Episode 7 — We Are Pathfinders

Sprints & Milestones
Sprints & Milestones
17 min readJun 14, 2018


“Pathfinding” by Greg Storey
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Show Notes

We’re not box-checkers or micromanagers. We give our teams the agency to create and build without the burden of nagging process overhead. We find new roads to delivery while sticking to principles rather than following the words in a book or training. We forge paths on every project by focusing on the strategic vision first, while having a keen sense of process, timeline, and budget.

In episode seven of Sprints & Milestones, we talk about how project managers can move on from that rigid, box-checking way of working to being more open-minded, and strategic about the way they handle projects and teams. A few topics discussed include:

  • The evolution of the project management role
  • Having operational awareness, no matter your role
  • How having a better understanding of your work and team help you to make better strategic decisions
  • Doing more and being more helps your career long-term
  • Tools to help you to think more strategically

Links Mentioned in This Episode

Thank you to our program sponsors TeamGantt

Order the book — Sprints & Milestones comes from the pages of Project Management for Humans. Get your copy now at Rosenfeld Media, Amazon, or Barnes & Noble.

Transcript: Episode 7

Announcer: Welcome to Sprint and Milestones, a podcast where Brett Harned and Greg Storey share war stories, tips, tactics, and anecdotes on navigating the sometimes rough waters of getting digital projects done. If you're leading projects and want some help and reassurance that you're doing the right things, you've downloaded the right podcast. Enjoy the show.Brett Harned: This episode is sponsored by TeamGantt and Harvest, two companies who have supported me and the digital projects management community for some time now. TeamGantt is an online project management platform that helps you to create intuitive and beautiful project plans. For more information and a free account, visit TeamGantt.com. Harvest, if you don't already know, is a leading time tracking and reporting software that has helped me to keep many budgets and projects intact. For more information and to start your free trial, visit GetHarvest.com. On with the show.Welcome back to Sprints & Milestones. This week brings us to the final principle from my book, "Project Management for Humans", and this one's really important to me, because I think it's very much about where we're headed in the industry with the role of digital project manager. And it is "We Are Pathfinders". Here's the excerpt from the book:"We're not box checkers or micromanagers. We give our teams the agency to create and build without the burden of nagging process overhead. We find new roads to delivery while sticking to principles rather than following the words in a book or training. We forge paths on every project by focusing on the strategic vision first, while having a keen sense on process, timeline, and budget."So Greg, I mentioned this is kind of where I see things going. I want to see DPM, specifically, moving in more of a strategic direction. Is that your POV of DPM? Be honest with us.Greg Storey: Should I answer that in a bunch of acronyms?Brett: Yeah, please do.Greg: Yes. Short answer, TLDR, yes. In the work that you and I used to do, I always found that you were definitely not the box checker, with all the skills that we've talked about thus far in previous episodes. On top of that, you have always been very mindful of the strategic direction of not only the projects that you were overseeing and leading, but also just the company in general. And I can tell you that in the last two positions that I've held, one at IBM and one at USAA, I'm definitely seeing a trend of moving folks who would be more traditional project or product managers, and they are being given enhanced, or I should say evolved, responsibility, of where it's not just a matter of making sure that the project succeeds, but both strategic and situational awareness and understanding why are you doing this work? How does it fit in the industry? How is it competitive? How is it meeting user needs? There's just a lot more data points that in other companies that I've witnessed, those responsibilities are being put on the project manager.And I totally agree with it, because I think if you ... just as you said in the introduction, if you just simply read a book and take the templates from the book and do the templates and make the Gantt charts and check off the boxes, that's not leading a project. And I think that the PM, whether it's project or product, you have to think of yourself to some degree as being the CEO of that project, right?Brett: Right.Greg: If you and I were in construction and making very tall buildings, we would have different job titles, we would have way more responsibility, and there's a likelihood that you would actually be the CEO of the "company" that is building the building, because in bigger businesses, that's how they run things. And so while we're not working in that industry or maybe even at that scale, I think the best thing a project manager can do is to really look at this and say, "I'm leading this. I'm the CEO."And that doesn't mean, by the way, that now I get to tell people what to do, because both you and I know we've run into circumstances where in certain situations, the project managers thought that they were the people manager. And that's not it. That doesn't help either. You need to lead with commander's intent and just make sure that your focus is on the project and where this all fits in larger strategy.Brett: Absolutely. I think what I try to kind of get across most is that strategy is related to what a lot