our membership doesn’t include structured courses, training videos, internships, recruiting, job placement, guaranteed career outcomes, or personal introductions to employers.
It’s also not a technical support desk. I won’t be debugging your software, reviewing code, implementing projects, performing security assessments, or providing hands on consulting through mentorship tickets. Those are entirely different services requiring different commitments, resources, and pricing.
And while I’m happy to share what I’ve learned throughout my career, membership doesn’t include scheduled coaching calls or unlimited access to my personal calendar. Keeping the program asynchronous is one of the ways I can make experienced mentorship available at an affordable price.
I want people to understand these boundaries before joining because I’d much rather have someone discover that the program isn’t what they’re looking for than become disappointed after signing up. I have no interest in selling someone a service they don’t actually need. No surprises, no nonsense, and no promises of overnight success!
What Makes Someone a Good Fit for Mentorship? #
You don’t need a fancy degree, an impressive job title, or a collection of certifications. You don’t even need to know exactly where you want your career to go. Some of the most rewarding people I’ve mentored started with very little experience but had something far more important: curiosity, determination, and a willingness to learn.
What matters is being willing to take initiative, think about the guidance you receive, do some research, and put ideas into practice. I’ll share my experience and help you think through your options, but the decisions and the work ultimately belong to you.
That’s not me trying to make mentorship difficult. It’s simply how people grow. The goal isn’t to become dependent on someone else for every decision. It’s to develop the confidence and judgment to make better decisions for yourself.
And don’t underestimate what a good career can do for your life! We’re not just talking about job titles or collecting more certificates. We’re talking about building skills, opening opportunities, making better money, gaining independence, and hopefully finding work you actually enjoy doing. Nothing wrong with wanting all of that, my friends! I’ve enjoyed the financial rewards of my own career, and I’m certainly not going to pretend money doesn’t matter. Hahaha!
Ready to Have a Conversation? #
If you’re already one of my mentees, you know where to find me! Visit your Mentorship Tickets page and bring me something that’s been on your mind. Maybe you’re wondering about your next career move, how AI could change your profession, or whether that new opportunity is really worth pursuing. You don’t need to wait until something goes wrong to start a conversation. That’s what I’m here for!
And if you’re not yet a mentee, I’d love to welcome you aboard. Take a look at our membership options and see whether the program fits what you’re looking for. Whether you’re just entering technology, trying to advance your career, considering leadership, exploring AI opportunities, or wondering if it’s time to do something completely different, these are all things we can talk about together.
No hype, no promises of overnight success, and no magical shortcuts to a six figure paycheck. Just real guidance, honest conversations, and lessons learned from someone who’s spent nearly four decades in the technology trenches. I’ve had plenty of successes, failures, surprises, and a few expensive lessons along the way. Hahaha! If sharing those experiences helps you make better decisions and build a career you’re proud of, then we’re heading in the right direction.
Thanks for stopping by, my friends. Whether you’re already here or thinking about joining us, I look forward to hearing your story and learning what you’re hoping to accomplish. There’s a whole lot happening in technology right now, and I’d love to help you figure out where you fit into that future.
Mahalo!
Dave Parmelee
Founder, Cyberspace Innovations Inc.