EPISODE 010

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

Description

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. MPP-Essendrup-Full-NeedsApproval

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?” MPP-Essendrup-Full-NeedsApproval

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. MPP-Essendrup-Full-NeedsApproval

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. MPP-Essendrup-Full-NeedsApproval

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. MPP-Essendrup-Full-NeedsApproval

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. MPP-Essendrup-Full-NeedsApproval


🎧 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

Transcript

Host: [00:00:00] Welcome to the major project podcast, your inside. Look at the high stakes world of billion dollar projects.

Orion Matthews: Today we’re gonna dive into risk and specifically go over risk 1 0 1 for project management. I’m Ryan Matthews, founder of aquion. Uh, it’s a reporting data analytics and AI solution company. We work with, uh, major projects in the project control space. I’ve been doing that for about a decade. I’m really excited to learn from luminaries in the space, particularly those like Kim.

Kim is the co-host of the project Management Happy Hour, one of the most popular podcasts in the project management space. He’s also the founder of raid log.com. He’s been using RAID logs for years to help save broken projects and keep his own projects from getting broken. Uh, one thing to mention, if you don’t know what a raid log is, that’s great.

You’re in the right spot. We’re gonna learn about them today, so, hi Kim. Welcome. 

Kim Essendrup: Hi, Ryan. Thanks for [00:01:00] having me. 

Orion Matthews: Awesome. So, um, whatcha up to right now? 

Kim Essendrup: Really busy. So, you know, I’ve, I’ve always done, um. I found myself doing a lot of coaching and training in the project management space and, found that there were a lot of topics that, uh, I, I talked a lot about for a lot of project managers.

And so that’s really kind of led us to where I am today professionally, especially with Ray Log and a book is really doing that. So it’s really just trying to translate, uh, the, those kind of coaching topics into things that that I can get out to a broader audience really. 

Orion Matthews: And Kim just really quick, kind of curious to talk a little bit about your book, your podcast and Raid log.

Maybe you can share a little bit about that.

Kim Essendrup: Um, sure. So the, the, our podcast project management happy hour. It’s, uh, just some, it’s, it is just, it’s so fun. I guess it’s a passion project and I, years ago I, [00:02:00] I took all the coaching and mentoring topics that I frequently touched on, and I started a blog, but strangely enough, nobody wants to go to a website and read a 10,000 word blog postop project management.

It’s not the most fun thing. So I reached out to a long time colleague and friend, uh, and said, Hey, let’s try, let’s try and do a podcast. And we, uh, tried it out and funny enough, people other than friends and family actually started listening to it. And that was in 2017 and we’ve been doing it ever since.

We’re coming up on episode 100 pretty soon. I think so. 

Orion Matthews: Wow. Okay uh, that’s awesome and people can get that at Apple Podcast. Um, other places like that, I assume 

Kim Essendrup: anywhere you can get a podcast, you can find, uh, project management. Happy hour, that’s us. 

Orion Matthews: All right, awesome. I imagine many people, you’ll get a couple more subscribers from this conversation, I hope.

Super. Fantastic. All right so today what I was really looking forward to is discussing risk 1 0 1 with you. And I think the reason [00:03:00] I say 1 0 1 is I think risk is one of those areas where, you know, when you think about the project management triangle, you have sort of scope, schedule, budget, and then you have this thing called risk.

And I think some people don’t understand it really well. I think I’ve met people that have gotten involved in project management and maybe went years without even really. Sort of treating risk as a black box. So I thought maybe we could have a great conversation if I could find someone like you that’s a complete expert in the field that has clearly taken risk to its highest form of art, but bring it back down to earth and sort of talk from a very 1 0 1 perspective to sort of introduce risk and understand why it’s so important for projects and things like that.

So, with that said, could you define project risk for us? 

Kim Essendrup: Sure. And first I’ll say thanks for the kind words, but there are a lot of people who are a lot more skilled at me when it comes to risk management. I just have had a lot of risks go [00:04:00] wrong, and so I just have a lot of experience on the wrong side of that.