of project management already is. Creating a process and managing that process is highly strategic, especially if you're being the person who wants to check in on that process and make sure that things are working well. It's strategic when you're setting up meetings and preparing a team for how the presentation should go, and thinking through what the conversation should be and how you can facilitate that. There are very many strategic aspects to just basic project management.I think what's interesting is that there are definitely a lot of project managers out there who struggle with that. They struggle with being more strategic about the decisions being made, and I'm not sure if that's because they see themselves as the box checker or the person who's just maintaining a timeline that's been dictated to them or a scope that's been dictated to them, or it's because they're working on teams where they don't want to give the project manager a seat at the table so that they can contribute to the conversation. But I do think that no matter what, there are people out there who are less strategic for whatever reason, and I'm curious, how do you get someone up to speed? How do you get them to think more strategically?Greg: It's not just PMs who have this point of view or are in this situation. I find that designers, developers, pretty much all facets of a team, or all different players of a team, they kind of have this problem as well, and I would tell project managers the same thing I tell designers or developers, which is pull up. If you can't see past what it is that you're doing and you can't see the people to the right or to the left of you, then you've got to take your viewpoint and you've got to pull up.You need to go as high as whatever's required for you to see more of the world. And I think once you see more of the world, more of the people that are a part of that, and the other processes that are contingent on the work that you're doing to snap into. The business ... I tell designers all the time that you need to have some kind of operational awareness of the business that you are in. It's not simply enough for you to tell what project it is you're working on. I want you to understand, when this thing is launched, when it's out in the world, what does that mean? What does that mean for the business that we work for? What does that mean for the industry that we're in?That's not to say ... I don't want anybody to get the misconception that I'm asking people to put in extremely long nights and get subscriptions to The Wall Street Journal, although those things are very helpful. I think it just helps when your awareness is broader than the work that is in front of you, and that's to me the first way, the first step in trying to become, or get people to become more strategic, is change their perspective, change their point of view.Brett: Yeah. I would say that for project managers, it's more than just awareness about the world. It's experiencing it and trying to assert yourself in it, because there are many situations where the nature of the project management role is very internal-focused. Thinking about an agency where there might be an account management team or an account manager and the project manager, in cases where basically the PM is internally-focused, and they don't have much insight into what happens in the project outside of the walls of their office.But also, just being curious about what people do on your team, how they work, what kind of deliverables they work on, what their thought process is when they work on them, how long it takes them, why they do certain things. There's a lot to be learned as a PM just through basic simple conversations with team members.Greg: Yeah, conversations and ongoing relationships. It's kind of that project managers should not necessarily be lunching with other project managers. There's a lot of nuance in project management. There's similar levels of that in design, in development, in content strategy, all the types of work that are done on digital projects. There's a lot to learn. You don't have to learn it all. I don't hear you saying PMs have to become a designer or they-Brett: No, not at all.Greg: ... don't have to become a developer, but you can, if you learn just enough, you have a pretty good window into their world. If you can gain like a, I don't know, like an 80% understanding of what are the priorities for all of these different crafts, what are the things that they're looking out for across all projects, no matter what the type of work is. I think if you can ... you know, go back to that 80%. If you can get to that level of understanding, then you're just going to be a much more effective project manager, for one, and two, I think that builds on your idea of now you've got more awareness, which allows you to be more strategic, and how that team may respond to the work ahead of them. And you also have a better window into what the next thing should be, beyond the project that is in front of you at that time.Brett: Absolutely. I mean, again, it's another thing ... I feel like in every episode I say this or you say this. It comes back to really good communication skills, and in this case building relationships, getting to know people, getting to understand them, getting to know their work, asking them about their work. I feel like when you sit down ... and this is an experience that I've had, sitting down with a developer ... My background is clearly from the more creative side, so I don't really know that much about code, but when I can sit down with a developer and ask some pretty specific questions and have them educate me, it's kind of like a win-win situation, because I'm learning, they're teaching, so they feel good about it. They also feel good about the fact that I'm curious about