Podcast

Conversations about the calls leaders have to make.

Unfiltered discussions from inside high-stakes delivery. What holds up. What breaks. How leaders think through tradeoffs.

Each conversation connects to a common situation leaders face.

Recommended for leaders

Ep. 10

Nobody Who Hires You Cares About Technology

For two career technologists to say "technology is the easy part" might sound strange, but after decades in the industry, it's the most important lesson they've learned. The biggest challenges that derail projects and frustrate teams rarely have to do with code; they have to d…

Related Situation: The team is busy, but leadership cannot see delivery clearly.
17 min watch · Sep 2025·Watch
Ep. 02

'The Solution-First' Trap: Why Projects Fail Before They Start

What happens when a client asks for the latest tech trend, like GenAI, but you suspect it's not what they actually need? It's a classic scenario that can lead to wasted time, bloated budgets, and solutions that miss the mark entirely.

Related Situation: The platform works, but you are not sure it will survive the next phase.
20 min watch · Aug 2025·Watch
Ep. 20

Strong Opinions, Thoughtfully Held, With Dave Holbrook

What happens when a perfectly designed software system crashes in production because of a single deployment error? You learn the most important lesson in engineering: *If you write it, you run it.*

Related Situation: The team is busy, but leadership cannot see delivery clearly.
61 min watch · Feb 2026·Watch
Ep. 14

The Messy Middle: Navigating Engagement Drift

Projects start with a bang and end with a sprint. The messy middle is where engagement drift sets in: focus blurs, momentum stalls, plans go off the rails. Starters and finishers need each other. Scope creep is inevitable. The middle is the true test of alignment and resilienc…

Related Situation: The platform works, but you are not sure it will survive the next phase.
26 min watch · Nov 2025·Watch
Ep. 21

Vibe Coding vs. Real Engineering: AI As Help, Not Hope

"Vibe Coding" has become a popular way to describe building software by simply chatting with an LLM. It feels efficient, but it often lacks engineering rigor. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) discuss the difference between this casual app…

Related Situation: The next phase requires a shift in how the organization works.
28 min watch · Feb 2026·Watch

All episodes

Ep. 29

AI Coding Is More About The Experience Than The Model

The tools we use to write software are evolving at breakneck speed. Cursor recently dropped version 3 featuring a brand new agent-first interface, while Anthropic continues to push developers toward the terminal with Claude Code. But are these new autonomous workflows actually…

Related Situation: The next phase requires a shift in how the organization works.
24 min watch · Apr 2026·Watch
Ep. 28

Turning Top Performers Into AI Champions With Boz Vitanova

Rolling out AI tools in an enterprise requires a different strategy than a traditional software implementation. Because large language models are probabilistic and constantly evolving, top-down mandates often lead to poor adoption or employees quickly dismissing the technology…

Related Situation: The next phase requires a shift in how the organization works.
50 min watch · Apr 2026·Watch
Ep. 27

The Bar Is Low in Tech Consulting. Do the Basics. Stand Out.

Ever feel like basic professionalism (like returning a phone call, showing up on time, or actually listening to a client) has become a rare superpower? You aren't alone. In fact, it might be the easiest competitive advantage you can build.

Related Situation: The team is busy, but leadership cannot see delivery clearly.
23 min watch · Mar 2026·Watch
Ep. 26

Rebecca George on AI, Bias, and Change Leadership

Organizations everywhere are rushing to implement AI, often measuring success by how many employees are actively using the tools. But treating AI adoption as a simple numbers game completely misses the mark. When speed becomes the primary goal, critical thinking is the first c…

Related Situation: The next phase requires a shift in how the organization works.
50 min watch · Mar 2026·Watch
Ep. 25

AI Is Changing the SDLC: Coding Matters Less, Specs Matter More

The traditional software development life cycle used to follow a fairly predictable breakdown of time spent on analysis, design, coding, and testing. Now that AI agents are capable of generating the code itself, those old percentages are being completely flipped upside down.

Related Situation: The next phase requires a shift in how the organization works.
24 min watch · Mar 2026·Watch
Ep. 24

Shadow AI Is Here: Responsibility Matters More Than Regulation

The tech industry moved fast and broke things during the rise of social media, leaving society to figure out the consequences of screen addiction and algorithmic feeds years later. Now, artificial intelligence is evolving at a much faster pace, and the conversation around guar…

Related Situation: The next phase requires a shift in how the organization works.
24 min watch · Mar 2026·Watch
Ep. 23

Is SaaS Dead? Build vs. Buy in the Age of AI

The ability to generate software with AI has revived the "Build vs. Buy" debate. If a team can spin up a custom CRM or invoicing tool in a few days using AI agents, the value of paying for expensive monthly SaaS subscriptions comes into question.

