Galen Low is joined by Alyson Caffrey, CEO of Operations Agency, to unpack exactly how to find that perfect interlock between ops team members and project managers to grow the business in a way that everyone on the team can benefit from.
Interview Highlights
- Alyson Caffrey is the owner and operator of Operations Agency based out of Nashville, Tennessee. [1:26]
- Alyson is named as one of the Top Agency Coaches of 2022 at Parakeeto. [1:40]
- The Operations Agency is named exactly for what it is. It is an operations agency. They take a look at businesses and partner with the owners to create an operational blueprint that serves them, helps their clients get better results, and helps their team perform more effectively. [2:19]
- Alyson got hired out of college as an executive assistant into a brand new business. She ended up going from executive assistant to the CEO, to the operations manager of about 10 to 15 employees. Then later on she left the company because they moved to a different place at that time. [4:37]
- A few weeks after Alyson left the company, a couple of people who she had met through that business had come to her and asked for her help. And so, Alyson formed the Operations Agency out of a need. [5:13]
It’s really fun when you think about your business as another relationship in your life.
Alyson Caffrey
- Alyson shares that operations operate in two key ways. First is your standard. It is how we deliver on core services. How we keep our marketing and sales engine up and running. The second is the growth initiatives. Alyson thinks of it as the quarterly planning initiatives. [9:02]
Project management exists underneath ops, but in everything.
Alyson Caffrey
- For Alyson, the best way that a project management team supports operations is to meet standards. A project manager’s job is to meet the standards of the deliverable. [12:57]
- Alyson shares that if ops is unclear with project management around how they should be updating a project, what data they want to see from them, she encourages her clients and all of the operators she has worked with to get super clear on key performance indicators and data as soon as possible. [18:06]
- Some of the defining characteristics of an ops team and a project management team working well together is the rules of engagement. First is the standards. The second big thing is communication, and the third is data. [22:25]
- The first step that Alyson would take in setting the right path for organizations with operational problems is to communicate effectively. It’s how do you let them know specifically what you need and then how do you monitor that over time. [25:15]
- Alyson shares some of the conflicts and points of friction that she’s seen happen between an ops team and a product management team, and how she solved them. [29:49]
We need to create data visibility here, it’s the number one thing.
Alyson Caffrey
- If you’re in a position where you have a project manager and they’re not willing to agree with the standards and they’re not willing to meet your ops person halfway, or they’re not willing to meet you halfway on how you want things, then that person, unfortunately, might not be the best fit for your organization. [43:35]
- Alyson’s advice for organizations who want something to change is to have someone, a colleague or a friend who is an operator, to come in and say the things that you’re missing in your business. Take the tactics from today and start to have those healthy conversations with your team around improving ops and project management. [46:12]
Meet Our Guest
Alyson Caffrey is the founder of Operations Agency and co-creator of the Operations Simplified™ Framework. She’s commonly referred to as ‘The Wolf’ among her clients because she just gets shit done. Alyson is best known for helping streamline the back-end ops for a multitude of brands, but mostly digital and creative agencies.
As a fractional COO for many high-growth businesses, Alyson fell in love with the results that clear ops bring to a service business. She and the team at Operations Agency are determined to help businesses thrive profitably, serve more clients and create high-performing teams. Alyson is a new mom to a son named Frank and enjoys spending her time at home with her growing family.

Everyone’s ops blueprint is very different just like everyone’s business is different and every person is different.
Alyson Caffrey
Resources from this episode:
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- Connect with Alyson on LinkedIn
- Check out Alyson’s website
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Read The Transcript:
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Galen Low: Well, it's happened again. After weeks of being completely absent from your project, your COO has just sent a scathing email to you and the team about how disappointed they are about the project's progress and the way that things are being done. Now, everyone's scrambling to meet new expectations that they previously didn't know that they had agreed to. It's emotional and it's frustrating. And actually it's stalling the project.
Is this just the way of things? Or is there a way to get operations and project management in lock step?
If you've struggled to build clarity and trust between project managers and operations teams, keep listening. We're going to be unpacking exactly how to find that perfect interlock between ops team members and project managers so that everybody is singing from the same song book and are working in cahoots to grow the business in a way that everyone on the team can benefit from.
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 elevate the value of project management in a digital world. If you want to hear more about that, head over to thedigitalprojectmanager.com.
All right. So today, we are talking about finding that perfect interlock between Ops + PMO and what impact that can have on a business' team culture, as well as its bottom line. With me today is the one and only, Alyson Caffrey, owner and operator of Operations Agency based out of Nashville, Tennessee.
Hello, Alyson!
Alyson Caffrey: Hey, Galen! Thanks for having me.
Galen Low: Great to have you on the show. Great to see you, as always. And first of all, congrats on being named as one of the Top Agency Coaches of 2022 by our good friends over there at Parakeeto. That's so exciting.
Alyson Caffrey: Yeah, thank you so much. I was a little bit surprised, but ultimately just extremely flattered, right?
Galen Low: I mean, listen, everything I know about you, everything I've heard about you, your, your reputation precedes you. So, I was not surprised to see you on that list.
Alyson Caffrey: Thank you very much.
Galen Low: There it mentions your business, Operations Agency, and I'm wondering, could you tell us a little bit about Operations Agency and just the types of organizations that your team helps?
Alyson Caffrey: Yeah. So, Operations Agency is named exactly for what it is. It is an operations agency, and I know a lot of people think, uh, operations is everything and, you know, it's, it's, uh, getting things together behind the scenes and surely it is all that stuff. but what we do at Operations Agency is we take a look at businesses and really partner with the owners to create an operational blueprint that serves them, helps their clients get better results, and helps their team perform more effectively.