what they do, and it's building trust and building a relationship between the two of us.And that then allows me to be more strategic about decision-making, or at least proposing ideas, and getting to an endpoint or a decision more quickly because I have a better understanding all around. And to me, that's how a PM can be really strategic, or at least how you can start to become more strategic.Greg: Yeah, because if you've got more information, more inputs, having that view allows you to see things differently. So if you think about it, how do you become more strategic? You listen, you learn, you observe, and you read. You're just trying to get more data from more perspectives. And you just mentioned designers and especially developers, also your stakeholders.So I go back to wanting my designers to know more about the business. When you're on a project, and we all do some type of stakeholder interviews of some kind, but those stakeholder interviews consider that just doing it during the discovery process is just one time. But you really ought to go back and just ask them, "What do you do? What's important to you? What does your world look like? What are your dependencies?" Questions that may or may not be asked during a typical discovery process, during the kickoff of a project, but understanding more about the people that you're working with and working for also turns you into more of a strategic thinker, right?Brett: Absolutely. It's my favorite part about the job. I mean, honestly, the best part about being a PM, particularly a DPM in an agency, is that you get to work with so many different types of clients and witness different ways of working, different culture, different products and goals and business goals. To me, that's really exciting, and that just contributes to your kind of like general toolbox of understanding of how things work, why they work, why they don't work, and personalities and people. It's such a great job, because you learn so much and absorb so much just by experience, and that allows you to be a better strategic thinker and allows you to lead better. And I think it sets you up for a better career path in some ways, because you're put in a position where you've been able to witness so many people and so many activities that you kind of figure out what works and what doesn't in business. And that's kind of exciting.Greg: Right. Well, not only exciting, but it also means that you're providing more value. Let's be frank. If you're a project manager who's simply checking off boxes, that's not necessarily providing value.Brett: No, you get nothing out of that.Greg: Yeah, that your projects are, to some degree, your designers and developers, the folks that are related to a project, if you're hiring right, all of them are going to be as concerned about timelines and wanting to deliver good work in a timely fashion anyway. So the value that project managers and product managers, or now what are being called experience owners or offering managers ... those are two examples I've heard ... the more you can bring to the table in terms of the strategic thinking and the strategic leadership that we're talking about here, definitely the more value you're going to have for the business. And totally agree, you're going to be on a way better career path.Brett: Yeah. I think to add to that, I asked the question earlier, how do you make someone more strategic? And obviously, it's not that you can do that. That person has to be curious, they have to have a desire to kind of level up in some way. And I guess my personal experience of that was, when I worked at Razorfish, the PM role was very much behind the scenes. It was all about managing a timeline, managing a budget, and having to deliver ridiculous financial reports on a weekly basis, and then have finance meetings on a monthly basis, stuff that honestly scared me, because I was so new to it. But I learned a ton.But what I found was lacking was a full kind of picture of where my projects actually sat, because I was never allowed to be in meetings with clients. I brought that issue to my account director, who I'd built a really good relationship with, and she was like, "Well, we need to have you in meetings. It's obvious we need to have you there." And I had to go to her boss and my boss and say, "This is a void in this role that we've found, and I want to prove to you that it's going to be a good thing to have me there." And I did it, and I made it work. We had a great relationship, and the clients benefited from it, and I think the team benefited from it.But in the long run, that was just me. I was curious enough to put myself out there, and I wanted to do that. I wanted to do more. Not everyone in the company wanted to do that, and I didn't see that major shift coming with that role. That's why I moved on to Happy Cog. But I think that's all to say, a deep curiosity and wanting to be more involved is a part of what will help you to be more strategic, just with projects but also, I guess, with your career too.Greg: Well, I think that goes for any kind of career. Essentially doing more, being more, is always a positive step for anybody's career. But I want to go back to something you said about how do get people to become more strategic, because I could see this being a stretch. If this is not a natural inclination for you, or you hear Brett talk about some of these things and in your mind you're just thinking, "Ew, gross." But you know, I think that there-Brett: Are you thinking that?Greg: No, I'm not thinking that, but I bet you there is somebody out there thinking that. But I think back to a tool like the Business Model Canvas that's put out by the folks at Strategyzer, and that is just a single piece of paper that has some quadrants in it that ask you questions. You answer