Category Archives: Leadership

Enterprise Software Sales and the Role of the Startup CTO

Selling major Enterprise software is very different to selling “off the shelf” products.  Beyond the technical challenges, the startup CTO can make a major difference in winning these critical accounts. From the startup CTO’s perspective, Enterprise software sales are really … Continue reading

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Technical Leadership for Impossible Situations

We’ve all faced resource limited situations that just didn’t seem possible.  Here’s a story of grace under fire, and how sound technical leadership can make all the difference… The Setting This is a true story, but I’m withholding names and … Continue reading

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Achieving Software Product Maturity

Well established frameworks, such as the Capability Maturity Model (CMM), help us measure software development process maturity in a standard way.  But what makes the product functionality itself mature, and more importantly, how do we get there from “here”?  Software … Continue reading

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Paying off Technical Debt

Technical debt is very similar to consumer revolving debt.  It’s convenient, especially when you’re resource or time constrained.  But it has an ugly compounding effect, and must therefore be managed as often and as early as possible.  The long term effects … Continue reading

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3 Keys to Being Disruptive

This week I was invited to speak on a disruptive technology panel. I thought about what being disruptive actually means, and what the keys are. Your Disruptive Technology Has to Work Whatever the nature of your disruptive product or service, … Continue reading

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3 Steps to Leading an Agile Transformation

Agile Development is right for most organizations.  Modern, competitive release cycles are much too short for more traditional methods, and customers have grown accustomed to continuous improvement in the products they buy.  We live in an age where software updates … Continue reading

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Lessons from a Bachelor Party: Valuing Development Teams

Confession: I spent last weekend at a bachelor party, “off the grid”, about 140 miles northeast of Seattle, WA.  Ten savages (yours truly among them) left to their own devises, without a care in the world, honoring a very close … Continue reading

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Why Aspirations Trump Skills

I’ve given a lot of thought lately to what I consider to be a key pillar of leadership: matching skills with responsibilities.  As obvious as this sounds, I can’t tell you how many times I’ve seen leadership teams miscast talent … Continue reading

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