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Upskilling at The Speed of Relevance

Originally written by Santiago Holley, republished here with permission.

The rapid acceleration of AI and hyperautomation is fundamentally reshaping every industry, and cybersecurity is front and center. Maybe because it is the least professionalized profession where many decisions are based on vendor driven narratives or professional opinion, but that in itself is the topic for a different article. I believe it is now more critical than ever for professionals in cybersecurity to develop a voracious appetite for learning to remain competitive, and that upskilling at the speed of relevance is every professional’s priority to avoid obsolescence.

The modern business environment is characterized by instability, turbulence, and continuous creative destruction. Companies that fail to adapt quickly to disruptive innovation risk decline, emphasizing the constant need to innovate and evolve to remain competitive. In this dynamic landscape, learning and development aren’t just beneficial; they are essential for survival and growth. The 21st century has seen machines and computers automate routine tasks, shifting the human role towards creativity, innovative thinking, and complex problem-solving. This means that individuals who do not continuously develop new skills risk becoming irrelevant, as the demands of roles can accelerate faster than many can learn, the opposite of success isn’t failure—it’s boredom.

Productivity in 2025 and beyond isn’t about working harder or longer hours, but about making strategic choices and thinking differently. This underscores why a proactive, continuous learning approach is paramount.

Prioritized Skills and Attributes for Cybersecurity Professionals:

In my opinion, here are the critical skills and attributes cybersecurity professionals should prioritize:

I. A Voracious Appetite for Learning and a Growth Mindset

This is foundational. It means adopting a “growth mindset,” where intelligence and abilities are seen as continually developing through effort, rather than being static. You must never stop learning or developing your skills, remaining open to feedback and constantly striving for higher standards.

It also means embracing humility by acknowledging your potential for error and being willing to admit when others can perform a function better than you can. The willingness to express nervousness or concerns about new ideas can be extraordinarily compelling, signaling thoughtfulness and honesty.

Ultimately, the most valuable tools are thinking differently, being disruptive, taking big risks, being bold, and being imaginative. This requires the discipline to trust one’s intuition and stay true to one’s purpose.

II. Creativity, Innovation, and Complex Thinking

As routine tasks become automated, the human role shifts to innovative thinking and the ability to think outside the box. There is an urgent need for “fast originality”, fueled by insights gained through deep engagement.

Highly innovative companies are receptive to ideas from everywhere and act quickly on them, even if “partly baked”. It’s important to remember that many great ideas were initially considered “stupid ideas”.

While ideas are easy to come by, implementation is hard and where the true value lies. Your role isn’t just to generate ideas, but also to discern and “kill off all the bad ideas we generate, and most of the good ideas too”.

To find truly novel ideas, “go beyond Google”. Great ideas often stem from an “earned secret”—a hidden insight gained through firsthand, real-world experience that can’t be found through a simple search.

III. Adaptability and Agility

Professionals must be able to respond rapidly to external environmental changes, including new threats and technological shifts. This involves a willingness to “prototype now, seek forgiveness later”.

It also means embracing a continuous experimental approach, diving into new methods and adapting as you go, rather than getting bogged down in lengthy planning cycles. Productivity emerges when people push themselves to think differently.

IV. Strategic Thinking and Vision

The ability to “see around corners” and predict future trends is invaluable. This involves focusing relentlessly on what will be valuable in the future.

Adopt a “helicopter view” of problems and opportunities, observing orthogonal changes that could significantly impact your ideas. True visionaries “skate to where the puck is going to be,” accelerating existing trends rather than trying to create entirely new ones.

Understanding your “WHY”—your core purpose—can simplify decision-making, foster loyalty, build trust, and drive innovation.

V. Self-Awareness and Humility

This is about having the humility to realize you will often be wrong and to admit mistakes, acting on that information instantly.

Leaders and professionals who embrace “intellectual honesty” are data-driven and possess the courage to change their minds, rather than clinging to historical positions.

Being open to admitting risks and concerns suggests thoughtfulness and honesty, building credibility. It’s more interesting to “bask in the glory of others” and harness their gifts for mutual benefit than to try to do everything yourself. The right blend of confidence and humility ensures adaptability and openness to change.

VI. Effective Communication and Collaboration

Start talking about your ideas right away, as the more people you engage with, the richer your thoughts will become.

