Monday, August 25, 2025

Your First Week with an AI Intern: 3 Safe Tasks to Get Started


 "Nothing in life is to be feared, it is only to be understood. Now is the time to understand more, so that we may fear less." — Marie Curie

In today's fast-paced professional world, the to-do list is endless. Whether you're running a company or a department, you're constantly switching between being a strategist, a creator, and an analyst. What if you could offload some of that mental heavy lifting to an enthusiastic, incredibly fast intern?

Welcome to the world of AI. The best way to think of it is as your new "AI intern"—it’s brilliant, works 24/7, and is eager to help. But just like any intern fresh out of school, it has zero real-world experience. It has incredible book smarts but needs your guidance, feedback, and expertise to produce truly valuable work.

Ready to put it to the test? Here are three simple, low-risk tasks to assign during its "first week" to see what it can do.


✅ Task 1: The Brainstorming Session

Your AI intern is a powerhouse for breaking through a creative block. It can generate ideas in seconds, giving you a wealth of starting points to refine.

  • What to assign: Ask it to brainstorm something creative and low-stakes.
  • Example Prompts:
  • Why it's a great first task: There are no wrong answers in a brainstorm! This is a safe space to see how the AI "thinks" creatively and provides a ton of value with zero risk.


✍️ Task 2: The Simple First Draft

Routine writing tasks can eat up your day. Let the intern handle the first pass on simple communications so you can focus on strategy.

  • What to assign: Ask it to write a short, common piece of professional copy.
  • Example Prompts:
  • Why it's a great first task: This saves you immediate time. The AI produces a solid draft that you can quickly review, tweak in your own voice, and send.


🧠 Task 3: The Information Digest

Feeling overwhelmed by long articles, reports, or email threads? Your AI intern is a world-class summarizer.

  • What to assign: Copy and paste a long piece of text and ask for the key points.
  • Example Prompt: "Summarize the key takeaways from this dense market research report in five bullet points: [paste text here]."
  • Why it's a great first task: This is a productivity superpower. It allows you to stay informed on industry trends or digest internal documents in a fraction of the time.


Your Goal This Week

The point of these tasks isn't to get a perfect, final product. It's to understand how to ask questions and see how the AI responds. You’ll quickly learn that the quality of its work depends entirely on the quality of your instructions and feedback.

Now that you’ve met your intern, how do you train it to go from a generic helper to a truly indispensable assistant?

Coming up next: Training Your AI Intern: The Secret to Smarter, More Useful Results

#AIforBusiness #FutureOfWork #DigitalTransformation #Productivity #ArtificialIntelligence #CorporateInnovation

Monday, August 18, 2025

The Power of the Worst Case: Why You Should Try to Break Your Response Plan

 

"Everybody has a plan until they get punched in the mouth." - Mike Tyson

Mike Tyson’s famous quote isn’t about boxing—it’s about the brutal collision between a well-manicured strategy and a chaotic reality. In business, the tabletop exercise is our chance to simulate that collision in a safe environment.

Yet, many leaders approach these exercises with a desire for reassurance. They want to see a smooth test where the plan is followed perfectly and the team handles the challenge with ease. But a test where everything goes right is a wasted opportunity. The real goal of a tabletop exercise is not to validate your plan, but to get "punched in the mouth"—to find your plan's breaking points so a real crisis doesn't find them for you.

Designing for Discovery: The Power of the Worst Case

To truly test a team, you can't throw softballs. A valuable tabletop exercise must be a stress test built around an extreme, but still plausible, worst-case scenario. This is a concept that elite military units and emergency services have understood for decades. They don't practice for the best-case scenario; they relentlessly train for the worst.

The logic is simple: if your team and your plan can effectively navigate a catastrophic scenario, they will be calm, collected, and thoroughly prepared for the far more likely, less severe incidents they will actually encounter.

Imagine the difference in preparedness:

  • A team that practices for a single server failure might be overwhelmed by a ransomware attack that takes out a whole department.
  • A team that has practiced for a ransomware attack that encrypts the entire company, including their backups, will handle that departmental incident with practiced, confident precision.

A "worst-case" scenario isn't about fantasizing about meteor strikes. It's about taking a realistic threat and amplifying its impact by layering complications. What if the ransomware attack happens during a key product launch? What if your primary communication channel is compromised at the same time your key supplier goes offline?

Designing these scenarios forces you to uncover hidden dependencies, resource gaps, and communication breakdowns that would only otherwise be discovered in the chaos of a real crisis.

There is No "Fail" in Tabletop

This brings us to the most important mindset shift for leaders: a tabletop exercise is not a pass/fail test.