And so typically, how that looks is we usually jump in with service providers. That's probably our number one, because I find that, uh, service providers struggle the most with the, "I'm a freelancer too. I'm a business owner transition." And it's challenging to kind of maintain quality and maintain, uh, profit margins and grow the business at the same time if, uh, you know, the owner is kind of in the weeds of fulfillment and all of that stuff. So we really help bridge that gap.
Galen Low: That's super cool. And yes, I can absolutely relate from my sort of work history. Uh, worked with a lot of agencies that are owner operators, right? They came up with just, as entrepreneurs, solo with a small team and then still delivering the work and then having to then figure out that notion of, Okay, business operations. That's something I need to learn. It's not the thing that I started my business with. It's the thing that I need to learn now to grow it.
Alyson Caffrey: Yeah, most definitely. And I think it ends up being something that they fall into that seems unnatural to them. So I'm, uh, you know, I was, uh, I always say Operations Agency was born out of need. People just started coming to me and being like, Can you please just help me do this because it's not my language?
And, you know, I, I respect that. I really do. I respect when someone knows, Okay, this is a weakness of mine. And, you know, it's just something that I need to work through as an owner in order for my business to thrive.
Galen Low: I mean, it's, in this day and age, it's actually kind of silly to try and be all things to all people. There are areas where we can just, you know, learn lessons from the folks who've, who've done it before, who know it and then spread our wings from there. I think that's super cool.
Tell me a little bit about what led to Operations Agency?
I know you as this bad-ass entrepreneur, this business consultant, the wolf, right? but I wondered if you could give folks just a quick intro of just who you are at work and just in personal life. and also kind of what led you towards creating Operations Agency in the first place?
Alyson Caffrey: Yeah. Yeah. So I actually got my start, I got hired out of college as an executive assistant into a brand new business, right? It was an owner operator business and it was a lot of moving parts and there were really only four core people on the team. And we grew that business pretty significantly in the two years that I was there.
And I ended up going from executive assistant to the CEO, to the operations manager of about 10 to 15 employees, where we had a full sales team. We had a full marketing team. We grew rather quickly. And so when, you know, natural transition time in my life, we were moving actually at the time and, I parted ways with that company.
And within a few weeks, a couple of people who I had, you know, just met through that business had come to me and said, Hey, can you do for me what you did for that guy? And I was like, Well, I guess I could.
I kind of formed Operations Agency out of a need. I mean, I'm sure a lot of people listening can relate. I was like up at one o'clock in the morning. I remember thinking I have to create a proposal for my very first client and I wanted them to think I was very legitimate.
So I was buying my domain name and creating this like super fancy proposal in Better Proposals. And I was just like, I really want them to think I'm legit, 'cause he was legit, right? He was like, I need help growing my ops. And I really wanted to make sure that I seemed like the good fit there. So it was, it was pretty fun.
I think in the beginning, especially just kind of, you know, bootstrapping it together. And I did a lot of the same things that agencies that we work with do, right? I was the person who was marketing. I was the person who was selling. I was the person who was fulfilling. I was doing all the invoices and processing the payroll and all that stuff.
And I think it is important to go through a lot of that stuff, because you know, you get a deep understanding of, Okay, this is what it takes to run a business. And so I definitely always encourage my new clients. I'm like, Don't get upset that you're in this position. I know you feel overworked and I know things are crazy and you're like pulling your hair out in the shower, but you went through this because you really care about helping the people that you help and you really care about making a difference with your business.
And so that was something that I had to kind of learn through that process was, Okay, do I really want this? Do I really want the business? Because there were multiple times where people were like, Can you just be my full-time ops manager? Can you just like, can I just hire you? And I was like, Respectfully, no, but I'm open to offers. Like, respectfully, no, but yeah.
It was, it was, it was just super fun, but I think, it was funny. My, so my personal lifewise, I mean, it's just wonderful. I have never, in my life thought to myself that I could be working from home full-time and kind of, how do I put it, financially free to the point where like, we can create whatever we want to create, right?
We can say, Okay, this is what I want my business to be and I just have a clear path to grow that. when my husband and I chat about like our goals and our dreams and things, it's always so fun because we use the business as a vehicle, right?
We say, Okay, you get to help these people and we get to do these fun things with these projects. And it also helps us become, you know, who we want to become. Right? It helps us, you know, be able to like afford the things we want to afford and take the trips and have the experiences that we want to have.
And so it's really fun when you kind of think about your business as like another relationship in your life, which I totally do. So yeah, that's like behind the scenes ops agency, uh, how it is in Aly's life.
Galen Low: That's super cool. I didn't know. It was like, the thing that went through in my head, it was like, Oh, and just like that, Operations Agency. I was expecting a little bit more of like the run-up, but one thing that I think is really inspiring, especially if any of our listeners are, you know, in an entrepreneurial stage in their career.
I mean, you know, people who have two decades, you know, of experience in other businesses might not have that, might not have that perspective of doing all the things, tearing your hair out in the shower. Right? And pouring just blood, sweat and tears into something to make it work really, really well.
So I thought maybe, maybe let's give our listeners their bearings. What we want to talk about today is just the relationship between a project management team and an operations team and how that relationship has an impact on just the way a business grows, uh, with the way it scales, but also, you know, the culture of that business and the way folks work together.
But let's back it up. What exactly do we mean when we say project management versus operations and what is the relationship between the two?
Alyson Caffrey: Yeah, so I'll start with the easier one. operations is basically, in my mind, uh, a two kind of track, highway, right, if we think about the business. if it operates healthily, it usually operates in two really key ways.
The first is your standard, right? So it is how we deliver on core services. How we keep our marketing engine up and running. How we keep our sales engine up and running, right? The main things that are going to be the day in and day out. They're not changing, there are policies, our procedures, our standards. Right?
