Galen Low is joined by Olivia Montgomery—champion of the social sciences, a former PMO director, and a published thought leader—to talk about strategic planning and whether project management has a place at the table.
- Olivia talks about a survey she recently led at Capterra: “From Task Manager to Strategic Partner: How Project Managers Can Become More Influential” [2:16]
- The survey asked 300+ PMs if they are influential in the tech strategy at their company.
- 87% of people surveyed said they felt they could be more influential.
- PMs are trusted executors but not always valued at how much information and knowledge they have. [4:56]
Project managers sit between the business and IT. They know the struggles that operations are having and they know the capabilities that their IT infrastructure has.Olivia Montgomery
- PMs are great at keeping emotions out of decision making—when ops and IT teams come together, that’s where emotions can clash. PMs can help bridge that gap by translating and communicating between teams to find a solution. [6:35]
- When there’s more money involved, there are more emotions involved. [10:16]
- Trust yourself, and your knowledge. PMs have a toolbox that not a lot of other roles have experience with. [12:07]
- The same tools that you use as a PM in your team are also useful in strategic planning. [12:31]
- Leaders can often focus on what the IT team is capable of—but it can be out of sync with what the team is actually feeling and how the operation is actually doing. That’s your opportunity to communicate what you know about the capabilities and challenges being experienced. [13:37]
- When you’re in a strategic and influential position, you can be the one-stop-shop for information about what’s actually happening across the organization. [15:49]
- If you’re a PM who only does one type of project, you might think you’re not the right PM to be at the table. And you might be right, but that doesn’t mean you can’t become the right person. Come to the table smart. [18:41]
- If you want to get involved in strategic planning, talk to your boss—if they can be your top advocate, that will set you up the best for success. [20:26]
- Get to know who exactly is in the strategic meetings, find ways to get yourself into those meetings, and advocate for yourself. [23:22]
- Don’t get disheartened if you don’t immediately get invited to those meetings. You can build trust, and become a valued advisor. It’s going to take time but it’s not impossible.
Advocate for yourself and hopefully you can get your boss to advocate for you too.Olivia Montgomery
- If you’re an execution heavy PM and you want to be influential, Olivia recommends staying at your current company and working towards that position rather than looking for those specific roles elsewhere. [26:26]
- If you’re invited to the table, don’t be afraid to speak up. You need to be seen as confident and helpful to the group, even if you’re invited just to take notes. [34:39]
As PMs, you should know the objective of the meeting, and make sure that everything that’s happening is moving toward that objective.Olivia Montgomery
- Knowing how to structure the information you’re giving can immediately bring business value. [37:32]
- Learn who the players are and what their motivations are. [41:22]
- Olivia shares her experience from her manager who controlled their team using fear and division. [43:56]
Problems that are discussed are problems that can be solved.Olivia Montgomery
- Olivia’s top tips for PMs who want to be seen as a strategic partner for their organization are: 1. Know the lay of the land and have ideas. And, 2. be the person who speaks up and has a solution. [50:50]
Meet Our Guest
Olivia is a researcher and thought leadership analyst responsible for producing reports and insights on small business project management, supply chain trends, and technology strategies for Gartner Digital Markets (Capterra, GetApp, Software Advice). Specialized in qualitative research and analysis. Her work has been featured in Forbes, Supply Chain World, The Digital Project Manager, TechRepublic, CIO Dive, and more.
Background includes IT program and project management with Scrum Master Certification, Master’s degree in English, and Project Management Professional certification.
Olivia is passionate about incorporating more humanities studies with tech research and advancements – the liberal arts and STEM are stronger together.
Just because you don’t have a technical background doesn’t mean that you don’t have insight and you can’t help move decisions along.Olivia Montgomery
Resources from this episode:
- Join DPM Membership
- Subscribe to the newsletter to get our latest articles and podcasts
- Connect with Olivia on LinkedIn and Twitter
- Learn more about Gartner and Capterra
Related articles and podcasts:
Read The Transcript:
We’re trying out transcribing our podcasts using a software program. Please forgive any typos as the bot isn’t correct 100% of the time.
Galen Low: Strategy. It's a word that gets tossed around in almost any business context. Business strategy. Digital strategy. Delivery strategy. Communication strategy.
But where I hear it the most is in my conversations about project management. As a project manager, how can I be seen as more strategic? How can I influence my organization's strategy? Or, as a business, how can I get more strategic value from my project managers? How can I plan and prioritize projects that can realistically achieve our strategic objectives?
In other words, what I hear is a disconnect.
So if you're a project manager struggling to be seen as more than just executional, or if you're a business leader trying to de-risk strategic initiatives, keep listening. We're going to be exploring how project managers can play a role in strategic planning and what impact that can have on a business' ability to achieve its goals.
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 over to thedigitalprojectmanager.com.
Okay. Today we are talking about strategic planning and whether project management has a place at the table. We'll be talking through the pros and cons for businesses who involve PMs in their strategic planning, and we'll be talking through the do's and don'ts for PMs who are getting involved in strategic planning for the first time.
Back in the studio with me today is Olivia Montgomery from Capterra. For avid listeners, you know Olivia—she's a champion of the social sciences, she's a former PMO director, and she's a published thought leader who lends her human-centered perspective to the way enterprises execute technology projects.
Olivia, welcome back!
Olivia Montgomery: Thank you so much for having me. I really appreciate it.
Galen Low: You are a fan favorite on the show. We always love having you back. Thank you for coming back, time and time again to share your insights. I'm really excited to dig in today.
Olivia Montgomery: Yeah, me too.
Galen Low: Let's do it!
You once again, you've just published a report that is focused squarely at project managers this time, and I wondered if you could just tell us a little bit about it?
