DPM Podcast

Can Psychology Make You A Better PM? (with Olivia Montgomery from Capterra)

By 12/10/2021 October 19th, 2021 No Comments

Galen Low is joined by Olivia Montgomery, a Senior Analyst at Capterra. She shares how her blend of PM skill and background in social sciences helps her navigate personalities within IT projects. Listen to learn how psychology can make you a better PM.

Interview Highlights:

  • Olivia is an experienced IT program manager who is passionate about merging the worlds of social sciences and technology. Armed with a PMP, a CSM, and a Masters degree in the liberal arts, she now specializes in qualitative research and analytics, consulting on project management and small business technology strategies for none other than Capterra. [1:23]
  • Outside of work, Olivia is a competitive equestrian jumper and loves a good psychological horror film. [1:43]
  • Olivia dreamt of being an English professor. She also wanted to be a gymnast. She wanted to go to the Olympics as a horse jumper. [4:37]
  • Olivia’s jump into project management and IT happened after college. She took a job doing some writing for a payment processing company that also writes accounting software called Shift4. Their software development team is scrum style, and so she learned what scrum is, how teams work together, and what JIRA is. [4:51]
  • From working at Shift4, Olivia did start consulting as a business analyst gathering user requirements, writing QA scripts, and it just kept evolving from there. [5:43]
  • Olivia’s first “official” project was as a BA for the company going public and replacing their ERP to be SOX compliant. [6:45]
  • In Olivia’s last role when she was heading up the IT PMO, she was actually a client of Gartner’s. She was working with their analysts and getting help in how to mature her processes and everything. [8:58]
  • Moving from an operational PM role to an advisory role at Capterra, Olivia’s day-to-day work is to survey and talk to SMB leaders about their tech problems or software problems, and really getting to understand what they need help with. [9:36]
  • Executives and leaders are MBAs and marketing types, IT study computer science. So the two have opposite training in communication styles and value different types of communication. [19:13]
  • Olivia recently saw in Psychology Today (a publication that she reads regularly) Dr. Erin Leonard’s article called, “High EQ Is a Superpower“. Dr. Leonard is a psychologist, and she wrote specifically an example about a project manager and their reaction if they had high EQ versus a low EQ, and how that would have a compounding effect on their project. [20:24]
  • Studying language, narratives, stories, and characters for over a decade has given Olivia a “bank” of reference to pull from that helps her relate to more people than if she didn’t have that experience. [25:05]

“Social sciences promote and train a flexibility in the mind, unlike any other area of study that you possibly could.” — Olivia Montgomery

  • One aspect of stakeholder management in a technical project is requirements gathering. You gather requirements from your executives, department leaders, managers, supervisors, actual users of the software, the people writing the code, your engineers, your QA testers. They also have to understand what’s happening. [28:55]
  • The other aspect of stakeholder management in a technical project is meetings. It’s where you have all the personalities together and you have to be effective with your time, effective with your communication. You need others in the meeting to be effective with their time and their communication, so that’s when everybody finds it comes together and it can be either a really successful meeting or a very not successful meeting depending on the prep that you’ve put into it. [35:11]

“I am a very strong proponent of categorizing, labeling clearly the meeting type that’s happening.” — Olivia Montgomery

  • If you’ve done your meeting prep and the people know what’s expected from them specifically when it’s their time to share their information, you need to really listen to how they respond and what they’re saying. [40:47]

“Not forcing people to perform the way you want them to in a meeting is important, because they’re going to be scared to join your next meeting.” — Olivia Montgomery

  • Olivia’s advice for those who do not have a social sciences background and still be able to build it into their project management style is to balance out your team. If you get to hire or select your own team, don’t be afraid to recruit from social sciences for IT project management. [56:44]
  • Olivia’s tips for someone who wants to get better at being an emotionally intelligent project manager or leader in general is to find a mentor, watch films, read stories about people and pay attention to the characters and apply the lens of your role. [1:02:01]
  • Olivia recommends a television series from HBO called, “White Lotus“. It’s one of the current shows that she has seen to tackle perception, motivation, biases, and just like clashes of the characters up against each other in awkwardness. [1:06:38]

Guest Bio:

Olivia is a Senior Analyst at Capterra who is passionate about sharing insights related to project management and small business digital transformation. She pulls from her experience as an IT PMO leader as well as her background in humanities studies to deliver data-driven insights for small business leaders. Her work has been published in TechRepublic, CIO Dive, and TrustRadius. When she’s not researching tech trends, you can find her horseback riding or watching Jurassic Park.

Can Psychology Make You A Better PM Headshot

“If you’re in IT, you’re trying to make software and technology work for people, not work for robots.”

— Olivia Montgomery

Resources from this episode:

Related articles and podcasts:

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.

Read the Transcript:

Galen Low

Project personalities. We probably all have something pop into our heads when those two words are combined. Maybe you had a nickname for that one stakeholder that could never make up their mind, or maybe you played Buzzword Bingo whenever that account lead was presenting the team’s work. Maybe you had a big party that one time your otherwise unemotive project sponsor smiled a little bit and said, “Good job, everyone”.

It’s all good fun, but here’s the clincher: as project managers, navigating these personalities is our job. It is a core part of our skillset. It is the unquantifiable thing that makes us succeed or fail at delivering projects successfully.

So why isn’t it taught in formal project management training? Can it be taught?

If you’ve ever struggled to navigate the quirks and nuances of the various characters involved in your projects, keep listening.

We’re going to be taking a deep dive into some organic ways of developing a human-centered approach to stakeholder management by drawing from social sciences, your own lived experiences, and even pop culture, so that your projects feel less like a Dilbert comic and more like a scene from Cool Runnings.

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 lead our projects with purpose and impact. If you want to hear more about that, head over to thedigitalprojectmanager.com.

Hey everyone — thanks for hanging out with us on the DPM podcast.

