Episode Overview
Scope, schedule, budget. And then this thing called risk, which too many project people treat as a black box. Orion Matthews hosts a deliberate 101: Kim Essendrup, CEO of RAIDLOG.com and co-host of the long-running Project Management Happy Hour podcast, defines project risk from first principles, walks through where risk work starts and why teams avoid it, tells the 1980s origin story of the RAID log, and shares how his AI engine reproduced 75% of a real project's risk register in one click. Thirty-four tight minutes, built for anyone who has ever nodded along at the word "risk register" without knowing what's inside one.
Projects break. Plan for it
Projects are statistically almost more likely to go wrong than right, Kim argues, so the job of a project leader is to stop and ask, early: where can this thing go off the rails, and what can we do about it now?
A coach with scar tissue
Kim deflects the "expert" label in his first answer: "I just have had a lot of risks go wrong, so I have a lot of experience on the wrong side of that." The whole episode teaches from that side.
RAID: the run tool
Risks, Actions, Issues, Decisions in one place. Not your plan, schedule or budget: the tool that keeps those plans on track, flags drift, and course-corrects before the failure statistics catch up.
Everything attributed here was said on the record in episode 010, released February 17, 2026. Quotes are transcribed from the episode and lightly condensed for readability (false starts and fillers removed, meaning untouched), and timestamps are approximate. Biographical details come from what Kim says on-air, the show's published episode notes, and Kim's LinkedIn bio, the source for the career-journey chart and credentials. Industry statistics quoted in conversation are the speakers' from-memory citations and are flagged as directional where they appear.
Episode Timeline
The conversation as it unfolds: a warm two-minute welcome, then five topic blocks that build from "what is risk?" to "what will AI do to it?", closing on the simplest tip of the season. The strip maps each chapter's share of the 34-minute runtime; timestamps are approximate. Click any block to jump to its chapter.
A tight, fundamentals-first 34 minutes: from “what is risk?” to the closing habit.
Welcome & the Happy Hour
The intro, what Kim is up to, and how a 10,000-word blog nobody read became a podcast approaching episode 100.
Risk 101: Why Projects Go Wrong
The textbook definition, then the real one, and the failure statistics that make risk management non-optional.
Start at the Source
Back to the contract, charter and assumptions; the eyes-closed driving analogy; and the four things you can do about any risk.
Obstacles, Not Risks
Why organizations dodge the conversation, psychological safety, one word that changes the meeting, and the upside kind of risk.
The RAID Log, Explained
The acronym, the 1980s UK origin story, the anatomy of a risk register, scaling it, and a 20-to-1 ROI claim.
Careers & the AI Risk Engine
Paths into risk work, "project managers aren't made, they're born," and the AI that wrote 75% of a live risk register.
The One Tip & Close
Kim's own signature question, turned back on him, and an answer that sounds obvious until he explains why it isn't.
Who carried the mic
Measured by word count across the full episode, excluding the show's recorded intro/outro announcer.
The Guest · Kim Essendrup
Kim's path into the mic is a coaching story. Years of coaching and training project managers kept surfacing the same topics, so he started a blog, and discovered "nobody wants to go to a website and read a 10,000-word blog post on project management." In 2017 he and a longtime colleague turned those topics into Project Management Happy Hour, now one of the most popular podcasts in the space and closing in on episode 100. The same instinct (take what coaching taught him and put it in a broader-audience tool) produced RAIDLOG.com, a dedicated platform for the risk-actions-issues-decisions log he's used for years "to help save broken projects and keep his own projects from getting broken." Its AI risk-identification engine launched more than a year before this recording, "which in AI terms is a century."
The résumé behind the mic runs three decades. Kim (a PMP, based in the greater Phoenix area) started in 1996 as a project manager and telephony engineer at Syntellect, ran projects at Interactive Intelligence, then spent a dozen years building and leading PMOs: PMO manager at Darcomm, director of the PMO at Ensynch, and three years in Munich running Insight's EMEA project management office. In 2017 he came full circle, co-founding Kolme Group (in his words, "the PMO consulting team we wished we had when we led our project management organizations"), where he was a partner through 2022, alongside 13 years as principal of Dobré Consulting Services, a PMI Registered Education Provider for PM training and coaching. Since this episode was recorded he has added one more title: Managing Director of Implico Group's North American team, as of April 2026.
