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Organizational Politics & The Security Program
I first wrote the original of this post over 4 years ago. Having seen a new spurt of discussion about organization politics in various on-line and in-person forums I thought it was time for an update. At every stage in your career and in every part of your role you are going to have to deal with organizational politics. People often construe such politics as inherently negative. Yes, there are some organizations that have toxic cultures where organizational politics looks mo
Mar 2118 min read
Cybersecurity’s Need for Speed & Where To Find It
As we talked about in the last post , a world going through a massive AI-driven transition means speed becomes vital. This is the speed of adapting to change and the speed of dealing with a world of threats, who are themselves moving ever faster. It’s easy to say go faster but this has to be more than just wishful thinking or a line in a strategy document. You actually have to go do some things. You also have to push back against some of the defeatism that permeates a lot of
Mar 710 min read
Things Are Getting Wild: Re-Tool Everything for Speed
It’s not often that a force appears that totally re-orients everything in security. This is what we are facing with AI. 12 months ago I had an incrementalist view of the cybersecurity impact of AI. Specifically, that it will be very significant but things will change progressively and we’ll adapt to adversarial use while also using it to improve defenses. Now, I’m coming to a view that this will have a bigger negative impact than even our worst assumptions. But at the same
Feb 218 min read
2025 Year in Review - Top 10
The most read posts in 2025 coalesced around the concept that successful cybersecurity is fundamentally a function of business leadership, strategic design, and sustainable execution . The unifying themes across the top posts emphasize shifting security from an artisanal, reactive craft to an industrial-scale, proactive capability focused on building scalable, self-reinforcing systems (flywheels). Transformation requires leaders to manage stakeholder expectations carefully, p
Jan 104 min read
Everyone Has A Plan Until They Get Punched In The Face
Apparently what Mike Tyson actually said in a 1987 interview was, " Everybody has plans until they get hit for the first time". In any...
Aug 23, 20257 min read
Career Longevity & The Don't Fire Me Chart
One of the more common patterns of security program success vs. failure is how much leadership is prepared to stick with the work over...
Jul 12, 20252 min read
Cyber Insights Needed & Delivered
I thought I’d try something different and share some thoughts on the Cyentia Institute’s latest report, the Information Risk Insights...
Jun 28, 20254 min read
CISO / Cybersecurity Leader Job Description
There is a plethora of sample job descriptions for security leaders that are often strictly correct but can also be uninspiring or too...
May 31, 20253 min read
Why Stuff Fails (“The Thermocline of Truth”)
For many years I’ve observed the same pattern of failure in projects, programs, issue mitigation and indeed anything that requires more...
Apr 19, 20255 min read
Security Leaders’ Reading List
I have a regular set of go to books both for myself and what I recommend to others at all stages in their career. Here they all are with...
Mar 22, 20256 min read
Stressed Testing: Practical Operational Resilience
Operational resilience is a concept that has gained even further traction. It first came to prominence from financial regulators, in...
Feb 8, 202513 min read
Top Ideas and Posts from 2024
I managed to keep up the pace of 1 post every 2 weeks throughout 2024. Just when I think I might be running out of ideas, and the backlog...
Dec 28, 20246 min read
Regulatory Harmonization - Let’s Get Real
Every few months some association or other learned group of professionals makes a fresh call to action for cybersecurity regulatory...
Nov 30, 20247 min read
Lessons in Crisis Management - Top 10 Disaster Movies
I’ve previously posted about some of the best security movies made but I have to confess I’m not a big fan of the genre. They tend not...
Nov 16, 20243 min read
Risk Appetite and Risk Tolerance - A Practical Approach
If you work for a large organization, especially public or otherwise regulated companies, then you may well have faced the prospect of...
Nov 2, 202413 min read
6 Truths of Cyber Risk Quantification
I wrote the original version of this post over 4 years ago. In revisiting this it is interesting to note that not much has actually...
Sep 7, 20248 min read
Security Training & Awareness - 10 Essential Techniques
Security training is often considered a bit of a waste of time. Maybe this is unfair, but unsurprising in the face of the worst forms of...
Aug 10, 202416 min read
Why Good Security Fails: The Asymmetry of InfoSec Investment
One of the many paradoxes of security is that when you have invested appropriately (sometimes at significant expense) and you have less...
Jul 13, 20245 min read
Human Error
Several years after writing the first version of this blog I still see a repeated pattern of problematic events attributed to human...
Jun 29, 202410 min read
The Crucial Test of Security Leadership: A-grades vs. Pass/Fail
A major success marker of great security leaders and their teams is one simple prioritization technique: the ability to know what needs...
May 18, 20244 min read
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