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Galen Low: Hey folks, thanks for tuning in. My name is Galen Low with the Digital Project Manager. We are a community of digital professionals on a mission to help each other get skilled, get confident, and get connected so that we can amplify the value of project management in a digital world. If you want to hear more about that, head on over to thedigitalprojectmanager.com/membership.

Okay, today we're talking about the complexities of communicating effectively with different stakeholder audiences and whether generative AI can be trusted to tailor those project status updates that are going to get sent to that hyperactive executive, that disengaged VP, and your hawk-eyed systems architect — all with your name on it.

Joining me today is Devin Mahoney, a cybersecurity expert as well as the founder and CEO of software startup, QTalo. Devin's got a really interesting background. He started as Employee #10 at Kyrus Tech, where his division of the company helped earn 60% of the company's revenue, and helped make startups like Carbon Black and the Red Canary what they are today. He then went on to guide other ventures like Randori, and is now focused on his own platform, focused on making project communications easier.

Devin, thanks for joining me today!

Devin Mahoney: Galen, I'm so happy to be here. Thanks for having me.

Galen Low: I'm so glad we connected. So we are kind of each other's fans, actually. I know that you have listened to this podcast. I follow your newsletter. It just kind of made sense that we connect and collaborate. I'm really excited to dive in.

Devin Mahoney: Me too.

Galen Low: We've been chatting a little bit and in our last chat, you mentioned that as part of your research for your product, which is focused on project status updates, you've talked to 200 project managers about status reporting and other project communications, but specifically around status reporting.

And I'm like, that's pretty unique because I don't know, it's not always the hot topic of conversation when you're talking with project managers, but it is very interesting and very important. And I was just wondering throughout your conversations with these 200 project managers, what is one of the most salient and forefront pain points around status reporting that people just keep coming back to in all your conversations?

Devin Mahoney: You've got a good point, Galen. There aren't many of us who care about status reporting this deeply, but it was fascinating because everything that we were talking to project managers about started with a status report. They couldn't do budgeting until they'd done status. They couldn't do resourcing until they'd done status.

Obviously, they couldn't talk to their executives until they knew the status of their project. So I've spent a lot of time thinking about status, and there's two major pain points that we hear about over and over again. The first is tool sprawl. Project managers are going through a ton of tools to get the insight they need for these status reports and everything else.

They're looking through Jira, Asana, Notion, but they're also looking through Slack and email. And the second problem here is knowledge is scattered everywhere, especially as teams are remote versed. All this knowledge is in all of these different tools. And these are the huge pain points that we're seeing about creating status.

Galen Low: Honestly, I relate to that so much. There's two stages of status reporting for me. Stage one is exactly that, gathering all these things. It's an exercise, it's like an Easter egg hunt, right? You're like, okay, this week, what tools do I have to dive into to find that conversation where that person said that thing and like where's our budget at and all these other things and like it's like this assembly this like you know this almost creative pastiche thing that happens. And it's a lift like it is it's like it's enduring and then you have this like stage two where it's like this moment of being very honest with yourself, right?

Where you're like, project's going pretty well. And then you gather all this information together and you're like, Okay, now I need to like, communicate this out to people who are gonna scrutinize it, to people who maybe aren't even that close to the project and are gonna grill me about it, to people who, are kind of sick of receiving status updates every week, and maybe don't read them.

But you kind of have to like, be like, Okay, is this actually like a clear picture? I've gathered all of these things from all over, all these tools, my tool sprawl, which everyone is, a bit susceptible to. And now, is it accurate? Is it right? Am I telling the right story? And when that story lands, how are people going to feel about it?

So, I relate to that. I think that's in some ways, unsurprising, right? That tool sprawl. And just having to go everywhere to figure out what's going on with your project, you actually become like the translator of what's actually happening in the project. But, it's not always because you actually know, sometimes you're just like stitching it all together and then figuring it out in that moment as you're sending it out.

Devin Mahoney: Galen, I just love your analogy to the stages of grief here with the end being acceptance.

Galen Low: This is where the project is at. It is indeed over budget. I mean, it is kind of a painful exercise overall, like status reporting. I think, you know, in the circles I travel in, I guess we do talk about status reporting and status updates and stakeholder communication or just nerds that way.