“The thing about risk management is: as soon as you forget to stay on top of it, it will be on top of you. So it's self-correcting.”Kim Essendrup · on the show, ~33:30
Career journey
Several lanes ran in parallel: Dobré (2009–22) and the podcast (2017–) overlapped the day jobs, and the strip shows the primary seat per year; the cards carry full tenures. Also along the way: Race Everywhere, a triathlon-travel startup he founded (2013–18), and a board seat at Shee Atiká (2025–).
What he's building
- RAIDLOG.com
- A dedicated application that moves RAID logs out of the spreadsheets where "most organizations" still manage them: "a more robust technical platform" for the run tool of project delivery.
- The AI engine
- Describe your project and it recommends risks: description, potential impact, estimated probability, a 1–100 relative impact score, and candidate responses. Next up, per the episode: "chat with your RAID log" meta-analysis across portfolios.
- The coaching arc
- "I found myself doing a lot of coaching and training in the project management space": the podcast, the platform and a book he mentions on-air all grew out of translating those topics to a broader audience.
Voice & where to find him
- The podcast
- Project Management Happy Hour: "anywhere you can get a podcast," since 2017. "It's just so fun. I guess it's a passion project."
- His posture
- "There are a lot of people who are a lot more skilled than me when it comes to risk management. I just have had a lot of risks go wrong." The episode is better for it.
- Credentials
- PMP. Also on the LinkedIn ledger: PMI's Agile Hybrid Project Pro micro-credential, Neo4j LLM Fundamentals, and a published "Ultimate Guide to RAID Log."
- Find him
- LinkedIn: /in/kim-essendrup · raidlog.com · pmhappyhour.com
The Host · Orion Matthews
Orion is an award-winning programmer, entrepreneur and technology executive who has spent the last decade in the engine room of major capital projects. He founded Queryon in Washington, D.C. in 2015 with a focus on data analytics and software for the construction industry, starting with bellwether client BP, whose project-controls solutions his team deployed globally, from the North Sea to Azerbaijan to Houston. Today he's a recognized expert in PMO data analytics and project-controls reporting, serving billion-dollar portfolios for owners including BP, Santos, Balfour Beatty and Turner & Townsend, a regular speaker at major industry conferences on AI and analytics in capital projects, and the host of this show.
Why this pairing works
- ROI vs ROI
- Kim cites a 20-to-1 return on risk-management effort; Orion counters from his own field ("that's higher than our stats, data analytics is a 13-to-1"), a rare on-air moment of two practice areas comparing receipts.
- Podcast craft
- Host interviews co-host: Orion closes by turning Kim's own signature Happy Hour question ("what is your favorite tip or trick?") back on him, and briefly stumps him with it.
Beyond the PMO
- The builder’s arc
- Founded Introspect Software out of high school; built and sold Design-PT (acquired 2015). His software has run from McMurdo Station to aircraft carriers, with write-ups in Scientific American, CNN and Maxim, and a BP Helios Award.
Risk 101: Why Projects Go Wrong
Orion frames the gap: people learn the project management triangle (scope, schedule, budget) and treat risk as a black box for years. Asked for a definition, Kim gives the textbook one a single sentence, then throws it away for something more useful: get real about the base rates.
