Has hybrid project management become the new sweet spot? As organizations balance structure, speed, and emerging technology, hybrid methodologies are rapidly becoming the go-to approach. Olivia Montgomery joins us to talk about why hybrid project management is rising so quickly, what “hybrid” really means in practice, and how AI is accelerating this shift. Project management isn’t “one size fits all” anymore, and today’s teams are proving it.
Table of Contents
00:00 … Intro
02:15 … Hybrid Project Management
04:35 … Project Management Software Trends Survey
06:09 … The Rise of Hybrid
08:20 … Blending of Waterfall and Agile
12:12 … Hybrid Growing Pains
15:44 … Source of Truth and Software Tools
18:47 … Pick One System
21:54 … Ensuring Tool Integration
25:26 … Scheduling Integration Testing
27:43 … A Word from Jess
28:27 … Team Culture and Collaboration
30:23 … Leadership Traits of Successful PMs
34:15 … AI Benefits in Hybrid Settings
39:50 … Is Hybrid the New Normal?
42:15 … Get in Touch
44:36 … Closing
Intro
OLIVIA MONTGOMERY: People are pretty willing to try out something as long as they know why they’re doing it, that there’s an incentive for them to do it, that they’re clear on the expectations, and they feel confident that they can meet those expectations.
WENDY GROUNDS: Welcome to Manage This, the podcast by project managers for project managers, and anyone else out there trying to keep their projects on track. We are so thrilled to have you joining us today.
I’m Wendy Grounds. In the studio with me is Bill Yates, who is the expert in all things project management. If you’re enjoying the show, we would love to hear from you, whether it’s on our website Velociteach.com, Velociteach’s social media, or your favorite podcast app. Your feedback helps us keep inspiring and supporting project managers like you.
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Project management isn’t “one size fits all” anymore. As teams juggle structure, speed, and emerging tech, hybrid methodologies are quickly becoming the new normal. In this episode today, Capterra’s Olivia Montgomery joins us to explore how hybrid project management and AI are reshaping the way we plan, collaborate, and deliver results.
Olivia is an associate principal analyst at Capterra and a leading voice in the project management software world. Since 2018 she’s helped organizations make smarter technology choices through data-driven research and real-world experience. She has led IT PMOs, guided ERP rollouts, and now studies how hybrid methodologies and AI are reshaping the project landscape. Her insights have appeared in Bloomberg, Forbes, and Tech Republic. And she actually spoke at last year’s PMI Global Summit in Los Angeles.
Hi, Olivia. Welcome to Manage This. Thank you so much for joining us today.
OLIVIA MONTGOMERY: Hi. Thank you so much for having me. I’m really excited to be here today.
Hybrid Project Management
WENDY GROUNDS: We are looking forward to this conversation. We have a lot of questions. We may not get to them all, but we’re going to give it a bash. We’re going to see how far we get. I think perhaps there are some in our audience who don’t know the word “hybrid” when we’re talking about project management. So, could you explain just briefly what hybrid methodology means in a typical project setting?
OLIVIA MONTGOMERY: Yeah, absolutely. So, hybrid blends elements of your more traditional waterfall type of methodology, and agile, and it can also be a blend of something totally custom and in-house that the business itself has kind of come up with. So generally, you’re going to be taking the pieces of all the methodologies that are out there and blending them together that works best for your company, your culture, your maturity level, the type of projects that you’re running, how much compliance you need, regulations you’re under, how fast and quick you want to be moving. It helps you kind of, like I said, pick and choose what you want to use.
You can also offer hybrid tracks for different types of projects. So, you might have very high-visibility, high-risk projects that run along a more traditional, predictable waterfall path; but then you also have project tracks that move a little quicker. Maybe they’re a little lighter in their overview, lower in budget, lower in risk, and so they can move a little faster. Then that gives you flexibility, especially if you have like a project management office that kind of oversees and manages everything. That way they can be providing as many resources and options to make the project manager and the project as successful as possible.
An example you might think of is, I like the analogy of cooking, projects as cooking. So, if you’re doing hybrid cooking, you have a recipe, and that’s going to be your waterfall, more traditional outline. Like you know what you’re going to make, you know your general ingredients, you know about how long it’s going to take and what the cost is. But along the way you’re going to be doing your taste test. So, you’re blending your sauces and cooking everything up, and you’re like, oh, I need to tweak the recipe a little. Oh, I need to make this change.
So again, it’s kind of like, yeah, you have a recipe that you have, and you follow and you get agreement from everybody, and everybody knows what they’re working on. But you taste test along the way and make sure that you can get feedback and iterate and make changes as needed.
