How to Work as a Freelance Project Manager (#236)

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Hey, it’s Fei Wu, creator of the phase world podcast and marketing services. And you’re listening to a new miniseries on phase world called how to freelance for independent Creators. In this series, we speak to the tactics of working as a freelancer, from health insurance to taxes, incorporation, but also the human side of things such as marketing, negotiation, downtime or burnouts, all inside a bitesize miniseries. Each episode is 15 minutes or less.

Hi there, this is Fei Wu and you’re listening to another episode of how to Freelance. And today I want to talk about a very specific role as a freelancer, which is known as a freelance Project Manager. Now, if you don’t work as a freelancer and this is the first time for you to hear about this title, you may be a little surprised too, because guess what? Many project managers who are working full time now highly question whether this is a feasible career or a path. And it is.

So I got this great question from Jenny Lisk, and I’ve known Jenny for a couple of years now and I really love her work. You can find her on Jennylisk.com Lisk and she has created a wonderful podcast called the widdled Parent Podcast. I think it’s very brave to do something like that. And you know, even though I am not a widowed parent, I couldn’t help actually listening to a number of episodes just to understand what some of these parents are going through. And I also know a number of my friends who have been going through that and I absolutely, without a question, directing them to check out the show as well.

So Jenny sent me a question and I want to read that to you because it has a lot of details. And to be honest, I’m quite excited to record this episode because I have been working as a freelance project manager up until I would say the end of 2018. And I’ve been doing that since the beginning of 2016 and also a decade before that. Therefore, I feel like I have so much to say about the transition even between the full time project manager into a freelance project manager route. So Jenny asked me, I’m qualified to do such work.

20 years in corporate It as a project manager and business analyst with a current PMP certification. And also, I’m a Certified Professional Scrum Master. Levels One and two. That’s awesome because I am also certified as a Scrum Master, but I do not personally do not have PMP. But her question continues.

I have no idea what a freelance project manager would do and what types of organization would hire such a person. I guess maybe you’ve either talked about this type of work in this realm or maybe you’ve interviewed somebody else. And if you could please adjust some episodes and please dive deep and that’s give us some real life examples of tech and also nontech work that freelance project managers actually do, and also that organizations actually would pay for. I spend so long in large corporations and internal it that I just don’t know what options are out there. All right, awesome.

Let’s get started. I’m really excited. And guess what? If you stay to the end of the episode, I’ll share what I think of as a very cool project not created for a traditional freelance project manager. However I got it.

And actually, as a result, I was able to continue that relationship with this particular client well into the future. And first, I want to just say a few things about my background in case you didn’t really line up the years and to have a good understanding of my experience. So, again, this is Faye. Before I started this podcast and during the beginning of the show, I was already working as a fulltime project manager. My career started as a computer programmer because of my degree in computer science and math, SAPN Corporation.

So I was there for six years. Half of that was consulting technology, and the later half was three years in digital marketing. And out of those six years, even though I started as a programmer, but I only worked as a programmer for about a year and a half, so four and a half years. For the rest of my experience, there was associate project manager when I started and very quickly transitioned into a regular project manager and later a senior manager before I left the company. And then I moved on to Digital Influence Group and just by the name and the definition, it was a digital company.

So I was what’s called a digital producer. That’s also what I want to mention because the title and the names although would change, but the roles are actually very similar now, by the time I moved on to Arnold Worldwide, that is an ad agency, and I worked inside an ad agency as a digital producer as well, a senior digital producer. So what it means, as all these producers and project managers what it means is my projects are largely focused on the internet of things, meaning mobile apps, website design, development and a lot of web apps. Which means it’s not just a very simple, straightup website that you have seen, but it has a lot of these applications built in, therefore it’s called web applications. So I hope that helps.

And after I left my full time job, as of January 2016, I worked as a freelance project manager between then all the way through the end of 2018. So my experience as a freelance project manager is about three years. So I can give you a bit of a variety, because when you work as a freelancer, the variety of the projects actually is quite vast. Because as opposed to working for a large corporation, that kind of puts you on a specific project. As you become more senior, more experienced, you tend to stay on that project until you fight your way out of it.

But it’s not the case when you’re a freelance project manager. Now, first I want to clarify the titles you will hear project manager, digital producer, or even project director, which was also a title I had. These are all freelance roles I had and specifically what I did as a freelance project manager include first I want to just break it down by the phases of the projects or the types of the projects. So number one, new businesses and sales. So it means that before a project is closed, sometimes clients will hire me to help close that project, or sometimes is closing a brand new client.

