How Solid Program Management Helps Organizations Scale

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Galen Low: Surprise. The executive leadership team has emerged from days of strategic planning and it's been decided that several initiatives will need to be executed in the coming fiscal year to achieve new heights in rapid organizational growth.

You've been selected to organize the initiatives into a series of programs and oversee their delivery, which is exciting.

Congratulations. But when you look around the room, you can tell that while some folks look eager and inspired, others look downright afraid. Because when done right, rapid growth can mean new opportunities, parabolic increases in revenue, and a higher quality of life for everyone involved. But when done poorly, it can mean instability, imbalance, pain, and burnout.

As person meant to plan and deliver these transformative initiatives, you realized you're the unlikely protagonist at the center of a story about change. How can you leverage your positioning between the leadership team and the rest of the organization to ensure that the goal of rapid growth doesn't come at the cost of people's well-being?

If you've ever struggled to harmonize ambitious growth targets against the han side of delivering strategic initiatives, keep listening. We're going to be diving deep into the role of the program manager in creating a framework for people-centric change, and how organizations can support that role to achieve healthy, sustainable growth.

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

Today, we're going to be taking a deep dive into how a solid approach to program management can help an organization scale. With me today is someone who has been leading strategic programs within large consultancies as well as startups for well over a decade. She's also one of my favorite recurring guests on the podcast.

Please welcome, Sarah Hoban. Hello, Sarah!

Sarah Hoban: Hi, Galen! It's so great to be here.

Galen Low: It's great to have you. It's always great to have you. I always love our discussions.

I'm excited today to dive into program management. We were talking just earlier. It is a big topic and this is almost just like scratching the surface, tip of the iceberg.

But I do, I am excited to, to really get into this program management mindset and what it means for rapid growth in general.

Sarah Hoban: Me too. This is totally one of the areas that I nerd out on. So I'm so excited to talk about it.

Galen Low: Awesome. Let's nerd out. Let's, let's, let's get folks their bearings, first.

So here's the thing that I know about you, that I would like our listeners to know. You're a bit of a Swiss-army knife, I would say, in the world of digital transformation. So you've got a bit of background in project and program management. You have a background in product management and also you have a background in technology strategy.

Can you tell us a little bit about that journey? How have you managed to, to accrue all that diverse experience?

Sarah Hoban: Yeah, absolutely. I think working in a large consultancy helps and that's where I started my career in program management. I didn't quite know what it was called, or what I was doing, but I knew that I loved it and I was good at it.

So I managed projects when, I was at that consultancy. Some were a couple of thousand dollars, some were a couple million dollars. So the gamut in between. And I found myself kind of gravitating towards emerging technology projects or projects that were a little bit off of the beaten path of what, my company at the time was, was doing is its bread and butter work.

So things like, transportation in emerging technology space, where there wasn't a blueprint for regulation and how do you manage that. Or international development projects, which were not, again, bread and butter for my company, although there are others. And I continued that journey into the cerebr.

I've always been interested in new technologies of the future, including the future of work. And that's really informed a lot of what I've done as a program manager.

Galen Low: I love that. And I think you're like, I can absolutely relate to that sort of consultancy view where you do get a lot of diversity in what you work on.

That's super cool. I wonder, could you tell us a bit about your experience, just like scaling organizations through programs? Like how has your background in program management and strategy influenced how you approach that sort of thing?

Sarah Hoban: Yeah, absolutely. I think a big component of a program manager role is people management, whether you're doing that formally or informally.

So because we are across workshop partner to so many different groups, I think there's a natural ability that we have to kind of make the culture on a team. And I think a lot of that has to do with scalability and so that when, whether that looks like coming into a Greenfield space where it's a new type of project you've never done.

And, and to me, that's, that's creating a program and scaling it, or if it's truly like, Hey, this team or this business is growing and, and you're responsible for effectuating that growth. I think from both of those angles, I've had the opportunity and the pleasure to do that type of work.

Galen Low: I like that nuance about like the people and culture side of things.

And kind of, you know, we're almost, we're definitely across, right? Different areas of a business, in some cases like a hub in the middle, connecting people together, but also driving that vision of like, what, what is the impact of the work we're doing? It's not just sort of hdr business as usual stuff.

It's actually leading towards something, more grandiose, I guess. Inspiring people to kind of, to rise to the occasion in that particular scenario.

Maybe I should take one half step back, because we're talking about programs or we're talking about program management, and a lot of our folks are listening because, you know, we are the digital project manager, but could you talk a bit about how you define a program and like, how is it different from project management?

Sarah Hoban: Oh, absolutely. Yeah. I think I get asked this question a lot. I think there's two answers to it, which makes it even more confusing.

One is, I think that the terms are interchangeable, right? So a lot of project management roles in the tech space, they can be labeled as program management and it's really an interchangeable term. So that's one nuance.

And then the second is, you can also have it as a meaning where a program, it is a larger, you know, either portfolio or group of related projects. So it's kind of one step up from your, you know, project that you're leading. It's thinking about it in terms of how does that project or group of projects impact the larger business?

So, I prefer program management as a term because I think even if you're managing a single project, having that perspective is very helpful, as you advanced in your career and as you are, you know, being a strategic thought partner, which I think is such a fun and interesting part of being a program manager.

Galen Low: I really like that. And yes, I know what you mean, right? Like potentially two conflicting definitions. Are they interchangeable? Are they not? But kind of what I'm inferring from it, choosing to infer from it, is this like complexity, right?