And so that is what keeps the business at the same level, or growing at a small, you know, a small percentage rate year over year. That's like the safety net, if you will. That's number one.
Then the second is the growth initiatives. And so that is our quarterly. I usually like to think of it as your quarterly planning initiatives. How do we plan to grow a certain product or service? Are you planning on launching a book? Are we doing a live event? Are we doing something that we don't typically do inside of our standards to either improve upon standards?
It's an initiative to either approve upon standards or create something potentially new in the business, right? Whether it's a new revenue arm, if we're hiring a brand new CMO, if we're doing, you know, whatever it is that we're doing there. Something that didn't exist already.
So that is operations in my mind. It's usually in two kind of buckets and usually it's comes in standards and then it comes in your initiatives. Now, project management lives under both of those hoods, in my opinion. And so that's why project management, I think, can get a little bit, I think that these things can get intertwined often and I think that they should be intertwined.
But unfortunately, everything in a small business and everyone always comes to me and they're like, Oh, my team wears so many hats and I wear so many hats. And I'm like, Congrats, you're in a small business. You know, until you're, up in the crazy numbers, right? Until you're in a position where you've actually got, you know, a really huge organization. And it's really important to keep people in their lanes.
In this case, right, if we start to think about the small business and the fluidity, we can think about projects as any finite initiative. Whether it's repeated or whether it's unrepeated, right? Whether it's an initiative or not.
For example, like if you're, if you're a project-based service company, and you take on a new client, even if it is a project, but it operates in the standard operating procedures category, right? You've got a project manager who has a set level of SOPs and a set amount of time or a set team, that they're going through this kind of rinse and repeat process with. If you have a project manager on the initiative side, that person might be in a position where they need to fill in the gaps a little bit more. Right?
So I think that PMOs in kind of both of those areas might need to even have different competencies, but that's kind of an aside. But nonetheless, so those, that's kind of, I think the difference between, you know, project management and operations.
And it's important to note that project management is nested kind of underneath operations, right? So if we think of operations as kind of the hood of everything that you do, project management exists underneath ops, but in everything. You've got marketing projects, you've got sales projects, you've got fulfillment projects. You've got, you know, anything, right? HR projects, if you're hiring a new person.
And so in my mind, it's anything with, again, a finite initiative base, right? We have a start date and an end date, and this is what it's going to get done.
Galen Low: Some stuff is just, the hum-drum day-to-day and some stuff is like the, bigger leap forward, in terms of, uh, you know, an initiative to grow the business.
I think we can like anchor around that, because as a project manager, sometimes I do feel separate from ops, even though I know I'm within it. It's like, Okay, the way I'm measured, the way I do my job, the reason why my role exists is to go and execute this plan. But sometimes I'm actually like I lose sight. And I think project managers can be guilty of losing sight of what that project does for operations.
So I thought I might just ask you, what do you feel is the most important way that a project management team supports operations?
Alyson Caffrey: Yeah, I think the best way is just to meet standards, in my opinion. Right?
Creating a standard that says, If this is, let's just say, a service initiative, right? If I am a digital marketing agency and I have an SEO project that I'm fulfilling on, the project manager's job is to meet the standards of that deliverable. Right? Which, in essence, affects so many different things operationally.
The client will stay for longer, which increases our revenue, right? The client will maybe refer us business if they're in a position where they've had a really great experience. We can grow potentially month over month, you know, monthly recurring revenue of the business. So that is directly operationally, you know, and financially included.
And so I think that if we can position in front of PMOs, you know, the standards of fulfilling on a project like this, and what it actually does mean for the business. I always take a look at Delta of time that we go over on projects.
That's like a huge number for me that I always look at. And in my mind, I can say if we can get at our Delta under one day, which is zero days, it's a fancy way of saying zero days. Then we can be in a position where the company can grow. We can obviously take on more clients. We have better trainable ways to fulfill on some of these projects.
And so, I like to encourage that type of rhetoric around standards and around things like that. I think it's, it's easy to lose sight and I think that, is it specifically with the standard operating procedures, right? Because I think the initiative side of things, if a PMO is, you know, launching, let's just say a new product, right?
We know what this means for the business. We know it's like a big new thing and everybody's excited and there's going to be errors and omissions and changes and all the things. Right? But then the person just needs to kind of stay on top of things.
And so I find that it's easy to lose sight in standards and I think that with initiatives, as long as we have a kind of project management rules of engagement, understanding, meaning that, we know that we're updating a project at a specific frequency. We're meeting about a project at a specific frequency. They have access to a specific team with these specific skill sets, right?
And so kind of situating the project manager to say, Hey, listen, this is huge. You are kind of the direct accountable person. However, here's what you have in your toolbox and here's what we expect from you. I think that conversation between ops and project management at that level becomes a lot healthier, because then they kind of are understanding, Okay, I am a function of getting this, this thing live, right?
They might be in a position where they're not doing any of the building, obviously, cause they're project managing, but they're in a position where they're kind of the glue. They're like gluing everything together and making sure that everything is cohesive.
Galen Low: I think that's just a, it's such a massive point, that, you know, I think a lot of the time we're like, Okay, we've got our iron triangle, like the triple constraints. Okay, I gotta keep this on budget and on time.
And that's where the challenge ends versus the perspective of, because I am an agent of growth either for my clients, if it's a services-based business or for my own business, or even if it is a services-based business, like, like you said earlier, if you're delivering that, you know, without an overage, you're allowing that business, your business to grow and do more and scale.
And I think as an agent of, of growth, I think that's what you mean in terms of like that it's such a healthier conversation. It's not like your job is to just to deliver this thing. There's a really big mission, on time, on budget and at a level of quality or to our standards. good luck.
It's, it's kind of like, if you do do that, we are going to grow as a business, we are going to retain clients. We are going to have better margins that allow us to do more. That's super cool.