My guest today is an experienced IT program manager who is passionate about merging the worlds of social sciences and technology. Armed with a PMP, a CSM, and a Masters degree in the liberal arts, she now specializes in qualitative research and analytics, consulting on project management and small business technology strategies for none other than Capterra.

Outside of work she’s a competitive equestrian jumper and loves a good psychological horror film.

Folks, please welcome Olivia Montgomery. Hello, Olivia!

Olivia Montgomery

Hey, thank you Galen for having me. I’m really excited to be here. The DPM has been a resource that I’ve gone to for a majority of my career, so very excited to be a part of it.

Galen Low

Awesome and great to have you here. I’m so glad to hear you’re a fan. I’m so glad that we were able to help you out, because I’m also very impressed with what you’ve done with your career, which we will get into. So great to have you on the show. And you know, it was really fun that along the way we actually found out that we had something else in common, which is film.

And you were saying to me that actually before your life as a PM, you actually wanted to be a Director of Photography?

Olivia Montgomery

I did. I love movies. And I just love getting into how they set a mood and a vibe and how it’s shot. And yeah, absolutely love it.

Galen Low

I love that. I, so my background is I did my degree in film studies and before I wanted to be a PM, I want it to be actually someone who edited trailers. I wanted to be a trailer editor. That was my dream job. So a little snippet about me.

Also, a little bird told me that you manage one of the most complex and yet the most organized spreadsheets that she has ever seen. And I’m wondering, do you consider yourself like an Excel guru?

Olivia Montgomery

Guru? I don’t know, but Excel is my favorite software program probably ever.

I know it’s weird, but I can tell you no other program has ever come close to being able to manage that much data and help me out, and it’s just speed things up. I even sometimes use it for qualitative data analysis, not just quantitative. So it’s amazing. I love it. There’s no other replacement for it.

Galen Low

You know what? Honestly, I am with you.

I feel like it’s a reflection of how our brains are actually structured. I’m saying just not from a scientific standpoint, but I feel like some days I think in spreadsheets, and dream in spreadsheets and yeah, there’s something comforting about a spreadsheet. So I am completely with you.

Olivia Montgomery

Yeah, absolutely. The best.

Galen Low

God bless spreadsheets.

All right, let’s get into it. One of the things that you and I have been talking about lately is like this wide spectrum of personalities that are involved in any modern enterprise IT program. And just how important it is to have not only strong project management skills, but also really strong people skills to drive outcomes effectively.

But to start, I wondered if maybe you could just tell us a bit about the professional version of you. When you were young, did you want to be a project manager like I did?

Olivia Montgomery

No, don’t be shocked, but I did not. I dreamt of being an English professor. That’s what I always wanted to do. Hence, my background in that but I also wanted to be a gymnast. I want to go to the Olympics as a horse jumper.

Project management was not on my radar, even through college. My jump into project management and even IT happened pretty quickly after college. So I took a job doing some writing for a payment processing company that also writes accounting software called Shift4.

And they’ve been in the news lately as the CEO is currently orbiting the earth for three days in the first civilian mission. So it’s a pretty innovative company and I’m proud to have kind of gotten my, cut my teeth in IT with them. Their software development team is scrum style. And so I learned what scrum is, how a teams work together, how it all, what JIRA is.

And I loved it. I really loved my experience there. From there I did start consulting as a business analyst gathering user requirements, writing, you know, QA scripts, and it just kind of kept evolving from there.

Galen Low

Yeah and for folks who are interested, my space buffs out there yeah. Inspiration for documentary on Netflix now. Documentary, episodic, it’s a, it’s a whole show, isn’t it?

Olivia Montgomery

Yeah, whole show. Yeah.

Galen Low

Super cool. So then he’s in space. Awesome.

All right, back on topic. I wondered, I mean, yes, learning about scrum and IT, and all that so can you tell us a little bit about the projects and programs that you’ve managed in the past?

Olivia Montgomery

Absolutely. So when I say my first “official” project I was a BA and for an IT project manager in the IT PMO and I was brought on as the company was going public.

So they had to overhaul their ERP system, the blue we replaced it actually to one that would be SOX compliant. And we had to get that done before, before the company went public. So it was a pretty hard deadline and pretty critical to get right, and I loved it. During that, at that company, even they purchased a lot of other companies just kept bringing them in and I was on the projects to help integrate their systems, replace their systems, deprecate the ones that we didn’t want.

And then if we did keep their projects their systems, we also had to integrate into the data lake that we’ve had. During my tenure at the company they also started building homes, just started this entire new ARM and it was so much fun, cause then we’re like, you have like a whole new company that we’re like starting to build out.

And I was lucky I was the head of the IT PMO by that time. So it’s super fun to work on building out an entire new branch of the company.

Galen Low

So to sum it up, you work on very simple, low stress projects, and very static environments that never changed.

Olivia Montgomery

Absolutely. Shoestring budgets, stuff that nobody pays attention to.

Galen Low

The same thing day in, day out. You know, IT then building homes, your average boring stuff. That’s such a cool journey. I love that.

And then today you are a research analyst at Capterra, which doesn’t really sound all that project management-y, but actually sort of is. And I wonder if you could just paint a picture of what your day-to-day looks like and what you love most about your current role?

Olivia Montgomery

Yeah, absolutely. So in my last role, when I was heading up the IT PMO, I was actually a client of Gartner’s and was working with our analysts and getting help in how to mature my processes and everything. And I loved Gartner. So when they reached out and they were like, Hey, Capterra needs, you know, an SMB focused and we like you. I jumped, sold our house, moved off in Texas, and jumped all in.

I couldn’t believe the opportunity. So yeah, so moving from an operational PM role to an advisory role, at Capterra I, day-to-day I’m working on you know, I survey and talk to SMB leaders talking about their tech problems or software problems, really getting to understand what they need help with.

And from there I design a research approach that always includes surveys of maybe users, other SMB leaders, IT folks, IT leaders, and come up and do my, you know, data analysis and then write a report. What I really love about Capterra is we’re able to publish those reports at no cost to anybody who wants to read them.

