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WHAT HAPPENS WHEN AGENTS MEET?

AI agents create system-wide effects when they operate at scale. Designing them requires population-level thinking, not just better individual interfaces.

HARD TRUTHS FOR B2B IN 2026

If AI doesn't re-accelerate revenue, it doesn't matter. Agents are creating a winner-take-most dynamic that's crushing the middle of B2B SaaS.

SHOULD TEAMS USE THE SAME TRACKER?

Transparency matters more than shared tooling. When trust drops, teams get managed through proxies, and delivery suffers.

Book time to chat with the team.

THE AI DELEGATION MATRIX: WHAT PARTS OF YOUR UI SHOULDN'T EXIST?

Designing with AI is deciding who is accountable at each moment. Use a repeatable score for risk and payoff to choose between human control, AI assistance with approvals, or constrained autonomy.

HOW TO BUILD AN AI NATIVE PM OPERATING SYSTEM (61 MINUTE PODCAST)

AI-native PMs win by building an operating system, not a tool stack. Centralized context and MCP-powered workflows eliminate friction and unlock new leverage.

PROGRAMMING WITH AI, WITHOUT THE HYPE

Programming with AI works best when treated as a tool, not a philosophy. Its real value comes from pairing it with strong context, clear planning, and human judgment.

FRAGMENTS

AI should help humans find answers, not pretend to be one. As coding gets cheaper, judgment, incentives, and civic responsibility become the real constraints.

SAYING “NO” IN AN AGE OF ABUNDANCE

AI removes building constraints, not user constraints.

WHAT, THEN, ARE WE PAYING FOR?

Generative AI makes building software easy, but owning the underlying problem remains hard.

HOW DOES AI IMPACT SKILL FORMATION?

AI slows learning per task but meaningfully increases output. Overall skill growth may remain intact if higher throughput offsets reduced depth.

FORGET TECHNICAL DEBT

Technical debt is only one contributor to cognitive load, not the core problem itself. Improving software speed and stability requires addressing broader organizational, process, and human drivers that often outweigh technical debt and cause it to accumulate in the first place.

PARKINSON'S LAW AND AI: DOES AI MEAN...MORE WORK?

I HATE FISH

Most productivity systems fail because their maintenance costs exceed their value. A deliberately hostile, minimal system that relentlessly prunes irrelevant tasks keeps focus on work that actually matters.

A JTBD-FIRST PATTERN FOR AGENTIC TOOL SYSTEMS

Strong agentic systems start with a clearly defined job and a small set of task-oriented tools. Verification closes the loop, turning one-off execution into continuous improvement.

LATENT SPACE ENGINEERING

Beyond context engineering, shaping an AI's mental frame can significantly improve results. Latent Space Engineering uses emotional, stylistic, and motivational cues to push agents into more effective modes of reasoning and execution.

RETHINKING SLACK

Slack became too complex as features accumulated without a coherent information architecture. A dedicated redesign effort restored clarity and scalability through rapid prototyping, intensive customer testing, and deliberate rollout planning.

CLOUDED JUDGEMENT 1.30.26 - SOFTWARE IS DEAD...AGAIN!

SaaS valuations are falling because AI is eroding confidence in long-term retention and terminal value. As software becomes cheaper to build, competition rises, and investors reprice risk across the sector.

VIBE-CODING IS NOT NEED-FINDING

Vibe-coding makes it easy to build polished solutions to nonexistent problems.

AI CHANGES THE BOTTLENECK FROM DELIVERY TO SOMETHING ELSE

AI makes it easier to ship faster, but speed has never been the bottleneck.

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THE MIGHTY METAPHOR

Strong metaphors let executives reason about technical trade-offs in their own language. When they hold up logically, they turn explanations into shared understanding.

ONE YEAR OF AX

As agents become primary users, products must optimize for Agent Experience. Access, context, tools, and orchestration will determine which platforms remain relevant.

DON'T SOLVE PROBLEMS THAT DON'T EXIST

Uncertainty drives people to solve problems that do not matter. Real progress comes from focusing on the single task that actually creates value.

AI PROTOTYPING IS CHANGING HOW WE BUILD

AI prototyping enables faster learning by turning behavioral ideas into functional products that teams can test immediately.

BUILDING AI PRODUCTS: LESSONS FROM PRODUCTBOARD SPARK

Winning AI products are built by teams that prioritize guidance over automation and invest deeply in continuous quality improvement.

DECISIONS TO MAKE BEFORE A POSITIONING EXERCISE

Good positioning starts with clear decisions before the work begins. Without them, teams waste time and dilute the outcome.

THE INTENSITY DIAL: KNOWING WHEN TO ESCALATE AND WHEN TO BACK OFF

The best communicators treat intensity as a dial, not a switch, escalating deliberately to drive change without breaking trust.

REAL TALK IF YOU'RE LOOKING FOR A JOB AT A HEALTH TECH STARTUP

In today's startup market, the winners are opinionated builders with real agency who understand growth, not resume polish or cool titles.

ROUTE AROUND BIG EGOS

The strongest PMs optimize for outcomes, not ego.

KEEP A WORK JOURNAL

A public daily work journal turns invisible work into visible impact and makes performance reviews trivial.

3️⃣ Tooling evaluation framework + scorecard

Tackle problems early in the lifecycle by accelerating your

prototyping strategy. Get the guide to learn how.

THE LINE BETWEEN AI-FIRST AND AI THEATER

AI-first work fails when it stops at impressive demos. Real value comes from product ownership, clear outcomes, and responsibility once AI touches the product.

WHY EVERY EXEC SHOULD BE VIBECODING

Vibecoding keeps executives close to the work. By building with AI tools themselves, leaders can move faster, align teams better, and turn ideas into impact without layers of process.

AI'S MISSING INGREDIENT

AI will not win through speed alone. The companies that succeed will be the ones that use design to turn raw capability into products humans actually understand and care about.

MY TIME AT AMAZON, PART I

Big Tech turns ambition into a constant state of striving that rarely satisfies. Status feels validating at first, but the cost to identity, family, and peace becomes impossible to ignore.

LIFE OF A BIRB

Finch's success comes from designing onboarding and monetization around fast engagement and habit formation. By removing friction and guiding users to an early payoff, the app turns curiosity into retention.

WHAT MAKES GENERATED UI WORTH KEEPING?

AI-generated UI only becomes valuable when it reflects real product constraints. Designing with brand, data, and existing patterns from the start turns AI output into something teams can actually build on.

I COULDN'T ADAPT TO BARCELONA'S MEAL SCHEDULE FOR THE SAME REASON YOUR PROCESS CHANGES AREN'T LANDING

Culture change does not fail because people are confused. It fails because beliefs cannot shift without lived experience and the right context.

UX STRATEGIST: THE ONLY JOB WHERE SAYING ‘IT DEPENDS' IS CONSIDERED EXPERTISE

“It depends” is often used by UX strategists to avoid making decisions. This avoidance slows teams down and keeps real product problems from being fixed.

DESIGN TOOLS ARE THE NEW DESIGN DELIVERABLES

Design deliverables are shifting from static assets to custom tools.

AVOID “ASAP” AND OTHER HIGH-STRUNG, NON-SPECIFIC WORDS

Vague urgency language leads to stress and miscommunication.