Guide
Insights
Straight answers about IT, security and AI.
Field notes, guides and news from Circle Square, written in plain language for owners and operators.
Latest
Nothing's Wrong With Your IT. That Might Be the Problem.
Ask most owners how their technology is doing and the answer is "fine, no complaints." But nothing being wrong and everything being right are two different things.
Read the field noteTools and downloads
Something to take away.
Checklists, assessments, whitepapers and calculators. Free, and useful whether or not you ever call us.
Legal · 15–75 attorneys
Law firms
- ChecklistThe Renewal Checklist: 14 things your carrier may ask about AIDownload the PDF
- Assessment · twelve questionsThe Renewal Readiness Assessment
- Whitepaper · six pages, PDFThe AI answer on your renewal is a written representation about your firm. Decide now whether it is true.
SEC-registered · $250M–$5B AUM
Financial and wealth management firms
- ChecklistPre-exam AI checklist: 14 things a CCO should be able to answerDownload the PDF
- Assessment · twelve questionsThe AI Evidence Assessment
- Whitepaper · seven pages, PDFYou have the AI policy. The question is whether you can produce the file underneath it.
Manufacturing · $10M–$150M
Manufacturers
- ChecklistThe Quote Clock: 12 numbers to pull from last month's RFQsDownload the PDF
- Assessment · twelve questionsThe Quote Clock Assessment
- Whitepaper · six pages, PDFThe quote is the constraint. The estimator is the risk.
Every industry
Any business
- Tool · about ten minutesAI Use Policy Starter
- CalculatorThe Downtime Ledger: what does an hour cost you?
- Sample report · four pagesSample Downtime Ledger ReportDownload the PDF
Guides
Guides you can use Monday morning.
- A worksheet for owners who would rather know the number before they need it.Learn more : What an Hour of Downtime Costs
Guide
The Continuity Plan Most Businesses Don't Have
What a real continuity and recovery plan contains, and how to tell if yours is one.Learn more : The Continuity Plan Most Businesses Don't HaveGuide · Signet
Bringing AI In Without Losing Control
A plain guide for owners whose teams are already using AI.Learn more : Bringing AI In Without Losing Control
Field notes
All field notes
- Signet$145,000 in one quarter. The AI sanctions cases are not about AI.
- SignetNobody expects valuations to rise. Diligence friction is one of the few variables still yours.
- SignetBefore you automate anything, find out whether your ERP will let you
- SignetA machine makes chips. Software doesn't. Here is the exception.
- SignetYour notetaker is producing records. Rule 204-2 does not care that nobody sent them.
- SignetWhen a client's outside counsel guidelines arrive with an AI clause
- SignetThe quantity typo that shipped 2,000 parts
- SignetEighty-six percent of you wrote the policy. Fourteen percent have an incident response plan that mentions AI.
- SignetBoth Reg S-P dates have passed. Can you produce the record for each service provider?
- Signet69% of legal professionals used AI last year. 9% of firms enforce a written policy.
- SignetThe cyber clause in your supplier quality agreement
- SignetWhat a small law firm should automate first, and what it must never automate
- LegalThe Friday Afternoon a Law Firm Learned It Had Tools, Not Security
- SignetAI for SMBs: The Strategic Framework That Separates Results From Noise
- NewsInc. Names Circle Square to Its 2026 List of the Fastest-Growing Private Companies in the Northeast
- SecurityBlocking Your Mom Is a Good Thing: Smart Cybersecurity for SMBs
- SignetDoing More with Less: A Practical Guide for SMBs to Start Their AI Journey Responsibly
- StrategyRide the Wave or Get Swept Away: How Digital Transformation Will Define Success in the Silver Tsunami
- Private EquityThe Pros and Cons of Modernizing IT Across Private Equity Portfolio Companies
- SecurityMastering Information Technology Risk Assessment Strategies
- Managed ITManaged Services vs Professional Services: What’s Best for You?
- CloudCloud Database Benefits Driving Business Innovation
- StrategyA Manufacturer’s Blueprint for Digital Transformation Strategy
- LegalWhy Every NJ Legal Firm Needs a Digital Transformation Consultant Now
- HealthcareHow Digital Transformation Services in NJ Improve Healthcare
- Financial5 Steps to Drive Digital Transformation in NJ Financial Firms
- HealthcareSecuring Patient Data: Managed Services in New Jersey's Healthcare Sector
- FinancialShielding Financial Data from Spam with IT Managed Services in New Jersey
- Private EquityNavigating Cloud Security in Private Equity: Managed IT Services in New Jersey
- Managed ITChoosing the Right Managed IT Service in New Jersey
Find out what an hour costs you.
Book a Downtime LedgerAbout 60 minutes. Your numbers. You keep the result.