Thing is, he's sent his manuscript out to three agents (somehow costing him $25 per 'query package') and was rejected. He's now convinced that the sci-fi market is dead and that it would be cheaper and more successful to self-publish. I tried to explain what things to watch out for in self-publishing, and he listened. He's now frustrated because he sees how difficult it would be to achieve his dream of selling his self-published book widely and getting noticed by a traditional publisher. Before I even mentioned it, he understood the needed to edit his manuscript, and he asked me who I used to do the job.

The next day, he hands me the first 45 pages of his manuscript (improperly formatted, using a dot-matrix printer with faint ink). Unsure of what he wanted, I asked if he wanted a line edit. He reluctantly said, "only if you see a real problem."

He's a decent writer. But his work is not publishable right now. The problems really wouldn't be hard to fix, but I'm afraid that all the red comments will do more harm than good for a writer at his stage of writing. Beginners don't understand that every writer has their problem blind spots and that my taking the time to make a lot of comments means "I believe in your ability to make this great!" And I really did try to edit as lightly as possible, but he has a bad habit of putting necessary-to-understand-the-scene information about two pages too late.

I think the big question is whether this person is coachable, whether they're looking to you for coaching, and whether you have some credibility with them and willingness/ability to mentor.

As an unpublished writer myself, I would have a hard time giving a detailed critique to another unpublished writer who feels he/she knows more than me (although seeing an MS rejected by 3 agents and thinking the market is dead is a bit of a strange conclusion to reach...)

It sounds like he's willing to listen to you, but begrudgingly. This is a hard person to coach, if they accept your feedback but only with coaxing. It might be simplest/easiest for you to just lay it on the line. "Here, Joe, I was as gentle as I could be, but I need to be honest with you. I saw a number of problems with your MS and can see some reasons why agents would reject it out of hand. To summarize my points, I see some problems in storytelling example a, b, c, and some issues with over-reliance on adverbs. Here are some tricks I have used to try to escape these tendencies in my own writing. I have found these two books (no more or he'll run screaming from the room) to be important in helping me hone the craft of writing. I think you have plenty of potential here, and a great story in need of polish and some additional work. I am giving you this feedback with the intent that it motivates you and helps you improve. I am really worried, though, that by seeing all this red you're going to think I thought your work is trash. That's not the case at all. I wouldn't have spent the time if it were just trash. I hope you can take this feedback in the spirit it is given, as a means to improving your skill. In my experience, writing is a lot of teachable skills, a little bit of talent, and a lot of perseverance. If you want to reach this goal, you can do it."

The key here is you have to believe he has the skill/talent/potential or the above is all going to sound false. So...if you don't believe it, cap up that red pen and step away from the manuscript. If you do, then by all means spend the time, and then spend the time explaining the feedback. Offer to dialogue about it, explain your thinking and offer examples of how to fix something (i know there are certain types of feedback I get that i wholeheartedly agree with and yet feel powerless to do anything about because I don't know how to fix it!)

Good luck to you. You are a good friend to want to help this writer. He's lucky to have you in his circle.

The other day, I looked at some of my writing when I was 16/17 and involved in a creative writing group I ran at sixth form. The basics were all right. The prose was enagaging, the plot well structured and the characters interesting.

Then I looked at some of the writing I did during my BA, when I was writing in isolation. The writing style ranged from excellent to beyond OTT. I'd gone away and cast everything I had learned to the wind, in order to experiment and do what I thought was 'writing as art'. In retrospect, it helped me hone my voice. But nothing I wrote during that period would be publishable without some serious work. I was being far too indulgent and had simply forgotten everything I'd learned. When I couldn't get it published, I felt people just didn't 'get' me.

In the last 9 months I packed in my part-time job to do freelance writing full-time (I've been doing non-fiction freelance for 3 years). I've joined multiple workshops and nearly completed an MA in Writing for Performance & Publication. I've relearned everything I once knew, and it gave me a wonderful perspective. In these few months I've had short stories published and written much more than I ever did in the three years of my BA. Everything I've written since has been stronger, and I can see that now.

Your friend is at the stage I was at during my BA, I think. He's taught himself a lot, and so thinks he knows it all. He's writing in isolation and is therefore lacking that critical eye being part of a workshop provides, and is lacking the objectivity offered by critiques. I'd crit his work as honestly and vigorously as you can. Knock him down a few pegs (but kindly). He'll soon see all the technical mistakes he's made, and will probably be resistant to your feedback at first. He'll say it's intentional and you don't understand him. Then he'll secretly see you're telling the truth, throw his novel in a cupboard (or the bin) and join a bunch of writers' websites. Then he'll flower and grow, and he'll always remember the wonderful help you gave him.

(Where you hold your story out from you and point to the right thing at the right time.)

If he's going to do much in writing he's going to need to develop the taste for red ink. If you don't want to be the one to thicken his skin that's fine. (Also you are the only one close enough to this situation to really judge how he's going to take it, so don't listen to us just do whatever you want.)

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And I really did try to edit as lightly as possible, but he has a bad habit of putting necessary-to-understand-the-scene information about two pages too late.

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I think you have the right ideas in mind. A full line-edit would be depressing to receive, a lot of work for you--and largely redundant, because if he starts revising it properly, much will change and many line edits will become irrelevant.

I would suggest finding a few nice things to say about it, being specific about phrases, segments or ideas that work. Then I'd suggest indicating (with a few examples) five or six of the most damaging common habits, such as "putting necessary-to-understand-the-scene information about two pages too late".

Also, as others have suggested, tell him about Hatrack, books on writing by OSC and others--and that revising several times is the way things are, even for experienced writers.

He's intelligent; he'll figure the rest out by himself and later come to the realisation that much was wrong, and you simply and sensitively told him the worst in an encouraging fashion--so he'll come back to you with requests to read later, better revisions.

Also, try giving him some of your stuff to rip apart. Let the cutting, slicing, and bashing on the writerly ego go both ways. That way it's not just you beating up on him and being all smug and superior (not saying you are, but that it may be perceived that way if the criticism is a one way street). Besides, who knows? He may actually have something to teach you, too.

Tell him he's like a new rock band trying to book stadiums before they've even started out playing bars.

I've also already let him take a look at my first chapter. He requested it the moment he heard I was a writer, and he had his go at me weeks before he handed off his work to me. However, he only had one minor change to suggest. I'm pretty sure he's not used to getting critiques (or harsh critiques, at least) back from people because of the way he commented about my work.

On the up side, he finally started asking the self-publishing companies the hard questions I told him to ask. Yesterday, he talked with me and profusely thanked me for saving him from getting ripped off. He's not going to self-publish anymore. This also means that he's now got a much higher opinion of my knowledge of the publishing industry and will probably be more open to critiquing.

I've decided to hand back the unmarked parts of his manuscript and give him the overview of his main problem, give him a few examples, and include a pep talk. If he wants the other sheets back, I'll warn him that I marked more heavily than he asked for so he needs to be prepared if he really wants to see them. I just didn't want to pop those pages on him without him mentally being prepared for the critique.