Alyson Caffrey: And fill in the blank there, right? With, with the team, and I always talk to my team about this. I'm like, If you guys want something, I said, come to me and we can figure out how to make that happen.
Whether that's more time off, whether that's, you know, different responsibilities in the business, whether that's a raise, whatever it might be. My opinion says to me, Okay, if I have a project manager that comes to me and says, I would like to make more money. I would say, Okay, let's look at the Delta of what, how projects go over, because agencies usually, typically, right?
They accrue revenue on a time basis for the most part, right? And so in my mind, if I'm finishing projects on time, that's adding directly to my bottom line, which means I can pay my people more. Right? And so if you're upfront and transparent with your team about this, especially your project managers, they can be firing on all cylinders and whatever is important to them, work-life balance, more cash in their pocket, whatever it is, they can be in a position to help.
Galen Low: I love that just openness to have that conversation. Businesses are businesses, you know, and it's, and jobs are jobs. And usually, you know, we, we do a job because we love it, but also because we get paid and, aligning those goals, I think overall like, What's in it for me? That question, I think is what sort of drives that, that healthier conversation, for sure.
Alyson Caffrey: Oh yeah, definitely.
Galen Low: That's super cool.
Let's flip it. Let's, let's ask the question, what is the most important way that the operations team at largest, uh, is supporting project managers?
Alyson Caffrey: Oh, yeah. I mean, ultimately with that product management rules of engagement, right? If ops is unclear with project management around how they should be updating a project, what data they want to see from them, I encourage my clients and all of the operators I've ever worked with to get super clear on key performance indicators and data, as soon as humanly possible.
Because there's really no clearer way to say, This is what I expect from you, than to line it out for them and then take a look at a number with them, weekly, biweekly, whatever the cadence might be on the project.
In my opinion, it's just such a huge, a huge, huge addition. And if any operations team is in a position where they find themselves looking for a good way to have that conversation, a good way to be like, Hey look, how do I help you? That's probably the first place to start, is to just go to your project manager and say, What do you need from me in terms of clarity? Really, what do you need from me?
And I think starting there and saying, Okay, look, I absolutely know that we need to update this project in this way. Here's how we communicate about the project, right? Here's the budget for the project. Here's who you have on your team. I think just kind of, again, situating the project manager and kind of this, this bubble of, I expect this from you, but here's what I've given you in terms of resources to help you complete some of this stuff.
So I don't like when operators are like, We just expect this project to be done by the end of the month. And then we just have to kind of figure it out. Then unfortunately, what ends up happening is there's no cadence, right?
They come back in to let's just say their Asana and they're like, Where's this? Where's that? Where's the other thing? Where's this and the other? And then Slack gets blown up and then all of the team members are like, Wait a second, bro. You haven't been in this project for like two months and now all of a sudden you're just like, where is everything? Right?
It's because they get stressed out. And instead of having the weekly meetings and having the numbers that they can go look at and the standard ways that you operate in a project, they start searching. And when they don't find something in the place they think it should be, then they get upset with the project managers.
And then the project managers come back and say, Well, you never told me you wanted it like this. And then round and round we go, right? So that's operationally an absolutely an ops problem. That is 100% an ops problem. I am telling all my project managers listening that that is not your fault. If you get blown up on Slack because nothing is in the right place, but no one told you where to put it, you're safe with me. I promise you.
Galen Low: And I know a lot of, a lot of our listeners just sighed with relief, like thank you.
Alyson Caffrey: I hear you.
Galen Low: 'Cause it's such a common challenge and I think, that absolutely makes sense. what is the best way for an operations team to support project managers? Well, support them. Give them clarity, give them a cadence too. Yeah, provide information and gather information.
And then on the project management side, you know, I know that some, some folks will be like, Oh, another layer of reporting, like to police me and how I do my job. But I think what you said earlier, right? It's like actually just transparency about what this means for the business.
If we are behind schedule, well, guess what? We can't start that, you know, other big project with client X. you know, when we expected to wrap this project, we have to push that. And that's going to change our revenue picture and that's going to limit our ability to grow, because we don't have as strong of a capacity nor do we have as much resource to deliver more work at the standards that we want it to be.
And those measurements, those data points, help the business grow. And therefore I need to orient the way I work around those, rather than just being like, Oh, that's silly. This is just a number I need to report up. That's not even how I, that's not even how I manage projects. You know, I'm a bit more organic than that, but like having the maturity to understand that, Yes, this is and should be a very clear and therefore mostly objective thing.
Alyson Caffrey: Yeah. It's a relationship, right? It's a relationship. You're in a relationship. You say, Okay, I care about what this person wants from me and I'm going to augment the way that I potentially behave to give them that thing.
Galen Low: Awesome. Speaking of relationships, let's, let's zoom in to just that ops team and project management team relationship. You work with a lot of different businesses, uh, and from the many organizations that you work with, I'm just wondering, what are some of those defining characteristics of an ops team and a project management team working well together?
Alyson Caffrey: Yeah. Yeah. So I think it's obviously the rules of engagement, right? The standards. The, 'Here's what I expect from you' type of thing.
The second big thing is the communication, right? So we gotta make sure that we're communicating effectively and communicating consistently. it's really tough, I think when folks leave communication to the back burner and they only communicate when something is wrong, instead of building out a cadence. Because then let's just say, if we're meeting weekly and nothing's wrong, you get to say, Hey, good job today, guys. So that's really helpful for morale.
The third kind of big bucket is, uh, is data, like it's truthfully. It just is, data visibility. And so I think, data visibility in my opinion helps with the other things as well. So we can say, Okay, if my standard is that we need to onboard a new client within 24 hours, however, if my data is telling me that that's totally impossible based on the way that we do projects, I need to go back and I need to augment how I'm positioning my standards to the team.