Olivia Montgomery: Yeah, absolutely. So my latest report titled, "From Task Manager to Strategic Partner: How Project Managers Can Become More Influential". So I surveyed 319 IT project managers asking if they are influential in the tech strategy at their companies. If they're not, why not? And just asking insights about, you know, where they think they can develop what their company is missing out on by not having them at the table.
Yeah, so I wrote the report for those who are looking to become more involved and influential in the tech strategy at their company, specifically of which, in my research we found that 87% of the project managers thought that they, their company's missing out. That they should be more involved in influential, that they could be more influential in discussing, setting and executing the tech strategy.
So this report is specifically for that 87% that's looking to get more involved.
Galen Low: Very cool. I find that set interesting and yet somehow unsurprising from a project manager perspective. Because I think, you know, there is this undercurrent of the value of project management being a bit underestimated, a bit undervalued from folks who are thinking strategically about their role, who are sort of strategic delivery leaders in their own minds and maybe are not necessarily perceived that way because there's this sort of flatness of the title or the role of project manager.
That kind of lends itself to being like squarely middle management and not necessarily involved in like the inner workings of the business to the point where there are, you know, insights to be had or gleaned for strategic planning. That's really interesting.
Can you tell us a bit about the, like, the research behind it? Was it kind of like a pull where you're interviewing folks? Like, did you get juicy stories?
Olivia Montgomery: Yeah, mix. So we send out a survey to IT project managers and we just ask them like, Hey, are you willing to answer these questions?
Luckily, yeah, hundreds of them are usually pretty happy to talk to me. And then I can do follow up if somebody had, you know, specific, it's a mix of, you know, answering like, you know, select from the answer options. And then they're also are always write-in options. So if they had an interesting story that they shared in the write-in option, you know, I can follow back up with them.
For this I really was focused more on aggregating the total trends cuz I wanted to know kind of in general what are people feeling. So I didn't do too much of a deep dive with individuals on this one. I'd like to do that as a follow up report, hopefully. This one was really focused on systemically where are we at as project managers, as a career?
What we're starting to be seeing as, like you said, we're in very execution heavy roles, and we're trusted executors, but not always, you know, valued at how much information and knowledge we have. So project managers do sit between the business and IT. They know the struggles that operations is having and they know the capabilities that their IT infrastructure has.
So they're often really quickly able to assess, you know, what can be done, what should be done, what direction, you know, projects should be going in, which projects should be green light, which need to be reworked. They have that, that like perfect blend of sitting between, yeah, the business and IT that pretty much no one else in an organization typically has.
And that's exactly why they should be included in the strategic planning process. It's not usually enough just to have your IT director and your operations director coming up with your, you know, the company strategy. They often don't speak the same language, and they don't even know exactly where their blind spots are. But project managers usually do.
Galen Low: Hoorah! And I totally agree. I have my bias, obviously.
Olivia Montgomery: Same.
Galen Low: But I think there's a lot on offer and we're gonna dig into that. One of the things that strikes me is that I feel like in some ways this is not just another report for you, it's something that you feel quite passionately about.
And I'm just wondering why is it so important for you to fly this flag of getting project managers at the table for strategic planning?
Olivia Montgomery: Yeah, absolutely. So it really is that in, personally in my career and in my research, I've just found that it is that miscommunication and misunderstanding that operations people and IT people tend to have.
In our previous episodes I've talked about the importance of emotional intelligence and how project managers are really good at decision-making and requirements gathering and keeping emotions out of discussions. That's something that when IT personalities and operations personalities come together, they can kind of come clash and emotions can run high.
And so already being a bridge that operates consistently, you know, every day in your job between those two when you get into strategic meetings, you're able to continue that role and help bridge that gap and help see like, okay, well, they're actually saying the same thing. Just using different words or coming at it from a different point of view, but it's, product managers are just really good at getting to like the root issue and being like, all right, yeah, you know, we hear both sides.
Let's now talk about the solution. Where sometimes, you know, operational leaders and IT leaders can get stuck in the problems. They can get stuck in what went wrong, you know, why it went wrong, who's to blame. And as a project manager, you can come in and just be solution-oriented.
Galen Low: I really like that facilitation aspect and more, but also I've seen that. I've been in sort of strategic planning sessions that are either quite passive aggressive cuz there's a lot of water under the bridge between personalities. And I've seen some very overtly, like quite aggressive, quite adversarial shouting, very much just like a much more combative environment, which naturally reduces its productivity in a lot of cases.
Not always. Sometimes that's good, right? Healthy, loud debate can still get to results, but also there's that whole culture of loudest voice in the room wins at some of these meetings. And that's not necessarily going to make great decisions for an organization, unless the, you know, the brightest person with the best judgment also has the loudest voice.
No, that's that's really cool. And then, I mean, I feel like your journey was that as well in terms of like navigating this, trying to find where you are valuable, but also like, like making that proposal to the right people to say, I ought to be here because I have some insights that I can share, I can help, you know, provide perspective, I can help facilitate.
What did that journey look like for you?
Olivia Montgomery: Yeah. So my career path was kind of a winding one, a bit of a non-traditional, especially as far as IT people. Tend to be, I don't have an IT background, liberal arts. We've talked about this in previous episodes, and it's something that I think is a part of my strength and it's not always seen immediately as a strength coming from the outside because I don't have the IT pedigree or a technical pedigree, which is still, you know, seen as very valuable.
And it is, it absolutely is. But it needs to be complimented with, you know, the social skills that a project manager tend to develop. And even people with strong social skills and technical skills can usually end up in project management roles, which is what I did.
Coming from technical writing, business analysis, being a project manager. At each of those steps, I did have to use my ability to get people to communicate clearly and stay on topic and reduce the emotions from what was being discussed. And my ability to do that was seen as pretty valuable quickly.
