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Making Your Deadlines


Freelancers face two giant challenges at the beginning of every new job. They need to agree a price for the work they’ve been asked to do; and they need to agree a deadline for the delivery of that work. Although a lot of attention is paid to the first challenge — calculating hourly rates, comparing the prices of competitors, dreaming of the check — it’s the deadline that’s actually the more important challenge and the hardest one to overcome. Pitch your quote too high and the worst that will happen is that you’ll lose that job. Pitch too low, and you’ll lose money… once. Miss a deadline though, and you could find that you lose a client forever.

Even that though looks welcome when you consider some of the consequences of missing deadlines. Of the roughly 35,000 lawsuits that clients file against lawyers each year, the second most common cause of the suit was that the lawyer failed to meet a deadline. A third of all claims result in damages and in one in six of those claims the damages top $100,000. That would be a high price to pay for being late.

Miss a Deadline, Pay $200,000

Nor are those high costs restricted to highly-paid and well-insured lawyers. When writer Douglas Brinkley missed the deadline for his biography of Jack Kerouac — and in the process, missed the 50th anniversary of the publication of “On the Road”  — Penguin, his publisher, sued. They demanded the return of his $200,000 advance, half of which Brinkley had already paid to Kerouac’s estate in return for access to the author’s papers. While that’s not a problem that’s likely to affect every freelancer, it is an issue for anyone who demands payments of 50 percent up front. Especially, if they spend the money before completing the project.

But missed deadlines are a threat to everyone, even the most organized of workers (and how many of those are there?) In part, that’s because the late freelancer’s favorite excuse — “It’s not my fault!” — might well have some justification. Ronda Muir, a management consultant with Robin Rolfe, notes that many of the typical management methods used in legal firms actually encourage missed deadlines. By setting dates that fall a long way before the item is actually needed, managers suggest that the deadline is soft and can be missed with no real consequences. And by micromanaging — checking in constantly to see if it’s ready — they take the responsibility for proper pacing away from the worker. If he falls behind, the worker thinks, then the client or manager will spot the problem pretty quickly… so they don’t need to do it themselves. That’s not a training routine limited to law firms.

There are technical solutions. Orbisoft’s Task Manager is supposed to solve the organizational problems that cause projects to fall behind. The Omni Group’s OmniPlan claims that it can make “project management painless.” And, of course, although Getting Things Done isn’t a piece of software, it is about as complex as one. It does seem to work for some people… and exasperate many others.

What all of these solutions have in common though is that they all demand time, something that’s always in short supply when you’re trying to reach a deadline, and seeing your schedule get tighter and tighter.

The Worst Kind of Deadline

The best solutions then might be the least technical and also the least demanding. One solution that many freelancers turn to is the imposition of milestones. Instead of agreeing to hand over the completed project on the final day, the two sides agree delivery dates for partial work. That allows the client to see the work as it’s progressing, ensure that it’s on track and ask for changes while it’s being created instead of waiting until the end. For the freelancer, it can also create a staggered payment schedule.

It’s also a solution that can help service providers to meet even the hardest kinds of deadlines: the ones that are a long way away.

While tight deadlines will always make a service provider sweat, when the time to the deadline is more than twice the amount of time it takes to complete the project, there’s too often a temptation to procrastinate. As smaller projects pop up in the meantime, the larger project with the distant deadline is continually pushed away… until it becomes clear that there’s only half the time needed.

Not all clients want to see half-completed work though, and not all freelancers are happy supplying drafts instead of polished projects that show them at their best, so an alternative solution is to set your own mini-deadlines. You can set a certain number of pages that need to be completed by a certain day, allocate a number of lines of code to write each week, or list the leads that need to be contacted each month.

While the occasional deadline might be missed, attempting to keep to them will always be a good discipline and an effective way of working to schedule.

Not even that though will solve perhaps the most infuriating kind of deadline: the one missed by other members of the team. If you’re waiting on someone else’s work before you can complete your own — or worse, if you’re managing a team of freelancers — it only takes one person to fall behind to put everyone behind schedule.

There’s not a huge amount you can do about that — beyond making sure it’s not you that’s causing the delay. Making sure that the team are in close contact might help. It’s one thing to let down a client or a colleague you’ve never met but when you feel you know the people you’re working then delivering late means that you’re letting down a friend, and that can be painful. Ultimately, though it’s up to the project manager to set deadlines that are tight enough to create focus but still loose enough to take the inevitable delays into account. It might also be possible to set overlapping tasks so that the Web designer, for example, can work with only some of the copy or the marketing team at least have a demo that they can show leads even if the final product isn’t ready yet.

But perhaps the best way to ensure that deadlines aren’t missed is to be honest. It’s never easy to say ‘no’ to a client but if you feel that the deadline is too tight and that you’re not going to make it, suggesting a more realistic date is always a better strategy than having to say ‘no’ on delivery day when the client asks if it’s ready.


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