So what you would do in that case is you typically work with what’s called a new business team as a project manager. And the scope of your work is really dependent on how big the company is. So if it’s a larger corporation, the scope of your work actually tends to be a little bit smaller and more specific. Whereas if you work for a smaller company, let’s just say under 100 people, that could be small or medium sized companies, you tend to do a lot more as a freelance project manager, meaning you may be reviewing assets, even giving input in terms of user experience, design, technology selection. I mean, you’re not really selecting or determine the technology, but you’re facilitating that conversation and you’re looking at your research data and conversations with these developers and technologists to help to make the best decision, basically.

Now the second category is what I call new projects. So this actually happens, I would say the most often for a freelance project manager. So these clients of mine have sold sometimes one, two or even many more projects. And then they look around, they realize they’re three, four project managers simply can’t handle that anymore. And I’m not talking about here in terms of skill sets, that’s another dimension.

But even if their current project managers can take those projects on, it will be a lot because they have ongoing projects they’re already working on. So in this case I step in as sort of that buffer and which is really beneficial for some of these clients because as a freelancer, they don’t owe me health insurance, they don’t have to manage my time or pay me twelve months out of the year. So I come in for specific projects. So these are brand new projects they’ve just sold. When I come into the project, typically I get briefed by a new business person.

I often get briefed by people who worked on the new business team that could be also a user experience designer, technologist or a designer, like a visual designer. And the third category of projects is ongoing maintenance and support work. So what it means is, for example, once you develop a web project, a technology piece, then what ends up happening is the client also needs maintenance work. So which is often really good money for the client. Also what’s called a retainer, right?

They know the set of tasks they have to take care of, and someone, in this case a freelance project manager, can manage it really well. So those are sort of, generally speaking, the three categories, just to simplify things. Now, I also want to talk about the DayToday work that overlaps. And I can assure you that overlaps a lot with what I was already doing as a full time project manager. And all those companies I listed, I don’t know, five minutes ago.

So, day to day as a freelance project manager working from home, by the way, sorry I didn’t call that out earlier. The location doesn’t matter. So let me actually talk about the location first. For largely for nearly all my clients, I was able to opt in and tell them to say that I prefer to work from home. All these clients, with very few exceptions, all these clients are based where I am, which is Boston, Massachusetts.

So specifically, I’ll give you an idea, right?

One client is based in downtown Boston. So what it means is, if I were to drive during rush hour, that will be an easy 45 minutes to an hour. And the other client I can think of is in Somerville, even though it’s not in downtown Boston. Still during rush hour, that’s another good 35, 45 minutes. Plus parking will cost me a lot of money, right?

And yes, I know I can take public transportation, but the reason why I decided to be a freelance project manager is I also want to gain that freedom to work from home. I know, again, this is an optional field for some of you guys. If you’re listening to this and you’re thinking about becoming a freelance project manager, perhaps you want to work on site with these clients. And you can certainly offer that as two folds. One is your own preference, and the other is also with a client prefers.

Now, office space can be pretty tight. You’ll be surprised that sometimes the clients don’t want you to work from their offices. Especially a lot of these locations I’m naming, you go there these smaller offices in Boston. I mean, literally, the floor plane either is not very scientific, or you go in there. People are running out of spaces all the time.

Yeah, so that’s a factor. Now, coming back to the day to day work on a day to day basis as a freelance project manager, I do the following planning an estimation, running daily stand ups via Zoom because I’m not standing up there if I’m working from home. Updating jira Board if this is a technology piece, often you work with developers and also in my case, I work with also copywriters and designers. All the work is in Jira. I review deliverables.

I sent deliverables to the clients with a list of things that are accomplished on a regular basis. I also set up meetings, allowed meetings, making sure to invite the right people, facilitating the meetings and prepping the meetings ahead of time, but also afterward. So afterward involved preparing notes and following up on the next step with different people. And also as a freelance project manager, I find myself to work as a strategic partner or thinker with upper management. What I really enjoy doing actually is working with some of the founders of these companies.

I enjoy my work as a freelance project manager, mostly with smaller smallish companies, between 25 or 25 to 50 people, or sometimes even smaller than that. And whenever they have new projects, especially the ones that they find themselves not having as much experience in, they tend to consult me or ask me to introduce often other freelance resources. The ones I can think of, including a lot of UX or user experience designers and developers. I’m also often doing the talking, talking to the team, talking to the clients on the phone or in person. I’ve run a lot of workshops and not just internal team meetings, but I’ve facilitated and prepared a lot of client workshops, especially before a new project gets kicked off.

I like to be part of that process so I can hear some of the original conversations and I’m there sometime I travel there. The farthest I can imagine driving from Boston was to Cornell and that took about eight to 9 hours. It was pretty miserable. But we had a good time. I had a good time talking to my clients.

