The Most Expensive Question You Didn’t Ask

Sometimes engineering has to do some rework. Usually, it isn’t caused by bad answers. This engineering rework is caused by questions that were never asked or the right questions answered with the wrong tool at the wrong fidelity.

Prototyping should be the antidote to that. But for a lot of engineering teams, it’s actually part of the problem. Not because prototyping is wrong, but because the way most teams practice it skips the thinking that should come first.

Here are three traps I see teams fall into, and they all share the same root cause.

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Local LLMs: Where to Actually Start, with Vincent Deeney (A Chat with Cross-Functional Experts)

If you’re an engineer or quality professional wondering how to actually start using AI beyond the chatbots and CAD plugins your company already provides, this episode is your starting point.

Vincent Deeney (technologist and AI enthusiast) joins Dianna to break down how to run large language models (LLMs) on your own hardware, why that matters for data privacy, and how to get real work done with modest equipment. No programming required.

This interview is part of our series, “A Chat with Cross Functional Experts”.

About Vincent

Vincent Deeney is a director who has spent the past five years helping organizations navigate complex software decisions. Before that, he built a nearly two-decade career specializing in data quality, master data management, and governance. He holds a Master’s in Organization Leadership and, perhaps most tellingly, an undergraduate degree in Philosophy. He’s someone who asks the right questions before reaching for a solution. Lately he’s been exploring local LLMs on his own time.

What Vincent and Dianna Talk About

They walked through the practical side of running local LLMs.

We covered why data privacy and token costs push people toward local setups, what hardware you actually need (from your existing laptop to a dedicated AI machine like the DGX Spark), and which free tools — Ollama, LM Studio, OpenCode, Hermes Agent — make it possible to get started without writing code. We dug into how local models compare to frontier models like Claude, and Vincent shared his approach to using both together: plan with the frontier model, execute with the local one.

We also talked about managing context windows, using sub-agents, and connecting local models to tools you’re already using. The episode wraps with a practical challenge to get you started this week.

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The Knowledge Your Team Has That Nobody’s Using

You’ve been in this meeting before. Engineering is three months into detailed design when someone from manufacturing finally sees the concept and says, “We tried this two years ago. Here’s why it failed.”

The knowledge existed, but it didn’t have a path into the conversation when it actually mattered. We often treat this as a “people problem” or a failure of a database, but it can actually be a structural problem: when you engage for this information in product development. After all, it’s significantly cheaper to change a piece of paper during concept development than it is to retool a production line later.

In this episode, I share the results of an experiment I ran using AI agents to test two different development approaches across three distinct products: a solar service design, a medical device, and a field harvester. The results were clear: the traditional approach produces “answers,” but the structured concept development approach produces clarity.

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The ROI of Engineering Motivation with Cassie Leonard (A Chat with Cross-Functional Experts)

What if the career move that looks wrong on paper is actually the right call — and there’s an equation to prove it?

In this episode, Dianna talks with Cassie Leonard — aerospace engineer, executive coach, and two-time bestselling author of STEM Moms and Beyond the Pipeline — about why the traditional “linear pipeline” model of engineering careers is failing both people and the products they build.

Cassie introduces an ROI-style equation rooted in expectancy-value theory that explains why engineers make the career moves they do. And how leaders can use the same framework to retain talent, recognize top performers, and build more empathetic cross-functional teams.

This interview is part of our series, “A Chat with Cross Functional Experts”. Our focus is speaking with people that are typically part of a cross-functional team within engineering projects.

About Cassie

Cassie Leonard is an engineer, two-time bestselling author, and dedicated working parent with 19 years of experience in technical leadership and executive coaching. Through her company, ELMM (Engineers, Leaders, Moms, and Mentors), she helps working parents and allies in STEMM grow fearlessly, connect wholeheartedly, and design careers that actually work.