You post them on the Capterra website, and that way SMB leaders who don’t have tens of thousands of dollars to do custom research, market research, you know, advisory, and just get recommendations from professionals, I’m able to provide all of that at no cost to them. That’s what I love. I love helping those innovative, driven SMB leaders ’cause SMB’s just a whole other, you know, they’re not Coca-Cola. They’re not NASA, you know, they’re out there, they’re gritty and they need all the help they can get. And I’m really excited to just be able to provide them the resources they need.

Galen Low

I love that. And you’re so right. I mean like that level of data and reporting used to be, you know, only for that echelon of organization that can afford the really big budgets, that can afford to, you know, have Gartner on retainer.

But now data is just so important for making decisions and evolving any industry. So I love that. I love that mission. It sounds really exciting to be a part of that, to just make that data available so that some of these smaller businesses can really succeed.

Olivia Montgomery

Yeah. And I always try to blend best practices I pull from my operational experience. So it’s not just data analysis and dry survey reports, you know, for her to take it out of your chart. I really try to be like, yeah, this is what we found, but then pull from my personal experience. You know, I’ve been in with the exact begging for budget. Budget buddy, wanting everything to get approved.

And trying to balance I’ve been, I’ve been caught in the elevator with them when they’re like, Hey, what’s the status update on this? And you gotta be on it. You got to be there. And you’re like, oh my goodness. So yeah, I really try to blend my professional experience so that I’m able to offer hopefully the best of both worlds in the reports.

Galen Low

I love that you’re a researcher and you’re a practitioner. That’s so cool.

Olivia Montgomery


Galen Low

Okay, let’s do a quick level set just to give listeners their bearings. I think that a lot of people are really quick to oversimplify the personalities within a stakeholder ecosystem of an enterprise IT program.

I’d even say that a lot of PMs still operate based on like the satirical archetypes from the world of Dilbert, including that cynical dog. It’s really not about that. I mean, stakeholder management, even in your most technical projects is about bringing together really unique and disparate personalities, it’s about aligning competing priorities, and it’s about navigating a wide spectrum of emotions.

And in our working title for this episode we’ve actually used the term psychology, but I think what you’re really all about is just social sciences at large — the humanities — and how that should be a part of project management training.

So the first question is, what do you mean by social sciences, and what’s the relationship between social sciences and stakeholder management?

Olivia Montgomery

Yeah, absolutely. You nailed it that we work with people, you know, especially if you’re in IT, you’re trying to make software and technology work for people, not work for robots and people are complicated. They have different values, different motivations relating it back to social sciences, specifically, you know, my background studying language and literature, you’ve got different characters and they want different things.

They respond to different things differently, and you have to know. You have to know how to communicate based on how they’re going to best receive information.

And you can’t treat everybody the same cause it’s going to be a very unsuccessful project for you. And probably even an unsuccessful career, I would even venture to say.

Galen Low

I think that’s absolutely, yes. But I love that notion of characters too, right? And I’m like, yeah, actually sometimes you know what? You do encounter the dog from Dilbert. But you know what, most of the time, it’s not the person that you expected it to be. It’s like a little bit of a spin because everyone is so unique.

Would you say that social sciences needs to maybe be a little bit more at the forefront of technical project management and how it’s trained?

Olivia Montgomery

Absolutely. A hundred percent. You’ve got, you know, your business stakeholders are executives. They have MBAs often, they’re marketing leaders often that have been promoted up.

But then the people doing your actual work studied computer science, you know, formally or informally they work with IT in code and machines. Those are really different people that have to come together.

And when you have, you know, high emotional intelligence and a background in social sciences, you can be that bridge, and project managers are the perfect person to be that bridge. You don’t need the MBA executive. You don’t even want them to be giving requirements to your software developer. That would, both of them would be really frustrated immediately. So you need to be that bridge.

Social sciences are they’re, I think they’re kind of coming out as you know, as being important in tech and software.

I even recently saw in Psychology Today a publication that I read regularly. Dr. Erin Leonard has an article called, “High EQ Is a Superpower”. She is a psychologist. And she wrote specifically an example about a project manager and their reaction if they had high EQ versus a low EQ, and how that would be a compounding effect on their project. Little, you know, preview, the high EQ response was more successful than the low EQ response.

So yeah, we’re even seeing project management in Psychology Today, which is fantastic.

Galen Low

I love that. And thank you for sharing that article with me as well. I shared it within my community and I’m like, I just feel so seen right now. Psychology Today is talking about project management and not the reverse for once. And that’s awesome. I’ll actually put the link in the show notes so that we can give Dr. Leonard a little bit of a shout out from our side of the of the industry as well. I think that’s so cool.

And you know, we do, we talk a lot about you know, leading with emotional intelligence and I know it’s kind of like a trending topic right now, but what I love is that sort of incorporation of, you know, not just not just that high EQ leadership style and super power but also just like the background in terms of like, understanding like the characters in the mix and the motivations. And yes, there’s, you know, there’s a lot of material out there right now on, you know, emotional intelligence. But I love that connection with the social sciences.

And as you mentioned, your background’s in like literature and you know, what are we doing if not actually kind of living out a piece of literature that is our working lives in, in our professions. And I think that’s such a cool like thread to connect it all together. And then even I’m in the process of, this is a bit of a tangent, but in the process of reading the PMBOK 7th Edition which from the Project Management Institute, which is a pretty market departure from the last edition especially as it comes to stakeholder management and talking about like personality dynamics.

So it’s really good to see it coming like right into the mainstream of project management training. And I’m not through the entire PMBOK yet. But it struck me that like, yes, this is, it’s really starting to resonate and people are really starting to understand that like most of the job is actually people over process.

And I think that’s such a cool spot to be in.

Olivia Montgomery

Yeah, absolutely. I’m almost disappointed you didn’t finish it in one night. Should just like sit down with a PMBOK and just blast it out.

Galen Low

Cover to cover. Yeah. It’s super enthralling. It’s actually a lot more compelling and readable than I think when I did my PMP, it was the fifth edition.