Project Management Software Trends Survey
WENDY GROUNDS: Now, you work with Capterra, and they did a project management software trends survey. When was the survey? Was it last year, or this year?
OLIVIA MONTGOMERY: It was earlier this year. So, yeah, part of my role as an analyst, I actually designed the survey. We have a research lab team. We are a subsidiary of Gartner, and so we have the Gartner research as our backbone. So, we work with a research lab team, and I designed the survey. I wrote a lot of the survey questions. I helped oversee the cleaning of the data, analyzing all of that. And then I take all of that information. I write and publish an annual report based off of that.
And then I’ll also do offshoots, kind of deeper dives into some aspects, of which this is one. So, the rise in hybrid methodology is a trend that we’re seeing grow that’s kind of unexpected. You know, agile was definitely like the darling for project management for a good while there. And we always have known like waterfall is usually appreciated by executives and steering committees for the predictability. But we know that project teams have always kind of needed to change and pivot and alter course, oftentimes multiple times during a project.
And so, seeing this rise of hybrid, we’re actually seeing it like double in use for survey respondents in the past couple of years. So, every year I run this survey, kind of what we focus on and what we ask can change and shift; but I do always ask about methodologies. Yeah, pretty excited to see that hybrid, like, really taking off. It’s working for businesses.
The Rise of Hybrid
WENDY GROUNDS: Yeah. So, from the survey, the numbers we saw here was 41% of organizations now use hybrid approaches, up from 21% in 2021. So that is interesting.
OLIVIA MONTGOMERY: Yeah.
BILL YATES: And when you think about that, it’s super helpful to be talking to you since you have great insider information about the way the survey questions were asked and the responses and how you categorize it. So that’s exciting for me to be speaking with you on that. What were some of the reasons for that shift, do you think? That doubling is pretty significant. Is it flexibility? Is it complexity of projects? What were some of the main traits that kind of jumped out as the reasons?
OLIVIA MONTGOMERY: Yeah, for sure. So, I think it’s a couple of different things. First off, we saw tech companies like your big FAANG tech companies, they started developing their own in-house terms and processes in kind of everything that they do. Apple and Facebook, for example, they don’t even call their project managers “project managers.” They’ve come up with new terms and terminology, and they do in-house training of their own methodologies. And they were one of the first industries that we’ve seen do that.
And I think that that has kind of bled into other businesses. A mix of executives, you know, might leave the tech companies and take what they’ve learned and what works into maybe they go into construction, or they go into real estate, wherever, you know, they shift around to. They bring those methodologies and, like, what’s working with them.
And we’re also seeing more and more companies just rely on technology. And IT teams are being more, not just your help desk, but they’re really an integral part of giving the tools that your customers need, your clients need, and your employees need. And so, they also have a very different way of working. So, I think a lot of it comes from tech, and it’s kind of coming up into other aspects, as well.
I mean, I don’t think we’re going to see hybrid take off majorly for, like, home construction or, like, large enterprise building. You know, that needs to be pretty predictable still. But like I said earlier, there are still some projects, even within a highly, highly regulated environment, there are some projects that you can make a different kind of track that maybe is a little bit more flexible and adaptable and can pivot. And that flexibility is where the hybrid methodology comes about, I think.
Blending of Waterfall and Agile
BILL YATES: One of the things that we wanted to ask you about, Olivia, was experience you had as a PMO in the past. There was a blend of waterfall with executive approvals and closing phases. You know, some of the more traditional things that you would see with waterfall, blending that with agile for planning and execution phases. What were some of the key takeaways that you saw in that in terms of integrating those two methodologies?
OLIVIA MONTGOMERY: Absolutely. So, it was a really exciting time in my career. It actually – coming up with a hybrid methodology happened very organically. So, when I started, the PMO that I had entered into with this company was very new, and it was very small. And they were kind of the first time they were setting up a steering committee. So, I was lucky to be involved in a lot of those conversations.
And I saw how much structure and predictability the C-suite who primarily made up the steering committee, so the CFO, the COO, CTO, all of them coming together, they really expected project plans before anything got greenlit, of course, to come to them with pretty clear objectives and goals, and timeline and budget set out. That was what they really wanted. And they didn’t care too much about some of the other, like how it got done.