Like you could have a technology project, that is sort of you'd have to approach it at a program level, because there are a lot of different moving parts, because there are a lot of different cross-functional teams doing different things.

And in some ways that is that like, that is what we're trying to say at that level to say, like, not just a single thing to achieve a single goal, but maybe an ecosystem of goals and an ecosystem of efforts to actually deliver an outcome. And therefore, it is kind of similar to the other definition, which is like maybe a cluster of different projects that are interdependent, that are trying to achieve shared goals.

Sarah Hoban: Exactly. That was so well put. I wish I could like record that, except we just did. So that's perfect.

Galen Low: We just did this. We did it. All right. Let's get into it.

So there's a lot of organizations out there that I feel like are trying to achieve like rapid growth, but they don't necessarily think of the components of that growth as a program.

So I was just wondering, like, what are some of the key pain points of scaling an organization that you feel could be solved or addressed through like a program mindset?

Sarah Hoban: Yeah, that's a great question.

I think it's, it's incremental by necessity. So I'll start with saying that the definition you gave for program management, I think is a good way to think about it.

Even if your project, single project that you're working on is not at that stage yet. It's going to get to that stage, assing all goes well, right? So having that growth mindset is key and having the ability as a, as a program manager to see around those quarters to understand what that potential looks like, to articulate what that vision is with leadership.

And then I think a lot of times our role is just to ask intelligent questions. I just, I say just, but it's, it's this significant role, I don't mean to diminish it. Sometimes we can be the person in the room who's that neutral third party slash therapist who can ask, Hey, why would we want to do that, that way?

Why would our customer care about this? Or how would we realistically execute the solution internally? So I do think it is taking that bigger vision or strategy, whether it's handed to you or not. Oftentimes it's not, so it's working with your leadership team and stakeholders to tease that out.

And then breaking that down into a tactical plan, because it's great to have a strategy and vision, but if you have no way to execute it, you don't have the people, you don't have the money, you don't have the timeline, and you're not sure like what to do first. You wind up doing everything at once and then it gets abandoned, right? So I think that big strength that we have is branding for the future and for the longer term, and making that vision a reality, which people think is the simple part.

But as program managers, we know it's totally not. And there's a lot of things that go into it, even if they cannot always be measure.

Galen Low: A hundred percent. I love what you said about, like looking around corners and then also just that future perspective of, you know, maybe your project doesn't feel like a program yet.

, but I think like coming at it two different ways, right? Like sometimes as a project manager, you have that one project and it has its own sort of freestanding goals and you have these liberties of maybe not looking outside of that and not choosing to understand how it fits in within a bigger picture, even though it does, frankly, right?

As a project, it more than likely does versus coming out of the other way, knowing that, Okay, yes. This is part of a growth strategy. My job as a project or program manager is to, make the plan, make the tactical plan to deliver this as a reality, knowing that I also need to be thinking about beyond the projects.

I need to be thinking about like the broader organizational growth strategy, and I need to be asking the right questions and having the right conversation. It does not that as a program manager we suddenly become the people who create that strategy. We are the other ones who need to be able to look around those corners and look towards the future to be able to like achieve the, the broader initiative, the, the broader strategic goals, especially in terms of growth, because it is all sort of related.

And I guess what'd you say that that's kind of the program mindset is just like, really understanding where you are in the bigger picture and the role that you play and the questions that you have to ask.

Sarah Hoban: Yeah. I think that's a great smary. I think it's being that person who has that vision and is able to further that vision and articulate it.

And I think a natural step that comes out from that is the prioritization process. So, there's been many cases in my career where I'll come in and you know, here's the vision and the strategy, but it's really a collection of like 45 things that want to get done. And then the decision making is often not, nobody likes to make decisions and nobody is good at making decisions.

I don't think. It's challenging. It's hard. It's something that hans, they struggle with. Decision fatigue is like a real thing, from a neuroscience perspective. So I do think it's creating the conditions for people to make those decisions. Sometimes that's by asking the right questions, sometimes that's by showing the trade-offs of one path versus another path.

And then holding folks accountable to make those decisions and to stick with them. And then a natural, I think a natural outcome of that is prioritization, which is like, I've never seen an organization like do that perfectly. But I think that that's the goal, right? If you do have to make trade-offs, if you want to be, if you want to excel in one area and have a big picture vision, it does require focus for success.

Galen Low: I think that's a really good point about decision making and prioritization. And I think that's probably a whole other episode as well, because I would love to dig into that because I think you're right. I mean, it is fundamentally a bit of a compromise. I've seen it happen so many times, right? You do strategic planning, you distill all of your ideas into like these really clear goals that align with your mission and vision and values.

And then when it comes to like, Cool, what should we do? There's all these things that actually fall away outside of that. Like, I want to do this and we want to do this. And we're like, Okay, how does this actually support the big, the big goals? And those are tough conversations to have, because even at the leadership level, they're like, well, because we still want to do that thing, even though it doesn't ladder up to any goal.

And it's really hard at that point to be like, well, can't we just do it all? And I think the whole point is, no, actually, we need to be organized and we need to prioritize. We need to understand, like you said, right, the trade-offs of doing one thing, the opportunity cost of not doing something.