And yeah, it was like that, like Rita Mulcahy. Like bless her heart for creating a less dry interpretation of PMBOK, that edition that I was reading. Yeah, that, that helped me kind of treat it a little bit more like something I could read at night for leisure.

Olivia Montgomery

Yeah. They’re evolving, like we all are – learning and evolving.

Galen Low

Seventh edition is very cool. It’s very exciting. So, for those of you who are into it have your PMP or looking to get your PMP or just interested in the PMBOK. Yeah, it might be worth reading reading this has got some really interesting stuff in it. But I digress. Let’s get us back on topic.

You mentioned your background is in literature and language. I’m just wondering, how do you use your background in the social sciences to approach your IT projects? Like, do you employ some kind of frameworks or are you the kind of person who does like personality assessments for the team and for the clients?

Like, are you psychoanalyzing everybody? How’s your approach?

Olivia Montgomery

I actually, I feel it’s really important to not psychoanalyze everybody. You know, I’m not a professional psychologist and that can be kind of awkward in a work setting. So I’m not advising that. Though I, you know, it’s really good for self discovery, but I would absolutely never be in a meeting, listening to somebody and be like they are definitely the cynical dog in the Dilbert cartoons, and I’m gonna respond and work with them that way.

That’s awkward. I try to be really organic. But a lot of that is because I spent over a decade studying language and literature and books and characters and stories. Learning about different cultures, experiences, different aspects of people’s life from, you know, childhood to on their death bed. So I, it’s a lot more natural just having decades of research there. Social sciences promote and train a flexibility in the mind, unlike any other area of study that you possibly could. And that’s what’s really interesting, is it helps you listen to not only what somebody is saying, but also how they’re saying it. What they’re choosing to say, what they’re choosing not to say. So it gives you that flexibility.

So yeah, really understand the person and the motivations behind, because everybody values different types of information. They value different outcomes of a project and you have to be able to manage and balance that successfully. So I feel like my kind of bank of reference from all these books and characters that I have helped me to relate pretty quickly just by listening to how people are speaking. So, yeah, sorry, go ahead.

Galen Low

Oh I was just saying I love, I, I love how organic your approach is, because I think a lot of, we’re trained, right? Our training as project managers is so much about process and inputs and outputs and procedures and what you’re talking about, like a lot of people in the project management world, when they’re sort of reaching out to that, you know, high EQ sort of leadership and management style, they’re give me a framework.

Myers-Briggs me, you know, like give me something where I can then put everybody in boxes, but actually the whole point is to actually not. What you’re saying is that everyone actually is an individual, you have to pay attention to them as individuals, you have to draw from your library of like your understanding of humans, whether it’s from your experience or from like, even something like literature and film and understanding like how humans and characters or how humans are portrayed as characters and how they are actually characters and working that into the way that you approach project management.

And I love that. There’s like, no, it’s not like a, some kind of rigid framework that I’m going to teach you. This is actually, it’s an organic thing. And it’s the social sciences, like the way it’s taught, the way it’s trained is about, you know, what is being said and also what is not being said, like, I think that’s so cool.

Olivia Montgomery

Yeah, the personality assessments and that have their place absolutely. You know, I’ve been an INFJ since I first took the test, you know, in high school I still get that result, but that doesn’t mean that’s all of me. And somebody couldn’t go online and just read one or two sentences of what an INFJ is, and then be able to truly build a successful connection with me.

It helps, like I said, I think it really helps self-discovery not so much how to professionally relate and get somebody to, you know, give their best in the project. So it’s a blend.

Galen Low

I like that. I like that. I wonder if we can kind of like, scratch the surface on that and double click and, and maybe you can tell me more about some of the, like examples or scenarios, or you might be applying that approach, like in a project management setting.

And just kind of like your, like, let’s get a little bit more into your mindset and model for incorporating social sciences into the way you deliver projects.

Olivia Montgomery

Yeah, absolutely. What comes to mind? So there’s two specific areas I’d like to dive into. First being requirements gathering, because that is a one-on-one experience that you have with all kinds of stakeholders.

You gather requirements from your executives department leaders, managers, supervisors, actual users of the software the people writing the code, your engineers your QA testers. They also have to understand what’s happening. Your architecture, you know, designer needs to, your IT architecture designer needs to know what’s going on.

So those are all these one-on-one conversations that you or your BA with SMBs, it’s usually the project manager because they have smaller teams. It’s all these one-on-one conversations you’re having with a multitude of personalities and a multitude of job functions. And that’s where you need to be able to relate, get them to open up and get them comfortable and make sure you’re clear on what it is you need from them.

So yeah, that one-on-one is, it’s reality of project management and you got to nail it and understanding who they are and what motivates them and what they can offer. Just helps it, helps everything all around the end delivery of the project is going to be much higher the more successful you are at that one-on-one engagement.

Galen Low

I really liked that and your background as a BA and I’m like, the thing I’m thinking about is like, you’re eliciting the story from them and you actually need to be good enough at sort of understanding the story, leading the story, eliciting the story so that then you can translate it to somebody, you know, who was kind of expecting it to be like, oh, you did that requirements gathering session. Did you come back with like 18 really solid user epics that we can then break down into stories?

And you’re like, not really. That’s not what came out of their mouse, but I interpreted it and I was that bridge and I helped to kind of gather the right information so that we can now build some great user epics or great user stories that you can now run with with your development team or your design team, or what have you.

Olivia Montgomery

Yeah. And that’s where the flexibility comes in, is you might speak to, you know, if it’s an account. You’re going to go in and do your one-on-one requirements gathering whether with an accountant and you get the information you need, but then you go to the department head and maybe they have a slightly different idea of what’s going on or what they want to be going on.

And you have to be able to identify like, oh, there’s a miscommunication here. Oh, we need to kind of bring these two groups together. Or even with your software engineer that maybe your executive has watched a little too much sci-fi TV and thinks that tech works a lot more advanced than it actually does.

