Professionally, I’m a game developer. I focus on developing adventures. That means outlining adventures and assigning writing to freelancers, checking freelancers’ milestones, and developing the freelancer’s text before sending it to the editors. Let’s break those three things down! Second, the milestone.

What A Milestone Is. A milestone is a check-in point where I’ve asked you, the freelancer, to turn in about half your word count. This is to make sure you’re on track, and to make sure I have something from you in case you disappear suddenly the day before the turnover is due. This isn’t to imply you aren’t reliable; even very experienced freelancers submit milestones, as anyone can put things off for just a bit too long without the right prompting. I wrote about what makes a good milestone recently (you can find it here), but this post is more about what I do with it.

First: The Words Are There. At its most basic, if I’m most rushed, I’ll open your milestone and look at the word count in the bottom left corner of Word. If that number is at least half your word count (or within a few hundred words of that), I’ll respond with “got it, thanks!” and that’s it. If you know that word count is going to be lower than expected, you should have already warned me of that fact and let me know what’s going on (or you should have already told me that your milestone will be a day or three late while you get up to the halfway point). I'll note to myself that I need to check in on that, and I'll start to become really worried if that half doesn't materialize pretty quickly. 

Second: Questions, Questions. The milestone is a great opportunity for you to ask me any detailed questions about the project that have come up in your writing, or show off something that might be a bit of a variance and ask if it’s okay. If I’ve asked for an encounter with a barbed devil in a village, you might ask if the barbed devil could be possessing the leader of the town’s salt miners, maybe.

Some advice I received very early on in my academic career about asking questions, more broadly applicable than just RPG writing. “What should I do?” is always a less impressive question than “Should I do X or Y?”, which is always less impressive than, “I’m not sure whether I should do X or Y, but I think X is probably the better answer and here’s why I think that.” More simply, pose any question with your thoughts about the best answer. Even if you’re wrong, it shows you’ve put some thought in, and that’s impressive.

My role in this is to be sure to find and answer any questions you have. I might miss some, and need some reminding, but answering a freelancer's questions at the milestone stage is an important part of my job. I might also let you know if anything's changed, or there's anything I can now get you that I couldn't before (such as an advance copy of a new Bestiary coming out that you might find useful). Giving you the tools to make the second half of your writing easier is good for me.

Third: Course Corrections. Once I have time—which might be the first time I open your milestone or might be a couple days later—I’ll read through your milestone in more detail. This isn’t just to answer questions you have, but also to spot any troubles that I see that need you to correct (like “hey, most of your NPCs are men. Make some of them women to get a better balance,” or “you have too many solo foes in a row near the end, please mix some of those combats up with mobs of enemies.”). To be honest, I’m also flagging things that I’ll have to do personally when it gets to development, and I might not mention those to you at all (like “ooh, this town mines salt. That makes the salt fiend in the next adventure placed oddly; I’ll eventually have to decide whether to change the salt fiend to something else, move the salt fiend encounter to this village, or change what the town mines.”) That’s just making my life easier down the road. (At the risk of exposing how low-tech this is, I keep such reminders on sticky notes on my monitor stand and throw them away once I’ve followed up on them.)

I also try to point out things that I think are going extremely well, and that I want you to be sure to keep doing. If I think a particular social encounter with the captain of the town guard is neat, I might say, “hey, this is a really cool encounter, and might be even better if the visiting duchess tells the heroes about the captain’s sordid past!”

Finally: Respect the Writer's Pace. Personally, I take a day or three off once I’ve turned in a milestone, to recharge a bit and handle other priorities. I’ll then dig back into the work. So I want to get back to you quickly, particularly if you have some tricky questions, but I'm not going to assume that you've suddenly jumped from 50 percent completed to 75 percent completed in three days (or even jumped from 50 percent to 55 percent, to be honest). I'm assuming my writers work at a steady pace, with reasonable breaks, and I work to keep that in mind no matter how frustrating or rushed things get on my side of things.