And how does this all ladder up to something bigger? And I think that's kind of like a macro metaphor for like han collaboration in general, right? It's like, okay, how can we all, you know, rally behind this thing, in a unified way, knowing that it means sacrifice elsewhere. And that's, that's a hard decision to make as an organization, but I think that's really cool about the prioritization thing.

Sarah Hoban: Yeah. And I don't think it's, there's ever a scenario where, you know, there is a scenario where you can say, yes, we can do all of those things, but here is the outcome. You know, there's a recognition, you're probably going to be able to do all those things, but not well. We can do all of those things, but we need more people, money, whatever it looks like, or our schedule will change or people will burn out and we'll have attrition.

Like there is a scenario where that is a possible pathway, but I think it's portraying, again, what are, what are the trade offs? You know, what are the consequences of choosing that path and just being realistic and candid about what that looks like.

Galen Low: I think it's really cool. I wonder if we can, I wonder if you can paint a picture of how that begins, right? Like where does someone even start when it comes to like designing programs to drive strategic initiatives? We've been talking about things like prioritization. We've been talking about things like program managers, you know, creating that plan to tactically execute a program or a part of a program to drive strategic initiatives.

But like, how does it begin? How does one begin to sort of apply a program mindset to, strategic initiatives, especially growth initiatives?

Sarah Hoban: Yeah, I mean, I don't think there's a clear-cut answer. I can kind of walk through a practical of how you could think about approaching it.

I think it's, it's twofold. I think there's two different approaches and I usually do both of them in parallel. You know, which one I emphasize more than the other kind of depends on the situation, but I think when you come in there's two ways that you can go about it. So you're a program manager or you're, this neutral third party, and you may or may not even administratively report into the, you know, the team that you're supporting.

So you're, you're a relative outsider, formerly or not. So I think a big component of your success is going to be to build a trust with your stakeholders and your team, which is something we all, all of these listeners will know intimately well and understand how to do. And so I think it's being really deliberate about investing the time upfront in those relationships that's going to garner the greatest success.

So, it's coming in. If you're, if you're new in your role, it's even better because you can have that, that, independent perspective of the start of, I'm new here, I don't know what's going on. And be able to ask the questions that are maybe uncomfortable, but you don't know, your defenses, you don't know that they're uncomfortable, so you get some honest answers.

So I think that's a good starting point is to like collect a ton of information and work on building the relationships with the stakeholders. Then once you've got everything that you know of, you know, what people do for their day jobs. Areas that they find that they struggle with, or that are challenges for them that they find annoying.

It's like, okay, what am I going to do in the first, like couple of months, let's say it's a 90 day timeframe to solve some of these challenges? Here's the things I've heard over and over and over again, leadership team, you know, a non mine's of course. And so, you know, here's the things that I'm going to do in the first 30, 60 to 90 days to execute.

And I think a piece of that is identifying where there are those quick winds up front. So it could be something like this meeting that we have every week is like a complete waste of time. They're 35 people attended. Like, we don't know why. We used to have it as a stand up for five people. Now it's huge.

Like, I don't get what this call is. Okay. Let's like, get rid of the call. Let's figure out a way to do that easy. That's a huge victory that people will instantly like love you for it because who does a lp getting a meeting cancelled? And you can use that, even though it seems minor to kind of capitalize on continued success and get buy-in for some of the harder things that we need to get done.

So, I think building those relationships, identifying what that plan is, what those quick wins are, getting the buy in on that plan. And then I think it's a balance of bottom up versus top down. I generally like to work with the people who are most receptive to like getting help first because of like, Okay, those are my change champions.

Those are the people who are going to like say good things about me and then other people are going to want to work with me. So that paves the way. So I will usually start at that level. But then, in the meantime, I'm kind of like, Hey leadership, here's the things that you will need to do. I find it sometimes it takes a little longer for them to get on board.

So I tried to like, work the grassroots magic. , they're starting to hear things bubble up and then they can understand, oh, this stuff that, that Sarah has been telling me all along, it's probably something I should be doing, huh. And it kind of warns them up to the big things that, you know, the setting, the goals and the like prioritization of projects that are like hard and nobody wants to do things that are hard.

It's uncomfortable. It's daunting. So I think that was a very long-winded way of saying it's very much about, it's a bit formulaic really, but there's a lot, I think that relies on our emotional intelligence and our intuition, which is those program managers that are solid skills that we have.

So I think once you start to get in there and feel your way through the trenches, like things will start to surface for you and you'll know what makes sense to do.

Galen Low: Actually, I think it's a really nice crisp picture actually, of how we are sort of managing change from the middle. Knowing that, yes, our champions of change are probably the people, you know, a) doing the work within our project or program, and also who will need to like adopts this change.

And it is about trust building and you need to start from day one and you need those quick wins under your belt so that people want to work with you and are coming like, you know, along with you, like relatively willing. And also knowing that you are acting as a, I guess a bit of, a bit of a mouthpiece for them as well, up to leadership, that you are surfacing some of the insights and some of the things that they're thinking and doing and feeling, you know, as maybe boots on the ground versus what leadership team sees.

And then I like that overall, right? Like managing at as well as, because I guess a lot, your leadership team, all those execs, your C-suite, they're going to need to do things and make decisions based on the information that you're giving them. That might be a surprise to them, right? And it might be like, whatever we made the plan and strategic planning and just go do stuff.