Cuz like you said, especially the higher up you go in strategic planning meetings, there's more money involved and when there's more money, there's more emotions. And you can help guide those discussions so that they're more productive and, you know, grounded in information and less in emotions, but it's not easy.
And even seeing that need and seeing where I could fill that need was new and different. I didn't really have anybody as a mentor at that time to say, yeah, this is it. Like, yeah, you're speaking up at the right times. Yeah, you have something here. You know, there's not a business analyst school per se, you know, there's not enough focus on, Hey, IT and operations don't speak the same language.
And there are people out there that do, and we need more of it. So I wish I did have, you know, in hindsight, I wish I had a bit more of a roadmap or maybe a mentor who is coming along saying like, yes, this is value. Just because you don't have a technical background doesn't mean that you're not, you don't have insight and you can't help, you know, move decisions along.
So I had to kind of figure that out for myself, which is why it's really important for me to share this information and my experience, how I did it, what it looked like, what I wish I had done differently with people. It's why I'm really happy to be here and always happy to talk with you and your listeners because I know that there are other people out there that, you know, are probably either in the same position I was.
And they're looking to see, you know, what, am I doing the right thing? Should I be doing this? Do people want me to be doing this? And the answer is 'yes'. They might not exactly know, they might not know where it's gonna come from, they might not expect you to be the person, you know, that helps them see it, but it can be you.
And you should be trusting yourself, trusting your knowledge, trusting that, you know, project managers have a toolbox that a lot of other professional roles don't have. We have the skill set, decision making of even just gathering requirements and doing your racy charts. All of those are skills and exercises that a lot of other roles and a company they don't have any experience with.
And you can bring that. Yes, it's helpful within your individual project to structure your team and set everyone up for success, but the same exercises and tools are also useful for high level strategic planning.
Galen Low: I love that. And I think one thing that, that hearing is that like, facilitation was kind of your way in.
That's how you kind of got your foot in the door. But I think there's more to it than just being the person who is there in the room helping sort of facilitate dialogue, supporting, you know, being a bit of just that like lubricant. I think there's, you know, like as you're saying, there's skills that we bring to the table and there's also perspectives that we bring to the table, not just as facilitators of the dialogue, but actually contributors to that.
So I was wondering if we just dive in to just like, why is it important to have project managers at strategic planning beyond that facilitation role? Like what does delivery have to do with strategy and how can businesses start to see it that way so that they can benefit from having project managers at the table?
Olivia Montgomery: Yeah. Absolutely. So oftentimes the senior leaders in, you know, perhaps you have an IT steering committee. In my previous company it was an IT advisory committee, ITAC for short. Most organizations have some kind of steering committee for how IT will spend their money, and what IT projects get grain lit and not.
They often are also very execution focused and budget focused. So sometimes they can lose sight of business value and what's capable of their teams of what they're asking for. So specifically, so what I saw a lot was senior leaders would say, oh, the call center, you know, is capable of doing this. And maybe I'd run, me or one of my project managers had run, you know, a recent call center project and it doesn't quite line up with what they're saying.
And so you can be like, oh, actually, you know, they're really struggling at where they're at. They need more people or they need this new software. Whatever it is what the executive is saying is just a little bit out of sync with what's actually being felt and seen and worked on in operations.
And that's where you can kind of speak up and be like, oh, actually, you know, when I spoke to so and so, this was their challenges. Or no, they're ready. You know, they're ready to take this on. They're ready to move forward, you know, and update their system, whatever your specific project is.
The point is, you're going to hear inconsistency between what the higher ups say and think and what you as a project manager executing for the business knows our capabilities and challenges being experienced.
Galen Low: It sounds like it's a very good way of not playing that game of telephone in a multilayered organization with all those tiers where, and I have seen it. I've seen it where, you know, the folks in the room at strategic planning are so far removed from, to your point, what happens at call center, frontline support, boots on the ground, that a lot of their decision making sort of happens, you know, based on assumptions.
Olivia Montgomery: Yep, absolutely. Absolutely. And it's, I'm a big advocate of having the project manager, a very knowledgeable technical project manager, be that strategic person because you can be kind of a one-stop-shop for that bridge between their understanding and their hopes of how, you know, the business is operating.
So it would be really inefficient for that, you know, the call center director to come in and advocate for themselves at this meeting. And then you have to call in the head of accounting to come in and do the same for their project. That's really ineffective. So when you're in that strategic and influential position, you can kind of speak to all of the areas because hopefully you have exposure because every department uses IT, and you're probably running projects for every aspect of the business.
You already can be that kind of one-stop-shop for that information. And that's a really key aspect of it. Yes, you might have to bring in, you know, if the conversation gets heated and they're like, no, I know Paul in accounting and he says this, and you're like, oh, you know that it's kind of different.
And you can say, I'm a big fan of transparency. You know, as we discussed before, be like, Hey, let's break Paul in, you know, and have him, you know, talk about this or, you know, let's shelf this for the next meeting and we'll tee him up, you know, to come in. But it's more effective if you can be the representative for anybody that's, especially if you're in a meeting, a strategic planning meeting. And you should already know what projects are, you know, coming down the pipeline, what projects are, you know, currently underway and what ones have recently passed.
And if you don't have that information, you need to get it before you go into those strategic meetings. I'm sure we'll talk a bit about like prep. Maybe that's even, we should talk about that now. But yeah, you need to be prepared and be that one-stop-shop resource for them.
Galen Low: Like, I think there's two really important things there.
One is, you know, devil's advocate to your argument would be, well, you know, if we're gonna have project managers at the table, let's have accounting at the table. Let's have whatever, design at the table. Let's have all the folks here in the room. If what we're saying is the folks who are sort of boots on the ground have a great perspective, then maybe everyone should be there.