But I don't think I've ever met someone who's I love doing this. This is my favorite part about project management, putting together all the information from all the tools and telling the story to a bunch of people who are going to probably really grill me about it or really, might respond negatively to it.

Anyways, a whole world of work that happens beyond delivering that status report. But, I think you come from an interesting perspective because you're building this platform about project communications. And if I was just kind of like back up here in 2024, we're living in this world where we've got generative AI advancing like really swiftly, and here we are recording a podcast about project status updates.

And I guess maybe the question is, do we even need to worry about getting better at status reporting? Like, how far are we away from just status reporting being like an automated thing? Or do you think it's always going to be like a human intervention required kind of activity?

Devin Mahoney: Yeah. Well, Galen, I really appreciate the question because this is just such an exciting time with where generative AI is.

And you're right, like this stuff is coming. And so let's get ready for us because generative AI is giving us this huge opportunity to radically simplify the problem of status reporting to automate this thing. We are at the cross of having to automate all of this drudgery that we've been doing for years.

I mean, there's a couple of people who really liked it that I was talking to, but like it is drudgery. All right, so it's coming for status reports. But what does that mean for us, the project managers? We can level up, we can start asking the questions that our stakeholders really care about around our data.

And now we're presenting better status updates that are more informative. We do need to be cautious though. I mean, this generative AI, it does hallucinate. Yeah, maybe somebody is going to fix that, but like right now, human needs to be there. And so I think AI is getting really close to being able to automate this, but at least for the foreseeable future, the human needs to be in here to make sure you get the report that you need, but more importantly, the project manager needs to know what good looks like. It's not just creating the thing, it's knowing that when it is created, it's the right thing, and they can push it forward.

Galen Low: I like that. And I like this sort of even the word hallucination, I know we're using it a lot with generative AI, but I guess I could equally say it's always been applicable in that project status report sort of process, right? Like we've got PMs hallucinating a bit, right? Yeah, everything's on time. Nothing's wrong. Oh yeah, except this issue. Oh yeah, this risk is actually being realized. Oh, wait a minute.

I've seen some status reports from project managers that I've worked with that are a little bit of maybe deliberate hallucinations. The, everything's fine. Don't worry. Even if it's not.

Devin Mahoney: Maybe some self delusion in there?

Galen Low: Yeah, right? It's a very personal thing, right? It's here's my report card from myself to my stakeholders. And, it's this sort of moment of reflection and sometimes self reflection. But I do like that notion that, yeah, what does good look like?

And, what do people need to hear? I love the idea that, maybe we don't need to, trawl through all of our tools to gather this information and can use that time to do something a little bit more strategic. But there is that sort of notion of really just like sitting down and like living with the data a little bit, right?

And like kind of understanding what the story is for you, what the story is for, all your different stakeholder groups and sort of how you can communicate that effectively. And is it accurate? Because I think that's the other thing that can go unbelievably sideways, especially if you are working on a project where you might be subject to audit later on or, all other levels of oversight. But yes, I love that. I think it is an exciting time. I like that you're combining generative AI with status reporting, and we'll get into that.

But first, I just wanted to kind of like dive into the meat of what I think we wanted to talk about today. So at time of recording, the working title for this episode is 50 Shades of Red, Amber, and Green, which is our tongue in cheek way of saying that project status reports can mean a lot of things to a lot of different people depending on where they sit within your project.

And one of the things that your company is doing, QTalo, is helping project managers understand how to send the right message to the right audience. And I was wondering, can you give some examples of different kinds of stakeholders and why a project manager might package the same message in a different way to make their communication a bit more effective?

Devin Mahoney: Yeah, I sure can. And I appreciate the question, because project managers actually spend a lot of time doing this. After you've got the data together, you need to figure out how you're going to communicate. They create a lot of similar reports, but they're for different audiences. And so the reason here is that your audience is your stakeholder and whether they're going to read it depends on like how you present that.

And so you're looking for them to take an action or to receive information from the status update. And so your report had better give them the information they need. It had better lead them to the action that they need to take if you're going to be a successful project manager. So let me give you a couple of examples here.

So a daily stand up report, it's going to look a lot different than a report out to your boss. And that's going to look a lot different than a report that's going to your steering committee that is really at the very high level. So at a steering committee level, you're really about sharing what the problem is, and then recommending an action.

