Preparing for 2026... Cybersecurity, AI Acceleration, and the Cost of Uncertainty.

Jim Leone

12/16/20254 min read

As we close out 2025, it’s clear that the conversation around technology has shifted. This is no longer just about adoption or innovation. It’s about control, trust, and execution.

Artificial Intelligence didn’t arrive gradually. It exploded. And while the benefits are real --> productivity gains, improved forecasting, faster analysis... the speed of adoption has outpaced governance, security, and organizational readiness. At the same time, threat actors are moving just as fast, if not faster, leveraging the same automation to scale attacks across increasingly complex digital ecosystems.

Looking ahead to 2026, the organizations that succeed will not be the ones chasing the newest tools. They’ll be the ones that understand how risk, AI, cybersecurity, supply chains, and human decision-making now intersect, and who act with discipline in the face of uncertainty.

I Believe The Real Challenge Isn’t Technology... It’s Speed and Uncertainty.

One of the most overlooked impacts of AI’s rapid rise is organizational uncertainty.

Executives are being asked to set direction before risks are fully understood. Managers are expected to translate evolving guidance into day-to-day execution. Employees are unsure how AI affects their roles, responsibilities, or job security.

This uncertainty creates friction everywhere...

  • Decision paralysis at the executive level.

  • Inconsistent adoption across teams.

  • Shadow AI usage without guardrails.

  • Erosion of trust in systems and outputs.

Uncertainty itself isn’t the problem. Unclear direction is. Organizations don’t need perfect answers to move forward, but they do need principles, ownership, and boundaries. Without those, even the most promising technology becomes a source of instability.

Where is AI in 2026? Force Multiplier, Not Decision Maker...

In 2026, AI will be deeply embedded in business operations. That’s inevitable. What remains optional, and critical, is how it’s used. AI excels at pattern recognition, summarization, and acceleration. But it is not a source of truth. Without proper controls, organizations risk treating probabilistic outputs as facts. Key risks leaders must confront:

  • Hallucinations being mistaken for validated insight.

  • AI “slop”, low-quality or recycled data contaminating decision pipelines.

  • Data drift, where models quietly degrade over time.

  • Poisoned inputs, either accidental or adversarial.

In supply-chain environments, these failures aren’t academic. A hallucinated risk score, an inaccurate vendor assessment, or corrupted forecasting data can lead to missed deliveries, regulatory violations, or contractual breaches. I believe the question for 2026 is not “Where can we use AI?” It’s “Where must AI advise, but never decide?” Organizations that fail to define this boundary will find themselves automating risk at scale.

Right Now, Threat Actors Are Scaling Faster Than Defenders...

Threat actors don’t struggle with governance or ethics. They adopt technology as soon as it’s useful. AI has dramatically lowered the cost of attack with...

  • Automated phishing at scale.

  • Highly convincing social engineering and deepfakes.

  • Rapid reconnaissance of third-party ecosystems.

  • Faster exploitation of exposed vendors and suppliers.

Supply chains are particularly attractive targets because they offer leverage. Compromising one upstream provider can create downstream impact across dozens or hundreds of organizations. This isn’t just a security problem, it’s a business continuity and liability problem.

The Supply Chain Risk Is Becoming a Legal and Financial Event

Looking at my crystal ball, I believe in 2026, supply-chain incidents will increasingly bypass IT entirely and land directly on the desks of legal, finance, and executive leadership. A single breach can cascade into...

  • Data exposure involving customer or partner information.

  • Regulatory reporting obligations.

  • Contractual penalties or SLA violations.

  • Loss of customer trust.

  • Shareholder or board scrutiny.

The cost is no longer limited to remediation and downtime. It includes legal exposure, reputational damage, and long-term revenue impact. Organizations that still treat third-party risk as a checkbox exercise are underestimating the stakes. Vendors are no longer external, they are extensions of your attack surface and your liability footprint.

Source of Truth, Where Are You?

As AI systems consume more data and influence more decisions, source of truth becomes a critical control point. Without clearly defined systems of record, organizations risk...

  • Conflicting answers from different AI tools.

  • Decisions based on outdated or unverifiable data.

  • Loss of auditability and accountability.

  • Increased exposure during investigations or litigation.

When threat actors deliberately manipulate upstream data, or when low-quality data floods the ecosystem, the damage multiplies. You’re no longer reacting to an incident; you’re operating on corrupted assumptions. In 2026, data integrity will be as important as data security.

Enter... Quantum Computing

Quantum computing continues to generate dramatic headlines, but 2026 will not be the year encryption collapses overnight. However, there are real considerations leaders should not ignore.

The most immediate risk is harvest now, decrypt later, the idea that encrypted data stolen today may be decrypted in the future as quantum capabilities mature.

What matters in 2026...

  • Understanding where sensitive data lives.

  • Knowing which cryptographic standards protect it.

  • Planning for crypto agility, not panic replacement.

  • Building inventories and transition roadmaps.

Quantum readiness is a strategic planning exercise, not an emergency response. Organizations that start now will be far better positioned than those who wait for a crisis.

The Biggest Risk I See In 2026... Execution Failure

When you step back, you'll see that a pattern emerges. AI. Threat actors. Supply chains. Quantum. Data integrity. Liability. The common failure point is not technology, it’s execution.

Strategies fail when...

  • Ownership is unclear.

  • Decision paths are slow or political.

  • Metrics track activity instead of outcomes.

  • Cross-functional communication breaks down.

I feel that organizations that thrive in 2026 will treat execution as a discipline!

  • Clear accountability.

  • Defined decision authority.

  • Guardrails instead of ambiguity.

  • Feedback loops that surface reality early.

Execution maturity compounds. Once it improves, results tend to follow.

As we move into 2026, leaders don’t need to predict the future. They need to prepare for it.

Some Practical steps that matter...

  • Define where AI can advise vs where humans must decide.

  • Establish clear systems of record and data ownership.

  • Treat vendors as extensions of your risk surface.

  • Integrate security, legal, and operational thinking.

  • Communicate clearly to reduce uncertainty at every level.

People don’t need certainty, they need clarity.

I believe 2026 will not reward the fastest adopters. It will reward the most disciplined ones. The future belongs to organizations that balance innovation with control, automation with accountability, and speed with trust. Those are not technology problems. They are leadership problems, and solvable ones.

If your organization is navigating AI adoption, cybersecurity risk, or execution challenges heading into 2026, thoughtful planning and disciplined execution make all the difference.