But to your question, what what’s risk? So the risk is, you know, the textbook definition is an uncertain event. If that could happen to your project, but if we zoom out, let’s, let’s get real before we start talking. Semantics and definitions. Projects are hard, right? Projects are statistically almost more likely to go wrong than they are to go right.

The Harvard Business Review wrote up something where they found that one in six projects has a cost overrun of 200% or more. McKinsey found that 17% of large IT projects go so badly that they threaten the very existence of the organization that they existed for. 10% of project investment is lost due to project issues and waste.

The standards group has their chaos [00:05:00] report and they have some, their stats are something like 19 project, 90% of projects. Fully succeed. 31% utterly fail, and the rest kind of flounder in between. So the context is that we know personally things go wrong in projects, and so 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? And that’s really what it comes down to. You can get caught up in this idea of risk, 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, from the get go.

Orion Matthews: And how, so when you talk about that, like that makes perfect sense. We’ve got a project, let’s say. How do you even get started with the process of identifying those risks and [00:06:00] moving it forward? Let’s say that I’m a project manager, I know nothing about risk. I now understand what you said.

Um, how do I, where do you start to. Address them? 

Kim Essendrup: That’s a good question. So I think where you start is really, you have to back up to the very start of whatever this thing is you’re calling a project. So is this project based on a contractual agreement with the statement of work? Is it based on a project charter?

Is it based on a project initiation document? Whatever those foundational things are that this project came from, there were certain planning assumptions or dependencies between parties, maybe certain risks that were identified from the very beginning, and so the first place you should start is to go back to the source and say, okay, when when you decided to do this project, what did, what were your basic foundational assumptions?

Um, did you already realize that there were risks involved in this? And if so, what were those? Um, if [00:07:00] there are dependencies, who’s de responsible for what, what’s, what’s, depending on whom or what condition. And you need to start by capturing that information as the initial source. And from there you start to grow your research.

You start to look at, once you have your project team, you’ll get your project team in a room and say, okay, team, where are all the things that this thing this can go wrong? And what do we, you know, what can we maybe do about it? You can also look at past similar projects. If you’ve got past risk registers or, or records from past similar projects, they’ve already paved the way, maybe they’ve already stubbed their toe on the same rocks that are threatening you.

So it’s good to try to learn from those and even industry benchmarks. So there’s a lot of places where we can start to collect this information, but it’s certainly something that should have a very strong upfront focus as you get started. 

Orion Matthews: So question on that. So it makes sense, right? You’re saying like, [00:08:00] check the original contract and engagement, like what was the original idea?

Where were the risks identified from there? So if you’re building a road, was somebody talking about like a bunch of rattlesnakes that lived in a bush nearby that could like injure someone? So what about. What is it about identifying risks that’s important though? Why not just say like, Hey, if someone gets bit by a rattlesnake, like we’ll deal with it.

Like what is the advantage of even identifying risks at all? Like what’s the point? Because if it happens, it happens and you can just deal with it then, right? 

Kim Essendrup: Yeah. I mean, you could. Make an analogy to say, well, as I get in my car and drive, I could get in an accident, I’ll just close my eyes. And what happens, right?

If you do little things like, I don’t know, open your eyes, you can see what could be coming at you, and you could have a possibility of changing your route. Changing your direction and avoiding that, that crash. Or 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 [00:09:00] and smashed.

Or do you slow down and evaluate the situation? And the same thing goes for projects is that if we take a moment and look at what could possibly happen and obstruct our project or cause us problems, most of the time there’s something we can do about it. We can, um. Mitigate. Which means we are reducing the probability of occurrence of that, making it less likely, or we’re reducing the impact if it actually does happen, or maybe both.

We can try to avoid the risk altogether. So let’s say, uh, my project depends on shipping a lot of materials from overseas and there’s risk that might be delayed through shipment or some supply chain issue. I could remove that risk altogether if I go through the effort and try to find a local supplier.