Then when I started talking and getting involved with our IT teams, because I led an IT PMO, so IT is my background, those teams were like, “Whoa, it gets so restrictive. We don’t even know.” C-suite wants to know, you know, those details and that predictability, but the actual business owner and who we’re getting requirements from, they’re not providing us enough information that we can even give you what you’re asking for. So, it came about with negotiating and discussing, “Hey, can we make both work? Can we blend both?” And there were a lot of conversations. That’s how we got to hybrid methodologies for all of the projects.
Then within that hybrid, kind of like I mentioned earlier, we came up with multiple tracks, whether they depended on thresholds on budget, you know, if they’d hit a certain amount, they needed to be going through the steering committee and follow a bit more waterfall traditional methodology. But if they were under a certain budget, or maybe they were only going to affect one team, we established what our particular thresholds were.
And then we provided the project managers and the teams those tracks that they can kind of follow. It really did come down to your steering committee and your senior leadership. Like I said, they want to know how much it’s going to cost and what they’re going to get at the end of it.
So, if you discuss and negotiate with them, like, okay, we can give you, you know, pretty close, what you’re going to get we can probably tell you; but the budget, when you get into hybrid methodologies, budgets definitely, you know, creep. Scope creeps, budget creeps, it happens. And you do have to make sure that there is understanding and a framework in order to discuss these overruns, whether it’s scope or budget. So, you can’t just have, okay, C-suite has the budget and the timeframe, we’re good to go. And then your development team who’s doing the actual work and doing the execution phase, that they’re just like, oh, this is great. We can do what we want.
And it has to be very structured. Everybody needs to be clear and have clear expectations of why we’re doing things the way that we’re doing, and how it works. Handoffs need to be crystal, crystal clear. And, like, reporting needs. It’s a lot of work, a lot of one-on-one conversations of, “Okay, what’s most important to you?” “What’s most important to you?” “What’s not so important?” You know, “Where are you willing to give up a little bit of control, predictability, and where are you not willing to do that?”
So, it came up, yeah, pretty organically. And I haven’t been at that company for years now, and they’re still writing projects that way. So, they sound pretty successful.
Hybrid Growing Pains
BILL YATES: Yeah, that’s great. I think it leads me right into the next question, which I think your description of that project lines right up with it. Typically, you have two different groups. C-suite, they want predictability, they want waterfall. And then you have the people that are actually doing the work. Maybe it’s the dev team, and they want flexibility. They want, you know, let’s test something and then make a decision.
So more of a, you know, waterfall versus agile. What are some other typical growing pains that you see in those types of situations where people are trying to embrace hybrid?
OLIVIA MONTGOMERY: So, there’s innate mindset clash. As you just said, their motivations are different, and oftentimes they conflict with each other. So right off the bat, you have to acknowledge that there is a mindset clash, and that’s okay. You can still find a way forward as long as everyone’s willing to be forthcoming with their needs and expectations and willing to compromise a little bit.
There’s definitely always a way forward, but acknowledging that both teams or maybe even other teams have different motivations and incentives for what they’re asking for and why they’re asking for it. So, off the bat, being clear and transparent about that I think is really helpful and helps people bring up any stress and tension and issues and confusion that they have.
One of the other very, very critical things that needs to come up is a crystal-clear layout of roles and responsibilities, especially when you are running a hybrid project or a hybrid PMO. Everybody who is involved or discussing any part of the project needs to know what their role and their responsibilities are. They need to know about what handoffs, the timing, who they need to go to for escalation, who they need to go to for decisions. All of that needs to be mapped out.
I like using flowcharts. I like using policy and procedure documents. You can make a video that walks the team through. Your RACI charts are my best friend. I’m a huge RACI chart fan. Absolutely love them. And all of those are what’s going to help everybody understand in general.
People are pretty willing to try out something as long as they know why they’re doing it, that there’s an incentive for them to do it, that they’re clear on the expectations, and they feel confident that they can meet those expectations. And all of those are conversations you can have generally one on one, especially if you’re new to hybrid.
I definitely recommend having the majority of the conversations one-on-one. That gives everybody time to ask questions, get in the nitty-gritty of their day to day, like, okay, what do I do? What tools am I using? Who am I talking to? Where do I go for the information that I need? If you do that in group settings, especially if it’s split across a dev team and your operations team, it can get messy, and there’s not enough time and space for everyone to ask their questions and share their thoughts.
So, I really, really recommend, like I said, acknowledging that there’s an innate clash, and that’s okay, and being really, really clear with roles and responsibilities – make those RACI charts, guys – and having as many one-on-one conversations as it takes. It could be ongoing, often. They don’t have to be formal. They don’t have to be documented or anything. But just a touch point to make sure that there’s a lot of clarity of what, why, when, and where. What do you need to do to be successful in meeting the expectations of the business?