And then they start realizing that actually, Okay, these are all really valuable insights that we did not have to help us make smart decisions and de-risk some of this change because, you know, you mentioned earlier, right? Sometimes, especially in a high growth organization, there might be a temptation to do all the things and everyone's just going to burn out and they might do a whole bunch of things very poorly.

It might get them done, but they might not have the impact. I really, again, just kind of trying to manage from, from the middle. Like I think it is a very crisp picture of like what the role of a program manager is for an initiative that impacts like major sections, if not the entire organizational structure.

Sarah Hoban: Yeah. And I think there's also that element, that we hear a lot about, Oh, it's, you know, especially at a start up organization, right? There's a growing pains period. You know, this is a natural thing. Well, I don't know that I buy that argent, honestly, like, yes, every, I don't know if it's a growing pain, but every organization has a pain because every organization intends to be around. It should be growing, right?

They should be evolving their strategy or their approach no matter their size. They should be thinking about what their customers are going to want tomorrow, because if they're not, they're not going to be there tomorrow. Right? So I think a lot of that, that growing pains mentality is it's unfortunately like the way that many of us have to work now.

And that doesn't mean we sacrifice, you know, people's attention, time, energy. You know, there's such a thing as having folks all in and, and working hard, but there's only so long of a period that you can do a push like that. If it's sustained it's, it's a recipe for disaster, and you're going to have, you're going to lose that legacy information unless again, you're very deliberate about like, what does that framework for change look like?

Here's what our planning process looks like. Here's what our workflows look like. So if somebody is out of the office, someone else can do that workflow in that person's absence and it's docented, and everybody gets what that person's job is.

So again, I think that's an area where we can really help them future-proof, no matter the size of the organization or no matter, you know, the so-called growth trajectory. Even if they're relatively slow growing they should still be thinking about the future.

Galen Low: I think that's a really interesting, framing, whereas, you know, I think a lot of folks, when they hear that, let's say you're doing like a process docentation and optimization project, for example. I think a lot of people think that that's like administrative, right? It's just like, okay, well we need to docent our process. And then maybe some people were like, okay, coverage, right?

Because we want to de-risk the business if somebody, you know, takes an extended leave, you know, that's the sort of unplanned and we want to have that sustainability, but it's actually a high growth initiative. Because you are planning, or it can be a high growth initiative because you're planning for, how can we, you know, spend our energy wisely?

And how can we, if we need to like, keep the business going in, like these like, like urgent high effort, high energy, like sprints, for lack of a better word, but what I mean is just like big pushes, big pushes, big pushes. How are we giving some people a break so that, you know, another team can take over, right?

And keep that growth going. We need to docent a process so that other people can do other things and we can kind of valve our staff to be continuously growing, but not burning our people out. Like, I think that's a really interesting framing on something that I think a lot of people would be like process docentation, lame.

But actually understanding where that sits in the bigger picture, I think is also that thing, right? It's just like casting the vision that this is about achieving a goal that is related to, for example, growth or staying competitive in the marketplace.

Sarah Hoban: No, I appreciate that. Administrative is my least favorite program management insult that I've heard, and I've heard many. I hate when someone describes my job as administrative, because it is, Okay, yeah, it's like the, not the glamorous or sexy parts of things, but we are, the role that we play lays the groundwork for the company to do great things. And some of those process things, first of all, I think they're awesome because I'm super interested in like how things could work better.

I understand not everybody thinks that, but what I always tell my stakeholders is like, this is my thing and I love doing this thing. I am doing, I am working with you on this thing so that you can work on what it is that you are good at. Whether that's, you know, software development or department of designing a marketing campaign or make, you know, making some new collateral for our brand, right?

Like you do you, this is the, everybody wants to do their job more efficiently, more effectively. And that's what I can enable you to do, 'cause I'm that dedicated person who can spend the time thinking through, well, how can we like make this faster so that our designer has more time to actually do design?

Galen Low: It's funny because I'm actually like, I'm starting to paint a picture in my head of what it's like to have you as my program manager. And I can see some of these things coming through, right? Because like, I think you, you like, it's a really strong point that like administrative is not your mindset.

And actually I would say that, you know, that's not necessarily true of every project manager and maybe that's fine, but also this, when we're talking about a program mindset in the context of like organizational growth, like that is so valuable to have that vernacular to talk about your role in a way that is exciting and empowering and like almost freeing for the people around you to be like, yeah, like I'm not doing administrative stuff.

I love this stuff, like I'm here to nerd out about stuff that you think is boring so that you can do your thing so that we can grow together, right? Yeah, yeah, exactly. Like I am branding stuff, like you do that all day long. I think that's boring. We're all here to do a job. but then what I've started to see, like in the way even we're talking right now, right?

It's, it's easy to see how, how easy and not easy, but how efficient, I guess it could be to communicate a vision to your team, right? Yeah, this is not administrative. We're helping, like this thing grow. Might be all it takes to really inspire people and for them to get it, to like, understand that this is not a task, like within a project.

And we don't really, yeah, just get from A to B and then move on. It's actually, this is part of a bigger picture, like a program, a strategic initiative that's going to change things and it's going to make things better for the organization, but also for the people working will do that, right? And I think just framing those benefits, like, it strikes me that that's kind of like part of the way from a soft skill standpoint, from just being a han standpoint, that you're getting people on board and getting them to trust you because you are casting that vision and you are energized about it and it is for something and it's not necessarily just like, busy work. Right?

