Ask a Project Manager #12: What PM Skills Should Freelancers Know?

Hello Solo,

This is a great question! It’s worth saying first that many project managers have found their way to project management when they were asked to fill the role because there were no PM’s on the team, meaning they have limited or no PM training – so you’re kind of on a level playing field!

There are two freelancer scenarios you may be in. For the sake of this conversation we will be focusing primarily on the second scenario.

1. You are a freelancer who joins existing teams, who have some form of a process for their work

2. You do work for your clients as a one person team or you assemble small teams of other freelancers doing projects for several clients

In the first scenario, you may be seeking a good baseline of project management best practices so that you know: how to interact with each of the roles on the team you are joining; how to participate in solid planning and execution of a project, or maybe you want to know PM skills and methods so that you can more accurately gauge when a project is healthy and when there are red flags to address.

If you are a freelancer taking on your own clients or assembling small teams of other freelancers, you are likely playing many roles in addition to your core function (as designer, content creator, developer) and you want to know how to set up and lead healthy projects with great outcomes. 

In either case, a healthy dose of good baseline project knowledge is essential for all digital practitioners and believe me, the PM’s in your life will thank you for understanding and supporting them! On your quest to build your PM skills baseline you will unknowingly also be building your skills as a team lead. Much of a PM’s role involves communicating, facilitating alignment on teams, and understanding how the pieces of a project make the whole – read Louder Than Ten’s project management manifesto to get the full picture of what PM’s do. These are also some of the foundational skills of any good digital project leader. 

Freelancing: What is my “PM 101”?

Because responding to your question with ‘everything’ would not be very helpful, we will review some of the super essential PM skills and knowledge that will help make your freelance project life much smoother. 

• The art of wearing many hats Time-blocking and grouping similar tasks 

• Expert communication When and how to communicate with a wide variety of stakeholder groups – tools, timing, approach

• Establishing early project alignment and goals Stakeholder alignment on project goals, scope, and strategy

• Collaborative discovery and research Research methods: how much, who should be involved, and how

• How to have difficult conversations Prepare for approaching uncomfortable conversations confidentially

• Meeting design and facilitation When meetings are useful, how to design meetings to get to desired outcomes, how to facilitate healthy conversation

• Building project scope, estimates, and timelines 

• Tracking progress, scope, and changes

The challenge of wearing many hats

Assuming you are a freelancer managing your own projects, we know you will be wearing many hats. How will you prioritize and block out your time each week to check in on the project status, schedule meetings, AND serve the primary function of your role (design, development, content strategy, etc.)?

You might consider running a ‘team schedule’ workshop with yourself (AND your team!) to determine when you will be available for meetings and when you will be ‘offline’ for uninterrupted blocks of time. Finding this balance is one of the first steps to making your project life smooth sailing! 

Expert communication: understand your stakeholder and project teams

As a freelancer you are likely working with a wide variety of teams with equally varied levels of digital expertise and knowledge. A good project manager will immediately begin evaluating the team dynamics, level of digital expertise, communication styles, and goals of the teams they work with (whether internal teams or stakeholder teams on the client side). This sets them up for good communication with teams throughout the project.

One very practical, tangible way to start the practice of understanding your team is to put together an empathy map for each of the layers of stakeholders on your project teams. Use this template and take some time to think through the goals, drivers, motivators, and best and worst outcomes for each of the stakeholders. 

Onboard stakeholders and teams: the art of facilitating alignment

A crucial step in setting up healthy projects (one the full project team should be a part of) is running a solid project kickoff meeting and discovery phase. This is the point in the project where you establish roles, responsibilities, and guidelines for communication. It is also an opportunity for everyone to align around the collective goals for the project. 

As a freelancer running your own projects, you will establish your approach to goal setting and early project discovery. Make sure everyone knows what to expect in these early phases and why they are important.

You can use the following list as a start for your own project communication checklist. 