A developer, they need to know what tasks they need to accomplish for the week, but why it's important. And then your boss, you're more focused maybe on staffing and giving them the context for the project that helps them guide the resourcing that you're asking for in order to accomplish this.

And the language and context for each of these reports is very different.

Galen Low: I really like the angle of action because even when I was hearing it back, I'm like, Ooh, do I actually do that? In some ways, even just in the past, like 10 minutes, I've been framing it up as, yeah, you're telling the story about your project, but you're right.

It's it's not for the sake of telling a story. It's because you want someone to do something with this information. And for all of those like status updates where, folks are like, I don't even read your status updates. I mean, you want to argue that they're not shaped in a way that makes it obvious that they have something to do with this information as well.

They might need to go out and take some action or make a decision. It's not just, a chapter from that series that gets published in the newspaper week on week. Am I dating myself? I might be dating myself. It's not just, optional reading, but it's actually something that is part of the work.

It's like actually part of the collaboration process. And yeah, then when you look at it through that lens, then it's really clear, right? It's okay, well, definitely we need to be shaping this in a way that is clear of what to do. Because, if it wasn't a status update, it was just an email being like, Hey, can you make sure we're doing this thing?

Devin Mahoney: It doesn't go anywhere.

Galen Low: Yeah, we'd be focusing a little differently.

Devin Mahoney: Project managers are leaders. We are leaders. And this is how we provide our leadership is through the status reports and giving people the right action with the right information.

Galen Low: Love that. Preach.

I guess the other thing I could say is that there might be some folks listening who are like, I don't do that. My status report is my status report. Like why are you wasting all this time tailoring for all these different folks? Isn't that kind of the opposite of being strategic in the sense that, you're spending all this time reshaping the same data into different words for different people. They're like, I'll just send out one status update. That's all I do. But clearly like tailoring is sort of the thing that underpins your mantra, in a way, especially with QTalo.

I'm just wondering what are some examples of some of the chaos that tailoring your communications can help avoid?

Devin Mahoney: Yeah, now that's a good question too. When you're thinking about the messaging, if you send out the same message to everyone, like the example as I shared, the raw status, it's very similar.

But each of these reports really does have different goals and different communications needed in order to accomplish those goals. And so, let's take the C-suite. We want them to be involved as little as possible. They should know that things are going the way that we're expecting it to go. And if we exposed every little bug and potential problem to that high a level, they wouldn't know what to focus on, and we would lose trust in them.

We're using our judgment as project managers to give them the insight on what to focus on. Now, if we're talking about, let's say a set of problems that can be solved with resourcing, and we're trying to convince our boss to add a new person to the team. Well, we're going to present a certain set of risks that are risks to this project, and that's something that our boss needs to see. But the steering committee doesn't need to see that, the developers don't need to see that. We are avoiding a lot of chaos that gets around mixed messaging by directing the message to the goal that we want to accomplish.

Galen Low: It makes sense to me, especially in the sense of what you said, right? It's what is our goal? If our goal is to like kind of keep this person like from fixating on, unimportant details or, getting too involved because it starts like breaking their trust, then, we can message differently. In some ways I'm like, yeah, that sounds strategic, but to another person that might sound sneaky.

What is your take on like the sort of ethics of being very selective about, oh, what details are communicating to whom?

Devin Mahoney: Yeah, well first of all, don't lie about it. Like, when you're telling the C-suite that everything's okay, I mean, everything has to be okay. But be upfront, communicate early and often when things are shifting into that shade of amber so that the whole company can get on top of that and get behind you and the solution that you proposed.

Otherwise, you just lose all this credibility. So, a lot of this messaging is actually to maintain credibility, to know that when you as a project manager say something, that you mean it. And those limited number of words that you're using to describe what's going on are actually the most important things that they need to read.

Galen Low: I like that. Yeah, it's like you're almost the filter for them, not to hide anything, but to make sure that it's something digestible and readable and relevant to them, yeah, but not lying about it.

I wonder if we could dive into the tool that you're developing at QTalo. And, I've teased at the beginning about, generative AI do we need to care about the actual activity of putting together a status report? Will we have that robot soon? And if not, why?