Sarah Hoban: Right. I mean, what I always tell my, you know, the teams that I work with too is, could you do this without a program manager? Sure. But it wouldn't be as good. It's just like I could design a marketing campaign. Sure. But it probably wouldn't be as good. I would be like making my whole thing in MailChimp.

Like it wouldn't be the greatest thing ever. Right? So I do think that there's value in, you know, investing in your talent in the areas where you have folks with expertise to do that and remove some of the burden from people so then you can, you know, get them focused on the work that they're, the best suited to do.

I think that's just, that's true if program management is, as it is true of any other profession. And I guess the last point I'll make, which is like probably a tiny bit of attention, but you got me on my soap box now, so I'm going to go for it. Is that when I talk to friends who are totally outside of like what I do as a program manager and like, don't get it, I try to explain it to them.

Like this is the day in the life of like what I would do. Oh, I would go and talk to you and you know and ask you what, when you're going to deliver something and you would tell me, oh, well I can't make that date. So then I would try to understand why, like dig into your process, figure it out, like where it can, where can I help?

Like where can I unblock something? Where can I eliminate pain? And so many of my friends will be like, oh, but my PMs don't do that. Like, they'll just come to me and tell me, oh, like I just, I just need to know like when this thing's due, like, and I'm like, well, that's because they probably haven't been empowered to think about that bigger picture and like have that energy.

So I guess for anybody who's listening, like you should feel like you can do that and have those conversations and add that value. Because again, a big part of our job is like working with people and making their lives easier. And that's the part where I think it's the fun part of our job. Like I don't, I don't think any of us listening wants to just like go to a schedule and ask someone when something's due and like, have that be our job.

No one wants that. So even if it's not on paper, what you're assigned to do, have that conversation with your teams, with your leadership, with your stakeholders, and like, take that next step and start to think about it big picture wise, 'cause you have the insight, you're in the meetings, you see everything that's going on, you have the context that you need. So go for it.

Galen Low: I love that. I think it's a great soapbox and I think it's like, it's, it's entirely like it's very relevant here. It's hyper relevant, in the sense that, especially if you're like, let's say if you're listening and you're a leader of an organization, you're part of the leadership team, or you're an owner, there's a chance that you may be under utilizing the role of a program manager.

Because the generally accepted definition is what you said, right? It's someone who's going to make sure things are getting done on time. And we don't necessarily have those conversations very widely outside of our own circles about how we are using our people's skills. How are we leveraging leadership skills to help people do their best work and orchestrate this collaboration that leads to change or growth or some kind of outcome that is beneficial for everyone in the organization. And I think even just tweaking your perspective a little bit to see that and know that that's a possibility.

I think that is the beginning of having that high growth, program mindset where you could be like, oh, I get it now. I can like they're like ambassadors, not just like doers and checklists, keepers. There can be an ambassador of the vision so that everyone is, is aligned and rowing in the same direction.

That's super cool. We talked earlier about, maybe an example, and it occurs to me that I know like this notion of like rapid growth, and like strategic initiatives. I know like you and I will throw that around, but I wonder if you have like a concrete example that you could walk through just even from like that moment where you get handed the, the program, you know, and maybe that roadmap, it turns to the strategic initiative, like what might an organization be trying to achieve?

And then how does one make that into different programs? And what might an outcome of those programs be in terms of like achieving those goals?

Sarah Hoban: Yeah, no, I think one good example, I'll try to keep it a little more generic since I, you know, client info and all. But when where I, I worked on a couple of years ago was coming into an environment where it was a data management program and they had this vision for how they wanted to create an analytics, centralized analytics platform.

Great vision. They started out, I think they had a couple of products that were like overlaid on this platform and they wanted to expand and they had grown from a handful to like 50 plus. And they just kept hiring data analysts and engineers to support that, but they had never really taken the step back, as they started getting tons and tons of requests and demand for their services grew to like, think about how to structure themselves in a way that would one, make the existing work easier to achieve.

And two, enable continued growth. So they saw the need for that. They, they brought me in, it was definitely a white space environment. And I was like, and they were like, oh yeah, we, you know, we use JIRA, we've got ticketing in place, like we track our work. So I get there and there's like a backlog of like 1200 JIRA tickets.

And I'm like, When exactly do these JIRA? They were like, Oh, well, we tried. And I'm like, Okay. So it was really kind of sitting down with the team and being like, okay, how did, you know understanding how the work request would come in. Which as is probably familiar to many of our project managers and probably our other engineer friends listening.

But it's like a phone call or texts from a client. And it's like how the work request comes in. And so we'll just kind of do that in the side and abandoned whatever we had for the day, but we haven't described in any sort of way that that's how we've approached our work. So we have no docentation that we've done that.

So then when we go back to our JIRA, it's like, oh, we're going to give you all this new work. Why can't you take it on? You've, seems like you've got time. So I helped work with the team to help them understand that like well, doing JIRA tickets is not the most exciting or fun or interesting thing in the world.

This is the reason we're at the point that we are in, because from a client perspective, they don't get it. Friends, like we need to take the time to help get then get it so that we can defend our time. And so that we can continue to take on cool projects, as opposed to, we're gonna have to say no to stuff that's cool.

Instead of, you know, we're spending your time in this routine stuff. So it was working with them to really set up like, okay, how should this ticketing system look in reality? Okay, great. We've got that stood up. Okay, now we just have a free-for-all pool of engineers where stuff comes in and we don't really have a plan for who works on what?