• Project roles and responsibilities

• A communication plan When (e.g. weekly status calls, bi-weekly sprint planning) and how (e.g. daily standups in slack vs. status calls on Zoom) we will communicate

• What to expect in meetings (and how to set them up effectively)

• Simple breakdown of the project contract What we are we building and in what timeframe, how we will manage changes to scope, timeline, and teams

• How deliverable reviews and feedback cycles will work

• How our stakeholders’ actions will impact project timeline, scope, and outcomes*

• When and how they will give feedback on key deliverables and in what timeframe*

• Other tasks that will be required of them (e.g. content writing, photo selection)*

*Project stakeholders don’t often have a clear idea of how much or what kind of effort they will need to put into the project. This is your chance to let them know: 

Research and Discovery: Ask the right questions to define project value

An experienced PM will tell you that the most accurate, value-packed project agreements were built AFTER the team did the responsible thing, and conducted a (paid) discovery phase packed with just the right amount of research.

Many organizations sell a project for a fixed price and promise delivery in a fixed timeline without having taken the opportunity to actually talk extensively to their stakeholders and the people who would actually use what they built.

If you need inspo for how you will convince your client stakeholders, you can adapt this description of the value of research and discovery phases.

Teams will be building a truly valuable product based on realistic requirements and timelines. Your client will be receiving the value they had hoped for, and your end-users won’t be stuck with a confusing or useless experience!

A quick search will reveal that there are many resources available on how to conduct user-focused research for digital projects. For projects with limited budgets there are ‘lean’ ways to conduct meaningful discoveries that will still give you important data you need to write a well-informed project scope. 

Scope, estimates, and timeline: “Build the right thing and build it the right way”

It doesn’t matter how brilliant your teams are or how closely aligned your stakeholders seem, you will still need to practice clearly defining what you are going to build. 

Project managers know that in order to define the scope of the work their teams will be doing, they need to work closely with their teams to define the value, features, and constraints that meet both the goals AND budget for the current project. 

As a freelancer, you can prepare to build out well-defined scopes and estimates for your projects by determining how you will conduct the following: 

• Define each of the elements of the work you will be doing (e.g. work breakdown structures, card sorting) 

• Get alignment on scope with your team first, then with your stakeholders. 

• Break the bigger pieces of your scope into specific tasks (“Build a signup form” requires UX workflows, copywriting, design, front-end development, and back-end development)

• Provide enough detail to accurately estimate the level of effort it will take to complete that work

• Involve your team in providing level of effort estimate ranges for each task (consider running a planning poker exercise to hear from different members of your team)

• Capture estimates for tasks that are often missed (meetings, creating documentation, travel, trainings) 

Tracking progress and change

As a freelancer you can most likely already recognize mid-project changes and know from experience how they can positively or negatively impact the health of your project. In the process of designs you might discover a new way to approach a project requirement. If that approach has little impact on the timeline and estimates for the project and better meets your project goals, you have just improved the project outcomes and the project remains healthy. 

How did you document that change in approach? How will you document other changes to a project that might introduce scope creep or take you further away from your project goals? Do your client stakeholders know that part of your role is to raise project risk and work with them to address changes to a project plan? 

Earlier, in the kickoff meeting checklist, I suggested introducing a plan for managing changes. 

As a freelancer you can start learning how to recognize changes to a project (all the project ‘creeps’), understand the benefits or the risk they introduce, and develop a plan for how to address them. 

In advance of a project you should consider preparing: 

• A way to document change on a project (RAID logs, change orders)

• Scripts to talk about risk with your team and client stakeholders

• A section in your weekly status report that calls out any changes or risk (if it’s empty most weeks, congratulations!)

• Clauses in your contracts that address mid-project changes and minimize their impact (I list several in Ask a Project Manager #8: How Do I Protect Myself in a Project Timeline)

What’s Next? 

With a little exploration of some of these foundational PM skills, you will immediately start adding additional value to the work you do with your clients and teams. What next? Keep learning and asking great questions. Take the SuperHi DPM course! Ask PM’s you know what they would suggest you learn.

As you learn about the world of project management, remind yourself that this is an iterative experiment to learn what works and does not work for the kinds of projects you do and the teams you work with.

Then, on your next project, you will have the templates and checklists you need to more easily run a successful project. 

Welcome to the world of project management and on behalf of my fellow project managers, THANK YOU for asking the question!