Right, you want to choose the clients you love, but that’s a different episode altogether. Let’s see client presentations and also running retrospective. So if your PM are probably don’t explain what that is, but in case you don’t know what that is, it is about retrospectively talking to the internal team and sometimes with the clients too, about what went well, not so well, what to stop doing, start doing and continue doing things like that. And I want to address Jenny’s next category question like wait a minute, what types of companies will actually hire a freelance project manager? So the question actually has a lot of weight to it.

And it’s true because what you typically hear from most people is that they want their project managers on site, they want them responsible. You hear I mean, from now I’m going to say PM instead of project managers. So PM short for project managers. You see them working very long hours, you see them if you’re friends with them, if you’re not, I’ll tell you that they work nights and weekends, many of them. But it’s true that there are as many remote project managers sorry, there are not as many remote project managers compared to other remote workers such as designers, copywriters and programmers.

Therefore, to work as a successful freelance PM or even to get the job to begin with, you need a part of the entrepreneurial spirit to carve out new paths to convince people, companies hiring managers who aren’t used to working with remote freelance PMS, that you are a good fit. So I want to mention that because otherwise sure, I mean, because what’s normal right now doesn’t mean it’s the only way or it’s going to be normal in the next three to five years because I think the whole remote workers freelance labor is changing rapidly right now. And I’m recording this in November 2019, but we’re stepping into 2020 in no time. So smaller companies is what I would recommend that you consider smaller to medium sized companies. As I’ve been throwing hints all over this episode here.

They really appreciate your big company experience. And this is me pointing in the screen right now. Actually, you know, Jenny isn’t really sitting across from me, but I know that Jenny, for example, comes from a big company or big companies that she has worked for. Smaller companies really appreciate that to a certain degree. What they appreciate is your structure, is your experience and your visibility often into possibly more clients, higher level clients, Fortune 500 clients.

And also, guess what? Bigger project, bigger team. And you know, yeah, bigger teams are definitely tougher to manage. And sometimes they love hearing like, different time zones as well. I remember just managing India teams, us teams, that was to me very challenging because you have your standups all over the place.

You have to kind of meet in the middle, and people working from different times can be very challenging. But typically smaller companies don’t get to experience that. But anyway, I don’t want to keep rambling on, but there are certain complexity that you learn, you gain from working as a PM inside a big company that are appreciated. Now I want to talk about the things that they won’t appreciate as much or kind of rub them in the wrong way, which is coming from a big company. What you don’t want to emphasize, what you want to avoid saying are all these incredible resources, the biggest budget you’ve ever seen, you’ve ever managed to put some numbers out there.

It’s not unusual at all. Even back in the day. I’m thinking about like 2010, where a lot of the bigger budgets I’ve managed are starting with half a million dollars. Very, very common. That’s a very small team, too.

But there were a lot of budgets I managed were one, two, $3 million, and there were multi year projects that were closer to well above and beyond $5 million. Now, you’re not going to get that budget, and guess what? You’re not going to get the list of software things approved very easily with smaller medium sized companies because they work in a much more nimble way. So definitely try not to name too many resources or request too many resources because smaller companies won’t have them. So I recommend that you look for companies.

Also I think here’s a big hint, look for companies that already have remote workers. I can think of a client right away here in Boston by the way. I didn’t really know this until I was interviewed by them and the CEO brought that up right away because knowing that I not that I just prefer working as a freelance PM, I’m determined to work as one. You want to make your preference very clear and try not to be too much on the fence so like I can do this or that. Like I told them very clearly, I want to work from home as much as I can.

And I found out that company already has so many resources from or so many other people. I don’t want to keep calling people resources. They have a lot of people, a lot of employees working in other states, not just another neighboring, whatever city. So those people especially, they have their design lead and their tech lead. The design lead was working from Maine.

Again, I’m here in Boston and their tech lead and other tech leads that they hired are in North Carolina. And by the way, that setup isn’t super unusual in my space. But that was a great sign that since a lot of the people, a core members of the team aren’t already working in their boss in office, like it made no sense for me to travel there all the time. So yeah, that was pretty cool. So one note on the local companies and you fearing or worry that they want you to be there all the time if you want to work remotely is guess what?

From my experience, a lot of the local companies don’t always require you to be there but they do because you’re local. I know that there are fewer excuses you can give to not be on site, but they do like the option that you’re nearby because they will ask you to come in for important meetings, such as selling a new project or when things go sideways. And they’re going to invite their clients into their office, and sometimes they want you to be there. That’s all.