Okay, let's sit down with the team and organize it to small groups based on the type of tickets or the program, the project or program area where the tickets are coming from. And so we made small teams that were dedicated that focused on one area and they handled a certain pool of tickets. And like, we try to align them based on skills, a link to what people said that they wanted to work on with a clear path of like, you know, if you master some of this operational stuff, you can work on these other cool things eventually and there's like a way to do that.

So I think it was really sitting down with people, helping them see the value of the process. Starting this structure from scratch and then convincing leadership was, was relatively easy. Doing that initial juror analysis was horrifying because there wasn't much data, but I was like, ah, here's what our throughput is today.

It says that people are working 90 hours a week, but we're still taking in new requests. This doesn't add up here. So I was like, we either need to ask for more budget or we need to start to push back on things. And so we started to see a clearer docentation over time of like what people were working on with the true, you know, level of work was.

And then we were able to say, No, moves to senior client who came to us with a random off the wall request. We're not going to do that if you want this other thing to get done, but you tell us, which do you think is more important and we'll do it, but we cannot do both unless you bring someone else for us to hire onboard.

And then in like a month that we can like take this on because of training. And by the way, here's our training program that we also stood up on the side so they could see how we onboarded people and the amount of time it took. So, it was a lot of data analysis, docentation and stakeholder relationships.

And it was working with people grassroots, and then at the top. Right? So it's a lot of roles like you said, that ambassador, that bridge between the two groups, because leadership didn't get it. They were like, not at that level of detail, nor should they be to be like, why can't these people do more?

It seems like they should. They're telling me that they're busy, but I have no proof.

Galen Low: Right. Yeah. And all of this, like the analysis piece, right? That sometimes we don't really emphasize the value of, but you know, we're there boots on the ground, asking the questions, getting the real world insights, like elbow to elbow, realizing that there's so much undocented work happening that of course, like our dad is not going to be accurate because, you know, if we read a report in JIRA, yeah, I guess what it would say.

Our throughput is terrible. And then why are people working 90 hours a week? They must really be terrible at their jobs. But to be able to like go in and be like, Cool, part of my program was to understand, like, do this analysis and then like pick out those components of how we can like solve some of the problems, you know, lift people up, and start getting the better results.

And then I like that notion of like the training, right? Like educating and onboarding clients, training, like the leadership team. And I think now I'm starting to see what you mean about like program management. How do we define it? Sometimes it's because it's multiple projects like that are working together to achieve a goal.

But sometimes it's just a project and some people might've been like, that's kind of a cop-out, but actually when you think about the components of that project, there's actually a lot going on. Right? There's a change management piece. There is a training piece, right? There is the overall like the technology infrastructure, and building the processes around it to get a really clear picture of the work and then building the workflow around that, to make sure that we understand capacity organizationally.

And can make better decisions about either our relationships with our clients or how we hire or how we scale the business, or even whether we scale the business. And then you have that data there, but there's all these different components there, you know, in someone's world, that's one project.

In someone else's world, that's 5 projects. So like, it's just that mindset of knowing that actually to like lift the tide in an organization, you can't just lift it in one spot. You kind of have to lift across, from a change management perspective, from a, you know, a client interaction and relationship perspective.

It would have probably fallen on his face if it was just a, cool, well, like, just make sure everything goes into JIRA, okay? Like that would be the mini version that isn't looking at the bigger picture.

Sarah Hoban: Yeah, well, no one's going to do it cause they don't get why.

Galen Low: They don't get why, yes.

Sarah Hoban: Once people understand the why, they will generally doing.

And we figured out a way to make it, you know, a lot less painful. So they were like, well, we don't want to fill in all these 25 fields and like, well this is we have to fill in 25 fields. Let's pick three. And like that's our agreement. If we had more time to build the risks, great. But we probably don't, this is moving too quick. So let's like make a good and fast choice to do what makes the most sense.

Galen Low: I like that as well. Also coming back to that thing you said earlier where hans aren't actually great at making decisions. Probably no han is, but we can make small decisions that are, you know, less overwhelming so that we can still move forward instead of just staying still.

Sarah Hoban: Yeah. It's better decision making power, I think on like the decisions that matter, like automate what you do over and over again to the extent that you can. And to me that is always another incentive from a crew perspective. Right? Because then you automate the boring things you do, then you can do the work fun things.

There always be more work to do, like I promise you in any organization.

Galen Low: That is absolutely true and fair. Absolutely true and fair, for sure.

I wonder if we could talk, pitfalls. Like we're talking about this and I know that, you know, like you've had success in this area. But I know that there's organizations out there, that they want to do this.

They're like, Oh, great. This podcast has been great. I know what I'm going to do. I'm going to adopt a program mindset tomorrow, and then we're going to solve all the world's problems in the next week or so.

What, what kind of like, pitfalls or areas of caution would you have in terms of like pressing go on structuring like growth initiatives as, as programs?

Sarah Hoban: Yeah. So there's a couple, I'm glad you asked that. I think some of, some of it is embedded in what I already share, but I think there's a few things I haven't touched on. So just to recap what I already maybe highlighted a little bit, but not explicitly.

One is, make sure your insights are based on real world observations. Like you've talked to somebody or you have seen some data point that backs up what you're saying. It's not like, some leaders may occasionally do your opinion on what matters or what is important based on no data. And the data could be qualitative or quantitative. Right? But let's not do something just because someone thinks it's a good idea and that's like the only basis for it. So that's one.