The goal is not to get a perfect score. A tabletop where everything goes perfectly according to the plan is arguably a failed exercise. It means the scenario wasn't challenging enough or the participants weren't engaged enough to question the assumptions and stress the system.

A successful tabletop is one that ends with a long list of action items. It uncovers flaws in the plan, reveals a need for new resources, and exposes misunderstandings between departments. Every "failure" within the safe confines of the exercise is a critical vulnerability discovered and a priceless opportunity to strengthen your organization before it really matters.

When a team says, "We wouldn't be able to do that," or "We don't have a plan for this," the correct response is not disappointment. It's "Excellent. We've found something real. Let's dig in."

Conclusion: Stress-Test Your Strategy

Your plans for Business Continuity, Disaster Recovery, or Incident Response are built on assumptions. The only way to know if those assumptions are valid is to deliberately and methodically try to break them.

When you design your next tabletop exercise, resist the urge to create a scenario that will make your team look good. Do the opposite. Challenge them with a difficult, multi-faceted crisis that stretches their capabilities and pushes them beyond the comfortable boundaries of the written plan.

Don't just test if your team can follow a plan. Test their ability to survive when the plan falls apart. That is how you build a truly resilient organization.

Monday, August 11, 2025

Ditch the Dusty Binder: How to Run a Tabletop That Actually Works

 

"Plans are useless, but planning is indispensable." - Dwight D. Eisenhower

This famous observation from President Eisenhower, a five-star general who orchestrated one of the most complex military operations in history, contains a profound truth about preparing for a crisis. The value is not found in the static, finished plan, but in the dynamic, indispensable process of planning itself.

Too often, organizations forget this. Picture the scene: a dozen leaders gather for the annual tabletop exercise. A thick binder is placed on the table, and for the next two hours, they dutifully flip through pages. This ritual creates a dangerous illusion of preparedness. Often, this exercise devolves into an administrative audit disguised as a strategic drill. The focus becomes updating contact lists and confirming roles on a chart, mistaking the upkeep of a document for the readiness of the organization.

The fundamental mistake is thinking the goal is to have a perfect plan. The real goal is to have a resilient team, forged by the process of planning. A tabletop exercise isn't a test of how well people have memorized a document; it's a test of the organization's collective ability to think, communicate, and react under pressure.

The Plan Serves the Team, Not the Other Way Around

Many organizations treat their continuity and response plans as rigid, sacred texts. But a plan is a compass, not a GPS. It provides direction, but it cannot predict the exact terrain of a crisis. Therefore, the core principle of any exercise must be: The plan should adapt to the organization's needs; the organization should not be forced to adapt to the plan's rigid structure.

The tabletop is the forum where the plan breathes, where its assumptions are challenged, and where it is updated to reflect the reality of how your team actually operates.

The most valuable moments in any exercise are not when someone correctly recites a line from the document. They are when a leader pushes the binder aside and says, "The plan says to do X, but that would never work because..." or "To solve this, I would need access to Y, but I have no idea who provides that." These moments of discovery are the entire point.

The Anatomy of a Real Tabletop

A well-designed tabletop is not a performance; it's a dynamic, facilitated discussion where the plan is just one resource in the room, not the script for the play. The goal is to see how your team reacts when faced with a real challenge.

Consider the difference in approach:

  • The Old Way: "Bob, according to page 47 of the BCP, what is your first step?" This is a test of memorization and document navigation.
  • The New Way: "Bob, you just got an alert that the primary data center is offline. Your phone is blowing up with calls from your team and the media. What are you doing right now?" This is a test of reaction, prioritization, and critical thinking.

The facilitator’s job is to present a scenario that disrupts the neat order of the plan. The objective isn't to force adherence to the script; it's to observe the team's instinctive response. You then compare that intelligent, human reaction to what the plan says. The gaps you find—the places where the plan is outdated, unrealistic, or unclear—are the gold you are mining for.

Conclusion: Preparing for the Unthinkable

A modern tabletop exercise should never be a test of your people; it is a test of your organization’s collective ability to respond, adapt, and recover effectively when faced with a dynamic threat.

Static plans are designed for predictable failures. But history’s greatest challenges are rarely predictable. Who had a detailed plan for a global pandemic in December 2019? Who saw the events of 9/11 coming? Who could have documented the full, cascading system failure of Hurricane Katrina in advance?

No one. And that is the entire point. The goal of a tabletop is not to ensure people have memorized a script for a foreseeable event. It is to build the collaborative muscle memory, communication pathways, and adaptive leadership required to handle the completely unforeseeable.

