I've sat through enough software contract reviews to recognize the pattern. The vendor presentation is polished. The sales team answers every question with confidence. The legal team confirms the terms are standard. Finance signs off on the budget. IT says the...
Thought Leadership in Software Project Risk
Our consultants explore the structural drivers behind software project failure—and how to prevent them. We publish practical analysis on IT contract risk, RFP design, governance frameworks, delivery feasibility, vendor dependency, and pre-signature decision control.
Is Your Software Development Proposal Overestimated? How Executives Should Push Back Without Blowing Up the Deal
Software proposals often look inflated—but reacting emotionally destroys leverage. This post explains how executives should analyze a suspected overestimated software development proposal using structure, not accusation. It walks through evaluating staffing models, role allocation, contingency padding, vague discovery phases, duplicated effort, and unrealistic effort multipliers. Readers learn how to request transparency around assumptions, delivery mechanics, and dependency sequencing without triggering vendor defensiveness. The article also explains when a proposal is genuinely high due to risk concentration versus artificially padded. The goal is simple: reduce cost exposure while preserving delivery integrity and negotiation control.
Delivery Promises vs. Delivery Physics: How to Spot an Unrealistic Software Timeline in 30 Minutes
I've watched too many executives sign contracts based on timelines that looked aggressive but achievable. Six months later, the project is bleeding budget, the team is burned out, and the vendor is explaining why "unforeseen complexities" pushed the delivery date. The...
Your Software RFP Is a Risk Document Pretending to Be a Buying Guide
I've watched executives sign software contracts thinking they bought protection. They ran a competitive RFP. They got three qualified vendors. They negotiated price. They felt confident. Eighteen months later, the project is over budget, behind schedule, and missing...
The Assumptions List Lie: How “Standard” Contract Language Transfers Risk to the Buyer
I've reviewed hundreds of vendor contracts over the years. The assumptions section always looks harmless at first glance. A neat bulleted list. Professional language. Standard terms everyone uses. Then the project starts. The vendor needs something you thought was...
The Assumptions List Lie: How “Standard” Contract Language Transfers Risk to the Buyer
I've spent years reviewing contracts that cost organizations millions in unexpected liabilities. The pattern is always the same. Someone signs what looks like standard boilerplate language. The project starts. Then the invoices arrive, the disputes begin, and suddenly...
The $122 Million Blindspot: Why Your IT Risk Assessment Needs Independence
I've watched too many executives sign contracts they thought were solid, only to discover the risk assessment came from the same vendor selling the solution. The math tells you everything you need to know. For every $1 billion invested in IT projects in the United...
Governance Is Not Bureaucracy: The Escalation Structures That Prevent Software Project Collapse
I've reviewed hundreds of software contracts that ended in litigation. The pattern is predictable. The Statement of Work looks professional. The Master Service Agreement has all the legal language. Everyone signs with confidence. Then the project starts falling apart...
Sign, Fix, or Walk Away: An Executive Decision Model for High-Risk IT Contracts
I've watched executives sign IT contracts they shouldn't have signed. The vendor presentation was compelling. The sales team answered every question. The timeline felt urgent. So they signed. Six months later, the project is 46% over schedule, 75% over budget, and...
Agile Theater: How Jira Backlogs Hide Unpriced Scope and Future Change Orders
I've reviewed hundreds of software contracts over the past decade. The pattern repeats itself with eerie consistency. A vendor proposes an "Agile approach" with a fixed budget. The executive team signs off. Six months later, the project balloons by 50% to 60%. The...
FREE GUIDE: 10 SOW Secrets Every Executive Should Know
This PDF guide exposes the hidden SOW risks that decide success or failure before work even starts—and shows you exactly what to look for, what to challenge, and what to fix while you still have leverage.