As we know, we all still struggle with our internet. Come on so stuff doesn’t always work quite as they do in the movies and they’ll have expectations or requirements that way. And you don’t want your software engineer to feel like they, their work isn’t valued. So you need to be able to yeah, have that flexibility of like, okay, I’m going to return back to this person respectfully showing their value, but changes need to be made.

Galen Low

I like that. I have this note here that says, ‘Good PMs are Babel fish.’ So for all the Douglas Adams fans out there for folks who don’t know that the Babel Fish like a fish you can drop into your ear and suddenly you understand and speak every language.

And sometimes we have to do that. I mean, yes, as a business analyst, but also as PMs because we are driving that compromise in a way, right? Where we have to have that hard conversation of, okay, that’s not how it works, or we could do this, but it’s going to cost you like twice as much, it’s going to take twice as long and really doing that translation in a way that is going to really like get the response or at least be heard and understood the way we need it to be.

And that takes that human touch. That takes that understanding of a person as a whole person, not just as an INFJ not just as a Virgo, not just as a, you know, this kind of personality type. But as somebody…

Olivia Montgomery

Are you a Virgo?

Galen Low

I am not, but I find it they’re like the most stereotyped I find. Are you? Okay.

Olivia Montgomery

Most stereotype, yeah. You got me. That’s me. I am.

Galen Low

You know, my wife’s a Virgo. My, my sister’s a Virgo, all very organized lovely human beings that actually kind of do fit into that stereotype for better or for worse, but also so much more, right? So like all their experiences are different. The way they approach a problem is different. And all of these things are things that we kind of need to factor in when we’re like managing stakeholders.

You know, it’s like these two simple words, stakeholder management, like expectations management, right? It’s like a simple sum up of something extremely complex and extremely difficult to do well. And it’s funny that we actually have these frameworks of training to teach these sort of things without actually going into what we’re talking about today, which is like the personalities, the individualities, the nuances that we need to navigate to do that a little line item, right? That says stakeholder management.

Olivia Montgomery

Yup. Got to do it. Yeah. The other, the other aspect of project management so with requirements gathering, that’s your one-on-one relationships. The flip side of that is meetings as performance. That’s where you have all the personalities together and you gotta be effective with your time, effective with your communication.

You need others in the meeting to be effective with their time and their communication, so that’s when everybody finds it comes together and it can be either a really successful meeting or a very not successful meeting depending on, you know, the prep that you’ve put into it. And that’s where I feel like social sciences and your ability to identify and adapt quickly to personalities really shines. Or falls apart. Both happen, absolutely.

Galen Low

Yeah. Meetings are that thing that I find people loath partly because not many people do it well. And like you and I we’ve talked about this and like, there is this sort of performative aspect for sure, right in the room, always personalities, but like also it’s about like prep.

I wonder if you can maybe dive in a little bit like your sort of human-centered approach to setting up a meeting for success.

Olivia Montgomery

Yeah, absolutely. So I am very strong proponent of categorizing, labeling clearly the meeting type that’s happening. I want a decision-making meeting or a working session, or it’s a status update. Luckily, I feel like the pandemic has helped us learn that the status update types can usually be emails which is great, but that’s not always the case, especially, you know, with, you know, scrum stand-ups, that’s ideally in person. You have to say, and not just assume that everybody’s going to know this is a decision meeting, like no, name it.

In your meeting title, say, decision making the objective of the meeting is you’re making a decision on X. Be very explicit. The next is letting every person know who’s attending the meeting. What their role and expectation in the meeting is.

And that also helps you design the meeting that’s going to be effective because if you put someone’s name down and you don’t have specifically what they need to be bringing, maybe they don’t need to be in the meeting. So it’s a really good way to step back, prep.

I know it sounds like a lot, but it’s truly not. As a project manager, you know your project in and out. You’re able to really quickly do it. Sure it takes, you five minutes to write up your meeting, you know, objective and state who’s in it and what they’re expected to do. It takes some time, but it’s natural. It’s not scary. It’s a good habit to get into.

Galen Low

It’s like when you’re painting a room and you like, don’t do the masking and don’t do it like a coat of primer. And you keep wondering why paint always sucks because it’s annoying to do that work. And not many people want to do that work. They want to just like, get everybody on the invite and have no agenda and get everyone together because we’re just going to chat it out. Don’t worry.

Which is also why so many meetings fail. And so we went back to our theme it’s because we’re not sort of thinking that doesn’t incorporate the sort of like the motivations and emotions of humans, right? You’re going to drag everyone into a meeting where they’re not clear on what they’re supposed to do.

And it’s not going to go well because you didn’t do the prep and actually the superhero skill is taking the time to do the prep.

Olivia Montgomery

Yeah. Exactly. I love that analogy. Yes. I’ve redone my kitchen and tried to cut corners of, yeah, it’s spot on.

Galen Low

I like that, like you have these categories and that they don’t mix because I’m like looking at the list and I’m like, yeah, I think my entire career I’ve been trying to do all these things in one meeting. Let’s do a status update and get some work done and make a decision.

And and yes, that’s why it’s convoluted and exhausting. And, you know, even just like, you know, our fragile human minds switching gears so much even in that meeting or like tuning in and out, because it’s not relevant for me at a certain point. And I’m just gonna, I have to like bring myself back in after I’ve like checked my inbox for 10 minutes during a meeting or whatever.

It’s so important to kind of segment that out and like clearly label it, like literally in the title of the event. It’s like, this is a decision meeting. And here’s your role, right? I think that’s so important.

Olivia Montgomery

Exactly. State, write it out. Don’t assume anybody knows don’t, no assumptions. Write it out exactly what’s happening.

Galen Low

And what impact do you see in the actual sort of meeting itself? The real-time aspect, the performative aspect when you’re kind of facilitating, like how does that prep end up helping you?

Olivia Montgomery

Yeah, absolutely. So when, if you’ve done your meeting prep and people know what’s expected from them specifically when it’s their time to share their information you need to really listen to how they respond and what they’re saying.