I can also think of transferring this risk, so it’s still my risk, but maybe I can transfer responsibility and some of the financial impacts [00:10:00] to another party by giving the responsibility to a third party who’s responsible for doing it for a fixed fee or getting insurance. Or sometimes we may actually look at that and say, you know what?

It might happen. It might not. Maybe there’s nothing I can do about it. Even in that case, I can look and say, okay, if that happens, what would I do? Should I have a little bit of an extra contingency in my budget just to cover, just in case? And maybe that’s how I cover it. So the answer is, planning ahead lets us potentially plan for that and reduce the probability or the impacts of those risks.

Orion Matthews: Okay. And then. 

Kim Essendrup:

Orion Matthews: so that makes sense. Obviously, I just sort of tee you up for that. I think identifying risks early and often good, like the ability to avoid them makes a lot of sense to me. I think it makes a lot of sense to stakeholders. Maybe some people prefer not to see them because it potentially shows big dollars that could come down the road, but by and [00:11:00] large it seems like it’s better to know what those.

Potential impacts are rather than ignore them and never have the conversation. 

Kim Essendrup: It is. But you know, that happens more often than you might think in a lot of organizations where they’re not accustomed to confronting or talking frankly about risk. If you start talking about where things can go wrong, it can really sour the conversation in a lot of people’s minds.

They don’t want to think about if things could go wrong. They don’t want to stop and consider that or invest time in it. Which, you know, considering the fact that you’re probably gonna have issues is not a wise thing to do. And so 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 uncomfortable, potentially uncomfortable conversations to the, to the surface.

Orion Matthews: Well, so let’s dive on that a little bit. ’cause that’s a really interesting question for people involved in projects in general. Like, what is the right culture? You wanna create around [00:12:00] risk for a project team or for a company. Because like you said, it’s not a fun conversation for people talk about. But it’s a really necessary one.

So is there a way to have you found there’s certain ways to create a good culture around risk that that’s more effective I guess, than other cultures that sort of avoid that problem? 

Kim Essendrup: I, I think there’s two pieces of this. There are some tactical things that we can do, but there’s still, there’s the broader context and it’s, it is very challenging if you’re in an organization where there isn’t the.

I think maybe the phrase is psychological safety to actually bring up and say, Hey, you know, this could be a problem, or this could be an issue and not be smashed, you know, smashed down when you try to bring those up. And so as a, as a project leader, what we can do is at least try to foster that open communication within our teams and really build that trust.

And that takes some time and there’s a lot to that. But you need to really prioritize that. But a more tactical [00:13:00] thing that we can do is we can change the conversation in a very subtle way that has a big impact. So when we talk about risk, we all come in, we hear the word risk, and we have a lot of connotations, right?

Sometimes we think, okay, a risk is okay, yeah, there’s a risk. I could be struck by lightning. I’m not gonna stop going outside because of that, so I’m just gonna live my life. 

Orion Matthews: Mm-hmm. 

Kim Essendrup: That’s not necess, but you know, that doesn’t always translate to the project world. So 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. And so there, there’s hesitancy to address it from right on. If you change the language just a little bit, and this is something I learned from Dr. Josh Ramirez who is a, he’s a, a forefront thinker in the area of, of psychology and project manager. And what he suggests actually is to call them obstacles.

So if my obstacles, if I feel like my team has [00:14:00] connotations or they don’t really like to deal with risk very well, instead of saying what are the risks of this happening? I don’t know. This could happen. That could happen. But if instead I rephrase that and I say, okay guys, what are the obstacles between us and success?

An obstacle has a much more real, almost tangible 

Orion Matthews: mm-hmm. 

Kim Essendrup: Uh. Think to it. And so now we can start thinking, oh, okay, well there’s this obstacle in it. A lot of times our shipments from overseas for this material get delayed. How are we gonna overcome this? And so it really changes the dynamic, it changes the discussion and you can have a, sometimes a more productive conversation with that approach.

Orion Matthews: Okay. That’s, that’s interesting. That’s really also there’s I have seen in the past, and I’d love to get into sort of the. The risk how you actually build out the table, so to speak, of risk, but sometimes do the people match up risks and opportunities in the same space? In a way where you’re saying like, make sure to identify project risks, but also [00:15:00] identify opportunities like to save money or you know, or, or, or do this quicker.