Two, I think is trying to move too fast, too soon. I know we're talking high growth here. Things move quickly, but I think sometimes we tend, or a program managers can tend to over brand and overcomplicate, 'cause that's like, you know, I love to do that too.

I'm like, I would love to have this perfect control group, world where everything operated in this way, but that's not how life is so, it's one thing to aspire to something, but you got to meet the team where they are. So, like in that example, I talked about with the JIRA tickets. There were 1200 tickets, if I came in and I was like, we have to fill out 25 fields for all the tickets and we have to go back and categorize all the old ones.

And then we need to make a really rigid structure, like, and we have to follow every day or you're going to be in trouble. That would have never worked. So instead I was like, let's delete all the 1200 tickets. They're like, what? And I'm like, well, if it's important, we would have updated it in the last like week.

So we'll just make a new ticket. Let's just wipe them all out and like start a fresh and like, let's agree on what we need to do and why. And it's only going to be these three things. And in two weeks I put a reminder in the calendar, we're going to revisit it. And if you guys hate it and it sucks, we will never do this again.

And B) don't be afraid to iterate, like try something. If it doesn't work, try it, try something different. So I think it's taking them bigger picture and then breaking it down into steps where the team is ready. I've also heard horror stories. I haven't experienced this myself, but from colleagues of like, people who come in are like, we're going to have all of these reporting requirements like that you must follow. Like, nobody wants to do that.

Like start with the bare minim and ask yourself why you need that information, and then make it a requirement. Do not just like, come in and do a report for reporting sake. Like, especially if the nobody has ever done a report before. So I think it's, it's starting slow, change management.

Galen Low: Yeah, there you go. Change management and, like, and meeting people where they are. I think, and even as you're saying that, like it's occurring to me that like, that is the program mindset, actually, because if we're thinking about programs as I've got this mental model, I don't know if it holds up, but like, you know, like if...

In the definition where a program is actually a collection of projects working together, like this is, it's almost this like cellular model you can look at it at. Okay, these cells come together to do a job. Right? , but then you can even go smaller than that. You can go, okay, just because this is broad organizational change doesn't mean that the program and all the projects within it have to be broad and sweeping.

You can actually start, it's all these little steps together. And it's actually, when you can look at it as yes, this organism is our organization and we want it to grow, but what are all the smaller component parts? And we don't have to say, you know, we don't have to like, you know, pull out a whole piece, and plug in a new one just to enact change.

Sometimes it's making iterative, changes that are, I don't know, digestible for hans, 'cause like you just don't really like change, right? You say change management and we all kind of like nod and we know that, what that means. But I think we, we don't say it a lot enough that what we mean is people can resist change, change, you can really do change wrong to people.

And that might be the cause of failure. And meeting people where they are like, I know it's kind of like catch phrasee in a way, but it's like, it encapsulate something much bigger. Because I think it was just like, yeah, it is, we're talking about hans here.

We're talking about people doing work, their livelihoods and yes, we're talking about organizational growth. But we are still talking about people even in that, even in that context as well.

Sarah Hoban: Yeah and I think also people are overly ambitious too. So I'll leave with a lot of folks who are like, oh yeah, totally, like, I want to set up this really elaborate workflow and some project management tool and say it's in Asana.

And like, I wanted to do all of these five things, but I've literally never made it to do list before. I'm like, okay. So why don't we just start by like capturing what it is that you work on in a daily basis and like, try that half for a week and see if we're like keeping up with that, then we can expand it to like, you know, quarterly planning and like how you interact with these five other teams and then get them embedded in the process.

Unlike, I think people want to have this thing set up and like had grand aspirations for how they're going to use it. It's like, you know, you buy lead equipment and you're like, oh, I'm going to use it every day.

But like, maybe you don't cause you were going to schedule like when you're going to work out. So you haven't made the time for it, so it doesn't really work. So I think it's kind of that analogy of like, okay, like, here's the, here's like the goal and the end state we want to get to. Let's not be prescriptive about what that looks like, but this is generally the outcome we want to see.

And like, here's the daily thing that I'm going to do to get me closer to that, and working with people to see that. I think organizations are a lot like that.

Galen Low: I love that analogy, right? I'm going to get fit about the gym pass, bought a Peloton. Yeah, this is all going to happen. And then, yeah, not if you don't have the framework to actually, you know, do it or you're gonna start doing too much and you're going to hurt yourself. Right?

And I actually think it's a it's apt because I wanted to swing back to this notion, right? You talked about growing pains early. And, you know, is it, is it a fallacy or is it not? How can somebody either, like avoid this growing pain, versus accepting it or transform it? But I think like some of that comes down to the fact that actually, like the word pain, I think in English, it's just like, it's not that useful of a word, right?

It's like, does it hurt or does it not? And it doesn't really have that scale, but, even just coming back to this analogy, like yeah, working out to like whatever, grow a muscle, right? Requires tiny little bits of pain and a framework around that, right? So that you know that you are going to create tiny tears in your muscle. And yes, that is a form of pain, but you're not going to like break your arm.

Like that is a different kind of pain and in the world of like growing pains, I don't know what I'm, what I'm kind of inferring here is just this notion of, yeah, change kinda is painful, I guess? But you need to like have that framework around change so that you're limiting the level of pain so that it's still productive. Not that it won't hurt, because change always kinda hurts in some way. Right?