Aerospace is at her roots. With degrees from UCLA and the University of Sheffield, she spent 16 years climbing the corporate ladder from entry-level analyst to Senior Aircraft Integration Leader. Today, she pairs that technical grit with mom skills to help clients reverse-engineer their own version of success.

As Editor and Lead Author of Beyond the Pipeline: Redefining Value, Success, and the Future of Women in STEMM — Together, Cassie collaborated with women and allies worldwide to create an insightful, practical, and action-oriented exploration of today’s technical workplaces. Beyond the Pipeline has been an international bestseller since its launch in August 2025. Her first book, STEM Moms: Design, Build, and Test to Create the Work-Life of Your Dreams, launched her into this global conversation with stories and
solutions for solving the partial differential equations of life as a mother in a male-dominated industry.

Learn more at ELMMcoaching.com

What Cassie and Dianna Talk About

She shares how a simple ROI framework, rooted in decades of research, can explain the career moves that look surprising from the outside. And how leaders who understand it stop losing their best people to decisions that could have gone differently.

You’ll walk away with:

• A six-factor equation for evaluating career decisions — and how to apply it to your team, not just yourself
• A new way to think about retention that goes beyond compensation and titles
• One conversation starter you can use in your next 1-on-1 to uncover misalignment before it becomes an attrition risk

This isn’t about forcing engineers into a five-year plan. It’s about understanding what actually drives the people on your team so you can build the kind of environment where great engineers choose to stay and do their best work.
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The Quiet System: Why Your Lessons Learned Aren’t Sticking

It’s incredibly frustrating when your team faces the same exact problems over and over again. You spend months untangling a complex project issue, only to discover someone two cubicles down solved the exact same thing three years ago.

This continuous cycle of rediscovery isn’t happening because your team is careless. It’s happening because most organizational systems are accidentally built to be reactive and protective—focusing on stopping the bleeding rather than preventing the next injury.

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Shannon Cummings on Why Marketing Should Be in the Room Before the First Prototype (A Chat with Cross-Functional Experts)

You’ve probably been there: a team of brilliant engineers, a clear roadmap, and months of work, only to launch a product that no one uses. The customer needs were never fully understood. Marketing showed up too late. The “why” got lost in the “how.”

This isn’t a failure of talent. It’s a failure of process. And more often than not, it’s because marketing (so often seen as a “support” function) wasn’t part of the conversation until it was too late.

In this episode, Dianna Deeney speaks with Shannon Cummings, a seasoned product and marketing strategist who’s spent his career bridging the gap between Marketing, Product, and Engineering. He’s launched life-changing medical devices, cut development time in half, and done it all by bringing marketing into the room before the first prototype.

This interview is part of our series, “A Chat with Cross Functional Experts”. Our focus is speaking with people that are typically part of a cross-functional team within engineering projects.

About Shannon

Shannon Cummings is a seasoned product and marketing strategist who helps organizations bring clarity to complex markets and build products that truly resonate with customers. He’s known for bridging the gap between Marketing, Product, and Engineering: translating customer insight into actionable product direction and strengthening cross‑functional alignment.

What Shannon and Dianna Talk About

Shannon doesn’t just talk about alignment. He lives it. He shares how early customer insight, shared processes, and intentional collaboration aren’t just “nice to have”. Instead, they’re essential for building products that matter.

You’ll walk away with:

• A clear framework for involving marketing early in product development
• Real-world examples of how cross-functional teams achieve breakthrough results
• One actionable step you can take today to reduce misalignment and build better products, faster

This isn’t about adding more meetings. It’s about building smarter teams, where everyone speaks the same language, and everyone is working toward the same goal.

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Stop Being a Witness to Decisions That You Should be Helping to Shape

You’ve been there. You walk into a design review, a planning session, or a phase gate meeting. You’re ready to contribute, to challenge, to solve. But within minutes, you realize: the decision was already made. The room is a stage, the discussion a script, and you’re just an audience member.