Source of Truth and Software Tools
WENDY GROUNDS: So, Olivia, how are software decisions changing? As more teams are going hybrid, are there organizations that are looking for kind of a one tool that can do it all? Or are there several specialized ones that work together?
OLIVIA MONTGOMERY: Yeah, that’s a great question. I think the instinct is often to try and find a one-stop-shop solution. But it’s just not a reality for most businesses. If you have a very small team or a small organization, I would say like under 15 people, that’s doable. You might have some limitations as far as every tool has strengths and weaknesses. That’s just a fact of technology.
So, if you have, yeah, 15 or fewer people, you can probably get away with one tool. But even then, generally teams are going to find that they have needs that aren’t being met by the tool, and that the tool set’s going to expand. So generally, I would recommend companies not being too afraid of having multiple tools.
I think our last study found the average number of project management tools businesses have is four. So, it’s the average. That means some have 15, and some have two. But our average across the survey respondents was four. That’s a lot just for project management. So that’s not including, you know, the CRMs and the ERPs and your email and your messaging apps.
There’s so many other tools being used. And I think that that’s okay if you’re clear about why you’re using the tools that you’re using, and you have identified your sources of truth, and that everybody using the tools knows which of those tools is the source of truth, how to maintain it being the source of truth, why it’s the source of truth, what that means. So having clarity at the business level of what every tool, you know, what service it’s giving you.
There are going to be teams, maybe your marketing and sales team, maybe they want a different project management tool than your IT devs and DevOps do. I think that having that flexibility and being adaptable is important, and really focusing on the integrations needed.
So, it’s just kind of a matter of fact that employees are going to have to use a lot of tools. The most that you can do to limit that, of course, is ideal. I think companies should always be doing audits of all of the tools that are in use, official and unofficial. Any way that you can do that, you need to be auditing what tools are out there and following up with teams of how they’re using them; why they’re using them; are they using them; are they happy with it.
And always be evaluating your tech stack, looking at, like, how can we simplify, but not making simplification or going all in on one product or one vendor a goal. I don’t think that that’s exactly realistic. And I don’t think it’s necessary, either, especially as integrations are getting, you know, generally easier. Lots of tools have native integrations with each other. A lot of these vendors are very cooperative and collaborative with each other. And it’s great. I think you should take advantage of that.
Pick One System
BILL YATES: One of the statements that you made, or your phrase of “source of truth,” really hits home with me. That’s so good. Some of the most frustrating projects that I’ve been on have been where the metrics got muddy because we had more than one source. And I can think of specific instances where it’s like the project team was looking at one specific tool for the source to say how it’s performing. So, this was the performance report that they were using.
The customer was using a different means of measuring it. And at first, I think it was one of those where the team was like, you know beginning of the project was when it should have been addressed; right? We should have just had the battle right then. Which we have to have one source of truth. Let the one source of truth be named now. And we didn’t.
And then throughout the project we’d say, oh, man, this piece looks good. It looks like we need to spend a little more time on this, but our reports show this. Customer on the other hand says, “Eh, I don’t quite see that. So, then you’re wasting time. We’re spinning our wheels on something that we shouldn’t be. We should have insisted on one source of truth from the beginning. I like the way you say that.
And to me, it’s not the name of the tool so much as it’s going to depend from project to project. But if there are two sources, then a customer may point to one that tells a better story for them, where the team will do another, and we need to have one source of truth. So…
OLIVIA MONTGOMERY: Yeah, not having an agreed upon and understood source of truth, like you said, it hurts that project. When you’re in the project, everybody’s confused. Expectations can be missed. But it also hurts you later on if you ever need to audit that project or you want to glean lessons learned. That can complicate things even more.
And then if any of those KPIs need to be reported at a portfolio level or higher up, sometimes those two systems or more than two systems that you’ve got, they don’t even have the same actual definition for a KPI. So that’s one way of picking one source of truth. That means everybody’s looking at the same dashboard. They have the same information and the same definitions of what we’re looking at. Because that can get split really quickly.
That’s one of the main things I see is like, oh, well, the start date is this in tool one, but the start date’s this. And you’re like, oh, we actually have different definitions of what a start date is. The best way to do that is, like you said, to pick one system. It can, depending on, again, your maturity level, your IT environment, your ecosystem, that might mean as a project manager that you’re kind of doing some manual collation of information.