To your point, that would be really inefficient. And I like what you're saying about the fact that, you know, project managers are somewhat uniquely positioned as this hub or the bridge between various teams and they have that line of sight. The other thing you touched on that I thought was important is that, you might be a project manager who doesn't have line of sight, you know, maybe you're only running one type of project.
And, you know, even, and we will get into it later on in terms of, you know, getting to the table and preparing for this sort of thing if you are going to be at the table. But there is also this lens of, Am I the right PM to be at the table? You know, if you're running just the, you know, just one type of project and you haven't really taken an interest or had exposure to other types of projects or what the business is trying to achieve, like you might be not the right person.
Doesn't mean you can't make yourself the right person. And I think that's where we can get to later on in this conversation in terms of just being prepared and coming to the table smart.
That's probably a pretty good segue. We've been talking a bit about how project managers are perceived, also how project managers perceive themselves. We've been talking about this notion that we're kind of seen as executional and oftentimes, you know, we're reliable to, to get underestimated.
So for project managers listening, what advice would you give to someone who's very much seen as executional, but wants to get involved in strategic planning?
Olivia Montgomery: Yeah, absolutely. So in my research, I found that PMs are spending about 40% of their time on essentially task management activities, status reports, administration update, you know, hunting down task updates from everybody, herding cats. I even had, so it's about 40% collectively of our time is being spent as a task manager.
And you need to try to, you know, delegate the tasks and, you know, get a bit more creative in how you're managing to eat away at that 40%. The report goes into quite a bit of detail about that. So anyone listening for specific actions of what it looks like to, you know, reduce that chunk of time you're spending on admin task, I recommend checking out the report.
But for your question about exactly like what first step you should take. I strongly recommend talking to your boss first. Tell them what your goals and your plans are. Tell them what you're thinking. If you can get them to be your top advocate, you're set up the best. Ideally, you know, they'll hear you and they'll be like, yeah, this is great.
You know, I love it. What can I do to support you? And then you can give them, you know, your list of asks. It might not always go that way. One of the top barriers to being influential in my report that we found was that another program or portfolio manager holds that responsibility and they kind of go in and they represent, you know, the PMs.
So they pretty, somebody already has that spot that you're looking for. Talk to your boss, you know, openly and say, is there only room for one of us? Probably there is, and that's okay. What's that person looking to do? Are they looking to move to another company? Are they looking for another position?
Are they happy where they're at? That's gonna give you an idea of kind of timeline. Honestly, if somebody else is already in that position and everybody's really happy with them, don't expect to replace them or be that person anytime soon. You might even need to switch companies in order to move into that role cause you don't want to, you know, take somebody else down.
That's awful. And your boss can give you that information. And you can also ask the portfolio manager, you know, talk to 'em about, Hey, I wanna do, you know, how did you get here? What do you like about this role? Like, how can I help support you when you go into these meetings?
Any exposure you can get to what senior leaders are thinking about as far as IT projects, and even just how IT is delivering business value in general. You need to hear that. So yeah, talk to your boss, try to get their support, and then be specific in your ask for them. You know, if you need to increase your technical knowledge, which was another of the top reasons that we found. It's like over 30% of PMs or it's like I just, you know, I don't have the technical knowledge quite yet to be in those meetings.
They probably have more information than they know. So sometimes I can see that being as a lack of confidence. You probably know way more than you think you know, but that's fine. Be specific in asking your boss, like, Hey, this is where I wanna be. What certifications, what classes, you know, who can I shadow?
Can I get a mentor? You know, maybe your company's willing to bring in, you know, an external mentor for you. Or they can set you up with an internal one. You need your boss' support is the long and short of it. That's going to determine how quickly this shift can happen for you. And spoiler, it's probably not gonna happen overnight.
Highly doubt you're gonna approach your boss and they're gonna be like, yeah, awesome. Next meeting, you're on the docket. Not gonna happen. And that's fine. Don't expect it. You don't need it to happen right away. The next thing that I would recommend doing is getting to know exactly who is in that meeting.
So even if your boss isn't so supportive of you taking on that role, maybe they like that role. Maybe you can ask, you know, for the meeting notes, maybe you can take the meeting notes. Anything to get yourself in that room is gonna be really important. So it's gonna be, you know, specific to your relationship with your boss, your company culture, if somebody's already in that role or not.
But yeah, advocate for yourself and hopefully you can get your boss to advocate for you too.
Galen Low: I think that's the really key sort of expectation management in terms of, you know, I talk to a lot of project managers who are like, oh, I wish I was more strategic. I wish, you know, I could be more influential.
And the bottom line is there's this practicality to like, okay, well, you can't, you know, you can't just ignore some of your other responsibilities, right? Like, yes, you probably are spending a big chunk of your time managing projects and everything that comes with it. You need to be able to make room for it first.
It's not gonna just magically happen where you are suddenly a strategic leader and you don't have to do all those things that you're doing yesterday. I think the other one is just like, yes, you could talk to your boss. Hopefully, they will support you. They might not, you might kind of get kind of, you know, brushed off.
There are other ways to do that. Talk to other people, win hearts, you know, have your advocates. But it's gonna take time. And then also there's only so many seats at the table, right? If every project manager in an enterprise was like, I wanna be at the table, you know, there's not 25 seats for project managers at strategic planning.
But to your point, there might be other roles. If somebody is already there at the table representing project management or delivery, then there's other things you can do just to be in the room, soak up that knowledge, get exposure to the process so that you are at the very least learning and either within that organization or within a different organization later in your career, you can say that you have that or you can actually bring that knowledge into the way that you are approaching your new role.
But I really do like that overall perspective that this is not an overnight thing. This is not a, When's strategic planning? Can I come? Oh yeah, it's next week, here's the invite. It could be, but generally just to, you know, level set expectations, it also might not be.