Okay, so I talked about a lot of things and I want to summarize a couple of things real quick. The answer of industries, so the type of industries in terms of the companies am I hire you including, including digital agencies, ad agencies and also tech companies. So tech companies can be very big, medium or small. And I’ve seen even though I personally haven’t worked in all sizes in all industries and verticals, I’ve definitely come across a lot of freelance project managers who have personally my experience has always been smaller companies. Now the types of projects I’ve worked on including higher education, I e universities and colleges, insurance companies, also health care, investment companies and investment startups.

Now these are the questions that Jenny didn’t ask, but I want to add which are what I think are the benefits, but also challenges of working as a freelance project manager. Number one, let’s talk about benefits. I personally think that there is a much better work life balance for anyone and especially for moms. I remember, even though I want to say this because I’m not a mom and I still find that to be helpful, to be able to make my own coffee, make my own healthy lunch as opposed to having that 30 minutes lunch break, walk over somewhere and buy whatever’s near you. So for me that’s really important.

Workout is important. Food is important to me and for moms. I heard from freelance moms who say that to be able to throw in a load of laundry at home is really important and do some cleanups and be able to prepare and pick up obviously drop up their kids in the morning, pick them up at the end of the school day. So another benefit I would say is your team won’t be able to rely on you by contacting you every second. If you’re a PM, you know this, right?

You have people come over to your desk all the time and becoming and because you’re remote, your team will have to grow more independently. They have to grow more independence and really improve the ability to think on their own more. Now that’s a really good thing for strong team and team members. But for people who are, you know, I don’t want to say people who are shy, but people who are new, sometimes there are younger team members who have a lot of questions that you can address that could be a little troublesome as well. So let’s talk about challenges.

Sometimes it does take more time to get things done right because you’re remote. And I know that it’s beneficial to have face to face conversations, which isn’t as easy when you work remotely. You may also hear from some folks to say that they would love to see you more where work side by side. You know, I think that can be decided on a casebycase basis. Plus tech these days help a ton.

Working through zoom you can see each other facetoface. I know that’s not the same as sitting next to each other, but it gets you a long way there and it will save a lot of time. So those are my quick thoughts on benefits and challenges and all right, as promised, last but not least, the first project. I was hired as a freelance project manager. I had a very unusual role, which is what I really love the company for.

And I was hired by their director of operations to have a project and they didn’t even have a name for the project. They said that over the years, over the course of establishing the company for nearly, I think it was 15 years, nearly 20 years at the time, obviously they hired a lot of people. There are a lot of deliverables and they want to establish a norm where they want to establish a set of templates for copywriting user experience documents, project management documents, development document, you can think of it. And also all these new business processes. So they want someone to be in charge.

So I took on my project and I even written an article about it. So I’ll list that in the description below for sure. And I conducted a ton of interviews. So an addon to the project I worked on, I actually got to speak with everyone as opposed to just talking to the project manager and say, hey, what works? Just give me the list, let me clean things up.

So I took the long route to find out where people were into what each of the departments thought about the documents that they used. They created what they should retire, what they want to keep and what they want to do to enhance them. And then I created a list of tools and that project ended up being called the creative toolkit because this company also is working in sort of, I would say kind of a creative agency. And they loved it. And I found out six months later during their annual review and everybody voted this project to be the most valuable project during that year.

I was really touched by it because I love the honesty and the intimacy of this company. It’s about 25 to 30 people. They didn’t have to tell me as a freelance PM or anything, some of the companies think that already paid you and I don’t want to give you all these accolades and talking up so you’re going to increase your rate. But they told me how the team, everyone felt and you know what they just want it just made me want to do much, much better work. So I always love that love of transparency.

And something I encourage you to do as a freelance PM is seek feedback. When people say constantly seeking feedback, okay, what means by constant? You want to do that in the middle of a project and also at the end of the project, right? You don’t want to do that every other day and where every week? That would just be way too much.

And if the project is short, some projects are just a month long. You could do that check in like in the middle second week and a second week and then once again during project close. The reason why I want you to consider checking in with a client during the middle of the project is you have a chance to see how they feel when things are going really well or not so well. And in the end you can kind of balance that and have a different set of feedback. Some people wait until the very end.

Even the clients or their clients will forget what actually happened. So seeking that feedback as a freelancer is quite important and if the project has gone really well and you have received all these praises, make sure that you kindly ask your clients to submit a testimonial as well for you on your LinkedIn, which you can then copy and use on your website. And that’s my way of saying and telling you that it’s really good to kind of gather that information while you can and that will lead you into even better and more projects later on. So I feel like I’ve been blabbing for a long time but this is an area where I feel really passionate about. I would love to hear your experience, how you have been working as a freelance PM or how you find out that other people are doing it really well.

So thank you for listening and I’ll see you in the next episode. Take care. Bye for now.