But it’s really, really critical; and you don’t want your teams frustrated. You definitely don’t want your customers confused or frustrated. And yeah, it can be a little hard; right? You know, you might want to, like, not have that conversation. You might kind of push it off. But knowing that it’s just going to hurt you and the entire team more, like just rip the Band-Aid off, get agreement.
BILL YATES: Man, absolutely. Just do it.
Ensuring Tool Integration
WENDY GROUNDS: Talking about tools, talking about the integration of these tools, how can you ensure that they talk to each other?
OLIVIA MONTGOMERY: Absolutely. So, integration is actually the top challenge and point of frustration repeatedly every year that we’re running this survey; right? So, it is where a lot of, like, new software implementations fail. And it’s often one of the top reasons businesses replace their PM tool or any tool, honestly. It’s not just PM tools. Integration is an issue across the board.
So, one thing, if you’re looking for a tool, one of the most important things you can do is, before you engage any vendor or you look at any solutions, try to identify exactly what systems you need your product management tool integrated with, and the level of integration. What type of information, what kind of data is being sent, what direction, how much, where is the data going to live? How often?
There’s a huge, huge difference between building an API that has near real-time data exchange both ways versus, you know, maybe an overnight upload of your job and so that daily your reporting is updated or something. That’s a huge, huge difference in usability and cost and maintenance.
So, before you buy a tool, hopefully, you have worked with your, like, IT architect, whoever is kind of overseeing your entire tech stack, and worked with the end users and the business leaders to identify, okay, these are all the systems. Accounting wants this kind of visibility and this kind of data. Sales and marketing want this kind of information. We want to show the client or customers this type of information. You do want to have a pretty clear roadmap and like another flowchart, another diagram of your environment.
And again, you want to do that upfront before you’re even engaging vendors because you don’t want to fall in love with a product usually based off like a marketing campaign, maybe a fancy demo. And then you get in there, and you’re like, oh, this is a very expensive integration to our CRM. And that’s, again, that specific example comes up so, so often. It’s just often more complex to keep up these integrations. So do that work upfront.
And then when you send a request for proposal and RFP to hopefully multiple vendors, ideally, like, at least three, state all of that as clear as possible, as much detail, technical detail that you can provide to them, and then make sure their responses make sense and are clear, and that they’re definitive.
You want to definitely stay shy of vague terms like, yeah, we will integrate with that. That’s not enough information. State the name of the tool. State the level of integration. State the data management policies. Be really clear about all of that. And then, if everything’s magic, okay, you’ve got your requirements. You’ve found a tool that meets it. You’re excited. Make sure you test, test, test before you put those integrations into your production environment. You want to test them in a lower environment, multiple times with multiple people. before you roll out into production.
So that’s kind of the best way you can try to avoid – there’s always complexity. There’s always frustrations. And being empathetic to that and knowing that it happens, the best thing you can do is just be open, be communicative, and have a mindset that we can fix any problem we know about.
Scheduling Integration Testing
BILL YATES: Yeah, right. Olivia, I think a lot of the projects that I did before working with Velociteach involved a lot of data movement from old legacy systems into our new software system. And we got bitten so many times we learned, we’re going to prototype this. You know, we’re going to test the integration, we’re going to test the API as soon as we can. You know, we’ve been bitten by this too many times.
So yeah, we would work that into the very early stages of the project because many times the customer was like, we’ve got a lot of data, you know, this project has created more projects. We’re going to clean up our data. We’re going to do all this stuff to it first. That sounds great. Give me a test file tomorrow.
I don’t need all one million records. I don’t need them to be pristine. I just need something I can load. I need to make sure that we have all the right data, that what we’re calling, you know, a certain field is what you think it is, too. So yeah, just do it as early as you can. Come up with the source of truth and test that integration.
OLIVIA MONTGOMERY: Exactly. But make sure you give yourself enough time. You know, IT integration isn’t going to be one day. And don’t do your testing on, like, Thursday or Friday night. Your teams will not be happy with you. Have an understanding and agreement with your larger IT group and your larger business group about when is a good week to be testing this because you’re going to be having people’s attention taken away. They’re going to be giving feedback. They’re going to be thinking about, you know, testing the new tool and the integration. So, they’ll be a little less focused on their other work. And you might break something. It happens. You can break stuff.
And so, you want to make sure that you’re scheduling it within a week that makes sense for your team, that everybody’s there, that they can be responsive, that your IT team is right with you when you’re pushing. I mean, they should be pushing it live anyway. And that the business owners are also there too so that they can see the bumps and snags that you hit. Expect bumps and snags. And like I said, make sure you pick a time of the month or of the year, whatever it is, where everybody can focus on it, and that expect it to go wrong. And then if it doesn’t, that would be amazing. And I want to hear what you did.