Olivia Montgomery: Yeah, we found in the research too, we found over 30% of PMs say that only senior leaders are allowed in those meetings, and that's the company culture that they just don't want.
You know, they don't see the value of having anybody else. They only want C-suite and above in there. And that's, I'd say don't get disheartened if that's the case. You can work toward, you know, building trust and being seen as a go-to advisor and, you know, a value add. Pretty much you're gonna try to position yourself as like, you know, I can see your all's blind spot.
But that's gonna take time, but it's not impossible. I do strongly recommend that if you are a, you know, execution heavy project manager and you want to be more influential, I do recommend trying to stay at your current company and building that relationship and getting to that spot where you're at now.
I don't recommend knowing that you wanna be in that role and go and look for job listings that are like that and applying for them. The next company's probably not gonna wanna take that risk on you. And it's gonna be really tough and it's probably gonna be really frustrating. And you might be a little honestly under-prepared for it.
So I do recommend trying to get moved up in your current position at your current company. The exception to that would be, if someone else is already in that role, if there's a portfolio manager, say you're a project manager, you're not portfolio level, you're gonna first need to get to be a portfolio manager.
And then you can, but that's a longer road. And like I said, talk to that person who's in the role and see. You never know when somebody's gonna leave the company too, and then they could be left, the company's left in a lurch and you can, I've had a lot of success by people leaving. You know, I've twice actually, moved up in my career because my immediate person quit and everybody was like, oh my god.
Here, Olivia, you do it. And I was like, yes, I'm on it. So don't give up unless somebody is already, you know, committed. They're a lifer for the company. They have that role and try and learn as much from them as you can. And then you're gonna have to apply probably for another company to take that on.
But the long story is don't jump ship. Don't think you're gonna need to switch companies. It's gonna be a much healthier road for you to take to build and develop that relationship within wherever you're at right now.
Galen Low: I like that sort of invested time because what we're doing actually is building trust and that takes time.
Olivia Montgomery: Yep. And it's gonna, you know, when you do that in your current company and then when you go to apply to be, you know, portfolio manager at another company, you're coming in at a position of authority. You have the credibility with that company. They're not having to take this leap of faith with you. Because they probably aren't going to be willing to do that.
Galen Low: Fair enough.
I wondered if we can dive into the next stage though. So in some cases, you will get invited to the table and when you get invited to the table, especially for the first time, it's gonna be new, it's gonna be exciting, but it's gonna require some prep. And we've been dancing around this throughout the conversation, but you know, specifically once you've been invited to the table at strategic planning and it's your first, like how do you prepare for it?
Olivia Montgomery: Yeah, absolutely. So first thing you to need to know what the other people, you know, who on the committee, what do they think your role and your involvement is going to be. So it might be really clear, maybe they invited you and they're like, yeah, you're gonna take notes. Okay, that's great. So you're automatically gonna know that you're gonna be a little bit more passive, at least the first time.
You'll wanna speak up, you know, and show a presence, but also you're gonna need to fulfill the role that they've asked you to fulfill during the meeting. Or maybe they're like, yeah, you know, in my case, my boss, I was reporting to the CIO at the time and he was who was putting together the presentation slides for the meetings. And he was moderating and driving the discussion and he was fantastic and said, Hey, yeah, I'll help you with the first one, but you do it.
And so then I had a very clear objective. I knew what I had to do. So you need to satisfy whatever the expectations the others have for you in that meeting is. You can go and beyond that, but do not lose sight. If you go in with an ulterior motive and you don't meet their expectations, they're not gonna invite you back.
No matter how witty or fun or helpful or resourceful you thought you were, if you missed the mark on the basics of what they needed, they're not gonna trust you. So know why you're there, know what they're expecting from you. The next is, I recommend trying to connect casually with every member of the committee before the meeting.
I say very casually, you know, if you're in office together, try to, you know, maybe stop by their office or see when they go to the break room. If they go to the break room, catch 'em on the elevator, something you wanna just be like, Hey, you know, I'm really looking forward to the ITAC meeting on Wednesday.
I'm excited to be involved. You know, can't wait to, you know, be there. Very quick, very casual. Essentially, you don't want your presence there to be a surprise. Hopefully when you say that, when you're like, Hey, excited for the meeting on Wednesday. They're like, yeah, you know, you're gonna rock it.
That's great. They might be like, oh, what are you gonna be doing there? And you'll be like, oh. You let them know, you don't want any surprises. You don't want the strategic meeting to be like, oh, anybody braced against you. Try to already work all that out before you get into the room. If you work remote, or you're not located together, shoot them a message.
You know, be open, like it can be intimidating. You're like, oh, I don't wanna like Slack the CFO, but you're gonna be in the strategic meeting with them on Wednesday. You need to. Send 'em a Slack. Again, I'm excited to be a part of it. I've got lots of ideas. Again, depending on what the role is that you're going to take in that meeting, make sure you solidify that and be like, oh, I'm, you know, I'm excited to be involved.
Anything, just get them to know your things and that you're gonna be there. So it's not a surprise when you're there. My last hit, like triple check any presentation materials you have. It has to be perfect. No mistakes. Every number needs to be accurate. Reward needs to be spelled correctly. That presentation needs to be perfect because if anybody is, you know, on the offense about having you be included, it's very quick and easy for somebody in nitpick and discredit you.
And essentially, you know, try to be, it's like gate keeper behavior. Just to be like, oh, well, that slide was a hot mess, so we're not inviting her back. She doesn't know what she's talking about. Do not give anybody that opportunity. Quadruple check any presentation materials. It has to be right.
Galen Low: I love that's resonating with me so much because I do hear it a lot, right?
