Mailander Podcast
The Mailander Podcast is a film room for high-stakes decisions.
In each episode, strategist and author Chris Mailander sits down with leaders who have been tested under real pressure to replay 2–3 pivotal choices that changed the trajectory of a company, career, or market.
The show is built around decision intelligence—the discipline of designing the processes, frameworks, and systems that make consequential choices better over time. Guests are typically CEOs of private mid-market companies (roughly $50M–$5B+ in revenue) or founders of AI and technology platforms (roughly $5M–$50M ARR) who have already navigated major inflection points: exits, strategic investments, AI transformations, turnarounds, or elite program builds.
Instead of surface-level origin stories, conversations slow the game down. Chris and his guests break down what they saw, what they missed, the trade-offs they wrestled with, and how those decisions shaped enterprise value, culture, and competitive advantage.
If you’re a performance-driven leader—CEO, investor, operator, or emerging founder—and you treat judgment as a craft, this is your room. Episodes are produced in long-form video and audio and released across Apple Podcasts, Spotify, Audible, YouTube, and major social channels, with selected clips cut for precision delivery to the audiences that matter most.
Mailander Podcast
Curate Friction: The Good Fight You Should Be Having
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There is a fight for influence over your decision-making process amongst your internal teams. This is how to curate a healthy fight, and harvest its benefits for your company.
There are competitors amongst those on your team who fight for influence over your decision-making. The battle can be overt, passive-aggressive, or quite subtle. It can be unhealthy. If curated well, it can be very healthy to your stewardship of the company.
There will be several camps. In one, there is a strong preference for creating routine rhythms to the decision-making in the company, with a routine cadence, common language, and well-defined metrics. In another, the preference is for the sort of irregularity where creative, innovation, and risk mitigation flourishes. One wants patterns to work within. The other prefers no patterns at all. They are both necessary and essential to the organization.
The friction between these camps should be carefully curated to ensure each contributes well to the overall decision-making prowess of the company. Doing so leads to improved argumentation, better options analysis, stronger playbooks, the development of more diverse decision arcs, the ability to find the lines that blur between emotion and logic, and perhaps most importantly, the ability to evaluate how individual contributors think, react, and perceive.
For the CEO, key components for curating this friction include
- Intentionally observing and managing this process;
- Managing the ‘blend’ between those who flourish in regularized decision-making versus those who prefer irregular ones; and
- Measuring the performance of each camp, which for the former can be evaluated against MoM or QoQ financial performance and operational efficiency, and for the latter, which can be measured by their contribution to sustained increase in the long-term enterprise value of the company, able to both capture emergent new opportunities as well as forestall the risks that lurk beyond.
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Original Music by Billy Goodrum