If there's one AI article you read today, make sure it's this one: https://www.forbes.com/sites/jasonwingard/2026/04/23/vibe-coding-will-break-your-company This isn't an anti-AI or AI-is-terrible take. This is a real & grounded take on the very real problem that AI is allowing us to move faster that the decision-time is compressed. Over the course of my career, I learned that the shift towards "seniority" isn't just that you have more of the core skills and are faster and better. It's that you become wiser about when to use those skills. You ask fundamental questions like: What new problems do we create by solving this? If we build this, who will maintain it? If we build this, will this distract us from our priorities? If we build this will we set some new expectations that we'll have to uphold? Just because something has value doesn't mean it doesn't create a form of debt in the long run. And these were all important to consider before  G...

There's a scene from the movie Big, I always think back to: Tom Hanks' character is sitting in his first big important meeting about a new toy launch, and he stops everyone in their tracks by saying "I don't get it... what's fun about playing with a building?" His question isn't meant to be antagonistic. It's honest, it's earnest, and (most importantly) it gets right to the point. One of the challenges we run into in our adult corporate lives is leaning so heavily on politeness that we introduce ambiguity ("we" should get this done...), and we combat that ambiguity with frameworks (OKRs, KPIs, SMART goals, etc.) But sometimes, we need a bit of Tom Hanks in the mix. That's the power of the Rude Q&A - a document that captures all the blunt, direct, and even rude questions. It's great for after the ideation, research, analysis, refinements and iterations. It challenges, stress-tests, detects contradictions, revalidates assumption...

I'm starting to think generative AI is a proxy for revealing skills gaps. Regardless of field, if you are a high performing, critical thinking, strategic and effective individual then AI is a time saving augmentor of your existing capabilities. Your high degree of skill lets you use AI tactically. You quickly iterate with prompts, better orchestrate, evaluate outputs, and immediately identify when you've been received a quality output. Alternatively, you will quickly revert to the traditional non-AI way of doing things if needed while offloading the more discreet and deterministic tasks to AI. And all that is great... If you're great at what you do. On the flip side, AI has also allowed for us all to easily fake that we are skilled in areas where we've not spent any time honing our craft. To our untrained eye, AI has given us passable-quality outputs that are in need of a trained eye to call out the risks, challenges, issues, or problems. At best, despite our lack of sk...

When I was a software engineer, I strengthened my delivery by also asking product questions. When I turned product manager, I strenghtened my delivery by also asking engineering questions. There's plenty to suggest that AI is blending the roles - but I want to propose an alternative theory: Software Engineering doesn't go away, Product Management doesn't go away. Instead, AI helps us fill the gaps in our individual perspectives so we can better engage with one another. It's not a replacement, but an enhancer. Whether PMs, Engineers, Designers, Operations, Marketing, or Millennials grappling with no longer being responsible for defining what is cool, and navigating a changing landscape of hip new vocabulary and memes (seriously, who references The Office anymore???), AI can be pretty handy for bridging divides. Said differently, AI helps you be "low-key goated, but only if your vibe check passes and your intentions aren’t sus."

You're walking in the forest and come upon a bridge. A mysteriously cloaked figure jumps out holding two envelopes. "Each of these envelopes contains a different number. You may pick either envelope. I will only let you cross if you can tell me whether the number in the envelope you pick is larger or smaller than mine"  Despite being put off by the disruption, you take an envelope and ask: "Can I look inside my envelope before making my guess?" The cloaked figure is surprised because, until now, everyone has ignored him and his envelopes. After some consideration, he says: "Sure." You open the envelope, thinking: "I don't even know how large a range he's picking from. This is a total 50/50..." OR. IS. IT?? What I love most about the solution is it doesn't come from gimmicks, hacks, or any external information. It is, in its purest form, a strategic decision framework. You magically improve your odds with something equally random....

I've been coding pretty intently on something in my off hours (I'm excited to share more once it takes shape). Like the carpenters I watch on YouTube working almost exclusively with hand tools, this is very much a labor of love, so I'm being very deliberate with when, where and why I use AI. I've very sparingly offloaded the soulless, non-creative, non-gratifying code to Claude in the same way the carpenters I watch will occasionally use a power drill when they need 32 precise holes. What I haven't accounted for was, as I've been working on this, my daughter taking a keen interest in watching me code. She's enjoyed watching me iterate, refine, expand - and she's asked with a lot of curiosity about design-thinking that goes into building something from the ground up - or, more precisely, as things have gone from generic to specific. To simplify the principles, I related things to grammar: Describing our weekend to a friend we can quickly and succinctly en...

I'm afraid we're losing our fingerprints. I love using, experimenting and making myself more efficient with AI. And I love being creative with AI - but only where AI is in the early stages of creativity, part of the brainstorming, refinement, and iterations. The final result, I try to make fully my own. (Admittedly, in the early and still novel days, I was regularly generating images and just using them as-is but this was before developing a more discerning eye for AI. Since then, I use AI as a launching pad not as the final product.) What worries me though, is how much I'm seeing AI get used right out of the box in our everyday lives. Posters on community bulletin boards. Homework assignments from elementary schools. User groups promoting meet ups.  What used to be a rich tapestry of people's individual tastes - from the poorly designed posters with clashing colors and excessive use of Comic Sans, to hand-drawn photocopies, to really well made amateur designs - is now ...