But I wondered if you could just tell us a little bit about the workflow of the tool and maybe just like how you've categorized different types of project communications and different groups of stakeholders and like how a project manager would go in and like tune that up just like, I don't know, just walk us through the flow.

Devin Mahoney: Sure. So first of all, the cool thing about QTalo is it's read only. Our tool is not another tool that you have to go and update. It is taking every piece of data about your projects. It's taking it from all of your PM tools. It's taking it from all of your communication tools.

You don't need to have your inbox organized to make sense of this. It really knows what a project is and what communication is involved in that project. And it gives you back the information that you could have found anyway, but it's much, much faster at that. So as it's bringing all this data together about a project, it's giving you this full picture of everything that's happened recently on that project.

And since it anticipates what your project communication needs are, like you've got a weekly report, or you've got this ad hoc stand up that you need to do. It's generating these status reports that you need, before you need them so that you can engage your stakeholders most effectively. And, it also allows you, in the workflow, to customize these updates for the stakeholder.

And, I just want to say again this really isn't another tool that you need to update by hand. You can take it, you can use it, you can do a quick update, and then you can leave it alone until you need another update.

Galen Low: I like that. It's like the stitcher. It's not trying to replace any technology.

It's funny because tool sprawl is kind of that thing where I don't know, it comes up a lot in our community and in our content about, how many tools are you using? And then everyone's oh man, like a dozen. We're like, wow, a dozen. And at the same time, then we look at ourselves and we're like, yeah, we use a dozen too.

I don't know if there's any team out there, executing a project that isn't using, a dozen different tools or more. You see some software companies trying to move in the direction of yeah, we're here to replace all of that sprawl, but the uphill battle that I think they're up against is we like these tools yes, we have to go all over the place to grab information from different tools, but the reason why we have all the tools is because we like each of them.

So, what I like about it is that it's gonna go in, it's gonna, as you say, read only, it's gonna pull it in from the tools that you're using, and it's going to make a suggestion, I guess, on here's how your project is going?

Devin Mahoney: Yeah, it's gonna give you the update, and we'll help you customize that so that it's the right update for your steering committee, or it's the right update so you, you show all the risks about your project to your boss so you can actually have a productive conversation about that.

Galen Low: And is there a nosy executive, like setting template?

Devin Mahoney: Oh, hope you don't have one of those nosy executives, cause honestly they have better things to do. But this is about credibility, right? We're trying to give project managers the ability to demonstrate credibility. This is what's going on with the project. This is exactly what you need to know. If you need more detail, we'll give it to you. But stick at the high level because the project is going exactly as we expected. Or, it's not, and here's the deviation.

Galen Low: It's really interesting.

One of the things I'm thinking about right now is I come from an agency background, so it would be not uncommon for us to have an internal status report and an external status report. And nothing too fishy, but just, as you say, it's like, there's only so much we need to disclose to external parties versus internal.

It's going to be a different message. But to the point where we actually had internal Jira, and internal Jira was where we could just cut loose. It was cuss words. It was, we weren't trash talking anybody, but it was definitely the not safe for client chat versus, formal project communications.

And I'm just in my head, I'm thinking, I'm like, Oh, what if QTalo goes in and pulls all these conversations, the four days worth of us going back and forth on this, like API integration and how much it sucks. And why is this requirement a thing? And then, how much control do you have, I guess, as a project manager, to pull in all this stuff, even if it's all accurate, no hallucinations, but to the point where it's so accurate that it's actually all the dirty laundry, like, how does that come to bear in your tool, and how are you approaching that?

Devin Mahoney: So, first of all, there was a study, I think it was just maybe two months old of open-source software, how often curse words are used in the software, and the code quality. And there's a positive correlation here.

Galen Low: I love that.

Devin Mahoney: I'm just saying this is like kind of a good thing that you're letting loose. You're being honest with yourselves. Look, QTalo is your view. Executives don't have a view into what you can see. You are fundamentally presenting, you're using your judgment to say, this is what's going on. I will abbreviate the status. I will make it like just so it's the actionable ones so that they get to see it.

Or maybe you want to expose, a couple of the inside jokes as a way to show the team camaraderie that is going on. I mean, executives kind of need to let loose a little bit too. But it's all so customizable, just as it is in real life. Just as it is, like, when you as a project manager without this tool get to present or not present. Because you're using your discretion and you're using your leadership to decide what goes in.