Like technical difficulties, you know, like poor presentation prep, you know, mistakes in the reporting in the data. And then just that like, that awkwardness of like, why is this person in the room? Like, all are things that on their own or together can just, I've seen them be career limiting, like legitimately career limiting.
Because the folks in the room are like, yeah, we'll won't have you back. And that's all it takes. That's really all it takes.
Olivia Montgomery: That's all it takes. Don't give 'em that excuse. You know, you can come back from a lot of things. But inaccurate, unthoughtful presentation material is a, I don't know how to come back from that.
I'm, I don't know. That's another podcast.
Galen Low: Then you start again. See you in a few years, everybody. I gotta.
Olivia Montgomery: Just quit and start somewhere else. I dunno. That's your losses.
Galen Low: Yes. But I think even with the preparation, I think, you know, the other element is something that we're talking about already, which is just in the room.
How can you, sure, preparing for it. Make sure you come to the table smart. Make sure there's no mistakes. Make sure that you've kind of set that expectation and you're ready to do what is expected of you in addition to, you know, whatever contribution you hope to have.
But then once you're in the room, like what's the best way for a project manager or anyone new to strategic planning, what's the best way for them to contribute without just seeming like they're just this like awkward, passive observer sitting in the corner? Like, how can they make themselves heard and also get taken seriously?
Olivia Montgomery: Yeah, absolutely. So one of the first things is don't be afraid to speak up. You need to be seen as confident and helpful to this group, and you need to be showing business value to them in that meeting, pretty much right away.
Even if you're invited just to take notes and that's how you know, ensure way into the door. There's still going to be points when people are asking questions or there's a discussion and you know that there's a point of view they're not considering or there's information that they don't know.
That's where you can like very, you know, respectfully and helpfully interject and be like, Hey, let me, you know, share some insight that I have on this. So don't show up to be a note taker and only take notes, because that could be solidified as your role and it can be tougher. The second time, you know, around to like inch forward, try to inch forward in that meeting.
So speak up, you know, know that you need to be seen as a go-to resource and extremely helpful. Helpful people speak up when it's needed. So don't be afraid to say something, and do say something, in fact. Keep in mind that this group, the IT, you know, ITAC whatever steering committee, whatever name, you know, your company uses, they meet regularly.
They meet about other topics. They probably golf together depending on what kind of company environment you have. They're comfortable with each other. They already see each other as peers, and you're entering into that dynamic as an unknown. And that's gonna be taken by different people, different ways.
So just know that they're gonna be comfortable and confident and relaxed when the meeting starts. You need to match their energy. If you're coming timid or meek or overbearing and trying to, you know, control everything, it's not gonna go well match their energy. Other thing is just show your passion, show your knowledge, but yet also be succinct.
As PMs, you should know the objective of the meeting, and make sure that everything that's happening is moving toward that objective. If, you know, conversations are getting sidetracked or emotional, remember the meeting objective, just like you would do in your project team meetings. And try to like get everybody back to the conversation.
Another thing is if you are doing presentation slides, which often people are, again, use your PM knowledge and experience of running meetings and know which information needs to go first, what needs to go last. If you know there's a contentious yet really important project up for review, cover it first.
Those are all the kinds of things that maybe even whoever was previously doing that work, they weren't doing. And so you can immediately be given business value by even just knowing how to structure, you know, the information that you're giving. So really rely on your own experience, you know, and your ability to lead teams and what works for them.
We're all still just people. So remember to be passionate, be engaged, be helpful, speak up, but match their energy so that you're not, you know, seen as meek, nor threatening.
Galen Low: What I think is great about that is this notion of, you know, we say know your audience a lot. And sometimes it's like, well, what does that really mean? But all the things you said there in the prep as well, right? Understanding who's gonna be at the table, what are they like? Understanding that some of them have relationships with one another.
You're the newcomer. Knowing that you've got to sort of match that energy so that you are part of the conversation and not this, just this awkward, you know, intrusion into it. And then just that whole, like understanding what's important. And what I like about it is, like that is strategic.
Like you wanna talk about being strategic for an organization. Well, guess what? It has to do with being strategic with the people around you and the people in the room. And if you're gonna say, Hey, I know this project is contentious. Let's talk about it first. Like, that's already a thing that's like, okay, all right.
Like that's a different way. You didn't just blather on about your slides in order, you know, you've been thinking about this. And I've seen that be something that the folks in the room, senior leaders will respect. I've also seen the opposite. All those things together go wrong where, you know, kind of that timid or overly sometimes emotionally charged, sometimes blathering on and taking up too much time on stage and not really being clear and succinct with your point and not really understanding what's important to that audience.
I've seen that, I hate to say it, but I've seen it be like a career limiting move. And those folks are not invited back for a while for what seemed like petty reasons, but actually are the core of being strategic. Period. Like not just strategic planning, not just, you know, ITAC stuff, nothing to do with technical knowledge.
It's like people knowledge and, you know, for better or for worse, it is a high stakes performance. But guess what? So is every interaction at that level. So I think all those things, what I really love about it is just that whole know your audience. You just really put a whole bunch of structure within that for folks who are like, I don't, you know, I kind of know what that means.
Everyone just keeps saying it. What does it actually mean? Those things you said.
Olivia Montgomery: Yeah. I have a couple tips that I like to share specifically for, you know, what you just brought up. So it's a couple of things. If you've not been in a strategic planning role in any level company meeting, do that first multiple times.
Hopefully, you're a project manager who has managed multiple projects and you're already used to kind of discussing, maybe depending on the size of your business, hopefully you're already kind of discussing things at a program and portfolio level. So you need to be having the discussions with somebody other than C-Suite multiple times.
Otherwise, you're probably not ready. Like, don't jump into this too early. Otherwise, exactly what you said, you're gonna be uninformed. You're unprepared, you're not gonna have the finesse, you know, whatever. It's gonna be different for every person, but make sure that you've done this multiple times in smaller, you know, lower stakes meetings.