So like by pairing your good potentialities with your bad potentialities, maybe it’s sort of. Helps balance them out a little bit. 

Kim Essendrup: Exactly. So, uh, and that’s a, that’s a, a really good comment. So the risks by definition, especially the Project Management Institute definition, a risk is an uncertain event.

Mm-hmm. It could be good, could be bad. So the idea is that when you start evaluating risk, what could go wrong, you should also be thinking of, well, what is the upside? What are some things that we could turn this around and turn it into an upside? So our shipping example, I’ve got a risk that my overseas materials might be late.

Maybe we can flip that. Turn that into a positive, because maybe if I can find a local distributor, I can, not just for this project, but for future projects I built, I could build a new supplier relationship that helps me get faster, materials [00:16:00] better. And so there’s a, a potential upside. So at the same time, you’re looking at negative downside threats.

You should also be looking at opportunities. Um, the reality is when most people say risk, they don’t usually think of the good kind of risk. So the language you used should be specific to your organization, but you might find that you have to talk about risks and opportunities as opposed to just saying risks and assuming everyone else has a PMI certification and understands you’re talking about threats and opportunities.

Yeah. 

Orion Matthews: Well, okay, so lead in here. I think we promised that we would talk about what a raid log is. Can you maybe break it down at a 1 0 1 level? What is a RAID log? 

Kim Essendrup: A RAID Log Raid is an acronym for Risks, actions, issues and Decisions is commonly how it’s, it is today long ago and in, in its origins.

And in some places still it’s risks, assumptions, issues, dependencies. And [00:17:00] so if you think of your risk register. An action list and an issues log or register and a decision log. Put that all together in one place, and that’s a raid log. And so, but it’s more, it’s much more than the sum of US parts. If we go back to the origins, the deep, dark origins of the raid log, it actually came about in the eighties.

When in the UK there was a big effort to outsource some government functions. And the problem that they had to face was the fact that there would be these long negotiations between this government contractor and a government agency, and they would identify assumptions, dependencies, they would identify risks and inherently it’s in their contract.

But of course, that contract is a hundred pages long, maybe more. So they hand the, they sign off the project and they hand over to the delivery team. So now the delivery team has to go through this a hundred page document and try to [00:18:00] find it. It’s tough because the delivery team has imperfect knowledge of the origins of the project and the negotiations.

So the tool they developed to take all the risks, the assumptions, the dependencies. And to put those together in a way that the delivery team could manage to them and stay in line with the terms and conditions of the contract. That was the RAID log. Since then, it’s evolved to become the run tool. So it’s not your plan, it’s not your schedule, it’s not your budget, it’s not your communication plan, but what it is.

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. So that’s how, that’s how the, the raid log is used for almost like a sub methodology for project delivery. 

Orion Matthews: Okay. And then so of each one of those sort of, when, just to sort of like, the word log, I think could be, is sort [00:19:00] of a de deceptive, right? We’re talking about table in a way, right? Like rows and columns, each one of those acronyms. So your risk log would be your, like a risk, a table in Excel, for example. Not saying you should use Excel to manage your projects.

That might have like the risk name and Id perhaps like a short name. They, uh, use a trigger of what might cause the risk to happen, and then the sort of potentialities of like what you would do, uh, to avoid it. Things like that would go in that like risk log. And then is it connected to the other logs or like how does that, like maybe just help me visualize the, the raid, the.

A bit here. 

Kim Essendrup: So the origins of RAID logs, they, of course they were spreadsheets, like the origin of everything else that we have today. And you know, up until recently, most organizations managed them in raid logs or raid logs in spreadsheets. And that’s actually why we launched our dedicated application was to try and advance [00:20:00] that tech put it into a more robust technical platform.

But yes, so you can think of each one. Let’s talk about the risk register as it’s just a big table of data and you’d have your, what is the risk? You’d have a description area. You got descriptions and some, maybe some tags and categories and things like that. Uh. Then there’s a section of fields where it’s about the qualitative assessment.