BILL YATES: Yeah, that’s good.
OLIVIA MONTGOMERY: Right. Expect some bumps and that’s okay.
BILL YATES: Yeah. Yeah, yeah.
A Word from Jess
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Team Culture and Collaboration
WENDY GROUNDS: If you are adopting a hybrid approach, how does that affect team culture and collaboration? What have you seen?
OLIVIA MONTGOMERY: Yeah. So, in general, teams are pretty excited about it. I think there’s still a lot of kind of baggage of waterfall and project managers just being very strict and very processed. There’s still a lot of that that we kind of have to fight against and be like, “No, we’re here to help you. You’re not here to slow things down unnecessarily.” The structures that a project manager in a business puts in place should be to support the team to get the work done the best that they can. And I think even coming at business problems and trying to get business goals and changes made to your business in a hybrid way is usually pretty received as exciting by most teams.
You’re like, “Okay, we hear you. We hear you, steering committees and executives. We’re not going to make you approve a project that you don’t really fully understand or that might cost five times as much as we tell you upfront. We respect your expectations and your needs, and we’re going to meet those.” But then also with your dev team or your execution team, we also respect that this is difficult work, and people don’t usually know what they want until they see it. So that means you need iterative development process.
Whatever your project is delivering, having those check-ins to make sure, “Okay, is this the work we want to be doing? Is this the quality that we want it to be at? Is this what we should be actually working on? And what should we be doing next?”
That, again, people know that if you’re in a waterfall and very traditional environment, that that’s going to be stressful and really hard. So generally, teams are excited, leadership and teams are excited when you’re like, “Hey, guys, we’re going to come up with something more flexible and adaptable that meets everybody’s needs.” So, it can be pretty exciting, which is probably why it’s doubled.
Leadership Traits of Successful PMs
BILL YATES: Yeah, that’s true. So, Olivia, thinking back on some of the successful project managers that you’ve seen in the hybrid environment, you know, maybe there were leadership qualities or communication skills that they had. What stands out to you? What are some of those traits that kind of set them apart?
OLIVIA MONTGOMERY: Yeah, that’s a great question. So right off the bat, a willingness to have those one-on-one conversations. It can take, depending on your personality type, maybe that is you have to be a little more brave, a little more confident. For me personally, it definitely was like, all right, I want to talk to everybody. I want to have these conversations. But sometimes, you know, it can be intimidating, especially some of the people, you know, like your senior IT architects.
BILL YATES: Right. You’re like, I don’t even know how to ask you a question. Yeah.
OLIVIA MONTGOMERY: Yeah, exactly.
BILL YATES: Yup.
OLIVIA MONTGOMERY: So, and then maybe on the other side, maybe you are very, very outgoing, and very, very extroverted, and you’re excited to have those one-on-one conversations. But maybe you’re not the best at scope management that way. And so, the conversations can be cumbersome to the person that you’re talking to. They’re usually short on time.
So, the best project managers I’ve had are willing and able to have very focused, action-driven, outcome-driven conversations in a very low risk, a lot of psychological safety, and just having a very natural conversation, being very clear, direct, and forthcoming as possible. Even, again, like having that mentality, if we can fix any problem we know about, that opens the door to sharing, being forthcoming about issues and concerns and confusion.
I think a lot of times in business, people don’t want to acknowledge, or they don’t feel comfortable or safe acknowledging when they’re frustrated or confused, and product managers should open that up. And again, that’s where the one-on-one conversations can help. So, yeah, you don’t want to waste time by having fluffy conversations because your stakeholders might not meet with you the next time you need their attention, but you also need to be brave and confident. You’re going to talk to some people who are a lot smarter than you, a lot more experienced than you are. You might say the wrong thing, and just you’ve got to do it anyway.
In general, you’re going to be happier, everybody’s going to be happier; and it can build that sense of trust, especially when it comes before you have a big decision meeting, for example.
That’s one time I really recommend and appreciate when a project manager kind of intuitively knows, all right, a big meeting’s coming up. I’m going to individually touch point with everybody, every stakeholder in that meeting so that they know what the meeting is about, what they’re expected to bring or say or do. And that can help so, so, so much.
But also on the other side, too, I want to say I focus on one-on-one conversations a lot, but it’s also important to support those one-on-one conversations with talking publicly about the expectations that have been made, that any time there is a clear set of expectations or requirements, yes, you want to discuss and negotiate in those one on ones, but you also do want to be communicating those to everybody in your team, your project team meetings.