And then same deal inside of communication, right? If we're in a position where someone might be new to the team, if they're kind of still training and whatnot, the data is telling us that there are a couple of missed marks because of the fact that this person might not have been trained.
Then we might need to go back and say, Okay, could we add a couple more sessions in with the previous project manager or with the owner, or whoever needs to be a part of that to make sure that we can fill in those gaps? And so again, it makes things a little bit more objective for us.
So that's kind of the three, the three big buckets that I look at in terms of the most, uh, glaring success points, I guess.
Galen Low: I feel like data is going to be this like steal, at a sort of steal, which I love because in a way, data is intimidating, right? It's kind of hard to get. It's kind of hard to make that decision to be objective when what we're dealing with is, you know, people, but then data is a driver.
It is the reason to get together and communicate and it is the reason to keep that conversation going of like, you know, maybe some of the goals aren't realistic to your point, right? Like, and that warrants a conversation to say, Okay, maybe it isn't just this hard wall, let's make the changes that we need to make in order to make either that goal realistic, or to change the goal. Because, you know, we were unrealistic in setting that goal.
I think that's great, right? 'Cause then you have that relationship. You're communicating, you've got those standards. You are, you know, having those conversations at a regular cadence. To your point, even, even using those, uh, like moments, those touch points to pat each other on the back, if nothing's going wrong.
And then when, when an organization comes to you with, you know, like an operational problem. Whether it's like operational efficiency or project profitability and you go in and you see that those things, those characteristics of an ops team and a project management team working together just don't exist.
What are the first steps that you'd take to set them on the right path?
Alyson Caffrey: Yeah. So I would, I would sit down and I would say, Well, how are you guys doing this right now? If they're just like pulling their hair out and I need to just take a look. I'm like, Well, what's going on exactly? And I will, I'll look at those kind of three buckets of information. I'll say, Okay, are we clear about what we expect?
From the expectations, kind of pool of things. Do we have a clear standard for how we deliver on projects? Do we have clarity on the team that's involved? Do we have SOPs to support those things? Are all of our people, veterans, or are they newer or how does that work? Have these people been even trained on what they, what they need to do, right?
The next thing is what have you communicated? truthfully, there have been so many times where I have been hired into a project and they, they being the owner operator hasn't said anything to the project manager about how disappointed they might be in their performance. And I'm on the first meeting that we do that and it's very, very awkward.
It's so awkward, because you know, it's challenging everyone, and I'm the type of person that like, I can't, if I'm, if something's bugging me or whatever, not only can you physically see it, but also I just need to get it off my chest.
I'm like, Hey, listen, this thing happened and I just need to make sure that it's addressed, because if I fester with it, my mind starts going a little crazy. And I'm like, Okay, it just always ends up worse. So I think that when I come into a new project, I always tell my client, Hey, listen, let's just like find the easiest way to address some of these micro problems immediately so that they don't fester into larger problems literally into the business, or literally into the relationship with the team members. Right?
And so I'll typically look at how they're functioning now, what kind of standards currently exist? So I'll look at obviously, rules of engagement, how often they're updating the project? Do they have standards on where they want meeting notes put? Right?
Simple things like that where we can just kind of administratively make sure that the project manager understands what's expected. Then we'll take a look obviously at how they're communicating both actual project updates and feedback about the projects. Right? So that I think is kind of a, something that gets overlooked, is feedback on work and whatever else is happening in the project, needs to be addressed, right?
Because if we're looking at tons of revisions and things, that's going to slow the project down a lot and we need to make sure expectations are clear there. And then I take a look obviously at data with them and I say, Well, do we know if this is on time or on budget?
And when do we know that? Do we know that the day before we ship the thing? Or do we know that like, you know, one month in, or how do we, how do we kind of understand? And so if that relationship is bad, it usually means that one of the three is off or all three don't even exist, truthfully. And there've been so many times where I've come into a business and none of it exist.
And that's not anybody's fault. It just is something that they've had to kind of flow with because they are, they, the business it's growing crazy or everyone's kind of wearing a ton of hats and it just feels, you know, overwhelming. And, uh, and I understand that they've been kind of bootstrapping it until now, but I think coming in and getting really intentional, whether the relationship has been soured or it hasn't, right?
Whether you guys are still operating, functioning really well, like internally as a team, it's really helpful to kind of make that investment. I think of it, like, I keep saying this, but going to couples therapy, even if you don't have a problem, it's proactive. You're able to have, you know, build some good skills and hang out and actually have some time with them, you know, if you have kids, right?
Like you have some time to yourself actually, and you can like actually have a conversation with them and be like, Oh, I didn't realize that that made you feel uncomfortable. Like, I'm sorry, I'll never do that again. Right?
And so in my mind, it's yeah, it's, it's the, it's the, how do I communicate effectively? How do I let them know specifically what I need and then how do we monitor that over time? Right? That's like the colloquial way of making sure that the relationship there, it doesn't sour or get any worse than it already is.
Galen Low: That therapy session, for sure.
Alyson Caffrey: Exactly, it's the therapy session.
Galen Low: I mean, yeah, you're absolutely right in terms of like, you know, it is a relationship, and there's things that we need to sort of be in place. And, uh, I thought maybe, I'm just gonna put you on the spot here, but I'm wondering, what are some of the conflicts and like points of friction that you've seen happen between, you know, an ops team and a product management team?
Or an operator and a project management team that were actually pretty difficult to solve, but actually like opened the flood gates, opened the door of improving that relationship?
Alyson Caffrey: Yeah. I mean, I think the anecdotal example of just like the owner, operator coming in to like your Slack channel and being like, Where the F is everything? And like freaking out. That I think everyone can relate to. And I think this, this kind of, uh, how do I put it? Like intentional, like input into the business, right?