Crucially, this approach has a powerful side effect: it creates genuine engagement. When you ask leaders to solve a complex problem rather than recite a document, you get their full attention. They become active participants in their own preparedness, thinking critically and collaborating to find solutions, not just passively checking a box.

Stop auditing your plan. Start stress-testing your organization’s ability to think, adapt, and lead through a crisis.

Monday, August 4, 2025

The Two-Sided Coin of Security: Balancing Maturity and Effectiveness

 

"In theory, there is no difference between theory and practice. In practice, there is." - Yogi Berra

In the complex world of cybersecurity, boards and executives crave a simple answer to a difficult question: "How secure are we?" This desire has given rise to an industry-wide focus on maturity models. Frameworks like the NIST Cybersecurity Framework (CSF) Tiers or CMMC levels provide a comforting, color-coded scorecard. They create the illusion of control, allowing a CISO to stand before the board and proudly declare, "We have advanced from a '2' to a '3'."

This is the theory. And in theory, a higher maturity score means a more secure organization.

But as Yogi Berra wisely noted, theory and practice can be two very different things. An exclusive focus on documented maturity can create a dangerous blind spot. Conversely, a program that ignores mature processes in favor of pure, reactive defense is building on a foundation of sand.

True cyber resilience isn't about choosing between maturity and effectiveness. It's about mastering both. Falling short on either side leads to two common, and equally dangerous, failure states: The Maturity Trap and The Hero Trap.

The First Failure: The 'Maturity Trap'

This is what happens when theory outpaces practice. The 'Maturity Trap' snares organizations focused on looking good on paper. They chase high scores on frameworks, but the activities required to raise a score are often disconnected from the activities that actually stop an adversary.

This trap manifests in several ways:

  • The Tool Trap: Millions are spent on "best-in-class" tools to check a box, but the tools are poorly configured or the alerts are ignored. The presence of the tool grants maturity points, but its ineffective implementation provides no real security.
  • The Policy Paradox: Hundreds of beautiful security policies sit on a shelf to satisfy auditors, but they aren't part of the daily culture. The organization has mature policies but immature practices.

This is a hollow shell—a program that is theoretically mature but practically useless in a real fight.

The Second Failure: The 'Hero Trap'

This is the other side of the coin, where practice outpaces theory. Many organizations are highly effective at stopping attacks for one simple reason: they have a handful of brilliant, tireless security analysts. These are the "security heroes."

These individuals have the intuition, talent, and sheer grit to hunt down threats and keep the organization safe through what seems like sheer force of will. The organization’s defenses are effective, but this effectiveness is brittle. What happens when these heroes burn out, go on vacation, or leave for a better offer?

The security posture collapses. Because their knowledge was never institutionalized, there are no documented playbooks, no repeatable processes, and no cross-training to sustain their efforts. This is the 'Hero Trap': a program that is highly effective today, but utterly fragile tomorrow.

Uniting the Two: The Goal of Sustainable Resilience

The ultimate goal is to build a program that is both effective in practice and mature in process. These two elements should exist in a virtuous cycle, not in opposition.

This means using real-world performance metrics to drive the maturity of the program.

  • Core performance metrics like Mean Time to Detect (MTTD), Contain (MTTC), and Remediate (MTTR) are no longer just grades on effectiveness; they are data points that inform process improvement.
  • A Red Team exercise isn't just a test; it's a requirements-gathering session for your maturity roadmap.

When an ethical hacker gets in (testing effectiveness), the response isn't just to patch the hole. It's to ask: "What process failed us? How can we create a new, repeatable control (maturity) to ensure this type of failure never happens again, no matter who is on the job?"

This is how heroics are converted into a sustainable program. This is how a theoretical policy is proven to be a practical reality.

Conclusion: A Two-Sided Coin

Chasing a high score on a maturity model without proof of effectiveness is a waste of resources. Relying on the heroics of individuals without building a mature program to sustain them is a reckless gamble.

Leaders need to change the conversation to demand both. Start by asking your own teams, "What is our evidence of effectiveness?" and "How are we capturing those lessons to make our program more repeatable and mature?"

This extends to your third-party assessors. Challenge them to move beyond a simple audit of controls. The critical question to ask them is, "How are you measuring not just our documented maturity, but our proven, practical effectiveness?"

A security program that only shows you one side of the coin is giving you half the value and twice the risk. True resilience is found in the unity of theory and practice—a defense that is both proven in a fight and built to last.

Your First Week with an AI Intern: 3 Safe Tasks to Get Started

  "Nothing in life is to be feared, it is only to be understood. Now is the time to understand more, so that we may fear less." —...