Project Management, Blown Deadlines, and How Freelancers Can Help

5 min read

As a freelance writer, editor and proofreader, much of my work involves supporting a team to produce a final published document—bids, reports, white papers, articles, and so on.

Time and again, I receive emails from the project manager letting me know that the work isn’t ready for my input yet, because other contributors haven’t managed to complete their drafts or finalise their results.

Having worked with many managers on this, I can reassure you: if you’ve ever experienced the frustration of trying to keep a project on target for a deadline and felt as if coordinating the working group is an impossible task—you’re not alone!

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In a recent Freakonomic podcast, Stephen Dubner detailed some common project dynamics, and the reasons why most of your group tasks overrun—in terms of time, budget, or both. In this five minute read, I’ll identify four key issues which affect us in our planning, and how using freelance support can radically help you overcome these challenges.

The Planning Fallacy

You may be an experienced project manager, or perhaps you are new to overseeing a group piece of work—but in either case, you’ve managed your own workload successfully in the past. And yet, Nobel Prize-winning psychologists Danny Kahneman and Amos Tversky would advise us all to be on our guard against the Planning Fallacy: overestimating your capacity, and underestimating the size of the task.

Despite our best intentions and most rigorous organisation, managing a multiple-stakeholder project can be overwhelming, and we can all fall prey to the same inefficiency monsters. So, what are they, and how can we defeat them?

The Optimism Bias

Freelancers are experienced at working on multiple-contributor projects, and have seen a wide range of challenges; they can help you think through possible difficulties and strategise around them

The first factor which messes with our deadline is our instinct to assume things will go more or less according to plan. Your own competence and professionalism can impede your ability to predict the sheer number of obstacles your project may face—we are insufficiently comprehensive in our thinking when anticipating bumps in the road.

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You may be able to imagine a competing piece of work arriving at the same time as this project, for example, or perhaps running into a technical issue that burns a few (dozen) hours of re-work or delay, or even that a crucial colleague may have a day off sick, or get held up on a flight… but can you imagine all of these things happening at once? As well as, maybe, ten other minor disasters you can’t even dream up right now—but that could happen, and have a major impact on your schedule?

Our Optimism Bias—the expectation that things will pan out well, even in the face of negative past experiences—is good for our emotional wellbeing, and it allows mankind to undertake daring and bold endeavours… but if we're trying to plan a realistic project schedule, it can work against us.

That’s when an external perspective can make a significant difference to team productivity: firstly, because freelancers are experienced at working on multiple-contributor projects, and have seen a wide range of challenges; they can help you think through possible difficulties and strategise around them.

Secondly, factors which affect your immediate team will not impact in the same way on freelance support (software / hardware issues, dynamics within the team, competing priorities, etc.), and so they can bring speed and positivity to the project, regardless of what’s going on within your office.

Overconfidence

Planning Fallacy factor two is overconfidence: the well-established feedback loop which tells us that being upbeat about our ability or progress is always a Good Thing.

... and that is a lifetime of feedback we give people, where we’re rewarding them for overconfidence constantly
— Katherine Milkman, Associate Professor at the Wharton School, University of Pennsylvania
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In a competitive and fast moving world, it's beneficial to make bold claims, super positive self-assessments, and generally present a glass half full message—even if we know that the glass actually has a chip on the edge, a crack down the middle, and the drink inside probably should have been chucked out weeks ago for Health and Safety reasons.

The danger of overconfidence is that we start to believe our own hype, and lose sight of where we truly are on the schedule.

Whilst your freelancer will certainly want to impress you, we know that the proof of the pudding is in the eating—we don’t get hired back if we don’t produce the goods. One member of your team upon whom you can rely for 100 percent honest feedback is the one who—after the dust has settled and the project is complete—will depend on your recommendation for future contracts.

Coordination Neglect

The massive gains which come with a wide range of participants and specialist expertise are at risk of being undermined by the logistical challenges which accompany the ultimate reassembly of all this input into a coherent whole.

 
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Freelancers can provide excellent collaboration in designing a schedule and a system that allows work to be done in the right order, and received by the right people at the right time, minimising re-work and delays

Coordination neglect—underestimating the complexity of putting together the rich data and insight you've received from across your team—can be a major stumbling block in successfully making your deadline.

A freelance support can be invaluable in working around some of the difficulties here. We are well used to the process of coordinating multiple inputs, and can provide excellent collaboration in designing a schedule and a system that allows work to be done in the right order, and received by the right people at the right time, minimising re-work and delays.

Procrastination

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The fourth crunch factor which blows your deadline is that old desk enemy, procrastination.

There’s always something more interesting / urgent / easy to do than slog out the work—it’s human nature to put things off, especially if you’ve hit a tough patch.

This is another way in which utilising freelance support can really speed things up: when you hire someone to work specifically on your project (writing, editing or proofreading your reports, for example) they are completely focused on your work.

There’s nothing competing for our attention or importance, and all of our doodling, social media distraction, and displacement activity gets done on our own time!

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Freelance support for your project can make a crucial positive difference to planning your workflow and managing your timeline and budget—by contributing experience, rigour, an external perspective, and uninterrupted focused energy, moving the project forward on time, on budget.

For a free consultation or quotation, please contact me@isandrews.com, or give me a call on 07988 858873 to talk more.


Next time: Take Project Planning Strategy a Step Further

My next blog post examines a simple but brilliant technique proven to deliver accurate budget and planning predictions, slaying the Planning Fallacy forever!

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