Helps kind of alleviate some of that stuff. but I worked with a team once and they did a lot of launches. And they would, they had a, they had a course and a coaching program and they would do these launches, I think it was probably somewhere close between six and eight a year. So it was a frequent project that they did and the projects were, somewhat of a shit show.
They really weren't. They were, and I say this with love because they had really, really good people and their launches were, for the most part, wildly successful. But when it came to the point where they were basically launching, they kind of stayed at one spot for a little while. And they were like, Well, why is this happening?
And so when I came into work with them, they had explained to me that their tracking system and their kind of SOPs for how to set things up just basically didn't exist. And so what they would do was, they would fly by the seat of their pants and lean on the project manager to be closing all the loops and making all the things fire and making sure the emails were out and the Facebook posts happened and all the ads were running properly with the media buyers and all of that stuff.
And then at the end of the launch, they would look at the numbers and they would say, Okay, where did we come in here? And then it would kind of spark this, like, cause they would sprint too, internally, as kind of how they operated. And so they would take some time off and let everything fester about how they were upset about the launch.
And then the next time they went to go prep for the launch, it was like this pulling hair out. So that meeting, I was actually a part of. And I remember thinking like, Oh my goodness, everyone's still so mad about the last launch last month. And it was so crazy.
And I thought to myself, I was like, we've got to make this a better system. So what I did was I came in and I was like, Look, everyone is on the same page. Let's just say, for example, right? Everyone is trying to do the exact same thing and we're all in the same boat. And so what I want to make sure happens is I want to make sure that we've got a visible way.
Cause their launches would be about 15 days from like a promo to an actual card open to a cart close time. And it was very, and there were so many hands on deck, like emails, organic social, media buying, you know, just every, every little thing you can think of with a large launch like this. And they would do like a pop-up Facebook group at some point, and it was, I remember like all the interworkings were just like outrageous.
And they were just doing so many things. So I remember, talking with the project manager and she was saying to me, she was like, we need a way to, like basically tell what we need to change. Right? Like a little bit sooner in the process. And so I remember thinking, Okay, we need to create data visibility here, it's like the number one thing.
And that's what we did. We basically made them a scorecard for 15 days. And we said, every day you guys are going to have a micro meeting at the end of the day, review the day's data. And then it'll tell you guys what we might need to augment, right? Like if we're getting way more enrollments from, you know, email than we are from Facebook, we need to double down and send another email potentially, right?
Like the next day or whatever. And so I think that that was a little bit better in terms of just creating a healthy conversation around what to do. And second thing we did was we were like, these are the standards, right? Here's how we're going to run this project because way too much relied on the project manager, in terms of just filling those gaps.
And I think project managers, while a lot of them have the same competencies as an operator often, there are two different positions. There are two very different positions. And I think that, you know, it's challenging when we start to, uh, expect a PMO to be a COO or to be an operator of any sorts and start to create some of these procedures, because what they actually are supposed to be doing is keeping the project on pace. Right?
And making sure to tie up all those loose ends and kind of be the glue. They're executor's, they're not, creators for the most part. And so in my mind, it's hard to muddy those waters and that was what was happening with this business. So I know, maybe a little bit more than you bargained for, but it was a crazy, crazy time.
And probably one of the crazier, projects I've ever had to like comb through and really work out in terms of all the moving parts.
Galen Low: I love that story. I am, I also love this notion of a scorecard, especially when it comes down to just like bringing together that data day over day. With a launch, we want to see who's opening our email campaigns, we want to see, you know, what engagement we're driving on social media. but you know, for, for another project, a project of a different nature where, you know, maybe it's not accustomed to having data every day. How do you go about getting that data and building the process to record that data, capture it, and then have a conversation about it day over day?
Alyson Caffrey: Good question.
And truthfully, I always get this because I think, to your point earlier, you were saying that data makes you nervous. And you're like, I don't know about this. And I think almost everyone I talked to is like, Oh, that sounds great, but it sounds like it's a pain in the butt to get there.
And so how I typically approach this conversation is I say, Well, what do you want? What do you want to see? Ideally, in, in the perfect case, what will, what might we look at in terms of projects? We might look at, the time that it takes to, you know, deliver a project, right? That project Delta I was talking about before. Might take a look at how many times revisions come back in a project, right?
If you're a service business, you might be in a position where revisions are killing you. You might take a look at budget. And I think those are all like surface level, pretty, pretty like surface level key performance indicators and data points. And then what we always can think about, so we can think about data like Russian nesting dolls.
You've got like a big, big one and then you break it open and there's a little one underneath that tells the story about the bigger one, right? And so to me, I say, Okay, well, why are we getting revisions? Okay. It's because, maybe our, our task base. What's going on with our tasks? You know, potentially it's not clear on the standards of what we need to deliver.
So how might we take a look at those standards? Statistically speaking, the standards, if we move things out into the, kind of earlier part of the project, we could be collecting more data from our clients around their preferences, with design and, and all of those things.
Oftentimes with turnaround time, we might take a look at, you know, team availability. Might take a look at clarity of actual tasks. We might take a look at, overall budgeted time, like it is our, is our time budget just to completely off? Because we think it's going to take this time and it actually takes this time.
So I think if you start with the surface level data and say like, these are the big dominoes that I need to make sure are like, actually there, then you can start to layer in and go a little bit deeper and go a little bit deeper, go a little bit deeper. But ultimately you won't be able to, really find anything until you have those kind of initial KPIs in place.
Those initial data points. In my mind, it's, it's something too like, if it's not broke, don't fix it. Like, I always say, if data stresses you out, let's get four or five data points on this project. And then if everything looks fine, then there's really no reason to go deeper. Right?