This isn’t just frustrating. It’s a sign of a deeper systemic issue.

In this episode, Dianna shares a powerful personal story from attending a state-level congressional hearing that mirrored the exact same dynamic she’s seen in product development: a performance, not a process. She reveals why these “formal” meetings often fail, not because of bad people, but because of broken incentives and poor timing.

The real solution? Influence doesn’t happen in the meeting. It happens before it. By shifting your focus to early, intentional conversations with cross-functional teams, you can stop being a witness and start shaping the outcome. This isn’t about being louder. It’s about being earlier for upstream influence in product development.

Learn how to build credibility, surface risks, and align on problems before solutions are locked in. The result? Less rework, better decisions, and teams that actually move forward together.

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Karli Auble THRIVEs: Positive Psychology Meets Engineering Rigor (A Chat with Cross-Functional Experts)

In our latest episode of our interview series, “A Chat with Cross-Functional Experts,” we delve into the human aspect of engineering with Karli Auble. Karli is a leader from the defense industry whose unique perspective integrates systems engineering with positive psychology.

With a decade of experience under her belt, Karli introduces us to her THRIVE Framework, a holistic approach for engineers to balance technical and human elements effectively.

About Karli

Karli Auble is an Engineering Leader in the defense industry who has over a decade of experience leading high-pressure teams. She is also a Speaker, Author, and Coach. With her combination master’s in systems engineering and positive psychology, she created THRIVE: a six‑pillar framework whose name stands for Thoughts, Habits, Relationships, Instincts, Values, and Environments. Karli contributed a chapter to the book Beyond the Pipeline, where she shares how engineers can embed THRIVE into their everyday lives.

What makes Karli’s perspective especially valuable for you (whether you lead a design team, drive R&D strategy, or advise high‑tech organizations) is that she translates human behavior into more reliable engineering design.

Karli’s Insights

1. Engineering with Human Error Codes in Mind: Karli emphasizes the need for engineers to recognize the ‘error codes’ in their own bodies, akin to the ones in technical systems. By paying attention to physical responses like stress or anxiety in high-pressure meetings, engineers can mitigate burnout and enhance decision-making.

2. Instincts and Environments: Two pillars of the THRIVE Framework discussed extensively by Karli are Instincts and Environments. She shares personal anecdotes and practical tools like ‘box breathing’ to manage stress and avoid ‘fight or flight’ responses during critical moments.

3. Improving Communication and Coordination: Karli touches on the necessity of fine-tuning communication, whether addressing team dynamics or engaging in conflict resolution. She shares strategies such as meeting follow-ups and environment adjustments (both physical and virtual) to foster healthier interactions.

Karli Auble’s approach, which seamlessly blends positive psychology with engineering principles, provides a refreshing perspective for professionals seeking sustainable success. By addressing both the tangible and intangible aspects of work, engineers can not only solve technical problems but thrive personally and professionally.
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Constraints Unlock Creativity: Why Frameworks Beat Blank Slates in Product Concept Design

Too many product teams spend months chasing ideas that feel safe, generic, or simply “meh.” They brainstorm with no direction, leaving a blank canvas that overwhelms participants. Or they wait until a prototype is already built, causing “fixedness” where people can’t unsee the existing design. The result? Stagnant concepts, wasted time, and missed market opportunities.

In this episode, Dianna shows how the right frameworks act like a drum‑less track for a drummer: they provide structure, genre cues, and sections to focus on, yet leave the creative freedom to craft something new.

By applying the Goldilocks principle (neither too little nor too much guardrails) and using the Concept Space Model (inputs, process, outputs), teams can hit the sweet spot after business approval but before detailed design to generate high‑impact ideas that are both feasible and market‑loving.

You’ll walk away with a clear method to set up constrained‑creative sessions, concrete examples of how to map customer experiences into design inputs, and actionable steps to run your own framework‑driven brainstorming without it feeling like another status meeting.

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