What’s the priority, what’s the impact? And this is something where you use to prior you, you prioritize it, you give it, use heuristics to decide, okay, is this big, is this little, not necessarily a whole lot of science behind it. Mostly based on expertise and past experience. That helps you understand which of these you need to really prioritize for a much deeper analysis.

And then, so the next set of, uh, data we have is really if you’re going to be doing some more qua, qualitative, uh, quantitative analysis rather, where we’re gonna start trying to really analyze what is the. Actual [00:21:00] monetary potential impact of this, and why do we think this is the probability? And so as depending on the maturity of your organization, you may only need to use the first part where, okay, what’s, what’s, what could happen?

What’s the probability? And now let’s just figure out a response plan. How are we gonna address that? As the state, as you have a bigger, more mature organization and the bigger project or the stakes get higher and higher and higher, you need the additional rigor of qua quantification. And some other data on there.

So it’s, what’s nice about a raid log is just like I’ve described in the risk register, is that it’s extensible and it can fit the size or complexity of your project. If you’re, if you’ve got a four week technical project or if you’ve got a massive two year massive, uh, construction project, you can still get value out of this and scale it according to your needs.

Orion Matthews: Okay. And then so speaking of like those needs being scalable, is there a ratio for how much projects [00:22:00] typically invest in risk? And I’m sure it varies by industry, like nuclear power probably has a much higher budget. But in general, like for a major construction project, say it’s like $500 million, is it one to 2% of that goes to the risk team and they’re gonna hire a team and spend some money doing risk identification?

Is there any kind of sense of like what that looks like or best practices for organizations? 

Kim Essendrup: Unfortunately, I, I’m not aware of much in the way of statistics like that. In fact, even if you stand back and say, well, show me some statistics on the ROI for investing in risk management. Mm-hmm.

Something as fundamental as that. There is not a whole lot of data out there, which is unfortunate. And of course if you’re viewing this and you say, I knew a study, please share it, we’d love to see it. In my research I found a couple of studies, two different studies in different industries which came up with a very similar R-O-I-R-O-I number.

And what they found was that [00:23:00] the time and effort invested in risk management has an ROI of 20 to one. It’s ridiculous. 

Orion Matthews: Yeah. 

Kim Essendrup: Uh, and so I’m sure that there’s a point at which the benefits start to, uh, level off there, but you know, most organizations do minimal at best, even if that from around a risk management perspective.

And so a little bit of investment really goes a long way. 

Orion Matthews: That’s a, that’s higher than our stats. The data analytics is a 13 to one. But I could see how risk could pay off better because. Just a little bit, you know, just avoiding a few of those really big issues. Could, uh, like you said, one in six projects fail.

I’d be curious how off or go at 200% over budget. I wonder how many organizations fail due to things like. Failed projects that go 200% over budget. So, okay, so this is 1 0 1 again, and, uh, like we’re talking about the team, 

Kim Essendrup: right? 

Orion Matthews: What are the titles that what if this was a career path someone [00:24:00] was considering?

So perhaps a listeners looking at 1 0 1 saying, I like project management. I like risk, I want to get involved in this. Like, what job are they looking for? How do you get involved in this industry? How do you. Build a career around it. Like do you have advice for anyone that might be just starting out looking at this?

Kim Essendrup: Well, you know, if, uh, I guess it depends on where you’re coming from. If you’re coming from a project controller, project management perspective just really moving more and focusing more on risk management. There are kind of risk management type roles within larger organizations, larger pro, larger projects where you can have a little bit more of that focus.

Usually it’s, it’s hard to keep a, a full-time risk manager busy on typical, you know, projects, unless we’re talking about very large engineering or construction projects. Very often you need to have a little bit of maybe some statistics background when you start to really go up. But from a career perspective, you can either move into that sort of the, the quantification area or into [00:25:00] consulting and really get into the science of what is the real potential financial impact and.