But that is actually, again, don't, run, run in too fast and trying to, you know, go too big too soon because that's how you're going to hurt yourself slash hurt your organization by trying to like grow all at once, instead of understanding that there are steps to be taken first.

Sarah Hoban: Yeah, I think that's apt. And I think too, a lot of times when you hear the word growing pains, it's an excuse for like a toxic culture. And like, to me, there is no excuse for that. Like, there's a way to do things like you described in a healthy and slow way.

And by slowing being like it's adoptable, like, cause if you try to overwork the street too, by the time you like roll out the whole thing, it's like irrelevant. Like if you try to do this big grandiose annual planning exercise, but it takes you three months, well, like what the heck? By the end of the first quarter like you've already like, you know, you've already lost that portion of the year, like who knows what those goals are even relevant anymore.

So, okay, like makeup goaling, goal setting process that's later charge rate and some like condensed cycle, if that's a problem for you. So I think it's just being realistic about like, you may have these great ambitions or aspirations in a perfect world, but like it's not a perfect world.

So like let's just seal it back to what's doable and like be content with that, and like, let's move on.

Galen Low: Maybe to kind of like tie it up with a bow. Like, would you say that that is kind of the program manager's role in all of this? We've been talking about managing up, managing down, meeting people where they are, like, would you say that it's actually the program managers role to, give this structure and componentize things and provide the framework?

So that the big change from the top doesn't, get sort of passed down to the rest of the organization as, okay, we must do all these things right away all at once and have this big sweeping change?

Sarah Hoban: Yes, absolutely. I think it's making a tactical plan out of a big strategy and that involves like so many pieces. Stakeholder buy-in, like leadership consensus, decision-making about how people spend their time, upskilling and coaching of employees of like how they should work to fit this new narrative.

There's an, and you know, how do we decide or interact with other teams that may impact this program? You know, there's so many pieces and components to it. So that sentence, I think, highlights a lot of what we do in our roles. They can sometimes be behind the scenes. And that is the, the reason I would also recommend, and I've mentioned this to a couple other colleagues who've found that this has been really helpful for them.

If you're operating in one of these high glimpse environments, like I keep a journal of what I do every day at work. Like it's three bullets. It does not take me a lot of time, but I'll just be like, yeah, here's some things I did today. Because when you work in a piece that's that quick, sometimes you go back and you're like, what? I've been working on this for what seems like an eternity and we've done nothing, but actually like you've done a ton that you don't even realize.

So when I go back at, at the end of the month, I'll just review like my notes and I'm like, oh, we got a lot further on that thing this month than I thought we did. And I think that's helpful for like, you know, the individual psychologically. I think it's helpful for the team to see those wins. And then I think it's helpful for the business also to understand, you know, where they've come and where and how far they've come based to your efforts.

So career development wise as well. So I think that's your analogy about like constantly workout and, and the, and the constant kind of tearing and the muscle and all that stuff. I think kind of docenting some of that journey, just like you kind of, sometimes people will record, like, you know, I was able to get to this weight or this many reps or something like that.

I think it's, again, continuing this metaphor, a good way to like track progress, for what you're doing in this type of role.

Galen Low: I love it. That's awesome. And just because I know at more, I think our listeners might be curious this, this year a project, what was the overall outcome after, after it was all said and done, what did it do for the business?

What did it do for the people? What did it do for the clients?

Sarah Hoban: Oh, yes. So we were able to organize into smaller teams. People felt like they hadn't worked clarity over what it was that they were doing all day, so they felt less like frenzied and frantic. A couple of them said, Hey, I got to spend more time with my family because we set this structure up and I wasn't on call as much, which was like a huge win for me.

I was like, oh, I love to hear that. And then our, our clients had, you know, they had the, you know, the wherewithal to go back to some of their top, customers and say, Hey, look, you know, we can fit you in, but you know, it's not going to be for another month because I've already got this other thing for so-and-so.

If you can convince their leadership to prioritize your thing, like let me know. But like here's what I, you know what I said I can do. So what did it take away? Some of the, the hectic piece of the day to day like, no, it was still a busy environment. There were still fires that came up. But I think if people just felt less on, less frenzied and we were able to have conversations with our clients that were much more productive.

And we spent less time arguing about like, why something didn't get done and more time, like, strategizing about like, where are you guys trying to do next? And we could be better prepared.

Galen Low: I love that. Awesome. Sarah, always great to have you on the show. Really appreciate your insights here. I think we came up with six or seven metaphors, probably three t-shirt ideas. And again, like I do honestly feel, I feel like there was so many things where we're just kind of, you know, at the tip of the iceberg, I think it's a bigger, it's a bigger topic, especially around people and change.

And we've been doing that a little bit on this podcast. Not because we're shifting gears, but because actually, the projects that we're talking about, the technology product, projects, the digital projects, like they are about enacting change and they are about growth. So yeah, hopefully you, as listeners, found this very, interesting and compelling and insightful.

And Sarah, I just want to say thanks again for your time.

Sarah Hoban: Of course. Thank you so much for having me. This was so much fun, as always.

Galen Low: So, what do you think?

Is a well-structured set of programs the key to rapid organizational growth? Or is growth more about the people and culture behind the day-to-day business operations? Or maybe both?

Tell us a story: have you had a project where you and your team have struggled to see the bigger picture? Or on the other hand, have you ever had a project where the goals were too lofty and sweeping to be successful?

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