Managing Project Deadlines: Tips, Strategies, & Resources for Freelance Professionals 

Let's chat about one of the most basic tasks of managing a communications project - keeping it on track.

Business writing tends towards complexity creep. Content standards increase, audiences become more sophisticated, and expectations go up.

Blogging is a perfect example of this. Writing a blog post that met the highest writing, SEO, and UX standards used to mean blocking out enough time for deep research, writing, editing, and reviewing. As long as we spaced things out enough, we were good.

But now, writing authoritative and helpful blog posts can include interdisciplinary brainstorming, SME interviews, expert quote sourcing, and multimedia creation. We might need to collaborate with different departments, do some journalism and a little PR, liaise with designers (or DIY it), etc.

And that's just for a routine B2B blog.

Even simple freelance writing services can get out of hand if you don't have basic project management skills and procedures in place.

First, a look at what really sets back freelance service delivery.

Scope creep is a go-to scapegoat for project delays.

To be fair, it often is a factor.

Think another team should contribute to the white paper? That's scope creep. Enrich a finished blog post with data visualisation? Scope creep. Adding an extra round of revisions? Also scope creep. Changing direction mid-project? Still scope creep.

Scope creep isn't a problem per se. I consider it natural for clients to want the best freelance writing service possible. Sometimes that means adjusting things along the way.

The real challenge generally comes down to scope and project management.

Most of the "scope creep" problems I've encountered fall into one of these four areas:

1. Not being aligned on what the scope is. If we aren't on the same page to begin with, we're inevitably going to experience some form of "creep". It's fairly easy to prevent this using detailed project plans and briefs. It's also easy to slip into off-the-cuff collaboration routines and start assuming we're on the same page.
2. Underestimating work requirements. As a freelance writer, I enter every project with certain expectations around client preparation levels, ease of research, material handover times, and so on. If those expectations are off, the project will take longer.
3. Not accounting for dependencies or contingencies. Delivering business writing services is more collaborative than it used to be. More collaboration means more interpersonal dependencies, potential delays, and friction.
4. Working without established scope change procedures. As I said earlier, I think it's normal for clients to find things they want to adjust or add once a business writing service is already underway. Things get out of control due to poor communication, insufficient change management, and vague agreements.

Is this everything that can derail a freelance writing service? Nope, definitely not.

But I think it covers the most common issues. And having these under control sets us up for successful service delivery.

Tip 2: Use project management strategies to understand the scope and optimize your processes.

Most freelancers have work management methods in place. Even if those only live in their heads.

Pro's take it a step further into actual project management.

Here are some task and project management strategies I find useful for freelance communications services.

• Work Breakdown Structure or WBS: This project management technique is perfect for freelancers since it can be deliverable-based or phase-based. It breaks projects down into deliverables or phases, then tasks, and subtasks. From there we assess what it takes to get each project component (or work package) done, looking at activities, resources, dependencies, and other requirements. A WBS is a great starting point for managing any writing service.
• Gantt Charts: This old-school PM method isn't necessary for simple writing services, but is a life-saver when managing larger business communications projects. Gantt charts compile tasks and relevant information (like dependencies, etc.) into a visual bar chart. Unless you're super Type A, a Gantt chart is overkill for basic freelance writing jobs, but knowing how to put one together is a great digital skill.
• Project Task Hierarchies: This is like a simpler version of the WBS and it just means organizing tasks into their discrete subtasks. It's a nice project management technique that's basic but still effective. I like incorporating it into my personal planning even for freelance writing services that don't need full-on project management.
• Task Dependencies: Pinpoint which tasks can't be completed until something else happens. Map out those relationships then evaluate your tasks for risks, potential delays, and project management needs. E.g., moving from the first draft to the second draft of a case study might depend on technical fact checking and be at risk for interpersonal delays.
• Time estimation and task time tracking: Estimate timelines for tasks, wait times, dependencies, and any other factors. Then track the time, even on projects that aren't billed by the hour. This supports accurate scheduling, task management, post-project reviews, and personal productivity improvement.
• The Eisenhower Matrix: This classic time management method prioritizes tasks by urgency and importance. You can also do versions using effort levels or tasks with dependencies.

Tip 3: Set realistic deadlines with room for contingencies.

A deadline that isn't based on a good understanding of a project's workload, dependencies, or risks is far more likely to be missed. So once you have a granular understanding of the scope and other factors, use that information to set realistic timelines.

This alone makes a sometimes tedious breakdown worth it.

1. Find the critical path aka the longest activity sequence - inclusive of dependencies.
2. Estimate your task completion times + possible wait or delay times. Add this all up.
3. Build in some buffer room. Add a little extra.

Tip 4: Stay organized with productivity and project management tools.

Finding the productivity system that's right for you (and your team) changes everything. Freelance professionals might want to use three sets of tools: personal, client-focused, and team collaboration.

I have a minimal but effective stack.

• Personal: Amazing Marvin, Obsidian, smart speaker reminders, whiteboard calendars, and notebooks galore.
• Clients: Moxie, Google Docs, and Microsoft Office.
• Team: Moxie, ClickUp, and clients preferred tools, like Monday.com.

Mixing analog and digital gives you the best of both worlds. As far as memory goes, handwriting is superior to typing. It probably works the same for physical calendars, day planners, and to-do boards. There's also something to be said for having direct visual reminders within your working environment. (Whiteboards, post-its, and index cards are great for this.)

Digital productivity tools are beyond this blog post's scope. So, I'll just share what I look for.

I go for personal management tools that are super flexible, customizable, and robust. Right now, that's Amazing Marvin and Obsidian.

I look for client, team, and business management tools that are collaborative and feature-rich, without huge overhead or lock-ins - giving me the freedom to use whichever tools work best for each project. Right now, that's primarily Moxie, sometimes ClickUp, or the client's choice.

Tip 5: Give collaborators a heads-up.

Collaborators and stakeholders should know what a delay on their end means. Otherwise, it isn't fair to blame them for not responding in time, making last-minute changes, or doing something else that pushes the schedule back.

So, build that info into messaging, updates, and documentation.

E.g., when emailing an SME to gather thought leadership material, consider mentioning that your graphic designer is waiting to create interactive visualizations to accompany it.

Note: We're just sharing information - not micromanaging or put anyone down. Double-check your messages to see if the tone is severe or belittling.

Tip 6: Use scope change procedures and agreements.

Scope creep is a problem. Scope change doesn't have to be.

Integrating clear scope change procedures into contractual agreements keeps things on track and fair for freelance service providers and clients.

Here are some terms to consider:

• Deadline extensions for scope changes.
• No changes beyond a certain time or approval stage.
• Compensation for work that's in progress or complete.
• Rush fees for last-minute add-ons.
• Kill fees or full compensation for changes that eliminate substantial work.
• Subcontracting to other freelancers.
• Right to refuse changes.

Figure out what your terms are and incorporate these into contracts.

Wrap