For Big Projects, Try a Cone-Shaped Schedule

Procrastination is one of the most discussed topics in freelance circles. Tips on combating dread, getting started, and powering through abound. Some of the advice out there has value, but the very focus on procrastination is often misplaced. I’ve found that, in terms of productivity, there’s more to be gained from shaping your project’s trajectory than from shaping your anticipation of the work. That holds true whether you’re working for yourself or for someone else.

The single biggest motivator in getting a project done — and done well — is a sense of progress. Sure, there’s an art to getting started (as I’ve discussed previously), but once you’ve begun, awareness of your forward movement is what carries you through. One way to achieve that is to spend less time on each step than you did on the previous one so that your schedule looks like a cone turned on its side — with the broad base on the left and the pointy end on the right. That doesn’t mean scheduling work sessions to artificially force earlier and earlier quit times; that approach just leads to a marathon “final push” right before the deadline. The cone-shaped method, in contrast, means observing these five, more organic principles:

1. Survey the entire geometry. To identify where the base of the cone is, you first need to look at your project in all its initially shapeless complexity. That allows you to see what you have, what you don’t, and how everything might fit together. You can’t possibly create an efficient plan without knowing which end is up — or, in this case, which end should be on the left and which on the right.

2. Respect the inherent properties of the work. Every project has its own deep structure that may not match how the people who ultimately see the work will experience it. In short, the beginning is not always the beginning. Sometimes, working backward from the intended endpoint for your user allows the earlier pieces to fall into place more easily as you develop them. Other times, the most substantive part (the part where you should start) is in the middle. Bottom line: your process and the end user’s experience are often two entirely different objects. Your audience need never see that you’re really just a conehead.

3. Make gross movements before fine-tuning. As soon as you’ve identified the heart of your project, start doing the heavy lifting. The first full-fledged work session should be your longest and most difficult. At that point, the project is likely to feel relatively new and fresh, and fatigue won’t be as much of a limiting factor. Besides, you’ll feel freer to move things around and take risks with the basic structure when you haven’t invested yourself in minutiae and aesthetics, important as those things are in the end.

4. Gradually narrow the window between sessions. As the cone narrows, so should the time between the periods when you sit down (or stand up) to do the work. A key to creating momentum on a project is having session duration decrease as the gap between sessions also decreases. That creates the illusion of speed — like you’re walking downhill rather than uphill. And, actually, it’s not entirely an illusion. You are, after all, moving toward the end at a faster pace. It’s just that you’ve deliberately structured your schedule to achieve that effect.

5. Take pleasure in the polishing. With the toughest parts behind you, enjoy the little pleasures of the tip of the cone — the niceties, the trim, the tassels. Imagine yourself sitting in the audience at your own play and appreciating the small things. Doing that can make a deadline feel like the celebratory debut it should be rather than the exhausting finale it often is. A cone tip is most pleasing when it’s sharp and shiny. Take your finger to it (gently) and see just how good it feels.

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Your Freelancer Can Be a Low-Cost Consultant

As any project manager knows, finding good freelancers can be tough. Once you have one who efficiently delivers high-quality work, the seamlessness of the operation is addictive. Everything’s functioning beautifully, so you just keep running the well-oiled machine. That’s a success to celebrate, of course, but it can lull you into overlooking additional value that the freelancer could offer, if only you’d pause a moment to extract it. I’ve seen that value both as an in-house project manager and as a freelancer.

Where is the value hidden? It’s buried among the insights that the freelancer is constantly acquiring about your systems. Not every reliable freelancer will be able to articulate those insights in a form that can be put to practical use; that’s something you have to gauge based on your interactions with her. And even if she is a good candidate for this kind of meta-analysis, her time does mean money. But it’s a fraction of what you’d pay for a high-priced consultant, not least because the freelancer has already done the up-front investigational work. That’s low-hanging fruit you’d be wise to pluck.

Here are some small-scale assessments you can ask a freelancer to do. Different types of outsourced work are likely to merit different types of assessments, many not in this list. And, clearly, they cannot substitute for a consulting task that requires a very broad scope.

1. On an isolated job, have the freelancer keep a running catalogue of things that went better or worse than expected. Ask her to briefly explain why she thinks each outcome was unanticipated, focusing in particular on systems- and process-related obstacles.

2. Over time, have her note which parts of the work you deliver to her have become easier to handle, and which less. If she finds that the level of difficulty fluctuates, have her identify the contingencies, systemic and otherwise, that seem to be responsible.

3. If your relationship with the freelancer is especially trusting, ask her to identify one process or protocol that she uses with one of her other clients that she thinks would serve your needs. Have her explain how it might best be integrated with your existing systems, even if modest ripple effects would be unavoidable. Obviously, make clear that you are not interested in the name of, or any proprietary information from, the other client and that if either revelation cannot be avoided, she should skip this task altogether.

4. Ask her to write a one-page analysis of how your overall systems can be improved. The analysis should include both a brief narrative assessment and specific, bulleted suggestions. Encourage her to be honest yet practical in her recommendations.

Small-scale consultative tasks like these should be assigned to a freelancer only on a periodic, or even a one-time, basis. You obviously don’t want to gum up the gears of the well-oiled machine. Also, be clear about how much time you’d like the freelancer to spend. If in the end you derive value from her assessment, compare it — and the cost — with what you got from your last consultant. There’s no guarantee of comparatively better value, but the experiment certainly will have been worth the low price you paid to conduct it.

How have you managed to derive value from your freelancers, beyond the usual deliverables?