Figuring out how do we calculate an appropriate, uh, risk reserve. And you can really go into it there. But if instead of narrowing and going more scientific, you can actually really broaden your focus and go more into the corporate space and focus on corporate governance and risk management, uh, GRC area where we’re looking at governance and regulatory compliance.

And we’re not thinking there on a project level. We’re thinking about the organization where regulatory compliance, things we need to worry about. What, depending on where we are from a a locality perspective, what do we have to worry about? Compliance with local, local government and entities. So you could really take it either one of those directions.

Orion Matthews: So then, like if you were looking at going into school for this and you wanted to take one of those directions, what kind of degrees are we talking about? Like a going into accounting, it sounds like potentially MBAs for that sort of [00:26:00] corporate quant side and then. Construction management maybe if you wanted to get involved in construction.

I’m just curious, like do they have risk degrees that you could just go, 

Kim Essendrup: you know, I, I, so that I’m not so sure that that varies a lot. I think this area is growing a lot. Even project management as a degree program is growing very rapidly. So, I think it depends, but, if we take a step back, I, I think before you go and jump in the school and try to get your master’s degree and, and be an actuary, it’s good to get your hands on it.

Get involved. I’ve got my podcast cohost likes to say that, uh, project managers aren’t made. They’re born. It’s something you really wanna do and just naturally do most of the time. And then. That’s how you know that that’s for you. And I would say to some extent it might be the same. If you’re, if you like to think in these directions, like to do these kinds of things, I would say try it out.

Get in, get more engaged in, uh, risk profiling projects at your organization for your own projects or for, you know, larger projects in your organization [00:27:00] or with the PMO. Just start testing it, getting more and more involved, then that will probably lead you in the right direction. Awesome. 

Orion Matthews: Okay. All right, just one last question, I guess, well, maybe two.

I don’t think any interview is complete in 2024 without asking about AI and perhaps the future of your space as you see it. So do you, do you see maybe the risk field, how it’s gonna potentially unfold over in the next five to 10 years? And if there’s any impacts you’re seeing from ai good or bad for the space maybe you can share a little bit there.

Kim Essendrup: So I think I, we will always need the people with the good judgment. First because people have good judgment, and right now, and probably for a long time, AI won’t have good judgment. And even when it does, our managers and, and those who have responsibility for all the projects that we’re doing, they’re not gonna wanna to put their trust and maybe, you know, put blame or accountability on an ai.

It needs to be a person who’s in charge. And [00:28:00] so. I, there will still be people in this role, but where AI is really interesting, is it knows, I’ll say quote, uh, it knows a lot of things. A lot of diverse things. And what we found, actually, we launched our first AI feature over a year ago, which in AI terms is a century, right?

A year ago we launched our first AI feature, which was an AI based risk identifying engine. So you basically describe, here’s my project and give it, give it a, a description and the AI will recommend to you. Risks that could happen with that. It will give you, here’s what the risk is. Here is what the potential problem is, here’s the potential impact.

Here is an estimated probability. Here is a relative potential impact on the scale of one to a hundred. And here are some possible responses for that. And we came, like I said, we came out with that [00:29:00] and as we were beta testing that. One of my colleagues in, in a sister organization of ours was running a, a very large project to implement a formal project management function to an 80-year-old civil construction company.

So very people oriented project. Not the kind of thing you would think, well, an AI knows about this, right? 

So what I did was, without telling him, is I took his project description and I put it into our AI generator, and it gave me a risk register, and I sent it to him without telling him where I got it from.

And I said, Hey, so we are just kicking around some ideas, and I just wonder how close does this align with your risk register that you and your team have developed? And he said, oh, well this is pretty good. This is about 75% of what we already have. 

Orion Matthews: Wow. 

Kim Essendrup: In one click I had 75% of his risk register. Just absolutely mind blowing.

Orion Matthews: That’s awesome. What a well, I guess that’s a good tip for anyone getting in the space is to also add [00:30:00] AI to your list of tools, right? As they say, like, AI won’t replace your job, but people with AI probably will in the future. Yeah. Perhaps that holds true here. 