Like you don't have to be inundated with numbers. I personally, am just curious and I like numbers, so I'll go a little bit deeper, typically and say like, Okay, here's how we might do this. But really at that point, what we say is, okay, these are the, you know, big numbers we want to see. And then we just need to ask ourselves, what might this look like to get this number and get it to be the most accurate source of truth that we costly can?
So that typically comes with obviously using a project management tool, right? If you're doing repeat projects and you don't have a home for those projects, get one. Get one soon. And I think it's, it's challenging too, because people are like, Oh well, we work balance sheets and we work well and whatever.
And I'm like, that's wonderful for framing out a project. But unfortunately, coming in and being able to leverage some of the reporting tools that some of these project management systems have is wonderful. And, uh, it really missing out, I think if you start to deviate from that.
That's number one, that's our project management tool natively report this as my big question, typically to them first.
Second is how difficult would it be for us to find that number outside of our project management tool? Do we need to take a look at Harvest? Do we need to say, Okay, if our project is going this way and we've got a budget in Harvest, do I need to go into Harvest and can Harvest tell me? So I take a look at my systems first, right? My tech stack and can we report on this natively?
The second thing I look at is what my people are reporting. So I say like, Okay, are they ticking off boxes in the project management tool? What are they taking off? Uh, you know, how can that help tell a story to me through the reports of the project management tool? So I might need to augment the way that my project templates are set up or the way that my project in general is set up so that I can get visibility into the data that I need.
And then the third kind of a big one is, is this just going to need to be manual? Is someone going to need to just report on this and put the number in the box? And so really what we need to say is, Okay, I'm okay with first, starting with basically the, you know, reports section of things in my Asana or inside of my Harvest account.
And that's all that I'm going to do. I'm just going to do that because I don't want to weigh heavily on my team and then kind of trickle down from there. Because in my mind, even if the team needs to put in a number or two, it's going to help, I think just the overall cadence of the project, in specific, uh, in specific instances, right?
If you're in there saying, Okay, here's how much time I spend on this project, but it's already in Harvest. You should probably just report from it in Harvest. And instead of making them waste their time, going and putting these numbers in, but it's, it is really, really helpful, I think to have that conversation and then ask yourself, Okay, how important is this metric to me and how difficult would it be to get it?
Galen Low: I'm getting less intimidated by numbers as time goes on through this conversation. Some data, any data almost, helps you not have just a conversation about feelings and gray areas, you can actually measure something.
Is it the defacto number? Is it a best practice number? Is it, the data point to end all data points? It doesn't have to be. It just has to be a points that you can look at, unpack, you know, go through the layers and figure out if, if there's an adjustment that needs to be made in order to get the results that everyone is looking to achieve.
Alyson Caffrey: Yeah, absolutely. It'll change your life, honestly. It really will.
Galen Low: Let's use that, uh, to dive into, just some of the juicy stuff. So what I wanted to talk about is just where the lines can blur, for better or for worse, in terms of ops versus project management and the personalities in play.
And talking about some of the conflict that can exist and some of the problems that might create some resistance to some of the things you're saying, right? Creating standards, getting data, et cetera, et cetera, communication.
So, how can an organization that is trying to standardize its project delivery practices get their rogue of project managers in air quotes onsite?
Alyson Caffrey: Yeah. It's it's a challenge, right? It's it's like taming a wild animal in a lot of ways. I think, especially if you have a seasoned project manager, someone who's been in the business for a while, who's been doing things and who has been getting, you know, fairly good results, right? Leading the team and all of that.
And then let's just say the organization grows and a box on the org chart opens up for an ops manager and this person is suddenly reporting to someone who is brand new, right? And in this case, it could cause a little bit of friction. And I think that, you know, I think I said it before, uh, but, but just having an open conversation and saying, How can I help you achieve better things or aware that where are the issues right now that you see with project management?
I really do think that experience is king, like with pretty much everything. And in my mind, I think that if we have a really experienced project manager who seems to be doing something right, we have a conversation with them and we say, Hey, listen, how can we create standards around what you're doing?
How can we do that? And I think someone is actually listened to this audio book a few years back. It was fantastic. It was about expectations versus agreements and about how thrusting expectations on someone versus coming to an agreement about how things are going to work with them actually increased the capability of that person to fulfill on expectations.
And so it's really interesting to come to an agreement with a project manager and, you know, someone who might've gone rogue, right? And say, Hey, listen, I know you want to do things this way. How can we keep some elements and aspects of what you're doing that really are important to you and also are really driving business? But also how can we kind of come to a mutual agreement about some of the ways that you're going to either report on that or that we're going to communicate on that or how, how that's going to work?
And so I think that's really the big, the big idea here, right? Is to really come to a solid, solid place with your project manager and your ops person, because I think it's so challenging, especially probably prior to that relationship, the project manager likely had a lot more autonomy, right, then, then it's going to happen in the future.
And so that can be really difficult to part with. But I think what we spoke about earlier relating to finding people who are invested in the growth of the business, not just the growth of themselves or, you know, something I think it's just really helpful to identify those people, especially early on in the business.
So if you're in a position where you have a project manager and they're just not willing to, agree with standards and they're not willing to meet, you know, your ops person halfway, or they're not willing to meet you halfway on how you want things, then that person, unfortunately, might not be the best fit for your organization.
And we might need to be in a position where we need to think about re-staffing. And it's not a fun thing. I never recommend that people let other people go. It's never exciting. But I do think that, like what we spoke about, it does help us understand who's invested in the long-term. Who sees themselves as a pillar of the organization, not just a person here with a job that wants to go home at the end of the day, right?
And it's really, really going to, I think, change the dynamic of the team culture if those conversations can be had and if necessary, right? The folks who are still too rogue can be eliminated. and you know, maybe find success and meaning in another company.
