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Strategy

24 articles

December 07, 20257 min readsoftware developmentstrategy
Why Software Rewrites Fail and How to Do Them Right

The patterns behind failed software rewrites and a proven approach for successful system modernization.

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November 07, 20257 min readdesignstrategy
Why Big Software Redesigns Almost Always Fail

Why Big Software Redesigns Almost Always Fail. software redesign failure

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September 17, 20257 min readsoftware developmentstrategy
10 Reasons Software Projects Fail and How to Prevent Each One

The most common failure patterns in software development with specific prevention strategies.

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July 18, 20257 min readstrategycompetitive
Custom Software as a Competitive Moat

Custom Software as a Competitive Moat. software competitive advantage

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April 30, 20257 min readengineeringstrategy
Why Boring Technology Wins: The Case Against Trendy Tech Stacks

How proven, stable technology choices outperform trendy alternatives for business applications.

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April 09, 20257 min readstartupstrategy
Transitioning from Services to Product: A Strategic Guide

Transitioning from Services to Product: A Strategic Guide. services to product

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March 22, 20257 min readenterprisestrategy
Building Software Products for Enterprise Clients

Building Software Products for Enterprise Clients. enterprise software development

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February 26, 20258 min readstartupstrategy
Why Speed Beats Scale in Early-Stage Software

Why Speed Beats Scale in Early-Stage Software. speed vs scale startup

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January 28, 20258 min readengineeringstrategy
How to Choose the Right Tech Stack for Your Business

A business-focused guide to technology selection that serves your goals, not your developer resume.

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November 25, 20247 min readstrategytransformation
Why Most Digital Transformation Projects Fail

Why Most Digital Transformation Projects Fail. digital transformation failure

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July 09, 20247 min readproductstrategy
The Build Trap: Why Building More Features Hurts Your Product

How feature factories destroy product value and what to do instead.

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June 01, 20248 min readAIstrategy
Build vs Buy for AI Features: A Complete Decision Guide

When to build custom AI capabilities vs when to use off-the-shelf AI products.

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May 06, 20247 min readstartupstrategy
CTO vs Development Agency vs Technical Co-Founder: Which Do You Need

CTO vs Development Agency vs Technical Co-Founder: Which Do You Need. CTO vs agency decision

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April 12, 20247 min readstartupstrategy
When to Pivot vs When to Persevere: A Framework for Product Decisions

When to Pivot vs When to Persevere: A Framework for Product Decisions. pivot or persevere framework

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March 05, 20248 min readAIstrategy
When NOT to Use AI in Your Product: A Practical Guide

Not every problem needs AI. Here is how to evaluate whether AI is the right solution.

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February 27, 20247 min readstrategydata
Data Ownership and Portability: Why It Matters for Your Business

Data Ownership and Portability: Why It Matters for Your Business. data ownership portability

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November 11, 20237 min readproductstrategy
Building a Product Roadmap That Survives Contact with Reality

Building a Product Roadmap That Survives Contact with Reality. product roadmap

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October 06, 20237 min readstrategytechnology
How to Build a Technology Strategy for Your Business

How to Build a Technology Strategy for Your Business. technology strategy business

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March 23, 20237 min readstrategyquality
The Hidden Tax Every Business Pays for Bad Software

The Hidden Tax Every Business Pays for Bad Software. bad software business cost

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March 11, 20237 min readsoftware developmentstrategy
Custom Software vs Off-the-Shelf Solutions: The Complete Decision Guide

When to buy packaged software and when to build custom. A framework for making the right technology investment decision.

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February 24, 20237 min readproductstrategy
How to Prioritize Features for Your Software Product

Frameworks for deciding what to build first that maximize business impact.

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May 30, 20227 min readengineeringstrategy
Understanding Technical Debt: A Business Leader Guide

Technical debt explained for non-technical stakeholders with strategies for managing it effectively.

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April 23, 20227 min readoperationsstrategy
The Operator Guide to Custom Software Development

The Operator Guide to Custom Software Development. operator software guide

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March 11, 20227 min readinternal toolsstrategy
Build vs Buy: When to Build Internal Tools vs Subscribe to SaaS

A comprehensive framework for the build vs buy decision with cost analysis and decision criteria.

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