Stories from the Trenches

Real-world insights and lessons from decades of technology leadership

Cost OptimizationJanuary 20, 202611 min read
How to Find Ghost Users & Save Budget with a SaaS Audit Tool
Discover inactive user accounts draining your IT budget and eliminate wasteful software licenses with this proven SaaS Audit Tool. IT leaders have used this simple Excel-based framework to save tens of thousands annually while demonstrating value to executives. Perfect for IT managers looking to earn a seat at the leadership table—and essential for MSPs and auditors conducting client assessments.
By Bill Dotson
Cyber InsuranceJanuary 18, 202614 min
The Changing Cyber Insurance Landscape: Your 2026 Renewal Guide
CIRCIA reporting requirements and intensified underwriter scrutiny are reshaping 2026 cyber insurance renewals. Learn the new compliance requirements, logging standards, and action steps to ensure your coverage remains valid.
By Bill Dotson
IT LeadershipJanuary 15, 202610 min read
The IT Budget Pitch Framework That Gets Approved
Stop asking for budget and start funding projects. This proven IT Budget Pitch Framework has successfully secured approval with over 25 clients in organizations ranging from 50 to several thousand machines. Learn how to speak the business language, cut waste, reduce risk, and get your critical IT projects approved—often in under 30 minutes. Remember: this is the pitch deck framework, not your detailed line-item budget.
By Bill Dotson
IT LeadershipJanuary 14, 202612 min read
IT Independence Scorecard: Can Your IT Run Without You?
Are you the only person who can access critical systems in your organization? What happens if you win the lottery—or get hit by a bus? The IT Independence Scorecard helps IT leaders and managers assess whether their environment can truly run without depending on a single person's memory. Learn how to move from 'hero mode' to building a resilient, documented, and mature IT organization.
By Bill Dotson
IT LeadershipDecember 18, 20253 min read
Are you the CIO (or IT Leader), or the C-suite's personal Help Desk?
It's a common trap for IT leaders. You've spent years to get where you are only to find yourself at a fellow executive's house fixing a laptop or being treated like an 'order-taker' rather than a peer.
By Bill Dotson
Risk ManagementDecember 10, 20257 min read
The "Hit By A Bus" Test: How to Build an IT Department That Survives Without You
In many mid-sized companies, the IT department isn't a department—it's a person. Learn how to move from 'Hero Mode' to 'System Mode' using the IT Independence Scorecard.
By Bill Dotson
Cost OptimizationNovember 15, 20256 min read
How We Saved a Holding Company $4M Annually in IT Costs
A case study on how strategic IT leadership transformed a multi-company holding organization's technology spend while improving service quality and customer satisfaction.
By Bill Dotson
Risk ManagementOctober 28, 20258 min read
Navigating a Data Breach: Lessons from the Trenches
What to do when the unthinkable happens. Real-world guidance on managing a data breach from initial discovery through recovery and prevention.
By Bill Dotson
IT LeadershipSeptember 12, 20257 min read
Why Your MSP's vCIO Isn't Really a CIO
Understanding the fundamental difference between a managed service provider's virtual CIO and true strategic IT leadership.
By Bill Dotson

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