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Who am I?
I am Chris Conway and I’m going to help you understand the world of technology we all now live in.
Why Subscribe?
Because I’m really good at translating technology into something that you’ll be able to understand and can relate to.
I don’t just explain it. Every article I write ends with items to bring up at your Monday morning management meeting and some new vocabulary to go with them. If you’re going to take the time to read what I write, I’m going to make it worth your while.
No hype. No fear-mongering. Just the complicated thing, explained simply.
There are plenty of smart people getting talked over by jargon. Somebody needs to be on their side.
I’m volunteering.
Who is this for?
This is for fellow tech leaders, private equity professionals, middle-market executives, and anyone generally curious about the digital world. The focus will be on the messy, fascinating intersection of tech, business, and humanity—written in a way that is approachable, occasionally irreverent, and always practical.
What’s my background?
Becoming a CIO (Chief Information Officer) was never on my bingo card. The plan was flying F-14s for Navy, or becoming a Jack Ryan-esque CIA operative, chasing errant Russian submarines for the CIA.
Instead I spent 30 years walking into chaotic companies with technology issues, finding the core problems, and putting things in order.
I found that the hard part was never the technology. It was translation. I speak Technology, Business, and People, and I turn what each group says into something the others can act on. Most technology disasters are translation failures wearing a technology costume.
Technology in Translation is the newsletter where I do that in public. Plain language for the finance director whose company bought an AI platform, the manager asked to explain what a context window is to the CEO, and everyone who ever nodded along in a conversation hoping nobody asked what they thought.
What do I write about?
Each article is part of of series.
Tech Goes Plaid
The speed of technology is accelerating at ludicrous speed. I focus on where technology decisions collide with stakeholders, P&L, and the people who have to answer for them. long-form preferred. Business + technology intersection for stakeholders at all levels. Always starts with Substack and LinkedIn articles that then are turned into short form for other social media channels. Most formal series.
CIO Field Notes
Lessons from the chair. Management wisdom, tech/business/people interactions. Personal narrative-forward. Advice navigating the messy interaction of technology, business, and people, and the cognitive biases that wreck good decisions. Always starts with Substack and LinkedIn articles that then are turned into short form for other social media channels. Most informal series.
No Profit in Caution
The dangerous side of the current AI boom. Over investment, the unpleasant outcomes nobody is pricing in, and the case that the bust is part of the story. The argument other people are too invested to make out loud. Stuff I really should write under a pseudonym.
The Daily Comment
Short-form reactions to the day’s technology news. The “hey, check this out” of someone who can tell you why it actually matters in one paragraph.
Tech for Normies (Coming Soon)
Your IT therapy. Content for everyone who ever wanted to up their tech game in bite size digestible chunks. Without condescension. How-to’s that make your life easier.
Why am I doing this?
Why? Because I genuinely love talking, thinking, and writing about this stuff.
I hope you’ll join me for the ride. See you in the comments!