I've been writing some form of my blog for more than 25 years now - I think I started before it was even called 'blogging.' I'm that old. In 2026, when you have that much writing readily available on the internet, there's really only one thing left to do: Feed it to your favorite LLM, ask it to deeply analyze your writing, build memories for storage, and instruct that, hence forth, it should respond in your own voice. Why... why would I upload my thoughts to the machine overlords? I had a theory: A lot of my posts tend to be exploratory or pursuasive ideas, and (as observed by GPT) "favor metaphors, are often a bit playful, and grounded in shared experience rather than top-down instruction; warmth over authoritative;" and I think I write this way because it's also how I best receive and process information. I like a story, real-world examples, a healthy dose of self-deprecating humor and flexibility over rigidity. If GPT could explain things to me the...

5 years ago, I wanted to help the engineers on my team stretch their coding skills by presenting them with an entirely new set of challenges than the typical tedium that can come with building business applications day in and day out. Having built so many games over my own career, one unique element I've always enjoyed is building out the game's AI. After building the core engine, collision detection, and all that - building the AI was always a fun, and very different, challenge. I'd have to think it through: if I was a player, playing this character - what would my own in-game approach be? To be fair, what elements could my AI player see and interact with, and what would they not see, how could I scale my strategy to different difficulty levels. Expressing your strategy in code requires a different line of thinking. It may not directly translate to writing better business or consumer applications, but it stretches your computational thinking and problem solving. Plus it...

Can I be so bold as to create my own business acronym? What an apropos way to start this, because the acronym I want to create applies to that very question. Let me re-start by, somewhat apologetically, confessing that I'm one of those distracting types who gets an idea, feels really passionate about it, thinks it will change the world and will offer it up for consideration. Over the years, I've learned to balance out the negative qualities that come with it: I try to focus on nuance, rather than chase novelty; I started keeping more ideas to myself and doing more to vet my own solutions before offering them. While I'm a work-in-progress, I will admit I do love sitting in a meeting where there all problems and no solutions. The gears that start spinning at full speed in my brain can cause such a strong buzzing that people will look at their phones, thinking they're getting a call. One danger I learned long ago about getting so passionate about a new idea is that it can ...

It's always interesting to pit Gemini vs GPT using the same prompt and source data. There's never a clear winner - and it really points to how important the precision and quality of the prompt is.  Google's Gemini definitly wins on this one. It's really strong, but not great (zooming in, you can see the edges and there was overall quality loss) - however the speed of the update was impressve (<20 seconds!).

Will input change with AI? Speech detection with AI is remarkable and, in particular, the whisper-mode lets people speak comfortably in public. Folks are using it for everything from writing emails, creating presentations, and even writing code. But does that mean the death of my beloved keyboard? I like being as hands-free as the next driver (well, maybe not all drivers...) but right now it seems voice is meant to fill the gap when I can't use a keyboard, it's not the default.  There's the obvious social issue of talking outloud to a device. Whisper-mode and earbuds solves the privacy issue, but even then I've only found voice-input to be useful when I'm being conversational (researching, brainstorming, learning) or directional (send a short msg, asking for music to be played, requesting directions). It's a different story when I'm writing, editing, iterating, refining. It's hard to edit on the fly with spoken instructions. While reading is linear, writ...

  At some point in the early 90s I tried rebuilding a game I loved: Beast. It was written procedurally in Basic over couple of months of on and off coding. Clunky, filled with bugs but I felt proud. About 25 years later, with 12 years of professional experience, I tried again. In about an hour, I had a working version. No bugs this time. Of course, Beast is not a complicated game but by going object-oriented with multi-threading it was even easier. And then, another 8 years later, I built Beast again . In record time: 25 minutes using with 7 non-technical prompts. No logic or technical guidance - just plain-english rules. We're well past the point of arguing AI's abilities. Instead, I wondered: In those 25 minutes, what parts of my own experience did I leverage? Strategic Iterations: Even if the LLMs handles complex specs, doing things all at once will still overwhelm the human. There are too many things to track at once. The ability to break things down into discrete, logical...

I sense a lot of people are forming a love/hate relationship (or maybe, it's just become a hate relationship) with AI when it comes to creative pursuits. It intrinsically feels wrong to offload something so human to the machines. Being creative is so essential, so rewarding, that to use AI in any way evokes a primal knee-jerk reaction - as if we're trekking far too into the uncanny valley that our lizard brain keeps telling us "This is wrong. Go back." Am I fan of using AI to generate music, books, movies, or art? No. But do I enjoy using AI when I'm being creative? Absolutely, yes. Whenever I use an LLM (a good one, at least), I notice a few things happen: Even before I send my initial prompt, my creative idea is getting more refined. It's like talking to the rubber duck and critically evaluating your own thoughts - but, it's even better because the AI rubber duck actually responds. Putting emotions into words can be very hard. Capturing complex feelings...