If you’ve done meeting prep and your team is really solid, it all goes gloriously well and you hit all your benchmarks and you have a successful meeting, but that doesn’t happen ever. You’re going to see things in meetings where maybe someone is not talking and they’re withdrawn, or they’re not answering the question how you need them to, or how you expect them to.

Myriad of reasons, but essentially they’re under talking. That’s a red flag and you need to have a high EQ response to that flag. Don’t apply pressure to that person. Don’t try to force them into performing the way you want them to in that meeting. Meet them where they’re at. If something going on, probably miscommunication or confusion.

Often over-talking and under-talking is a sign of confusion on their role, their expectation, maybe the actual work. Sometimes it can be personal. I think Dr. Leonard, you know, touches on that in her Psychology Today article. So yeah, not forcing people to perform the way you want them to in a meeting is important because they’re going to be scared to join your next meeting.

If you apply pressure to them, that’s not, meetings aren’t the time for them to go exactly how you want them to. You need to try to accomplish your objective, but you have to be meeting each person where they’re at in that moment. An analogy I have going back, like pulling from my horseback riding.

We do all this training, I’m in lessons. My trainer is giving me information and I’m trying to incorporate all of it. Learning, practicing, training. When it comes time to go into the actual show ring, she has a way she wants it to go. Like she’s my project manager, right? And my project being a show. She has a way she wants it to go.

I go to the show ring and that’s my meeting, and she needs to be supportive and encouraging of what I actually end up doing. If I’m out there and she’s still trying to like train me during my show, I’m going to get confused. I’m going to get lost. I’m going to break my train of thought, like at that point in a show, in a meeting, she needs to just be supportive.

I know what I need to do, and I need to show up and do it. And if I don’t, if my horse stops at a fence and I go flying over a shoulder, it happens. That’s, you know, that happens and she needs to be supportive of what has happened. So it’s, don’t apply pressure to people and meet them where they’re at especially in meetings.

Be cognizant that you’re seeing their performance too. It’s not just about you, you know? Their responses are part of their professional reputation as well. And you need to be nurturing and supportive of that.

Galen Low

I really like that. We’re talking about defining roles for a meeting and sometimes we don’t think enough about our role actually as project managers, cause we’re like, okay, we’re casting, right? We’re like, we’re kind of control freaking out, right? We’re like, okay, you’re here to do this. And you know, and it feels very like, you know, like we’re kind of playing house a little bit, right?

Or it’s kinda like, okay. And then this happens and this happens. Okay? Got it? Go. But actually when you say go, your role is actually to make sure that the dynamics go towards the goal of the meeting, but that every personality and all the sort of interactions between these personalities, like it’s all improv from there.

You can facilitate but you can’t necessarily control and actually trying to over control. Well actually could take you a lot further away from your goal because humans are humans and they’ve got a lot going on. And like you said, it’s their sort of professional reputation that sometimes egos clash.

And if you apply pressure at the wrong time, you could actually have every, have it all, have it all shut down.

Olivia Montgomery

Yeah, and I think it’s important to think of meetings as not just, you know, the 45 minutes so long that hopefully your working session. That 45 minutes you’ve blocked off that’s the meeting but you need to expand your thinking to the meeting prep is part of the meeting and then post-meeting. Maybe in your environment you are required to send out meeting notes to summarize that’s something, you know, we all have to do, and maybe you don’t. But post-meeting, follow-up conversations are all part of the meeting.

So thinking of it a bit broader, I think can help someone who is controlling kind of loosen up control that they can be like, okay, I wanted this person to react a certain way and they didn’t and don’t freak out and be like, oh my God, my meeting’s ruined, like, acknowledge that no, you can follow up afterward and still get the impact that you need.

Get the information, you know, that you need from them, help them feel more comfortable knowing you have some time. So I think that can help loosen up that like “Right now the performance has to be perfect. Otherwise everything’s lost!”. Nope. It’s not. You can follow up afterwards.

Galen Low

That’s a really good way of looking at it.

Like in some ways a meeting is like a milestone in a conversation that is ongoing. And I’d like, your under-talking example, like I thought was a really good one because yeah, it might be a project manager’s instincts, you know, especially someone who’s motivated for this meeting to go well to kind of try to get that person to say what they expected them to say.

Whereas actually, I mean, you know, treating like humans as individuals, you know, we know that some personality types might not necessarily be that comfortable sharing in an environment that is a meeting, which is in some ways quite unnatural. And there are other ways to get that information or do a follow-up outside of that meeting rather than applying pressure and like, just that notion of creating more of an equitable experience in project communications or work communications and not necessarily like forcing everybody in the world to, you know, be an extrovert, for example.

We can kind of pay attention to that as project managers and find other ways to get that information out, that meetings aren’t really the only way to, you know, have to take decisions to, you know, share information, to have conversations. It’s just one way.

Olivia Montgomery

Yup. Just exactly. Just one way. And yeah, you really under-talking, you know, it’s really, I, like I said, a huge flag, red flag that you need to pay attention to as a project manager. Maybe that person’s behind on their work and they don’t want to be exposed and you haven’t had time to touch base with them.

Don’t apply pressure again, you know, it’s okay. Don’t expose them. Don’t make them expose themselves. Don’t just assume that they’re not paying attention, and that’s why they’re not talking. Don’t just assume that there are other reasons. Just talk to him after the meeting, sit down and talk to him, see what’s going on.

Galen Low

It’s funny. We we’ve been having conversations about you know, the reputation of project managers in general. Sometimes not always so positive of course, right?

Olivia Montgomery


Galen Low

You get things like, oh my gosh, project managers are the worst. And the reason why that reputation happens is exactly this, right?

You know, it’s funny, we kind of immediately jumped to, okay, bad project manager is probably somebody who, you know, loses control of the scope or the timeline or the budget. But actually the PMs to call them out right here on the podcast, the PMs who are driving that negative reputation are the ones actually that don’t have the high EQ that are just applying pressure, applying pressure, applying pressure.