Galen Low: Where my head goes is okay, well, there's so many things that can happen on a project and so many different types of communication that happened on a project. How are you training your software to kind of deal with all these scenarios?

But I guess even actually, maybe this is two questions is like, how are you training it? And where are there lines around like the privacy of it all? And sort of the integrity of all of it. And people are, speaking freely right now in certain tools. And, our software is learning from that, but at what point is it kind of, will people become like a bit like self conscious about the fact that, yeah, there's this kind of tool going in and learning from everything we're saying and all these tools, and could it like potentially stifle some of the conversation?

Okay. That was three questions, but...

Devin Mahoney: Well, let me tackle the kind of privacy question first, because I think that's a big deal. When you're using QTalo, we're giving you a view into what you as an employee can see. You can't see what your boss can see. You can't see what your employees can see. So if somebody's playing a surprise birthday party for you, it's not gonna come up until you're surprised. So that stuff is not available to you unless it's something that you can literally see. We're relying on the tool to restrict access that way. You know, so does this stifle your willingness to talk freely?

I mean, Slack sure doesn't, even though everything is recorded. Email sure doesn't. So I don't think this is going to do it. I don't think this is going to be the nail in that coffin. You asked another question about, how do we train our software to deal with different stakeholder scenarios? So we have a lot of different personas that just come right baked in.

We've got the executive, we've got the steering committee, we've got your development team, we've got other, counting and other overhead teams that are already baked into the software that are messages. And so we built the software already to handle, the variety of personas that we're just anticipating that you might have.

But you actually get to take those generalized profiles and you feed examples of your own writing to that stakeholder. And then we can modify the summary so it's more tailored to what you've written before. And then further, you can even update that messaging. So if we didn't say it quite right, you'd be like, okay, hey, try again.

You need to be a little bit more formal. Or, Okay, you lighten up a little bit. That's too long. Make it a little shorter. So, with that, we're able to kind of create these personas for you, where you are writing to a stakeholder, and produce the content that makes sense for that stakeholder.

Galen Low: I love that. And actually, it's one of the things that, I mean, we're recording this, obviously, at a certain point in time, so this might not age well. But I think right now the way we're using ChatGPT, for example, one of the things I see that's underutilized is exactly that. It's it'll let me help you be more like me, let me train you, try and use this tone of voice, and say less, say more I think that whole tweaking is a bit emergent, at least with the, in the circles I travel in, the people I talk to. They're they're using it like Google, ask a question, get an answer, okay, thank you, instead of actually taking the time to train it.

And maybe sometimes because they're a bit resistant to the idea that, this machine, this LLM can, accurately mimic how they would write an email to this particular client. And, in some ways there's this fear almost, right? Or at least like this hesitancy to be like, yeah, I'm going to invest the time to train this software to be more like me.

Because then I can say to myself, well, software in a matter of a few days, learned to be me, what does that say about me and my humanity? I think there's there's a sort of resistance to it, but I like that idea that, yeah, this is of course, something that's here to help you. It's not making decisions for you necessarily.

It's here to help and it can be more like you, at least in the communication to the stakeholder to make your job easier here to help, I guess.

Devin Mahoney: And I think kind what you're getting at is kind of interesting is okay, if AI is producing this stuff, and our job is to review these updates what are we doing here?

What's our purpose in life? I want to go back to maybe one of your earlier questions, because well, first of all, AI is coming, and it's going to be here. It's here, whether you, we like it or not. And so we might as well embrace it because it's going to make things better for us in a lot of different ways.

More specifically, it's going to enable us to level up the type of communication we can have with our stakeholders. We're here to establish trust and establish communication. We can take the AI, we can take its summary, we can go validate and verify what it's saying. And now that it's doing it, we can anticipate the needs of our different stakeholders and we can ask these more insightful questions and we can help drive the company forward and really get back to the point where we're leading the company from the middle from our own position.

So a couple examples here. So you can now ask, I've got a problem with my team. Who else in this company has tackled a similar problem? And you might find an answer from a year ago at a totally different team. And now you can bring this resource in to say, Hey, we've got something similar going on. Help us tackle this.