“The textbook definition is an uncertain event that could happen to your project. But if we zoom out, let's get real before we start talking semantics and definitions. Projects are hard. Projects are statistically almost more likely to go wrong than they are to go right.”Kim Essendrup · ~4:00
The numbers he rattles off
One in six projects runs 200%-plus over cost (he attributes it to Harvard Business Review); 17% of large IT projects go so badly they threaten the organization's existence (McKinsey); 10% of project investment lost to issues and waste; and the Standish CHAOS report's split: roughly a fifth of projects fully succeed, roughly a third utterly fail, the rest flounder in between. ~4:15
What the numbers are for
Not doom. Duty. "It's incumbent on us as project leaders, project controllers, to stop and take a moment and say: okay, where can this thing go off the rails, and how can I avoid that? That's really what it comes down to." ~5:10
- Orion's setup: risk as the fourth, unexamined corner of the triangle: "I've met people that got involved in project management and went years treating risk as a black box." ~2:45
- Kim declines the pedestal before answering anything: "I just have had a lot of risks go wrong, and so I just have a lot of experience on the wrong side of that." ~3:45
- The pivot from definition to duty: you can get caught up in what might or might not happen: "really it comes down to the fact that you're probably gonna run into issues. So let's try to avoid those from the get-go." ~5:15
The HBR, McKinsey and Standish figures above are cited from memory in conversation. Treat them as directional context for "projects fail a lot," not as precise citations.
Start at the Source
"I'm a project manager, I know nothing about risk, where do I start?" Kim's answer isn't a workshop or a template. It's archaeology: go back to whatever document this project was born from, because the first risks were written down before the delivery team ever arrived. Then Orion plays devil's advocate (why identify risks at all?) and gets the episode's best analogy for his trouble.
“You have to back up to the very start of whatever this thing is you're calling a project. Is it based on a contractual agreement with a statement of work? A project charter? A project initiation document? … Go back to the source and say: when you decided to do this project, what were your basic foundational assumptions?”Kim Essendrup · ~6:00
Then grow the research
Get the project team in a room: "okay team, where are all the things this can go wrong, and what can we maybe do about it?" Pull past risk registers from similar projects ("maybe they've already stubbed their toe on the same rocks that are threatening you") and check industry benchmarks. ~7:15
Eyes open, or eyes closed
Orion's rattlesnake challenge (why not just deal with problems when they bite?) meets Kim's driving analogy: "As I get in my car and drive, I could get in an accident. I'll just close my eyes. If you do little things like, I don't know, open your eyes, you can see what could be coming at you and change your route." ~8:20
- The yellow light: "Do you floor it and just hope, boy, I hope I get through this before I get T-boned? Or do you slow down and evaluate the situation? The same thing goes for projects." ~8:50
- The four responses, taught through one shipping risk: mitigate the probability or the impact; avoid it altogether by finding a local supplier; transfer it via a fixed-fee third party or insurance; or accept it: decide what you'd do, and hold a little contingency just in case. ~9:15–10:20
- The payoff line: "Planning ahead lets us potentially plan for that and reduce the probability or the impacts of those risks." ~10:20
Obstacles, Not Risks
The uncomfortable middle of the episode: most organizations don't have a risk-analysis problem, they have a risk-conversation problem. Talking about what could go wrong "sours the conversation," so nobody does it, which, given the base rates from chapter one, is exactly backwards. Kim's fixes are one cultural and one tactical, and the tactical one is a single word.
“That's where our role as project leaders becomes really important, because we have to be the ones that say the truth about the project and bring some of these potentially uncomfortable conversations to the surface.”Kim Essendrup · ~11:20
The cultural half: psychological safety
It's very challenging in an organization where you can't say "this could be a problem" without being smashed down. A project leader can at least foster open communication and build trust inside their own team: "that takes some time, and there's a lot to that. But you need to really prioritize that." ~12:15
The tactical half: change one word
Borrowed, with credit, from Dr. Josh Ramirez, "a forefront thinker in the area of psychology and project management": stop asking "what are the risks?" and ask "what are the obstacles between us and success?" An obstacle is tangible; teams start solving instead of shrugging. ~13:30
- Why "risk" fails as a word: it invites the lightning-strike shrug ("there's a risk I could be struck by lightning; I'm not gonna stop going outside") and the quiet hope that ignored risks won't happen. ~13:00
- The reframe in action: "Now we can start thinking, okay, a lot of times our shipments from overseas get delayed. How are we gonna overcome this? It really changes the dynamic." ~14:10
- Orion raises pairing risks with opportunities; Kim confirms it's in the definition itself: "Especially the Project Management Institute definition: a risk is an uncertain event. It could be good, could be bad." ~15:10
- The same shipping risk, flipped: finding a local distributor isn't just avoidance: it's a new supplier relationship that pays off on future projects. Threats and opportunities, evaluated together. ~15:30
- A practical language note: most people never hear the good kind of risk in the word: "you might find you have to talk about risks and opportunities, as opposed to assuming everyone has a PMI certification." ~16:10
The RAID Log, Explained
The promised centerpiece. RAID: Risks, Actions, Issues, Decisions (originally Risks, Assumptions, Issues, Dependencies). Take your risk register, action list, issues log and decision log and put them in one place: "but it's much more than the sum of its parts." Kim tells the origin story, defines what the log is for, opens up the anatomy of a risk register, and drops the episode's biggest number.
