Better Questions
What problem are we actually solving?
A deceptively simple question that exposes a surprising amount of wasted effort.
Bill Waters · AdviceGuy.net
I ask a lot of questions.
Usually some variation of “Why are we doing it this way?” I write about technology, business, systems, things I'm building, things that don't make sense—and occasionally whatever squirrel sent me down today's rabbit hole.
The fanciest technology in the world doesn't matter if the outcome still sucks.
Lately
I've been thinking about...
Questions, observations and experiments about the systems we build—and whether they actually make anything better.
Did Anything Get Better?
Technology isn't the outcome.
New tools are interesting. Whether they made the experience better is the useful question.
Building
Probe*
A digital business operating system designed to turn ideas into managed, measurable outcomes.
*Working name. Still deciding what to call it.
Right now
Things I'm building & exploring.
I learn best by making things. Some become products. Some become frameworks. Some become very elaborate ways to discover I should have asked a different question.
Building Probe* into a reusable digital business operating system.
Exploring how AI changes the work — and whether the outcome actually improves.
Collecting better questions, useful systems, and occasional side quests.
*Working name. Still deciding what to call it.
The recurring themes
What lives here.
Better QuestionsAssumptions worth challenging and questions people aren't asking.
Technology That Actually HelpsAI, software and automation judged by outcomes rather than hype.
Systems & ProcessesWhy things work, why they fail, and how they could work better.
Building ThingsProducts, prototypes, experiments and lessons from actually making things.
Life, ApparentlyThe human side: observations, family, side quests and whatever rabbit hole showed up today.
A useful second set of eyes
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About Bill
Technology is the tool. The outcome is the point.
I've spent more than two decades building, testing, fixing and improving technology, products and systems across e-commerce, travel, finance, FinTech and CRM.
Somewhere along the way I realized the technology usually isn't the hardest part. Asking the right question is.
Better questions tend to produce better outcomes.