Pitching is essential not just for funding, but for achieving agreement leading to sales, partnerships, and new hires. Be prepared and concise; if you can’t describe your business model in ten words or fewer, you don’t have one.

When pitching, focus 80% of your time on convincing yourself of the idea’s conviction, and only 20% on the presentation materials. Avoid bullet points when possible, as “fully formed paragraphs force you to explain why”

Proactively “steer into objections” by anticipating potential criticisms and addressing them directly in your pitch.

Crucially, share what an idea could be, not rigidly “how it has to be”. Invite others into the creative process to foster a sense of co-ownership, making them advocates for your idea even when you’re not present.

Build a “backable circle” of trusted individuals with diverse perspectives, including a “Karen” who will poke holes in your ideas, helping you get ahead of objections.

Rigorous debate within a team doesn’t break it down; it builds strength and fosters collective willpower and commitment. Multipliers actively foster such environments, asking for evidence and challenging conventional thinking to arrive at sound decisions

VII. Deep Expertise and Strategic Specialization

While generalists are useful, as an organization (or a career) matures, specialists who excel at specific tasks become more valuable. This means striving to know more about a niche area than anyone else.

However, don’t be afraid to pivot when necessary. The advice is “Don’t ever quit unless you should quit,” showing strategic discernment over blind persistence. The goal is to persist with your “company” (your career or overall mission) but be prepared to kill, revise, or evolve specific ideas.

VIII. Bias Towards Action and Persistence

The “essential thing is action”. This involves not just decision and preparation, but execution itself.

Understand that early efforts often involve “throwaway work”—material that isn’t immediately usable but is a vital part of the creative and learning process.

Leaders and professionals should be willing to do “whatever it takes” to convince others of an idea they truly believe in.

Cultivate “emotional runway” – the energy to keep pushing a new idea forward. Intellectual interest is rarely enough; you need to be emotionally invested, as conviction is replenished by passion. This means aligning your work with something you deeply care about.

Embrace the philosophy that “the obstacle is the way,” using challenges, failures, or disruptive events as catalysts for growth and new opportunities.

IX. Leveraging Others (Multiplier Mindset)

Recognize that success is a team sport. “Multipliers” are leaders who see and cultivate the intelligence in others, significantly increasing organizational capability.

This involves “doing less” of the controlling behaviors (less talking, less rescuing) and “challenging more,” allowing others the space and obligation to contribute their best thinking.

When people bring problems, ask them for their proposed solutions (an “F-I-X”), and then “give the ‘pen’ back,” clearly returning ownership and accountability for the work.

Conclusion

The foundational skills required go beyond technical proficiency, demanding a blend of a proactive learning mindset, innovative thinking, adaptability, strategic vision, self-awareness, strong communication, and the ability to inspire and empower others. By prioritizing these skills, cybersecurity professionals can ensure they not only remain competitive but also lead the charge in securing the future.

This article draws upon my experience, information and concepts from a variety of sources. I leveraged my own though leadership NotebookLM. Below is a list of the key books that I recommend and were used to compile the insights presented in the article:

  • Art of the Start 2.0: The Time-Tested, Battle-Hardened Guide to Starting Anything by Guy Kawasaki.
  • Awakening Your Ikigai: How the Japanese Wake Up to Joy and Purpose Every Day by Ken Mogi.
  • BE 2.0 (Beyond Entrepreneurship 2.0) by Jim Collins.
  • Backable: The Surprising Truth Behind What Makes People Take a Chance on You by Suneel Gupta.
  • Crossing the Chasm, 3rd Edition by Geoffrey A. Moore.
  • The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses by Eric Ries.
  • Product-Market-Fit: Der entscheidende Meilenstein eines Start-ups by Nils Stotz.
  • Smarter Faster Better: The Secrets of Being Productive by Charles Duhigg.
  • The 80/20 principle: the secret of achieving more with less by Richard Koch.
  • The Four Steps to the Epiphany by Steve Blank.
  • The Gap and The Gain by Benjamin Hardy & Dan Sullivan.
  • The Innovator’s Dilemma: When New Technologies Cause Great Firms to Fail by Clayton M. Christensen.

Republished with permission from Santiago Holley. You can view the original article on LinkedIn here

 

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