“It's not your plan, it's not your schedule, it's not your budget, it's not your communication plan. It is the tool that you use to track and make sure those plans stay on track, identify when they start to go off track, and course-correct when that starts to happen.”Kim Essendrup · ~18:20
The 1980s origin story
UK government outsourcing, long negotiations, and a signed contract "a hundred pages long, maybe more" handed to a delivery team with imperfect knowledge of how it was negotiated. The RAID log was invented to pull the buried risks, assumptions and dependencies out of the contract into something the team could actually manage to. ~17:10
Anatomy of the risk register
A big table: the risk, description, tags and categories; then qualitative assessment (priority and impact by heuristics, "not necessarily a whole lot of science behind it, mostly expertise and past experience") to decide what deserves deeper, quantitative analysis of real monetary impact and probability. ~20:00
- Orion's plain-English translation: the "log" is really a table (rows and columns, historically in Excel), and Kim confirms: "the origins of RAID logs, of course they were spreadsheets, like the origin of everything else we have today." ~19:00
- Why RAIDLOG.com exists: "up until recently, most organizations managed RAID logs in spreadsheets, that's actually why we launched our dedicated application." ~19:40
- It scales both ways: "If you've got a four-week technical project or a massive two-year construction project, you can still get value out of this and scale it according to your needs." Rigor grows with stakes and maturity. ~21:20
- Orion asks for the investment benchmark: is it 1–2% of a $500M project? Kim's honest answer: there's surprisingly little data on risk-management ROI at all. ~22:00
- The number that survived his research: "Two different studies in different industries came up with a very similar number… the time and effort invested in risk management has an ROI of 20 to one. It's ridiculous." ~22:55
The 20-to-1 ROI comes from two unnamed studies Kim recalls from his research. He invites listeners who know better data to share it. Orion's 13-to-1 figure for data analytics is likewise cited from memory. Directional, both.
Careers & the AI Risk Engine
Act III, in two movements. First, for the listener eyeing risk as a career: where the roles actually are, and the two directions the path forks: deep into quantification and consulting, or broad into corporate governance, risk and compliance. Then the AI question every 2026 interview owes its audience, and Kim arrives with the season's best demo story instead of a prediction.
“Without telling him, I took his project description and put it into our AI generator, and it gave me a risk register. I sent it to him and said, I just wonder how close does this align with the register you and your team developed? He said: this is about 75% of what we already have. In one click I had 75% of his risk register. Just absolutely mind-blowing.”Kim Essendrup · ~28:50
The career fork
Full-time risk managers are hard to keep busy outside very large engineering and construction projects. Go narrow (statistics, quantification, consulting, calculating risk reserves) or go broad, into GRC: governance and regulatory compliance at the organization level. ~24:30
Try before you enroll
"Before you jump into school and try to be an actuary, get your hands on it." Volunteer for risk-profiling on your own projects or with the PMO. His co-host's line applies: "project managers aren't made, they're born," and risk people may be the same. ~26:20
- Kim's AI ceiling, stated plainly: "We will always need the people with the good judgment… managers are not gonna want to put blame or accountability on an AI. It needs to be a person who's in charge." ~27:30
- What the engine actually outputs: risk, potential problem, potential impact, estimated probability, a 1-to-100 relative impact score, and candidate responses, from nothing but a project description. ~28:20
- The test case that makes the 75% story land: a very people-oriented project (implementing a formal PM function at an 80-year-old civil construction company): "not the kind of thing you would think an AI knows about." ~28:45
- Orion's aphorism in response: "AI won't replace your job, but people with AI probably will." ~29:50
- What's next: the AI learns your past risks, issues, lessons learned and decisions, then "chat with your RAID log": ask your portfolio what's really driving budget impacts and schedule delays. ~30:30
The One Tip: Use It
Orion closes by borrowing Kim's own signature question from Project Management Happy Hour (what's your favorite tip or trick?) and briefly stumps him with it. The answer Kim lands on sounds like a punt and isn't: the RAID log fails silently, one busy day at a time.
