I’ve written previously about firing your CTO in a hostile situation and how to survive your CTO leaving. In this post I’d like to talk about the process you as a CEO should go through before deciding to replace your current head of engineering / CTO in the case where it just doesn’t seem to […]

“Every system is perfectly designed to get the result that it does.” W. Edwards Deming When your product and engineering team is struggling to deliver consistently, it is tempting to go looking for answers in those two functional areas. You might start asking for more reporting and metrics, or ratchet up the pressure and ask […]

“Any organization that designs systems will produce a design whose structure is a copy of the organization’s communication structure.” Melvin Conway One of the questions I’ve been asked most often, either as a part of diligence or talking with CEOs, is how the product and engineering organization should be designed. Many times the question arises […]

On Decisions I was listening to the year-end episode of the All In podcast over the weekend. Though I don’t love these kinds of “recap” shows, this show was great because in the middle of it Elon Musk joined. After the initial pleasantries were exchanged, David Friedberg posed a question to Elon about how decisions […]

The most common complaints in software product companies are typically some form of the below: “We’re spending all of this money and I don’t know what I’m getting” “Our team consistently misses deadlines and there’s always some excuse as to why” “Every time we release something new, something else breaks” When these issues occur, the […]

Not too long ago, a company I know had a serious outage. The customer base was split across the old, legacy environment and the new public cloud, and there was a schedule in place to finish the migration in six months or so. The outage took down most of the legacy environment for an extended […]

“Humans tend to read things as events rather than an outcome of a system that can be predicted.” Thinking in Systems by Donella Meadows When software systems are failing, we tend to evaluate the causes as either a singular event or even a series of events, and often times we miss the opportunity to understand […]

Back in 2018, I started a company called Spellbound Partners with a business partner. Spellbound was started to address what we believed to be a gap in software company technology diligence, which from what we observed was focused on a list of “check the box” items rather than understanding how the business was set up […]

Hi there. It’s been a while now, hasn’t it? 2018 has been a pretty tough year. Regular blog posts and podcasts were a casualty of war. Thanks to all of you who asked about me during the second half of the year. Time to end the year on the upswing! Reading The Coddling of the […]

Every month I publish a list of blogs, podcasts, books, products or anything else I consider to be a must-have or must-do. Hope you enjoy this month’s list. In case you’ve not stumbled across it, I’m publishing a short summary of every book I’ve read on my website. My references to books going forward will […]