Galen Low: Yeah. Coming back to that sort of capability, ability versus maturity.
Yeah. Sometimes they won't be the right fit. But honestly, the other part, I wasn't expecting you to say that. The fact that, listen, yes, sometimes you're going to have a role in project manager and actually they might be doing something great that should be part of that standard. Can they just go and do their own thing?
No, that's probably not a good for operations. But can we incorporate some of those things and come to an agreement to get them onsite? I think that's great. I was thinking about it a lot.
Alyson Caffrey: Yeah. I'm not just trying to lasso and hog tie people. That's not what's going on here. Definitely not, especially, again, if it's working, right? If we're in a position where we've had a good PM and they're doing some crazy stuff, but maybe it's working for us, I think personally, that, that that's totally fine.
I mean, everyone's ops blueprint is very different just like everyone's business is different and every person is different. And in my mind, I think if we can find the good that's coming out of that rogue situation, then we can say, Hey, listen, I've understood and noticed what you're doing well. Let's, maybe meet in the middle and say that these couple of things that I need from you need to, need to happen.
Galen Low: Actually, probably a good segue into my last question, which is kind of zooming out, zooming out from project management and ops teams and how those teams grow and how those teams interact.
But for organizations, right, for organizations who want something to change, but aren't necessarily convinced that they need to invest in getting someone like yourself to come in and really look at things and, you know, create the standards to have that leap forward. What advice do you have for them?
Alyson Caffrey: Well, first, I would say, I can't want change for you more than you want it for yourself. So that's number one. so I think that the people who ultimately are ready to grow the business and have this change agent in their business, around project management and ops kind of, you know, synchrony, it, it happens in my opinion, like breaking your leg, right?
It happens all of a sudden, and there's a triage that needs to happen. And then you get in a position where things get a little bit hectic and somewhat out of control. I think if you can be in a position where you can treat it a little bit more proactive, and be in a position where you're not gonna let everything break before you seek to improve something like this, it'll help, obviously the business grow a lot faster.
And so it's, it's challenging when I meet with clients who are like, everything's everywhere and I have just lost all hope for projects and everything's off the rails and whatever. I mean, we can obviously still get them back on track, but it's obviously a way more difficult place to come from both business wise, mentally, emotionally, right?
You're just kind of like done with everything. And so I always say to the folks who are thinking, Oh, well, we could be improving on this. I don't disagree that you could do some of it on your own, especially if you're firing on all cylinders, your products are looking pretty good, your team is small, you guys are growing.
Those types of things I think a lot of what we shared here could really be really solid places for you to spend some time. and I really don't want this to be ignored, especially, you know, as you, as you're growing, because what ends up happening is when things grow, then, you know, they need to be moved to like, I'm thinking of like all my plants, like I just moved my one plant from like a smaller pot, into a bigger pot, had to like add more soil and like figure out how that was going to go.
And so it's really challenging sometimes when you are in the weeds of the thing and you're like, well, I'm not exactly sure, like what the new structure might look like. It's really helpful to have someone, like myself, or, you know, like a, you know, a colleague or a friend that you have, who is an operator to come in and say, Hey, look, I'm not in your business every day, but I think you're missing some of these key things.
It's my opinion that having that opportunity and that goes for anything. Ops, marketing, sales and all of that stuff, right? Having someone come in and expert who isn't in your business, come and speak into it and say, Here's, here where I see it. You know, the, the leaks might be right and here's where we might need to plug things up and figure things out.
I think it's just such a helpful conversation in such a helpful perspective to have. so if you're not looking to invest, that's fine. I say, take the tactics from today and start to have those healthy conversations with your team, at least, you know, to help kind of ease into this kind of conversation in the future around improving ops and project management.
If your leg is broken, call me. that would be totally fine because truthfully, I feel your pain. and, and honestly, if you're in a position where you have another colleague or someone who can speak into your business at a high level from this lens, absolutely take advantage of that and say, Okay, just come in and for a day and take a look at how things are moving around and tell me what I feel, what you feel like I need to do.
I think that action alone is, is a very micro commitment, but also such a huge impact.
Galen Low: I love that, for that perspective, for that perspective, for sure.
Listen, Alyson, these insights are all super valuable. I think the one that really resonated with me was just this notion of a data scorecard, but also this like cadence of, you know, project managers meeting with ops teams. You know, status meetings aren't just for, you know, a client's project manager relationship.
If we're not having those conversations regularly and looking at the data and expressing your expectations, then of course it's going to be this, you know, uh, what somebody might call a swoop and poop situation where, you know, suddenly someone's coming in, whether it's the client or the operator, uh, who's coming in and saying, Oh, I'm upset.
Things are off the rails. Uh, I'm just gonna, I'm just going to be a bull in a China shop for a little bit. having that cadence, having that framework from ops to have those conversations around data and not just about feelings, to really understand how a project is lifting up a business and allowing it to grow, to create a better, uh, a healthier business, but also a better quality of life for the staff, for whatever each individual employee wants from their role there in that business.
Alyson Caffrey: A lot of fun things we chatted about today.
Galen Low: And we really did. Hopefully, listeners found that insightful.
And again, Alyson Caffrey, from Operations Agency. Look her up, there's lots of things that, honestly, you and I, we could talk for hours and hours and hours, but I think instead we'll create an, uh, we'll do another episode.
Alyson Caffrey: Yeah. Most definitely.
Galen Low: Awesome. Again, thank you so much. Thanks for coming on the show. And, uh, hopefully we will talk with you soon.
So, what do you think? Are your PM and ops teams collaborating to their full potential? Or is the culture a bit more of a necessary detente? What would happen to your business and organizational culture if you could maximize the interlock between Ops and your PMO? Tell us your thoughts in the comments below!
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