A project manager. You can go in and say, Hey, what did we expect how this product was going to go? And how did that diverge? And what is the outcome of this? We're asking like really insightful questions and not relying on our memory of what might've happened, but we're relying on what our actual state of mind was then and start measuring ourselves.

And so, there's like a whole world of communications and additional skills that we can get to you here because AI is doing the basics.

Galen Low: What I love the most about kind of your approach is that it is communication oriented and I'm thinking about things like, two years ago, we're having conversations around like data driven estimation, right?

And it's okay, well, if you've got good data from your projects about did it land on time? Was it on budget? What was the scope? And can we compare apples to apples for this other project that we're scoping and estimating? And the answer was always, well, you have to have really good data, right?

In the sense that I worked with a lot of companies where they were struggling to figure out that exact, like sort of taxonomy and record keeping so that they could look along that column in a spreadsheet and go, this scored an eight, this scored a nine, this scored an eleven, whatever, right? And be able to compare this data based on, like quantitative style data.

Whereas, what you just said is kind of more it's this qualitative data that, to your point, gets recorded anyways mostly in the tools that we're using. And instead of necessarily having to, have a team go through and trawl through all of this and then give every conversation from every project a score so that we can kind of figure out, how to package this data and have some historicals, it's just a search through, doing some probably, natural language processing and figuring out kind of like certain sentiments around certain keywords.

And you can like, look at that and be like, Oh yeah, like I see the conversation of where this happened. Not, I see that it scored an eight, but I can actually see the conversation. And to your point, maybe it's not all personally identifiable, but what's interesting is that it kind of skipped that step of getting your data house in order, and like that huge lift that organizations need to go through in order to take advantage of some of this stuff. But actually all the conversations are happening anyways.

So that's all there. I think that's really interesting. It's really interesting.

Devin Mahoney: It's fertile ground for a lot of insight, so I'm just really excited about where we're going with this.

Galen Low: You mentioned something that I thought was really interesting. Just this kind of, the world of, what are we going to do with our time if we've got software that's kind of putting together a status report for us?

I don't want to kind of get into that, but I guess in the interim, the one thing I'm thinking is we're describing a world where instead of going through all your tools and your tool sprawl world and gathering this information, we're going to have a tool that does that for you, but also then you kind of need to train it.

And at the end of the day, you still kind of have to look at it and tweak it to make it right. And I think some folks, I know maybe even not at their core in their heart, this is not necessarily what they believe, but functionally they're like, I ain't got time for that. Tell me when the robot is done so I don't have to think about this at all.

I'm not going to train this software to be me and spend the exact same amount of time like putting together a status report, call me when I can spend zero hours on this. What would you say the biggest benefit is of having a tool like QTalo kind of go through and, put together a status report versus, the time that's going to be spent still reviewing it, still training it a little bit, like what's the upside?

Devin Mahoney: Well, I guess just to set a, a different stage here, you and I, we've been in project management a while we've mentored people. You take a new college grad, take somebody who's, you just got a couple of years of project management, they're going to do the wrong thing. They're not going to look in every different place, they're not going to know the tone to take with their boss, with a developer, if God forbid with a executive, you got to tutor them a little bit so that they can learn, grow and be better project managers for themselves.

And so I think that we as project managers, we're like, we've got a really good community and you demonstrated that Galen. I've been very impressed. Yeah, it's cool. Like we want to upskill each other. And so I think there is this desire to not just keep our heads down and just do our job, but to look for ways that we can do more. So I guess just to, I know I didn't quite cover your question here, but I think what I'm trying to get at is there's a desire to do this, and then also the effort is really low.

Because the effort and putting a communication together, you were going to send that email anyway. You were going to write that PowerPoint anyway. All we're doing is exposing what you've written to AI, and so AI can copy it and do a little bit better next time.

Galen Low: I like that you flipped that on me, and I was like, Hey, isn't it a waste of time training this machine?

And you're like, Actually, the machine is training you. One thing that I can connect it to, it blew my mind because I was like, when the pandemic hit, and everyone was in lockdown, and we were all working remote, there were a lot of conversations about like what's missing. And I know that there's still organizations wrangling with their return to office and trying to convince people to, do that 45 minute commute, 2 hour commute, each way to go and work.

