The SST Insider – December 2025

From the Helm

As we close out another month and year, one theme keeps emerging in client conversations: technology choices are outpacing budgets. In this month’s Unscripted with SST, we discussed what smart tech budgeting should look like for 2026 and why “keeping the lights on” no longer keeps you competitive.

Looking ahead, our approach is deliberate and disciplined. We are enhancing CIS Maturity to ensure asset inventory and secure configurations occur on schedule, not after an incident. We are strengthening Microsoft hardening strategies across identity and endpoints, including Conditional Access, least privilege, Defender baselines, and a consistent patching cycle to prevent the most common attack vectors. Additionally, we are improving incident response with clear plans and playbooks so that the first hour of a major incident remains calm, coordinated, and swift.

As we begin the new year, let’s align budgets with the most important outcomes: uptime, security, and confident recovery. If you want a focused start to the first quarter, we can create a simple 90-day plan around these priorities to keep your team moving with clarity.

— SST Leadership

Client Success Story

Reducing AI-Enabled Phishing Risk

A professional services firm saw an increase in highly convincing phishing attempts fueled by generative AI, including messages impersonating vendors and internal finance workflows. Although no breach happened, leadership recognized a higher risk of credential theft and fraud and sought immediate protection without delaying broader security measures.

During managed services onboarding, SST deployed high-impact, CIS-guided safeguards to reduce phishing risk. This included implementing Security Awareness Training based on realistic attacker behaviors and strengthening the Microsoft 365 tenant using CIS benchmarks. Identity protections, email security controls, and reporting workflows were enhanced to decrease dependence on user judgment alone and to lower the chances of successful phishing attacks.

After onboarding, SST established a regular schedule for CIS Implementation Group 1 (IG1) meetings. This led to an immediate reduction in risk and a clear, attainable plan for long-term cybersecurity resilience.

Key Outcomes

• Increased detection and blocking of phishing and impersonation attempts
• Higher employee reporting suspicious emails
• Reduced exposure to credential compromise through MFA and tenant hardening
• Clear roadmap for ongoing CIS IG1 implementation
• Improved leadership confidence in cybersecurity readiness

— Operations Manager

AI Corner

8 Ways AI Delivers Faster Value

• Right-size Microsoft 365 licenses
• Flag risky access policies
• Rank patch and config fixes
• Find shadow IT
• Summarize EDR alerts for faster response
• Verify backup recovery times
• Recommend tool consolidation
• Generate incident response runbooks

Proactive Insights

Why Weekly Business Metrics Are Essential

For many years, performance tracking was handled through monthly reports or quarterly reviews. Today, that pace is no longer enough.

Faster markets, tighter margins, and leaner teams mean small issues can escalate quickly if leaders are not watching the right signals. The most effective leaders are shifting to a short, consistent set of weekly metrics that reveal problems early.

Here’s why this approach matters now:

Early Warning Beat Crisis Management
Tracking a few leading indicators helps leaders identify cash-flow gaps, delivery delays, or sales weaknesses before they become emergencies.

Focus Improves Decision Quality
A small dashboard keeps attention on what drives outcomes rather than reacting to noise or anecdotal feedback.

Cash Visibility Protects Growth
Knowing cash on hand and upcoming obligations each week prevents overextension and supports confident investment decisions.

Teams Align Around Shared Reality
When everyone sees the same numbers, conversations become clearer, and accountability improves.

Consistency Builds Discipline
Weekly reviews foster a habit of proactive leadership rather than reactive problem-solving.

If you’re not reviewing a short list of core metrics each week, now is the time to start. Being aware today builds stability tomorrow.

SST News & Events

• Unscripted with SST Episode 12 – 12/2/25
• SST Christmas party – 12/5/25
• Right of Boom Cyber Call – 12/8/25
• LaCrosse Chamber Business Afterhours – 12/11/25
• Reedsburg Chamber Ribbon Cutting – 12/16/25
• Dubuque Weekly B2B – 12/18/25
• Unscripted with SST Episode 13 – 12/19/25
• New team member Matthew starts – 12/29/25

Is Your IT Strategy Aligned with Your Growth Goals?

Schedule your FREE Technology Assessment today and uncover hidden risks, inefficiencies, and opportunities in your current environment.