“This is gonna sound ridiculous and obvious, but: use it. And that sounds easy, right? It's not, because as project leaders we have so many things to do… and what inevitably happens is the RAID log starts to fall down towards the bottom of your priorities.”Kim Essendrup · ~31:45
- The failure mode, narrated from the inside: "If I don't update my RAID log today, it's not gonna be the end of the world. And sure, maybe it won't be. Maybe tomorrow either. Still busy the day after that…" ~32:10
- The driving analogy returns to close the loop: "You can go through a yellow light with your eyes closed and be fine the first time, the second time, the third time. Sooner or later, those project failure statistics are going to catch up with you." ~32:25
- He's lived it: "I got distracted, I got focused on other things, then bam, project issues. And the first thing I think of is: am I keeping my RAID log up? And the answer's always no." ~32:40
- The exit line, and the episode's most quotable: "As soon as you forget to stay on top of it, it will be on top of you. So it's self-correcting." ~33:30
The Big Ideas
Three ideas carry the episode. Sketched here the way a risk workshop facilitator would whiteboard them.
Kim teaches all four responses through a single running example: materials shipped from overseas that might arrive late.
Reduce the probability it happens, reduce the impact if it does, or both. Expedite, dual-source, build slack.
Remove the risk altogether: go through the effort of finding a local supplier and the shipping delay can't touch you.
Still your risk, but a third party carries responsibility and financial impact: a fixed-fee contract, or insurance.
It might happen, it might not, and maybe there's nothing to do, so decide now what you'd do, and hold contingency just in case.
Risk inputs scattered across founding documents and institutional memory converge into one managed table, whose job is keeping every other plan honest.
The tactical culture fix Kim credits to Dr. Josh Ramirez: the word "risk" invites a shrug; the word "obstacle" invites a plan.
“What are the risks?”
- Feels hypothetical (the lightning-strike shrug): it probably won't happen to us
- Invites avoidance: "if I ignore it, it might not happen; if it happens, I'll deal with it"
- Sours the room in orgs without psychological safety
“What are the obstacles between us and success?”
- Tangible and real: something standing in the way, right now
- Invites action: "how are we gonna overcome this?"
- Opens a more productive conversation (no PMI certification required)
Bookshelf & Links
Everything recommended or credited in the episode, plus where to find the people and the show.
From the episode
- Podcast
- Project Management Happy Hour: Kim's show, co-hosted since 2017 and approaching episode 100. Orion's on-air send-off: "If you're looking for more of Kim's amazing, insightful advice and the advice of his co-host, you can always join him on the Project Management Happy Hour."
- Tool
- RAIDLOG.com: Kim's dedicated RAID log platform, with the AI risk-identification engine behind the 75% story. "It just really empowers you, makes you smarter, helps you make better decisions, which is really our goal with our whole platform."
- Person
- Dr. Josh Ramirez, "a forefront thinker in the area of psychology and project management," credited on-air as the source of the risks-to-obstacles language reframe.
- Cited research
- Harvard Business Review, McKinsey and the Standish Group CHAOS report on project failure rates, quoted from memory as directional context (see the editorial notes in chapters 1 and 4).
The episode
- Listen
- Episode page · Apple Podcasts · Spotify
- The guest
- Kim Essendrup on LinkedIn · raidlog.com · pmhappyhour.com
- The host
- Orion Matthews on LinkedIn · Queryon
- The show
- themajorprojectpodcast.com: new conversations from the people building projects over US$1 billion.
Quote Bank
The best on-the-record lines, gathered in one filterable place. "Highlight" marks the lines most worth scrubbing back for; quotes are lightly condensed and timestamps are approximate.