them in a very simple way. If you don't know the information and you can't look it up, you provide your best guess, and it gives you, I'd say, one tool of many that can help you kind of inch your way into more strategic thinking. And again, by completing something as simple as that Business Model Canvas tool, what that's doing is it's broadening the horizon. It's getting you to think about information and inputs from areas that typically a PM does not provide. This is just a matter of changing your perspective to be able to change and go from tactical to strategic.Brett: Yeah, through an exercise that is largely based on conversation too. I mean, that's the power of it. It's like going to the right people to have the right conversation to inform yourself and the project to move forward on the right path.Greg: Yeah. But I think another exercise that I've talked about too is talking to other project managers who are in different industries, who likely have more responsibility as well. My wife, for instance, is a chemical engineer, who ... she does project management-like work, but there's definitely a heavy, heavy, heavy strategic part of her responsibility, or there are heavy strategic responsibilities on her job. And so she helps make rocket fuel. We make digital experiences. The process is different, the components are different, the players are a bit different, but in the end it's still making a thing. I think there's a lot to be learned by people who make things in completely different industries to help you, again, broaden your horizon, enable you to think more strategically.Brett: Yeah, I love that idea, especially because we all share the same challenges in some way. That's part of the power of the Digital PM Summit, is getting into a room with a group of people who come from a ton of different backgrounds, different places, different companies, in similar roles. You start to talk about, what are the things that really bother you? And we all share the same exact challenges. So I have to think that you get people who are operating projects in different industries in similar ways with different goals, the challenges are going to come down to communications, people, process, all of the same stuff. It's gratifying to talk to those people and hear about how they handle those situations, not to dwell on the challenge, but to dwell more on like, "So what did you do to recover?" and learning from those experiences. And it just, again, adds to that toolbox.Greg: Yeah, totally, and it's kind of how we used to talk about design in different industries and how one solution in fashion could be applied to e-commerce. And at the same time, when you talk to those folks who are stuck in their verticals, they're stuck in their industries and they never peek over the fence, when you bring these ideas in from other industries that apply to the work that you're doing, a lot of times you're just seen as a genius, because a lot of people don't think in that way. They don't think that, just as you said, the problems that are happening in other types of industries ... I think there's a bias of, "Well, that doesn't happen here," when if you break down the components, they're pretty much exactly the same thing. You know, everybody thinks they're a snowflake, when I think we're more like salt crystals. You know what I mean?Brett: Yeah, definitely. I think there's obviously a lot to be learned from other industries. There's also, I think, a ton to be learned just from yourself and your life experiences, if that makes any sense at all. You know, a lot of what I talk about in the book is applying personal experience to project management. There are times in my life where an expectation has been set, and it wasn't met. I can look back on that experience and say, "Hmm, how was that done or how could it have been done differently?" and apply that to a client situation or a team situation or anything on a project. So I think it comes down to just, on a personal level, connecting with someone, talking through those challenges, and again, dwelling on the solutions to those challenges.Greg: Yep, absolutely. One more point I have to make is, I want to double down on the getting involved in communities, and that could be a project manager community, that can be industry communities, but getting out from behind the screen and talking to people. Being a part of that is also going to help you become more strategic.Brett: Yes. Well, so I really hope that this is where we're headed with digital project management. I think making that role more strategic and recognizing that it is a strategic role is important. And of course, it's still equal parts strategy and tactics, but to me that's the makeup of a good DPM. I think the whole book summarizes that in some way. If you're someone who's looking to brush up your PM skills or even take on a PM role, you should embrace the idea of being strategic and having the big picture view, while also focusing on the details, because the details do matter.So I think that wraps up this episode. Thank you, Greg.Greg: Thank you.Brett: Everyone else join us on our next and final episode of season one of Sprints & Milestones. We're going to do a Q&A session powered by questions from our audience, and we'll talk a little bit about what's next for the podcast. Thanks again for joining us.Greg: Night.Announcer: You've sprinted to the end of this episode. Milestone complete. Thank you for listening. If you're looking for more resources on digital project management, check out Project Management for Humans, by Brett Harned, which is available on amazon.com or through Rosenfeld Media. And of course, don't forget to subscribe on iTunes. And check out our show notes and more at sprintsandmilestones.com.

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