Why Great Questions Lead to Better Results in Pentesting or IT in general

If there’s one thing IT and Cybersecurity have in common, it’s this: you can’t know it all. There’s no magic book with all the answers, no one-size-fits-all solution to every challenge. Each problem is unique, often requiring a fresh approach and a creative mindset. The key to success is asking the right questions and embracing the right attitude. Let me explain why this matters and how it can transform your learning journey.

Pentesting has not been an easy topic to me. Even though I’ve been in IT for many years and had clear understanding of many concepts. And I still do not consider myself very good at it. The reality is that theory is one thing and practice another one. So during the process, I’ve spent many hours looking at some command man pages, researching online, asking for help online. Granted. When I reached that point I’ve usually exhausted all my options.

However, not everyone approaches learning with same curiosity and effort as I do. I often see questions online like these:

- Why can’t I ping this box?
- Can I use SQLMap during the OSCP exam?
- My Nmap scan says the port is closed — why?

They come from people who haven’t researched or experimented on their own. They have skipped…