Kim Essendrup: I think that the, so our next phase of development, which we’ll have, uh, later this year, is we are gonna make it even smarter in that the AI will know about your past risks and issues and lessons learned and decisions made on your projects.

And what this will allow us to do is with the ability for AI to, you know, quote quotes, again, understand a large amount of data and pull. Sort of, uh, conclusions outta that is, uh, meta analysis. So it will, we have a feature we’ll be launching, which will be chat with your raid log where you can ask, okay.

For my portfolios this past year, what is the primary root cause for impacts to our budget? What are the primary causes of, of schedule delays and with a meta-analysis through the ai, it can comb through [00:31:00] past risks and issues, lessons learned, and they can identify those and pull those forward. And it just really empowers you, makes you smarter, helps you make better decisions, which is really our goal with our whole platform.

Orion Matthews: That’s awesome. Wow. Well, it sounds like you have a lot to say about AI and a lot coming out with ai and you were one of the early birds to ai, so that’s really awesome to hear. I guess we should maybe close this up. I know that you have a question you like to ask people on your podcast, so I’m gonna ask it for you, see what your answer is, which is, what is your favorite tip or trick for using a raid log?

Kim Essendrup: Alright. Well, I’ll say my favorite tip or trick is, uh, wow. You, you stumped me on the question that I asked, I guess. I guess it comes down to this. This is gonna sound ridiculous and obvious, but use it. And that sounds easy, right? Oh, just use it. Just use the blade log. But it’s not because as project leaders, we have [00:32:00] so many things to do.

I’ve got to go and I’ve got to, you know, I’ve got things I’ve gotta update. I’ve got meetings, I’ve gotta plan, I’ve got workshops I have to run and, and notes I have to do afterwards. I’ve got documentation. And what inevitably happens is you, the raid log starts to fall down towards the bottom of your priorities.

Well, 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. Do I What if I, you know, I don’t need to update. Okay. I’m still busy day after that. Still busy. You know, and you can do that the same way. You can go through a yellow light with your eyes closed and you can 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. And I have gone through this cycle myself, where I got, 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. That’s my advice is get get into a habit where you’re always using [00:33:00] it and make sure you’re using it. 

Orion Matthews: Awesome. Well, and as we know Kim, they can use your excellent raid log@raidlog.com. Also, if you’re looking for more of Kim’s amazing, insightful advice and the advice of his co-host, uh, you can always join him on the Project Management Happy Hour.

That’s available at project management happy hour.com, I believe. 

Kim Essendrup: It is there, or iTunes, Spotify, all those places where you get podcasts. 

Orion Matthews: Awesome. Well, I can’t thank you enough for taking the time to join me today to share your wisdom and teach us a little bit about risk. I found this conversation really insightful and I hope that, uh, you enjoyed going back through some of the basics with me today.

Kim Essendrup: I did. Thank you. Yes, the, 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. Uh, I hope this is useful, and thank you so much for having me on today, Ryan. 

Orion Matthews: All right, well, thank you [00:34:00] again, Kim. And please check out Kim’s website@raidlog.com and you can visit my company site at query on Q-U-E-R-Y-O n.com.

Thank you all for watching and have a great day. Sheriff, 

Host: thanks for listening to the Major Project podcast. Be sure to follow us wherever you get your podcasts and learn more at the major project podcast.com. Until next time, keep building big. 

ABOUT THE PODCAST

The Major Project Podcast

Every day, somewhere in the world, a billion-dollar project is underway, reshaping skylines, powering nations, and pushing the limits of what’s possible. But behind every megaproject are the people who plan, measure, and keep it all on track.



Hosted by Orion Matthews, founder of Queryon, The Major Project Podcast dives into the world of Project Controls — the art and science of delivering the biggest projects on earth. From energy and infrastructure to tech and space, we talk to the leaders managing billions in scope, risk, and ambition.



Join us as we uncover the lessons, failures, and innovations that define how major projects actually get built — and how data, risk, and human judgment come together when the stakes couldn’t be higher. 

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