Be very open and sharing. “This is what so and so and I talked about,” or “This is the new expectation for everybody.” You know, for example, getting everybody to update the PM system in time for you to pull your reports; or, you know, before you go to meet with the business owner, letting everybody know in that one on one, okay, guys, by 2:00 o’clock on Thursday I need you to update the PM tool. Say that in your one on ones and discuss, you know, negotiate as needed.
But then again, say it in front of everybody so that everybody knows that everybody else has the same kind of information. So, making it common knowledge. The expectations need to be common knowledge. Everybody needs to know that I know that you know that I know that you know what’s needed.
AI Benefits in Hybrid Settings
WENDY GROUNDS: Olivia, AI is transforming so many aspects of project management. I’m finding it helps me so much in my job. And there are so many benefits to it. What are some of the exciting ways that you’re seeing it used in hybrid settings?
OLIVIA MONTGOMERY: So yeah, I’m in the same boat. AI has completely changed my job. How I work is so different than even a year ago, and probably in another year it’ll look even more different. So, it’s very, very exciting. It’s also very scary, and there’s a lot of risk. There’s a lot of these tools, especially the LLMs, the large language models like ChatGPT and Copilot or Claude. These were kind of unleashed to, like, everybody. So even if your company maybe doesn’t have a specific in-house tool or version or instance that you’re using, we know pretty much everybody’s probably using a private version of it. And that is very exciting.
I will say one of my favorite things that I’ve seen is this just absolute fast jump in natural language processing and being able to talk to a computer like a person. I know if you’re a little older, like me, you remember the days of MS-DOS, and trying to, like, talk to a computer as if you’re a computer. And it is so bizarre. And you had to learn an entire new language to work.
And then we saw no-code and low-code options for more front-end configurations get more popular. And that was really helpful.
I think that this step in the NLP and LLM capability is skyrocketing that. So now anybody can be like, “Hey, help me figure this out.” And that can be filled with – you can literally type it like that. “Help me make a project plan. I’ve got two hours, and it’s due. I need you to help me out.” And you can make typos. You can make mistakes. You can say it wrong. And it still generally can figure out what it is that you need and what you want, and you can work with the tools. That’s something that I am super, super excited, and I think helps everybody, especially if you are working in technical documentation.
And there’s also a lot of synthesizing of communication. So so much of what a project manager does is getting all the information from so many different types of people with different, again, motivations, communication styles, different types of knowledge, different gaps in their knowledge. You have to take all of that in constantly so that you know the health of your project, the status of your project, and where everybody’s at. And I think these tools can really help you do that.
I do kind of warn people to really, really try and do their research and understand what these LLMs – how they operate. I think a lot of people are relying on what’s considered emergent capabilities of these tools.
So, what I mean by that is these LLMs, they are pretty much based on statistical prediction of word order. And so, they have all their training data, but they really are just kind of being like, “Okay, this word often, you know, is next in line. And then sometimes this word is next in line. And this person will probably like this sentence or this paragraph because my training data, this is the most often that it looks like.” And that’s incredibly helpful. But that kind of backend structure doesn’t mean that the tool knows anything that it’s saying. So, understanding that it doesn’t even know words, it knows tokens, that can be really helpful.
I find it doesn’t know what the word “summarize” means. It just is like, “Okay, summarize it for instance is probably three tokens, depending on how the backend” – I don’t want to get too technical. But that’s probably three different tokens. So, it doesn’t even know what the word “summarize” means. It knows, okay, these three tokens showed up in this order. In my training data, this is also where those three tokens show up together. And this is all the other tokens that are around that most often. Okay, I’m going to push this as my output to you. It is very good at making itself sound fun and engaging and lighthearted and friendly, which is great. And it makes your day a lot easier.
And like I said, talking to it is a lot less intimidating, and it can really help you prep for conversations. We just talked about, you know, having maybe low confidence going into a technical deep dive with your IT architect about your tech stack. That can be really scary. But you can have a practice conversation with these LLMs and, you know, learn some of the jargon, and have a practice like, “Okay, I’m not totally out of my depth.” It still might hallucinate, and it still might tell you something funky, but that’s okay. And so, using those tools to help prep for conversations, help write user stories, help synthesize all these different types of communication is incredibly, incredibly helpful.