Related Situation: The platform works, but you are not sure it will survive the next phase.
35 min watch · Mar 2026·Watch
Ep. 22

Ethical Billing: Time vs. Value in Consulting

"Billability," "Utilization," "Chargeability." For consultants, these aren't just buzzwords... they are the metrics that often dictate your worth. But is an hour worked always an hour of value? And where is the ethical line when it comes to billing for research, learning, or d…

Related Situation: The team is busy, but leadership cannot see delivery clearly.
28 min watch · Feb 2026·Watch
Ep. 21

Vibe Coding vs. Real Engineering: AI As Help, Not Hope

"Vibe Coding" has become a popular way to describe building software by simply chatting with an LLM. It feels efficient, but it often lacks engineering rigor. In this episode, Ben Griswold (Grizen) and Noah Heldman (OutcomeSource) discuss the difference between this casual app…

Related Situation: The next phase requires a shift in how the organization works.
28 min watch · Feb 2026·Watch
Ep. 20

Strong Opinions, Thoughtfully Held, With Dave Holbrook

What happens when a perfectly designed software system crashes in production because of a single deployment error? You learn the most important lesson in engineering: *If you write it, you run it.*

Related Situation: The team is busy, but leadership cannot see delivery clearly.
61 min watch · Feb 2026·Watch
Ep. 19

Making a Strategic Bet On The EDGE Operating Model

We all know the problem: a company sets a high-level strategy, but the teams on the ground have no idea how their daily work connects to it. Enter *EDGE*, a value-driven operating model designed to close that gap. But can a framework built for massive enterprises actually work…

Related Situation: The platform works, but you are not sure it will survive the next phase.
50 min watch · Jan 2026·Watch
Ep. 17

Shared Language or Shared Chaos: Why Words Matter

There are two hard things in computer science: cache invalidation and naming things. In this episode, we tackle the latter. A single word like "integration" or "account" can mean entirely different things to a COO, a salesperson, and an engineer, leading to confusion, rework,…

Related Situation: Decisions depend on data few people fully trust.
25 min watch · Dec 2025·Watch
Ep. 15

So, AI Is Going to Destroy Us All... Now What?

A book argues that superhuman AI would inevitably kill us. The core claims: AI could master biology, we cannot understand how it thinks, and the timeline could be 10 years or less. We walk through the argument, then pivot to a different question. If existential risk is on the…

25 min watch · Nov 2025·Watch
Ep. 14

The Messy Middle: Navigating Engagement Drift

Projects start with a bang and end with a sprint. The messy middle is where engagement drift sets in: focus blurs, momentum stalls, plans go off the rails. Starters and finishers need each other. Scope creep is inevitable. The middle is the true test of alignment and resilienc…

Related Situation: The platform works, but you are not sure it will survive the next phase.
26 min watch · Nov 2025·Watch
Ep. 11

Are Most AI Tools Just Fancy Wrappers?

What happens when you push an AI so hard with a real-world coding problem that it... gives up? In a surprisingly human moment, Google's Gemini admitted its approach was "fundamentally wrong," lost its user's trust, and promised to "stop." This wasn't just a glitch; it was a pr…

Related Situation: The platform works, but you are not sure it will survive the next phase.
23 min watch · Sep 2025·Watch
Ep. 10

Nobody Who Hires You Cares About Technology

For two career technologists to say "technology is the easy part" might sound strange, but after decades in the industry, it's the most important lesson they've learned. The biggest challenges that derail projects and frustrate teams rarely have to do with code; they have to d…

Related Situation: The team is busy, but leadership cannot see delivery clearly.
17 min watch · Sep 2025·Watch
Ep. 08

I, For One, Welcome Our Robot Overlords: Navigating AI Hype

Generative AI is grabbing all the headlines, from "vibe coders" raising millions overnight to tech giants replacing entire departments. But behind the hype, what is the real-world impact of AI on business, productivity, and the future of work? The answer is far more complex th…

Related Situation: The platform works, but you are not sure it will survive the next phase.
26 min watch · Sep 2025·Watch
Ep. 07

How Great Consultants Gain Trust and Credibility From Day One

You've landed the client. Now what? The first few days and weeks of a consulting engagement are a critical window to set the tone, build relationships, and lay the foundation for success. It's not about being the smartest person in the room; it's about becoming a trusted partner.

Related Situation: The team is busy, but leadership cannot see delivery clearly.
18 min watch · Sep 2025·Watch
Ep. 06

Beyond the Pitch - Spotting Great Tech Consultants

Hiring the right technology consultant can be the difference between a project's soaring success and a multi-million dollar failure. The stakes are incredibly high, but how do you see past the polished pitch and industry buzzwords to find someone who will truly deliver?

Related Situation: The team is busy, but leadership cannot see delivery clearly.
38 min watch · Aug 2025·Watch
Ep. 05

Feeling Bloated? Time for Some Lean Consulting

For decades, big problems meant hiring big consulting firms. The logic was simple: size equals impact. But what if that model is fundamentally broken? What if the hundred-page slide decks, massive teams, and staggering bills are a sign of waste, not value?

Related Situation: The team is busy, but leadership cannot see delivery clearly.
27 min watch · Aug 2025·Watch
Ep. 02

'The Solution-First' Trap: Why Projects Fail Before They Start

What happens when a client asks for the latest tech trend, like GenAI, but you suspect it's not what they actually need? It's a classic scenario that can lead to wasted time, bloated budgets, and solutions that miss the mark entirely.

Related Situation: The platform works, but you are not sure it will survive the next phase.
20 min watch · Aug 2025·Watch
Ep. 01

We Built and Launched an App for a Las Vegas Casino In 11 Days...

What happens when you’re asked to build a full-featured, secure, and high-traffic website for a Las Vegas casino in just 11 days to meet a Super Bowl ad deadline? You pull it off... but what if the project still fails?

Related Situation: The team is busy, but leadership cannot see delivery clearly.
27 min watch · Aug 2025·Watch

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