They’re not really, you know, using that empathy. They’re not understanding what people’s motivations are. They’re not really paying attention to what is not being said versus what is being said. And, you know, trying to drive that collaboration based on human dynamics, you know, it’s the ones that are just like blunt instruments that are like, Nope. Scope is this. Deadline is this. Can’t hit it too bad.

You know, those are the people that are creating really bad experiences for folks working on project teams. And it’s driving this reputation of like, PMs are just useless people who just stand over us and make sure we’re doing work and tell us, you know, bark at us from on high and don’t get it.

And fundamentally that’s not, I mean, okay. My, my philosophy is that’s not what a project manager should be. Actually, what we’re doing is we’re facilitating and empowering collaboration. Fundamentally, we are getting humans that are very different, that know very different stuff, that speak very different, you know, that speak very differently, that are interested in very different things. And we’re like, cool. Make a piece of Ikea furniture together, right?

You’ve got one Allen key. You care about like business side, you care about data, you care about the creative side. Hey, go play and we’ve got to build this, you know, Ivar shelf by this date. You know, it’s actually our job.

And when you look at it that way, you’re like, okay, so it’s not going to help me just like by saying, now listen, just grab the Allen key and, you know, keep driving that screw in you know, no matter what, even if your hand is bleeding, right? Like that’s not a great way to lead.

Olivia Montgomery

Yeah. And I think we see command and control as a management style was dominant through all of the 19 hundreds.

Is that weird that we say that now? Seems weird to me. But anyway, ever since the industrial revolution. Yeah. Like command and control management is what we all worked under. And, you know, I, we have to acknowledge that a lot of us still do work under managers and leaders who follow that. So it can be easy to think like, okay, you know, they’re command and control, I should be too.

And there’s a bit of that. You have to know that’s what they value. You need to be respectful of it. But I think in general, like teams, and people, and work has just evolved past that. So yeah, being able to identify like, okay, command and control is it’s out of fashion. If you’re listening and you do it, stop doing it.

It’s no longer effective, if it ever was. That’s a whole other conversation.

Galen Low

And then I’m thinking about it as, okay. You know, we’re two people actually who have a social sciences background and that’s all fine and good. But for folks who like don’t have the same background that we do, and really just like, don’t feel like this sort of high EQ approach is their strong suit yet what advice would you have for them in terms of how they can kind of build this into their project management style?

Olivia Montgomery

Yeah, absolutely. I, one of my first tips would be, you know, it sounds like hopefully you would identify that’s a weakness for you. It needs to be compensated for. Quickest, easiest way is to leverage someone who’s good at it. Don’t be afraid to recruit from the social sciences for your, from your team.

For example, I was struggling with a lot of challenging personalities on a project. It didn’t go as well as it probably could have. And we’ve finished that particular one, but then they asked for another, they wanted another new software system. So that’d be another new project. So thinking back about where things kind of went wrong, there was a lot of miscommunication. Requirements gathering was an issue.

So we actually, I found a a psychologist who, you know, is really tech savvy, and he’d been a consulting BA for a while. And I wanted him to be on this project. For all the reasons we’ve been talking about this whole time. And so I was like, all right I want this BA. I want to hire him as my IT PMO BA and everybody, executives thought I was insane.

They took one look at his resume and they’re like, what? Like, he’s been an addiction counselor. He’s a psychologist. What is going on? And I just was like please trust me. Luckily, I had built up, you know, years of trust with them. He’s fantastic. You know, short story now it’s, he’s still there. He’s still rocking the job.

He’s so good. And it’s exactly for all the reasons, you know, we’ve been discussing here, so don’t be afraid to recruit. They don’t have to have a computer science degree. Absolutely not. And if it’s a weakness of yours, they probably shouldn’t.

Galen Low

I like that notion of balancing out the team. I know it’s probably hard, it’s a hard conversation to have to convince, you know, a leadership team, the executive team that, you know, this is a smart hire.

But I think it’s equally important for hiring managers to be able to like, look at a resume and understand what it means, because I’ve actually, I’ve been that guy, I think? I’ve always been like, okay, yeah, English lit major. I get it. Whatever. Tell me more about what you’ve done, you know, for a digital agency, what is your project management experience?

And I’ll gloss over that without actually understanding what it means which is all of what we’ve been talking about today, right? That ability to sort of navigate nuances of people who are who’ve been frankly just been forced to collaborate, right? Whether that’s psychology or whether that’s like someone like yourself, who’s got like a literature background and understanding of the characters and their story arcs and where they meet and where they may sort of clash and navigating that.

Like, that’s what that should say to a hiring manager, like when they’re looking at it on a resume.

Olivia Montgomery

Exactly. Yeah, absolutely.

Galen Low

And then we started this off as like, I’m talking about like training, right? Why is it that we kind of get taught all of this process and procedure and protocol and aren’t really formally taught some of these like less quantifiable skills, right? Of just like emotional intelligence and navigating personalities.

So if it is someone, if someone’s listening and they’re like, you know what, that’s all great. It’s definitely not my strong suit. And yes, I can, you know, bring someone onto my team to balance it out, but I want to get better at it.

If there’s someone out there who wants to get better at being an emotionally intelligent project manager or leader in general, like what’s the best way to learn some of this stuff? And also convince their organizations that it’s worth investing in this kind of learning?

Olivia Montgomery

Yeah, absolutely. You know, to your point about it’s, it hasn’t been, you know, he’s not taught, there’s no training for it.

That’s, that’s a huge societal problem that we have. I think K through 12 needs EQ training learn how to balance your checking account and identify emotions. Now we need that. And it goes back also to all of our schooling has been about career and profession. And command and control management style has been the dominant style.

So you’re trying to train people who will be successful in that environment. So we’re doing a big disservice and I hope, we know we start addressing it and things start changing. But yeah, for today find a mentor for you know, there’s probably somebody in your organization maybe in your local, you know, PMI chapter, who’s good at it.