But again, I do caution people that we sometimes rely on them to do emergent capabilities. If you’ve ever asked it to count anything, you probably know what I mean. Or if you’ve talked to the LLM within a thread, you know, for five, six, ten prompts, it can lose the goose. Like it can definitely get a little wonky. And that’s okay. You start a new chat. But I think knowing how these tools are designed and how they work, and not trusting it to tell you how it works, practice and try, you know, talk to each other, that all can be really, really helpful. But yeah, AI is like changing everybody’s world really quickly.
WENDY GROUNDS: Yeah, yeah. I always like when it tells me I’ve done a good job.
BILL YATES: Very affirming.
Is Hybrid the New Normal?
WENDY GROUNDS: Olivia, do you see hybrid project management as a stepping stone? Or do you think it’s the new normal? Do you think it’s going to stick around for a long time?
OLIVIA MONTGOMERY: Great, great question. I think it’s going to really depend on the industry that you’re in. So, if you’re chemical manufacturing, you have an intense amount of risk and regulation, and you need a lot of predictability in your projects. So those kinds of businesses might not be, maybe their marketing and sales teams are taking on hybrid approaches, but their other teams might not. They might even stick with very traditional waterfall. But even embracing that is embracing hybrid methodologies, allowing different types of projects to run in different ways. That is hybrid methodology. So, I do think that it’s here to stay, and it’s going to continue to evolve, and it’s going to look quite a bit different.
We also see a lot of job hopping that we didn’t see maybe, you know, 30 years ago, 20 years ago. And with that, that also kind of spreads out the experience and preferences of people. People switch industries, especially, you know, maybe not just roles and companies, but they switch industries a lot more often now, too. And so, you’re going to see a lot of different opinions and a lot of different ways of working. And hopefully businesses do embrace like, okay, yeah, this is great. Let’s incorporate this. Or this hasn’t been working for us. I like your new idea you brought in. Let’s replace it.
And so, I think hybrid is going to be continuing to just take on more and more of a presence across all types of businesses, even if they think that maybe they’re highly regulated.
And like I said, I wouldn’t be pressing or recommending any business to move forward with hybrid if they’re not ready and wanting to do it. It’s not a trend, don’t have FOMO for hybrid. If your current methodologies are working, that’s great. No FOMO for hybrid. But if there’s dysfunction, if you’re missing your deadlines, if you’re going over budget, if there’s just so many problems that keep showing up very late stages of your project, all of those are signs that probably a more flexible and adaptable methodology is needed and will be appreciated by your teams.
Get in Touch
WENDY GROUNDS: If our audience wants to get in touch with you or find out a little bit about what you do, what’s the best place they can go?
OLIVIA MONTGOMERY: Yeah, the best place is LinkedIn. I am very active on LinkedIn. I share my reports. I make a lot of videos on there. I do a lot of webinars. If you guys are looking for PDUs, I do a lot of webinars. I try and give back as much as possible. I really love, one of my favorite parts of my job is that most everything I do is free and offered to anybody and everybody. And I’m very, very proud and lucky to be in a position to do that. So definitely reach out on LinkedIn.
Like you said, I am an analyst at Capterra. I also work for a couple other sister companies within Gartner. And so, you can always check my profile there. But LinkedIn’s probably the go-to place. And I am happy to hear from anybody.
BILL YATES: Olivia, thank you so much for spending the time with us. And for us to be able to speak with an analyst who, quite frankly, communicates well, you know, sometimes the analysts get so deep into their data, they can hardly come up for air and see the big picture and explain it to people. You have done that extremely well. We thank you for giving us some insight into how and why hybrid is growing. It’s very interesting to see the numbers and then hear the story behind it. So, thank you for explaining that to us.
OLIVIA MONTGOMERY: Yeah, thank you, too. That’s really kind of you to say. I think I’m very fortunate to have a background, a literature background. I have a Master’s in Literature, and that’s where I learned to research and write and communicate and to think in a million different ways. And then, right out of college, I went into tech because I knew tech needs research and communication. And everybody’s talking different languages. And I saw, especially IT leaders and business leaders don’t, they don’t speak the same language, and they don’t really want to figure out a new one.
And then on top of it, yeah, being an analyst is pretty introverted work. A lot of detail, like my whole life is spreadsheets and thinking and data and numbers. But I also think that it’s really important to try and get the message out and share what’s working. Being a project manager is difficult and complicated, and it’s nuanced, and there’s so much. So, anything that I can do to, like, help everybody out. So, thank you for the kind words. I appreciate that. And I was very excited to spend the time with you guys.
BILL YATES: Thank you so much.
Closing
WENDY GROUNDS: Thank you for joining us on Manage This. You can visit us at Velociteach.com, where you can subscribe to this podcast and see a complete transcript of the show.
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