Risk 101: Why Projects Go Wrong ~2:45–5:35
- Highlight“Projects are hard. Projects are statistically almost more likely to go wrong than they are to go right.”
- “There are a lot of people who are a lot more skilled than me when it comes to risk management. I just have had a lot of risks go wrong, so I have a lot of experience on the wrong side of that.”
- Highlight“It's incumbent on us as project leaders, project controllers, to stop and take a moment and say: okay, where can this thing go off the rails, and how can I avoid that?”
Start at the Source ~5:35–10:40
- Highlight“Go back to the source and say: when you decided to do this project, what were your basic foundational assumptions? Did you already realize there were risks involved, and if so, what were those?”
- “If you've got past risk registers from similar projects, they've already paved the way, maybe they've already stubbed their toe on the same rocks that are threatening you.”
- Highlight“As I get in my car and drive, I could get in an accident. I'll just close my eyes. If you do little things like, I don't know, open your eyes, you can see what could be coming at you.”
- “When you come up to a yellow light, do you floor it and just hope, boy, I hope I get through this before I get T-boned? Or do you slow down and evaluate the situation?”
- “Planning ahead lets us potentially plan for that and reduce the probability or the impacts of those risks.”
Obstacles, Not Risks ~10:40–16:25
- Highlight“We have to be the ones that say the truth about the project and bring some of these potentially uncomfortable conversations to the surface.”
- “There's a lot of times an idea that if there's a risk, if I just ignore it, it might not happen. If it happens, I'll deal with it.”
- Highlight“Instead of saying 'what are the risks?', rephrase it: okay guys, what are the obstacles between us and success? An obstacle has a much more real, almost tangible feel to it.”
- “A risk is an uncertain event. It could be good, could be bad… at the same time you're looking at negative downside threats, you should also be looking at opportunities.”
The RAID Log, Explained ~16:25–23:30
- Highlight“Think of your risk register, an action list, an issues log and a decision log: put that all together in one place, and that's a RAID log. But it's much more than the sum of its parts.”
- Highlight“It's not your plan, it's not your schedule, it's not your budget, it is the tool that you use to make sure those plans stay on track, identify when they start to go off track, and course-correct when that starts to happen.”
- “The deep, dark origins of the RAID log, it actually came about in the eighties, in the UK… that contract is a hundred pages long, maybe more. The tool they developed to put the risks, assumptions and dependencies together in a way the delivery team could manage, that was the RAID log.”
- “If you've got a four-week technical project or a massive two-year construction project, you can still get value out of this and scale it according to your needs.”
- Highlight“The time and effort invested in risk management has an ROI of 20 to one. It's ridiculous… most organizations do minimal at best, so a little bit of investment really goes a long way.”
Careers & the AI Risk Engine ~23:30–31:15
- “It's hard to keep a full-time risk manager busy on typical projects, unless we're talking about very large engineering or construction projects.”
- “My podcast co-host likes to say that project managers aren't made, they're born. It's something you really wanna do and just naturally do.”
- Highlight“We will always need the people with the good judgment… managers are not gonna want to put blame or accountability on an AI. It needs to be a person who's in charge.”
- “We launched our first AI feature over a year ago, which in AI terms is a century, right?”
- Highlight“In one click I had 75% of his risk register. Just absolutely mind-blowing.”
- “AI won't replace your job, but people with AI probably will.”
- “Chat with your RAID log: for my portfolios this past year, what is the primary root cause for impacts to our budget? … It just really empowers you, makes you smarter, helps you make better decisions.”
The One Tip: Use It ~31:15–34:00
- Highlight“This is gonna sound ridiculous and obvious, but: use it. And that sounds easy, right? It's not: the RAID log starts to fall down towards the bottom of your priorities.”
- Highlight“You can go through a yellow light with your eyes closed and be fine the first time, the second time, the third time. Sooner or later, those project failure statistics are going to catch up with you.”
- “I got distracted, I got focused on other things, then bam, project issues. And the first thing I think of is: am I keeping my RAID log up? And the answer's always no.”
- Highlight“As soon as you forget to stay on top of it, it will be on top of you. So it's self-correcting.”