What’s the deal with freelance project management?
This is an updated version of an article I originally posted back in 2015 on this blog. Some minor adjustments and updates have been made, and I’m working on a few more in a similar vein – so keep checking back!
A while back I was at a local meetup and had the chance to talk to a lot of people about what I do as a freelance, remote project manager. I’ve been contracting full-time for almost 3.5 years now, but I wasn’t surprised to get so many questions. Contract project management isn’t as common in the tech world as freelance design or development is, and it’s still somewhat of a novelty.
So, I thought I’d talk about what I do, how I got here, and how I do it.
How did you start contract project managing?
I was looking to leave my job at the time and had been pursuing job leads for a month or two. I received offers at a well-known agency in Boston and a few remote-based positions and realized a few things. The offer in Boston wasn’t what I wanted to do — I didn’t want to go straight back into crazy agency life, but I missed client work. The remote offers gave me the flexibility to live and work anywhere, but I wasn’t sure how much I’d like remote work in the long-term.
At that point I had started thinking about working for myself and the freedom that would allow me in how I led my projects. It was really appealing to me. Conveniently, several of the remote positions I applied to expressed interest in offering me a “trial” position for numerous reasons. At one company, this was their standard practice with potential new hires for 4–6 weeks before making an offer. At another company, they were unsure of the need for another full-time project manager and didn’t want to rush into anything — but needed help soon.
I decided that I might not get the chance ever to try working at not only several positions, but remotely, with the chance to move at any point I needed (I was considering a move to another city at the time), and it was a lower-risk way to slide into freelance should I want to do that.
This leads me to my next point:
Who even wants a freelance project manager?
This is the key to successfully freelancing — understanding who needs a contract project manager, why they need me, and how my skills can help companies reach their vision of project success. I’ve found a sort of “sweet spot” that works really well for me, my preferred type of work, the people I work with, my strengths, and my work style.
My best contract project management fit has been small development/design agencies that are:
Growing from ~3–10 employees (including freelancers and owners) to a larger staff
Moving from taking on a handful of large projects a year to several larger, more complex projects a year
Looking to add or restructure services that they offer
Taking on a new or unusual project but need more management capacity
Struggling to find a process, system, and/or software that fit the company’s project needs
At the point where these companies are expanding from “organized chaos” to the need for a solid, actual business process is usually where the owners see the need for a project manager to join the team. A frequent explanation I hear when hired is that the company founders can no longer manage to do the work, process and manage the work, and feel like they’re on top of things without a project manager.
What kinds of contracts do you hold and how many projects do you work on at a time?
I typically work on longer-term contracts — between 4–6 months for consulting, and 6 months–year for project-based work. So far, I’ve kept most clients 6+ months, with several spanning years. There are lulls and there are busy periods and I adjust my hours accordingly, but it’s much more flexible for myself and for these teams to hire me as an independent contractor. I work between 25–55 hours a week and have found that having 2–4 long term contracts (anywhere from 5–20 projects total, ranging from large web development projects to smaller support clients) at a time are the best for my own sanity, financial security, and efficiency.
The companies I work for have their own clients and web/development/design projects for those clients. I have two major functions with any team I work with:
Manage projects from start to finish (or in the middle if I’m taking over a project)
Help company owners create, solidify, or fix their internal project processes.
This second item includes things like choosing and setting up project management software, internal team communication development, auditing project processes, setting up and maintaining business development systems, developing and managing support and maintenance plans, and generally supporting the operations of a small web development business.
Remote work for me is an added bonus and great in contracting because it allows me to work across timezones and manage my work day a little more easily. It’s also amazing to work with teams across the world and be able to connect with them over chat, video, and email — it really makes me realize the constant importance of communication in our industry.
And finally, a slightly cheesy question:
Why do you freelance project manage?
I truly believe it’s a good project manager’s job to work myself into obsolescence (in the case of certain teams) OR be so great at my job that no designer/developer knows of the stress and issues that come up during a project cycle. Working across multiple teams not only keeps things interesting and exposes me to a variety of projects (and thus a variety of project styles, personalities, and management tactics to use), but also allows me to better utilize everything I learn across teams, across all of my teams.
Working as a contract project manager for small companies means that I can help teams that need a project manager but don’t necessarily need one for every project. It helps those teams be more flexible and efficient with their projects without compromising quality, timing or budget on a project. I get to form longer term relationships with contractors on these projects and make teams more cohesive. And, I get to work with many different management and project styles, call the shots, collaborate with incredibly smart people around the world, and decide to take on projects that seem different and interesting.