And it's it's a hard sell. But one of the things that I was chatting with one of my colleagues about was this notion of I don't know, just being able to kind of like witness the job being done at different levels. So like at a previous organization, I was lucky enough to sit next to like the managing director and like some very high up people running the organization and people would come by their desk, like other MDs come to their desk or like those, know, those big, you know, very influential people from the organization would come by and you hear the conversation, like eavesdropping per se. But you kind of see how that is getting conducted and how they're navigating those conversations, and for me, I was like, I'm not at that level yet.

So I'm just going to watch. And then that kind of goes away in a lot of like work and remote and like hybrid work environments, you can't necessarily bank on being able to kind of absorb information just through osmosis, just by watching it happen. But what I like is this notion that Oh, actually we have captured like many of these conversations and we've kind of done the sorting for you and here's how you might want to consider writing, an executive status update for this particular individual based on some other, updates that have been sent to them or other executive sort of status reports and that language.

I like that idea that it's not like a robot trainer. It's it's not just bringing together the data about your project, it's bringing together some of the conversations that are happening so that you can understand and kind of, only one step removed from just like overhearing some of these conversations live.

And honestly, I'd like, it didn't occur to me that, yeah what a huge benefit to be able to kind of capture that information in a world where you might never be, face to face with some of the people who have walked this path and sent a report to this executive or, I really like that. That's very interesting.

Devin Mahoney: I love this idea. It's cool. And we could be at the point where maybe I'm a new PM, I'm coming in and I can say, well, I'm going to try writing this email, but like, how would Galen do this? And you've exposed some of, enough of your writing that I can understand and see what you would have done in the same situation.

I would love to get to that point where we're giving people the opportunity to learn from people who've been there before.

Galen Low: I think it's really cool, like this like sort of exposing to mentor, right? And we'd probably do that, maybe some people are doing that right now selectively. Yes, would I want everyone to be able to look at my, sent items?

Probably not. But are there a few where I'm like, Hey, here's, I forwarded it to someone else on my team or, someone who has a direct report and be like, yeah, this is how I would communicate with this person. Here's an example. Whereas it instead of having to kind of, go through that manual process, maybe it's a little bit more fluid.

Maybe it's kind of built into the workflows. Maybe it's part of the software experience. I think that's actually really neat.

Devin Mahoney: Give me tilburton too, before we put that in.

Galen Low: There you go. As I add a hundred items to the backlog here? I mean, maybe in that same vein, right? I think to answer the mail on what I think will be the title of this podcast, but this, like the varying shades of status reporting, sometimes we're using these things strategically and, you mentioned it up top.

I've alluded to it as well that yeah, part of the strategic nature of the communication is that you might raise a red flag as like a, shots fired across the bow. This is urgent. Like maybe it's because it's that stakeholder who never reads your status reports and like never does a thing.

And maybe it's not maybe the software is not going to be like, Oh yeah, your status is it's definitely red here. But you're like, actually make it red, please. Because I want to like, get somebody's attention. I guess even like with what we were just saying that actually might just come across in the software because someone has done it before, right?

You'd be like, well, actually you could make this sort of like red status, send up a flag, but it gets into this gray area, right? Where we kind of, maybe we have this expectation of our AI tools of being like, so pure is not necessarily the word, but it has this like innocence to it.

It's okay, yeah, you're like reading all this stuff that, you're learning from all this stuff that we have out there. And, yeah, we kind of expect this very, sort of, middle of the road, professional, ethical response from them. But is there a world where the tool's hey, listen, you might actually consider changing this to a red status, because this person never reads your status updates.

Is that the role of a tool or is that still you in judgment?

Devin Mahoney: Yeah, oh man, you're going in so many directions. Galen, I'm going to ask you to hold two things in your mind here. One is that there's lots of views of the world where on the scale of, red, amber, green, there really are these 50 shades and people can be equally right about, where it is, even if they have different opinions.

And the other thing is that there is a ground truth and AI can really help you give a basis for what is really going on with the project. So this is really up to you as a project manager to decide, like, where do you want to set that shade of red, amber, and green? You are using your skills and experiences to decide that.