So whether that's your meeting with directors, or supervisors, whatever it is, make sure that you've had, that you've taken on that role in other meetings first. You need to be comfortable being seen as a go-to. You need to be comfortable answering tough questions. You need to have already practiced stereo conversation away from emotions and to, you know, facts and objective data.
Another thing that I have seen people do is they will learn who the players are and what their motivations are. So getting to know motivations was something we talked about in a previous episode. I'm a huge proponent, you need to know is somebody really driven by data? Is someone really driven by feeling?
Is someone really driven by themselves? Everybody has different things that they value. They have different types of information that they value. Hopefully before you get into that meeting, you've had enough exposure to that person, to each person on the committee to know what it is. You know, your CFO probably just wants to know how much it costs.
You know, what's the ROI? They want the numbers. So make sure you have the numbers very clear in the presentation. But do not say, oh, hey, you know, CFO, I know you're the numbers person, so I made sure to include this. Don't say that. I've seen a lot of people think that it's like, oh, I'm showing that I know you and I'm giving you the information that you need.
And from the person doing it, it does feel, it can feel like the right thing to do. But for the person receiving it, it often comes up, especially as a senior leader, it often comes off as, I don't know, it's not usually taken the right way. Just give the information. Just know that's what they want.
You know, you have the facts and numbers for so and so. You have, you know, the business value for so and so. You have the, who has the buy in and how good and fun and productive it's gonna be for so and so. But don't tell them, oh, I included it for you. I included this for you. No one wants to be typecast.
Nobody wants to feel like somebody else knows them in and out. Don't do it.
Galen Low: Yeah. That would be my reaction. Like, you don't know me. And also classic bond villain when they're like, here's my plan. And you're like, okay, well, now you've shown all your cards.
Olivia Montgomery: Right, exactly. It just, it doesn't go over well.
I'm not exactly sure how that disconnect happens, but I've seen it a lot. And like I said, as the person doing it, it usually does feel like the right thing to do. Like, oh, I'm so helpful. But it's not received well.
Galen Low: And you can also be wrong. That could be awkward.
Olivia Montgomery: That would be the worst. Yeah.
Galen Low: And one thing you mentioned was the fact that some people, they might shut you down because they feel threatened by you. Have you experienced that? And if so, how did you navigate it?
Olivia Montgomery: Like for example, I had an early on manager who used fear as his like, form of control. Everything he did was just sharing consequences. If this isn't done, you know, we might have to cut back head count. You know, promotions are gonna be on the line. He was very fear-driven. As I was getting more exposure to senior leaders, you know, this is when I was even still a business analyst, and only running like small IT projects.
People were like, oh, she, you know, she knows things like I can ask her questions, you know, she's really insightful and he was feeling threatened by that. He once went so far as to tell me that one of the C-suite doesn't want me in meetings any longer because I'm not helpful. And they just didn't, they just don't like me.
And I was heartbroken. I was shocked. It was awful. I was like, well, there's my career. I overstepped. I don't know what I'm doing. I don't have the support of my boss. Like, great, I need to go back to teaching English cuz I made a mistake. Right? But you know, I luckily, I talked to my mom about it.
I always recommend talking to somebody who's experienced and you know, has done stuff that you look to do someday. Thankfully for me, that's my mom. And she told me to just go head on, be transparent, be who I am and address the issue. She's like, if your performance is bad, you need to apologize and ask for feedback.
And I was like, okay, cool. And then she was like, and if they didn't say that, which I have a feeling they probably didn't say that, you'll expose, you know, the real feelings. So sure enough, I went through, I emailed each of, some of 'em were C-Suite too. I emailed them. I cc'd my boss, I apologize. I said, Hey, you know, my boss gave me the feedback.
My performance was lacking. I deeply apologized. Is there any specific feedback you can give me, you know, so that I can improve? I wasn't sure what to expect if, I didn't know what was gonna happen. But I know that doing that was true to who I am. I knew that I would either get honest feedback and stuff to improve on, and then at least I could have a path forward.
It ended up being, you know, what my fear every single person I emailed either emailed in response or came and talked to me in person saying, I didn't say that. No, I think you're great. We really like your work. Like, we're really sorry there's a miscommunication. Like, none of that's accurate.
And I was like, ha ha ha, validation. So I knew, and then I was seen to them like, oh, I'm not gonna let issues bubble up. You know, like, I'm gonna address stuff head on. And I always had that. That was always my approach. Like if anybody brought up something, I didn't just let it, you know, bubble and tension and fester and create drama.
I was like, Hey, I'm sorry, you know, this happened. What can I do? That Mander didn't stay with the company very long after that. Obviously there were other issues that were going on and he was building a rather toxic environment around him. And he moved on not too long afterward, and I stayed and got his job, actually.
So it works out sometimes, but yeah, again, it's just being who you are, being transparent, and always doing the work. Not just like letting stuff fester and bubble under. And then that way they also knew that I would be transparent and when I did get, you know, give back up, you know, into the ranks, like I said, they asked me to take his position when he left.
Because they were like, yeah, like you're not gonna take shit from everybody. You're not gonna let somebody manipulate you. And you're gonna get the facts out on the table. We saw you do it. So.
Galen Low: I love that. That's pretty wily. But also, you know, the thread that I'm seeing going through this whole conversation is that, you know, sometimes you have to take on those uncomfortable conversations and just tackle them because the repercussions of not doing those things are going to be a lot more uncomfortable.
Right? Letting it fester, right? Or, you know, not reaching out to somebody who is C-level and will be at that strategic planning in a couple weeks time, versus showing up in the room and being like, wait, who are you? Why are you here? Right? Like, there's some discomfort that you can endure in order to come out on top and really just figure out where you stand and set yourself the best stage to succeed.
