Dear Dr. Freelance: I’m a magazine editor at my wit’s end with a chronically deadline-delinquent writer. Not just a day, but a couple of days of excuses and delays. This freelancer nails every assignment and requires little editing, and I like her personally, so I’ve cut her slack. But I’m running out of patience. I’ve tried padding her deadlines, which she figured out. I’ve tried asking for daily updates, which has had no measurable effect. What can I do to motivate her?—Too Late Baby
TLB: I assume you’re providing her plenty of lead time and that she’s squandering it. If that’s the case, an editor-friend of mine has a system that will help you get the point across. Basically, her freelance stable divides into A, B and C categories, with the A Team receiving the most and best assignments. If nobody in A is available, a story trickles down to the best writer in B, and so on.
Normally, this all takes place behind the scenes; writers don’t know the system exists, let alone what their rank is. In your case with this freelancer, however, it would benefit you to make the system transparent. From your description, I am guessing she’s a perfectionist who prides herself on her writing craft. That’s something you can use to your advantage as you gently let her know she’s in danger of dropping into the second tier.
If I were to have the conversation with Deadline-Delinquent Writer Debby—and please note this MUST be handled in person or on the phone, not email!—it would go something like this:
“Debby, you know how valuable you are to my editorial team. Your stories are great, you always get the assignment right, we receive positive feedback from the readers. For the moment, though, I’m going to take my Editor hat off and put my Client hat on.
“Here’s the deal: You may not realize it, but we rank all of you freelancers, and you’re a strong A because of your writing talent. Unfortunately, your habit of missing deadlines is putting you in danger of falling into the B category, which would mean fewer stories and less interesting assignments. I don’t want that to happen, and I know you don’t either. But I’ve gotten to the point I’m catching flak from the other editors, graphic designers and production staff, and I can’t defend it any longer.
“So, from here on out, no late stories, no excuses, and I’m going to give you real, not padded, due dates. If you foresee problems completing your piece, call me at least 48 hours before the deadline and we can talk. You’re one of our best writers and I know you’re going to come through for me. Once you’ve proved that you’re on top of deadlines, I’ll feel comfortable giving you even more assignments than I do now.”
Debby is surely smart enough to know that the reverse is true: Missing deadlines is now going to impact her income negatively, though you’ll need to read her demeanor and your relationship as to whether you want to say that explicitly. Handle this deadline-delinquent writer with a respectful but firmer approach, and I think you can bring her around. If she blows it, you need to follow through on the consequences you’ve laid out, assign fewer stories to her, and remind her why. She’ll get the idea.