AI is providing this base layer and giving you the knowledge to make the decisions, but it's not going to make the decisions for you. And if you need to set it to red to get somebody's attention, well, I guess go ahead, but you're kind of masking a communications problem here. And like, if you could introspect a little bit deeper and actually you would have time to introspect a little bit deeper if you didn't have to spend all your time gathering data, you can really have an honest conversation with this person about Hey, I'm seeing a risk. In the past I've had to set this as red in order to get your attention, but let's talk about this risk.

And let's talk about like, How do we mitigate this so that it doesn't go to red? So that we're not pulling the fire alarm today.

Galen Low: I really like that. Actually, I'm reminded of a time where I did, like setting your email to like urgent, right?

It has a two exclamation marks in Outlook or whatever. I was having a communication issue with someone very senior in the organization. So I sent this link and it was like a reply all. And I went to 20 people with like urgent status. And yeah, boy, did I ever get that? I should have probably just solve the communication problem rather than, like to fire a shot across the bow like that probably wasn't the right move there, so.

Devin Mahoney: You learned something.

Galen Low: Yeah. Yeah. There you go. I did. I did. Indeed. I think that's fair. And I love that the judgment is still there with the project manager, but just to entertain an idea because, we did sort of raise this thought earlier of Won't there be a status update robot soon, and we don't have to touch it at all?

In your mind, is that going too far? Does it create some risks around communication, or is that the goal?

Devin Mahoney: Yeah, okay. So, just yesterday, I was chatting with another project manager, because I've done 200 of these interviews, and she was 201. But she was looking back at her history of project management, and every bug that had ever come into her code base from her engineers came down to a miscommunication, every bug.

It was an interface problem that no one talked about. It was a, an expectation setting here that wasn't set over there. It all came down to communication. I've been doing software development for a while. There's always been bugs. There's always been breaks in communication. They will always result in misunderstandings.

I don't think that we're going to get around that. But here's where AI comes in. AI comes in because these status reports give us a common picture of what's going on in our project. And it gives us the space to allow us to have this better communication. We've got to be realistic here. We can't be perfect. But when we're looking at the job of our project manager, their role is to lead, their role is to keep the communication smooth so the project can succeed. And I always see a need for that.

Galen Low: I like that. It's a good perspective. Nice. Listen, before we wrap, I'm just wondering, is there anything else that you maybe just want to share with our audience? Just on this topic of status updates, communications, misunderstandings, bugs, and the way projects go?

Devin Mahoney: Sure. I've talked to a lot of managers. I've talked to a lot of people who are not project managers. And the one thing I want to express to all of them is project managers work here to help people and teams succeed.

But who is here to help the helpers? Project managers, we get overlooked when things go right. And so we're not always given the tools that we need to work more effectively. But I'm personally excited about how AI can help us create these tools and help to solve this problem. And an investment and effective tool for a project manager, it pays dividends through all of the teams that they help to support.

Galen Low: That, I really love. Because, honestly, I very much believe in that idea that, a lot of our successes as project managers are actually quite invisible. And, as a result, we don't always get support. We always have these conversations in the community as well about firefighter, rescuer project manager who kind of goes in and like fixes all the problems and they get praised for it.

But the project manager who just runs all their projects so cleanly and then they're being very proactive and nothing's getting escalated. Like they're not even on the radar. So I do like this notion of yeah, I mean, helping project managers tell the story of the value that they're delivering through communication and that there's like more to it than just like typing a few words into an email and sending it to your stakeholders.

And yeah, I like the idea that, of us having more space to do more, because I think we do get bogged down in some of the admin and some of these tasks that we become known for, even though it's not necessarily like the superhero skill that makes us awesome. Great point.

On the roadmap, can you add just like a PR agent bot? Can you tell me, just like tell us the story of like how awesome you are and like sends it on the company's Slack channel?

Devin Mahoney: We all need that.

Galen Low: I love that. Devin, thanks so much for hanging out with me today. This has been a lot of fun. I love what you're doing and I'm so glad to have you on the show.

Devin Mahoney: Galen, thanks for having me. This has been so much fun to talk about this.

Galen Low: Alright folks, there you have it. As always, if you'd like to join the conversation with over a thousand like-minded project management champions, come join our collective. Head on over to thedigitalprojectmanager.com/membership to learn more. And if you like what you heard today, please subscribe and stay in touch on thedigitalprojectmanager.com.

Until next time, thanks for listening.