Reach out to them, you know, say, Hey, you’re fantastic at this. Could you help me out? You know, would you be willing to talk to me about it? Yeah. A mentor with high EQ is going to be, you know, immensely important to you. That’s definitely one of the first things I would recommend. Another way is read books, watch movies and just kind of get that exposure to different ways of speaking.

How people relate to each other. Just like I mentioned earlier, I have this like bank of references, of stories and characters from narratives from my studies, but you can do that now. You know, there’s amazing books and TV all over, you know, any streaming service you have. You can find it.

It’s really important just to get that exposure. And sometimes, and I think it’s totally fine if you prefer movies and TV over books. Totally fine. I would never, as an English major, I would never say that’s, you know, lesser in quality. So it’s not.

Galen Low

I like that and I think people don’t think about that enough, right? And you know, maybe I’m ruining Netflix for people by saying like, oh, it’s also professional development. And they’re like, oh, I can’t just put my feet up and relax, but actually like, it’s true. And I love this sort of like a thread of steel throughout this conversation that like people are characters and actually a lot of fictional characters are based in some, rooted in some kind of reality, right?

So it’s not just all necessarily made up. They are all qualities of human beings that can exist in reality, and that have to navigate other personalities. They even just putting that lens on. Okay. I just like did this, for those listening, I just did a hand gesture of like putting on a monocle, just apply that lens of, yeah. How can I listen to the story and enjoy it, or watch a story and enjoy it, read the story and enjoy it. But also learn something that I can apply in my professional life as well. Even if I’m just reading it for fun, even if it’s just that paperback novel that was just like on the aisle display before the checkout.

And it’s technically trash literature by most people’s standards, but also I can read it and pay attention and go, you know what? Yes, like this is deepening my understanding of how I can navigate like human dynamics and personalities and motivations and, you know, kind of appreciate other people’s stories and build that into the way I manage a project.

But I love that. That was part of your answer, cause I think a lot of people are like, where is the course where I can learn this? I’d like to just throw money at it and be done with it and get my certification in emotional intelligence. And the answer is it doesn’t exist right now, or at least not very widespread.

And actually the more effective way might be mentorship and might be just like taking in other experiences and applying that lens.

Olivia Montgomery

Yeah. You get exposed, you know, TV and movies and books help expose you to experiences you’ve never been in. And even if it’s hyperbolic and exaggerated, you know, for entertainment, you still get to see like, oh, that conversation didn’t go well. You know why and you get to think about, you know, like, okay, well, if something, if somebody starts to reacting that way to me, you have like, yeah, just a little bit more exposure and a little more, you know, reference to pull from on how to make it go your way.

Galen Low

I love it. Absolutely. You know what? These insights are all super valuable. I think those things that really resonated with me was just your story of like requirements gathering and being that bridge and being that translator. And I’m just, I’m picturing it, right?

It was like elbow to elbow, requirements elicitation session with an accountant. And they’re telling you, you know, the story of how they use the system, which is not told in requirements, right? You need to then capture that. You need to translate it. You need to be able to tell your team and you know, how it aligns to the goals, how we’re going to like prioritize it in terms of the backlog, what the actual requirements are and the definition of done.

And we kind of have to be that bridge. And as a result, we need to understand what people are saying or not saying. And that’s kind of part of that sort of navigation of human nuances that is this stakeholder management side of things.

That is the emotional intelligence side of things. That is the thing that’s going to, you know, make people understand that PMs are awesome. And not just kind like blindly barking orders at people, or, you know, standing over their shoulders.

Olivia Montgomery

Well, they don’t just herd cats. I mean, it feels to us they were herding cats, but it’s an art. You know, and it has to get done and it’s not just herding. It’s a lot of work, a lot of, yeah, nuance, balance, translation.

Galen Low

Awesome. I love that. Olivia, it’s been great having you on the show. Thank you so much for joining us. This conversation is so important just from a PM training standpoint and how we conduct ourselves, but also from an education standpoint. Generally, as humans and not even just professionals. As humans, what can we do better to have this part of what we are taught, you know. In K to 12 you know, in university, in technical colleges, on the job, like these are things that, yeah.

We need more outlets and avenues to get this training because it is really impactful and we see it working. And it is trending because it works.

Olivia Montgomery


Galen Low


Olivia Montgomery

Yeah. And it’s definitely the future of work where we’re going, so get onboard. Yeah. I’m so excited to be talking about this.

I’ve been passionate for years and years, and I feel like it is finally coming to the forefront of conversations, which is reflected in, you know, the PMBOK picking up stakeholder management and not just having a B in input and output you know, chapter.

Galen Low

Absolutely. Yeah. I feel like this won’t be our last conversation together on the podcast.

Olivia Montgomery

I hope not. This was awesome. I love it. I hope, you know, listeners are feeling inspired by it. I hope they have questions. I hope they value it. I’m so excited to be here sharing and talking about it. My coworkers aren’t always so interested. Researchers, you know, they’re not always, they don’t have the same, you know, some of them are CRM researchers and just different than project managers.

Galen Low

Nope. Absolutely fair. Listen, I really appreciate you coming and nerding out with us on the show and absolutely let’s like, keep this conversation going and let’s have you on again. It’s been a lot of fun.

Olivia Montgomery

I’m so excited. Again, thank you for the time. I look forward to more.

Galen Low

So what do you think? Should social sciences be a bigger part of project management training? What hacks tips and tricks do you have for applying social sciences to stakeholder management?

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Until next time, thanks for listening.

Galen Low

Galen Low

I am a Client Services Professional and Agile Delivery Specialist with progressive experience driving human-centered digital transformation in government, healthcare, transit, and retail verticals. I manage large, cross-functional teams and executive-level relationships within boutique agencies and large consultancies to drive tangible business outcomes and strategic growth. A few of my specialties: digital strategy, agile web application development, project management, human-centered design, design thinking, innovation & growth, digital government, career coaching, professional development.

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