So, they were doing "professional photos" at the office... And maybe it was my misinterpreting "professional photos" to mean "photos of you, taken by a professional" rather than the intended "photos of you looking professional..."  Or, maybe it was that I'd forgotten about it and so I'd failed to dress professionally ( still undecided which narrative I prefer... ) Either way, with only a few minutes to spare before my allotted slot I decided to have some fun - so I grabbed a few of my desk ornaments, and off I went. It was only after seeing the awesome final results (big shout out to Ted Warner !) that it had me wondering: Why, oh why, don't we (as adults) get "school photos" done anymore? Sure, I'm looking a bit older these days, but that doesn't mean the kids should get to have all the fun. Why aren't we getting fun photos each year and sharing them with our pals? Why aren't we autographing each other...

Was talking to a friend about their job hunt. My friend made an observation that (with their permission), they're letting me share: It's strange to call it a job "hunt." If you're hunting/fishing - you're usually sitting out there and waiting. And while you're waiting, you don't really have visibility into all the animals or fish passing you by. Job hunting is not like that at all. There's no waiting. You're constantly putting yourself out there, feeling each miss deeply. Imagine if you were fishing, and you could easily see beneath the surface of the water - seeing each fish as it swims past your bait. It gets you wondering: "Do they even care about my bait? Is it good enough? Is it me? What am I doing wrong?" Then imagine, they nibble on your bait - ever so slightly that you feel the tug on your fishing line... but then they dart off, and now you're wondering: "Why? What did I do wrong?" For the most part, it's a l...

I do my best at being handy around the house - and lately, I've been exploring how AI can help. For a few projects now, I've been using a mixture of GPT & Gemini to help me think through how to build things - especially when there are some weird complex things I hadn't anticipated (and there always are...!) One thing I really like is how easy it's become to visualize changes - and better than Photoshop. We've had this pointless ledge in our house... one of those designs from 90s that is just begging to be decorated with fake plastic trees and a green plastic watering can. After doing a quick sketch, I fed the original photo and my sketch to Gemini, and asked it to render it for me. I made some tweaks along the way - at first, it was a stained wood without any trim, then it had the back of the bookcases painted the same color as the walls. But within 5 minutes I had a close enough rendering of what I wanted (though, for the life of me, I couldn't get it to re...

Someone once told me how much they appreciate that I use the correct flow chart shapes. Now, at the risk of disappointing them, I am deciding to break convention. I appreciate the jarring disruption a diamond creates to highlight where a workflow may diverge, but I am done with the aesthetic tradeoffs. I don't want to make a larger diamond. I can't always shorten my text. Sometimes I need more than 3 divergent paths. Enter the hexagon. Easily matches the dimensions of the other shapes. Provides more space for text. Supports 7 paths! Sure - it may get trigger someone to question your knowledeg of conventions, as they spit out their coffee and arrogantly belittle you as they proclaim that hexagons are meant for initializations. That's why I'm sharing this post. It's time to build a movement. It's time to disrupt the status quo. If someone gives you any guff, you just point them here and let them know we're #DoneDecidingWithDiamonds . If hexagons are good enoug...

PSA to all my engineering pals... The worst (best?) thing you can do for an Engineer-turned-Product-Manager is giving them read-access to the databases & logs. Queries and joins and more joins for linking, Dashboards and charts to show what I’m thinking, AI and BI put the insights on springs, These are a few of my favorite things. 🎶

Throwback to almost 15 years ago when I made my funniest coding joke  on StackExchange.  Do people in non-English-speaking countries code in English? I'm from Canada, but live in the States now. It took me a while to get used to writing boolean variables with an "Is" prefix, instead of the "Eh" suffix that Canadians use when programming. For example: MyObj.IsVisible MyObj.VisibleEh

I use GPT & Copilot a lot for brainstorming and a sounding board to refine ideas. One thing that's bothered me is when it comes to generating images (for example ideas for logos) it can suddenly slow me down as I wait for an image to render. And then I make individual refinements and iterate much slower than if I were doing it independently. Today, I tried something different which worked spectacularly well: "Given the description, and aesthetic, generate 10 different possible logos all  within the same image so I can look at them all and compare." Ignoring the fact that it only provided me with 9 (where's #7??? 😅) I was then able to make targeted refinements and iterate faster. "I like number 8 - adjust the colors so the hand is more like the colors in #6 (but keep the lightbulb yellow and turn the element into a leaf)" A reminder that AI can multitask in ways that are typically harder for people.

I came across this article about how middle management is dead. While it reads a bit as an "advertorial" it does make a compelling argument. The future is not about building skills in managing people. Growth is not about how many direct reports you have. Orgs trees are flattening and growing wider. AI (+ plenty of productivity technology, and the many years of learnings from the evolution of Waterfall to Agile to Kanban/Continuous Improvement) has made the direct management (as in the organization, coordination, and progress measurement) less and less a thing needed to be done by people.  People Management is increasingly becoming unnecessary overhead while  Management of Tools, Processes, Strategy, Products - with a clear end goal of a value focused impact is what matters. That being said - Management and Leadership are two very different things. People Leadership still matters and, arguably, it matters more. We need to think more about how we probive guidance, mentoring, t...