Which is a whole different kind of strategy. We started talking about strategic planning, but you know, there's this whole interpersonal dynamic strategy that is important as well.
Olivia Montgomery: Yeah, it's some of the most important, because it's what can trip you up really quickly. Yeah. Projects can, you know, go over budget and, you know, miss their deadline and you can discuss all of that, you know, at the project level and with the strategic team.
You know, problems that are discussed are problems that can be solved. So you have to be the one that's willing to, yeah, make yourself a little uncomfortable depending on your personality type. And then on the other side too, if you're a really strong personality type, you don't wanna be overbearing.
You don't want to, I don't think it would've turned out the same for me if my boss had, you know, given me that false feedback. And then I came back and I was like, why did you say those things about me? Like, why did you do that? And I overcorrected to be like, nobody's gonna walk on me. It wouldn't have turned out the same way.
So it always comes back to, you need to know what are you trying to do and how is it gonna be received from the other person? You know, it comes down to we talk, you know, or there's idioms around that are, 'We judge ourselves by our intentions, but we judge others by what they say'. And that disconnect doesn't work really well.
You need to clearly share your intentions and also give other people, even if they say something, and it comes off wrong or you're not sure or you know, I was pretty confident these people hadn't have said my performance was terrible cause that's not how it felt in the meetings and in the rooms. So I was fairly sure, but I also, you know, wasn't certain, maybe they were being nice to my face and turned around and told my boss like, absolutely that could be happening.
So I needed to know not just what their words were, but the intentions behind it.
Galen Low: Love that.
All right, last question. I mentioned earlier that a lot of project managers I talked to want to be more strategic, but there's not that many seats at the table. Not everyone can be part of strategic planning. So outside of strategic planning, what is your top tip for project managers who want to be seen as a strategic partner for their organization or for their clients?
Olivia Montgomery: Yeah, absolutely. So I have two, and they go hand in hand cuz you, you can't successfully do one without doing the other one as well. So the first one is know the lay of the land. I mean that in the broadest sense possible. Know what your IT infrastructure is. What are your capabilities? What are the restrictions?
Know your IT landscape. Know what their roadmap is. Know the challenges of the business. You know, what's making money? What's losing money? Where is the company going? What challenges? What are we doing well? What are we not doing well? Know the lay of the land of the business at the very high level. And then also know the lay of the land of the committee.
What is your ITAC structure? Who exactly is in those meetings? What is their role? And again, back to the motivation. What is their motivation? Do they wanna know the numbers? Do they wanna protect the budget? Do they want to be seen as really competitive, you know, that the company's really competitive.
What information do they value? So you need to know, yeah, the business operations, the business value, the IT lay of the land, and the structure of the meeting. Who's in it? What do they care about? What do they want? The next prong of that is have ideas. So be the person who has enough information.
Like I said, you know, the lay of the land. So you should be able to answer questions, have ideas. So be the person that when, you know, discussions come up or decisions need to be made, or someone misrepresent a challenge that you speak up and you're like, Hey, I've got a solution to this.
Don't get into the nitty gritty of why the problem happened in the first place, who's to blame. Don't be that person. Be the 'has ideas' person. And like I said, you can only do that when you already kind of know the lay of the land. But two senior leaders, you need to be the person who always has good ideas and good too, of course.
That's why they're intertwined cuz you can't just show up and have ideas. But then people are like, oh, we don't even use AWS. Why are you talking about that? That's gonna be terrible. Don't do that. But also don't go in and just like, no. You know, be like, oh, I know the infrastructure of everything. I know the layout, I know our problems, but you guys figure it out.
Don't be that person too. You have to bring both to the table.
Galen Low: There you go. There you have it.
Olivia, as always, such a pleasure having you on the show. Thank you so much for sharing your insights and your stories. Congratulations again on the report. I will link it in the show notes because I just think it's such an interesting read and an interesting take that is specifically for project managers, but equally for organizations who are thinking about how to improve their strategic planning process.
And as always, just love having you on the show. And there's a couple threads in there that we could do a whole 'nother series of episodes on, just from that interpersonal side of things. And probably let's make a diabolical plan.
Olivia Montgomery: Yeah, I think I think we could. I would really love to see, love to help people with their specific situations.
You know, I share a lot of my stories about, this was a particular manager, and this was my case. This was, you know, my boss. This was my ITAC. I would love to also help people, you know, with their specific, you know, but, oh, my boss, you know, this is the problem. How do I navigate that? How do I figure out this person's motivations?
Or what even are motivations? I don't know my own. Yeah. I think, as specific and as applicable, you know, hopefully people can find, you know, my insights, my research and my stories, and kind of glean from it what is gonna help them in their roles. I don't wanna just be sending out information, you know, that's just worthless.
I wanna be as helpful as possible. That's always my thing. So, yeah, I look forward to discussing more and I hope people learn something and, you know, have ideas.
Galen Low: Love it. Thanks again.
So what do you think?
Should project managers be involved in strategic planning? Or does that sound more like overstepping the bounds of the role?
Tell us a story: how have you gotten yourself involved in strategic planning, and how did your first strategy meeting go?
And if you want to hone your skills as a strategic project leader, come and join our collective!
Head over to thedigitalprojectmanager.com/membership to get access to a supportive community that shares knowledge, solves complex challenges, and shapes the future of our craft—together.
From robust templates and monthly training sessions that save you time and energy, to the peer support offered through our Slack discussions, live events, and mastermind groups, being a member of our community means having over a thousand people in your corner as you navigate your career in digital project delivery.
And if you like what you heard today, please subscribe and stay in touch on thedigitalprojectmanager.com.
Until next time, thanks for listening.