I haven’t talked much about AI, because I haven’t liked much about AI. The aesthetic of contemporary AI is tacky and tasteless, somehow both try-hard and lazy. It makes me feel angry, then stupid, then angry again for feeling stupid. Three of my books were used without permission or compensation to train Anthropic’s model. And all of this is to say nothing of my general preference for clean drinking water and a broadly habitable planet.

Still, even before this particular hype cycle, there were plenty of AI-like tools and systems I found very useful. After all, OpenAI is only now rolling out its own answer to Google Translate, which I have happily been using for over a decade. I’m perfectly happy for Citymapper to ingest loads of transit and traffic data and tell me the best way home after a meeting.

In my quest to find some common ground between visceral disgust and intellectual honesty, I’ve been paying really close attention to folks who are A) excited about AI and B) thoughtful, tasteful, and generally good. People like Christina Wodtke, Teresa Torres, and my friend Dave Killeen. So, when Dave announced that he had built out an AI “Chief of Staff”… I decided to give it a shot. And two weeks later, I’m really glad that I did.

I’ll skip over some of the finer points of getting Dex up and running but, long story short, about an hour after getting started, I had a conversational interface running through Cursor helping me make sense of my calendar, documents, email, Trello, and accounting software. After a few weeks, I feel like I have a much clearer sense of where AI assistance is really helpful for me, where it’s confusing, and where I want to throw my electronics out the window, run away from the city and become a dirt farmer.

Here’s what I’ve learned and observed:

Being able to search and synthesize information across multiple sources via conversational interface is, indeed, an absolute game-changer.
I used to spend a lot of time digging around in Google Drive, Dropbox, multiple inboxes, etc. to find information. Dex can easily dig through all those sources with a single, plainly written search, and usually find exactly what I’m looking for. It’s amazing.

Being able to ask software to rewrite and enhance itself is, also, a game-changer, and a really cool one at that.
Even more amazing? If I need to incorporate a new data source, I can just ask Dex to teach itself how to interface with that source. For example, I was able to get Dex searching through old .mbox archives of email addresses I don’t use any more. It really does feel like the future of software. With a few necessary caveats…

Self-writing software makes a lot of weird choices that an even-remotely-experienced coder never would.
To be clear, I am half-technical at best, but watching Cursor spit out scripts in realtime, there have definitely been a few times that even I noticed some weird coding choices. For example, it took me several rounds of back-and-forth to get Dex to go from ambiguous definitions of “today” and “tomorrow” to managing tasks around specific dates. I’ve had to ask it several times, “hey, why can’t you access my email any more?” But every time, I’ve found a path forward. As ever, the future probably belongs to people who refuse to get stuck.

The “voice” of AI still feels obsequious and offputting to me, and I don’t trust it to write external messages on my behalf.
When I ask Dex to write a message on my behalf, it says some pretty weird stuff. It sounds robotic. It REALLY wants to tell people about how many individuals from their company are subscribed to this newsletter. It sounds… like AI. And I don’t like it. Maybe it’s my own insecurity, but I feel like it’s gaslighting me into doubting my own voice and instincts. Thankfully, there’s a really easy fix here: I just don’t ask Dex to write stuff on my behalf. And you don’t have to, either.

I’m always curious to hear about other people’s experiences with AI systems like this. And, for what it’s worth, I highly recommend you take Dex for a spin.

This April, I’ll be heading to Chicago by way of New York to run some client workshops and interview my friend Nesrine Changuel at ProductTank Chicago. I’ve got some availability around April 8-20 for client workshops and talks in those cities, so please do reach out if you’d like to explore how I can help your team put impact first.

Not to be a cliche, but sometimes you gotta spin the classics, and Guided by Voices’ Alien Lanes has been getting a lot of spins this week.

Thanks so much for taking an interest in my work. As always, you can reach me directly at [email protected].

(P.S. Fun fact: at least one character in Dr. Strangelove was based on General Curtis LeMay. My paternal family is… complicated.)