010 - Risk 101: How RAID Logs Keep Projects on Track with Kim Essendrup

Risk isn’t a scary “extra” - it’s the reason projects succeed or spiral. ⚠️

Kim Essendrup, co-host of Project Management Happy Hour and founder of RAIDLOG.com, joins Orion for a practical Risk 101 breakdown - and how RAID logs help teams stay proactive instead of reactive.

In this episode of The Major Project Podcast, Orion sits down with Kim Essendrup - co-host of the widely followed Project Management Happy Hour podcast and founder of RAIDLOG.com, a platform built around one of the most useful tools in practical project delivery: the RAID log. 

Kim brings the conversation back to fundamentals with a full Risk 101 walkthrough: what risk actually is, why projects are statistically more likely to struggle than succeed, and why risk management isn’t about pessimism - it’s about being honest and prepared. He shares research and real-world context showing how frequently projects face major overruns and failures, reinforcing why project leaders have to pause and ask: “Where can this go off the rails - and what can we do now to prevent it?” 

Kim explains that effective risk management starts at the source of the project itself - the charter, contract, statement of work, or initiation document - where assumptions, dependencies, and blind spots often begin. From there, teams should expand the conversation through workshops, lessons learned, and similar historical projects to build a realistic picture of threats and opportunities. 

He also digs into the culture challenge: why many organizations avoid risk conversations entirely, and how strong project leaders create psychological safety so teams can speak candidly about what might go wrong. One of Kim’s most practical tactics is a subtle language shift - using the word “obstacles” instead of “risks” -to help teams move from avoidance to action. 

A major highlight of the episode is Kim’s breakdown of what a RAID log really is: an integrated way to track Risks, Actions, Issues, and Decisions (and historically: Risks, Assumptions, Issues, Dependencies). He describes the RAID log as the “run tool” of project delivery -the place where project leaders monitor reality, spot drift, and course-correct early. 

Finally, Kim shares how AI is already changing the space. He describes how his team built an AI-based risk identification feature that can generate meaningful risk registers from a project description - sometimes matching 75% of what experienced teams create manually. He closes with a simple but powerful truth: the best RAID log tip isn’t complicated… it’s use it consistently, because the moment teams stop tracking risk, risk starts tracking them. 

🎧 You’ll Learn

• The true definition of project risk -and why most projects need risk management from day one
• How to start identifying risks using the contract/charter as the “source of truth”
• Why teams avoid risk discussions -and how leaders build a healthy risk culture
• The difference between mitigate, avoid, transfer, and accept risk responses
• Why “risk” also includes opportunity -and how to capture upside outcomes
• What a RAID log is and why it’s the operational backbone of delivery
• How to scale a risk process for small projects vs. billion-dollar programs
• Where AI is already helping: risk identification, meta-analysis, and portfolio insights
• Kim’s #1 tip: the best RAID log is the one you actually keep up to date

📌 Mentioned in This Episode

• RAIDLOG.com
• Podcast: Project Management Happy Hour