The Process Debt Podcast — Year in Review

A full year of uncovering the hidden costs of how work really gets done. 🎙️

In this special “Year in Review” episode, Chris and Toby look back on the first year of The Process Debt Podcast — from the early conversation that started it all (“process must be discoverable and transferable”) to exploring the strange collision of Elon Musk and government bureaucracy, to the ongoing battle between Try vs. Buy when building systems and change.

It’s a reflection on what we’ve learned about how organizations scale, stall, and sometimes survive on bubblegum and duct tape — and how great process thinkers are the real crown jewels of any business.

With year two ahead and new ventures through Magic Button Labs, the hosts share lessons, laughs, and the optimism to keep fixing the unfixable — one process at a time.

Listen to The Process Debt Podcast — where we make sense of the mess behind every business.

Welcome to year two of The Process Debt Podcast! In this episode, Chris and Toby explore one of the most complex—and timely—processes of all: how the U.S. government shuts down.

From “turning off the lights” in Washington to the ripple effects affecting families, communities, and the economy, the hosts analyze the shutdown through a new perspective they call P.U.M.P. — Process, Unintended Consequences, Money, and Power.

They examine how failures in process at a large scale mirror the same dysfunctions found inside businesses: lack of long-term vision, incentives that reward short-term thinking, and the painful cost of ignoring the machinery that keeps everything running smoothly.

It’s a sharp, balanced discussion that blends humor, curiosity, and critical thinking—complete with a few detours into tax policy, inflation, and even how Microsoft once forgot to renew an SSL certificate.

Tune in for:

• Why “process debt” is as relevant to Congress as it is to corporations
• The real consequences of halting the world’s largest organization
• How incentives influence (and sometimes derail) both politics and business
• A reminder that restarting broken systems is never as simple as flipping a switch

🎙️ Process. Unintended Consequences. Money. Power. Welcome back to The Process Debt Podcast. Year Two begins now.

One year of Process Debt is officially in the books! 🎉 In this milestone episode, Chris and Toby take a surprising detour from discussing Wall Street internships to exploring a lollipop factory in Boise, where defects are easy to spot (nobody wants a half-melted Rodman Pop). However, in knowledge work, defects often hide in plain sight.

What qualifies as a "bad lollipop" when your day is filled with emails, PowerPoint presentations, meetings, and dashboards? Is novelty the same as productivity? How can you determine if you're producing valuable outcomes or just cluttering the system with appealing but ineffective work?

Join us as we delve into why defining what is "good" in knowledge work is challenging, how invisible waste sneaks into our calendars, and why applying Six Sigma principles to PowerPoints might not be as outrageous as it seems.

It’s the phrase that pops up in every organization—but does “more” actually solve the problem? In this episode, Chris and Toby dig into the hidden meaning behind the call for communication. Is it really about emails and meetings, or is it about alignment, purpose, and clarity? From career-limiting questions to Zoom distractions and the five whys of team dynamics, they unpack why “more communication” is usually a symptom—not the cure.

From Amazon packages at the door to Slack pings in the middle of Zoom calls, distraction has become the default setting of modern work. In this episode of the Process Debt Podcast, Chris and Toby explore why our attention is constantly under attack—and what that means for the endless hours we spend in meetings.

They discuss how COVID blurred the line between connection and decision-making, why so many meetings lack clear purpose or roles, and how habits like assigning a rotating “scribe” could help us focus more sharply. Along the way, they talk about sitcom-worthy meeting culture, the rise of AI-generated communication, and how efficiency tools sometimes make us less alert.

At the core of it all: are we just tracking time, or creating real value? Tune in for a conversation that’s relatable, funny, and uncomfortably honest for anyone who’s ever zoned out during a Zoom call.

This week on The Process Debt Podcast, Chris takes us on a wild ride through “vibe coding” — using AI to sling code like it’s magic Lego bricks — until the whole thing comes crashing down. From lost database keys to endless AI apology loops, it’s coding that feels a lot like golf: hours of frustration, one satisfying hit, and just enough hope to keep you coming back.

We unpack how developers’ discipline of making small commits, branches, and using version control has lessons for the rest of us who are drowning in knowledge work. Why do we try to do everything in one shot when the pros already know the secret is iteration, validation, and rigor?

If you’ve ever built a system, wrangled a spreadsheet, or been stuck in an “AI says sorry” loop, you’ll laugh, cringe, and walk away with a fresh perspective on process debt.

What do birthdays, coin flips, and endless Zoom calls have in common? More than you’d think.

In this episode, Chris and Toby unpack the famous Birthday Paradox—how just 23 people in a room give you a 50% chance of a shared birthday—and connect it to something every business leader struggles with: complexity.

Why do we keep pulling more people into meetings, projects, and decisions—when more often, less is more? From the days of skunkworks teams in the 90s to today’s bloated virtual calls, we explore:

• Why our intuition about “more voices = better outcomes” often fails.
• How meetings became overstuffed and under-productive post-COVID.
• The role of clarity, purpose, and decision rights in cutting through process debt.
• What Toyota’s culture and even backyard deck builders can teach us about lean, effective collaboration.

If you’ve ever sat through a meeting wondering “why am I here?”—this one’s for you.

We all do it—chew on worries that may never come true. In this episode of The Process Debt Podcast, Chris and Toby dive into the hidden toll of personal process debt: rumination. Kicking off with Mark Twain’s line, “I’ve had a lot of worries in my life, most of which never happened,” the hosts explore how overthinking becomes a silent workflow that drains energy, creates anxiety, and produces… absolutely nothing.

From stories about misreading rooms at work to a 20-year-old’s confession about replaying arguments in his head, Chris and Toby shine a light on the very real costs of spinning on problems that don’t exist. Along the way, they unpack strategies for breaking the cycle—such as writing by hand, using the Five Whys, creating pro/con lists, taking walks, and asking the simple yet powerful question: What can I actually control?

The conversation ranges from imposter syndrome to collective rumination in organizations, even touching on EMDR and why movement helps reset the brain. Their takeaway? Clarity is kindness to yourself and to others.

If you’ve ever felt stuck in your own head, this episode offers both permission and practical tools to step out of the loop and reclaim your focus.

Decisions, Decisions: Why Business Choices Are Harder Than They Look In this episode of the Process Debt Podcast, Toby and Chris wrestle with one of the toughest challenges in business: decision making. From the small “what’s for dinner?” fatigue to high-stakes strategic moves that can make or break a company, they explore why decisions are so hard to evaluate—especially after the fact.

The conversation unpacks:

• Why great leaders like Steve Jobs and Obama simplified everyday choices.
• How businesses often miss the mark by failing to track the effectiveness of their decisions.
• The tension between purchasing vs. finance, short-term results vs. long-term strategy.
• Why not making a decision is still a decision—and sometimes the right one.
• How bias, politics, and poor prediction skills quietly build process debt.

With humor, hard truths, and real-world stories—from e-commerce purchasing metrics to massive enterprise launches—this episode challenges you to rethink how you (and your teams) make and measure decisions.

If you’ve ever wondered, “How do I know if that was the right call?”—this one’s for you.

Ever had a fix so simple you can’t believe no one thought of it sooner? Chris and Toby dig into why the best solutions only feel obvious in hindsight—sharing shipping fiascos, billion-dollar pivots, and a few rants about bad tools. Fast, funny, and packed with tips for finding your own “duh” moments.