There's a reason why messengers get shot. Nobody likes bad news – particularly if it's a list of perceived problems with a project someone has spent months slaving over, spilling their blood, guts and personality into it. To a writer exhausted by lack of sleep, persistent rejection and a life of lonely unappreciation 'sorry I just don't get this character's motivation' is likely to be the last nail in their coffin. It doesn't matter how long you've been in the business, the first reaction to a penetrating critique is at best defensive, at worst homicidal.
So before stepping into that emotional minefield you need to get your shit together – here's how:
1. Establish credentials
Sometimes you'll be giving feedback to someone you already have a relationship with, but often you may find yourself working with someone you don't know, or worse, someone who doesn't know you. Make sure you make them aware of your past experience with critiquing and/or successful writing projects, perhaps even giving them examples of your work. Bad news is bad to take from anyone, so don't give them a chance to dismiss your feedback out of hand, otherwise you're wasting your time.
2. Establish trust
If the writer thinks you're going to post snippets of their germinal projects online for trans-global mocking, or maybe even talk about them in the pub, it's hardly going to help strengthen what is an already fragile relationship. If the writer thinks you're not going to be sensitive to their hopes, ambitions and fears they may not end up submitting again. You need to be trusted and taken seriously.
3. Establish terms
Some writers just can't take it on the chin. My erstwhile writers' group had at least two full-on lost-it arguments that I know about, one of which involved me. If you've spent four hours working on a critique only to be shouted down by the writer every point you make then everybody's wasting their time. Make sure you work out with the writer the best way of delivering the crit – in person, over the phone, in writing, or a combination of all. That way you give the writer an opportunity to deal with the truth on their terms.
4. Understand the story
Remember that you're not writing your story – they are trying to write their story - and you are trying to help. Sure, you would probably enjoy a car-chase right through their Mills&Boon romance but saying so is no help to anyone. Leave your ego and your writing ambitions at home, try and understand the story they are trying to tell, and see what you can do about helping them tell it.
5. Look for the positives
Disrespecting someone's writing is easy. You can't help but notice all those problems in someone else's work that you can't recognise in your own, but your criticisms will be given far more weight if you can also recognise good writing, promising story-lines, and intriguing characters. Make those points too.
Sometimes your faced with a piece of writing so atrocious it's impossible to find any good in it whatsoever. Invent something. You need to sweeten the pill so that the bad news will be taken seriously - then hopefully next time you read it you will find something positive to say.
6. Don't react to defence
I don't care who you are – the first reaction to a bad crit is a defensive one – with the best will in the world, it's hard not to justify your creative choices – 'I had to write that passage abominably because...'. When faced with a writer defending the indefensible take a breath, smile sweetly, and move on to the next point.
7. Tell them what they need to know, not what you think you know
So you may have just learnt about deus ex machina, defamiliarization, subtext, dramatic irony, in media res, foreshadowing, foretelling, inciting incidents and god-knows-what-else, but no one cares. Don't pontificate about what you think you know, look hard at the work in question and tell the writer what they need to know.
8. If in doubt, leave it out
If you're not sure about a point it's probably not worth making. They'll be more than enough for you to pick on, so don't weaken the points you feel strongly about by articulating the ones you don't.
9. Don't make it personal
Treat it as a learning exercise. Assume that the writer will ignore everything you say. Focus on developing your understanding and your expression. Anything else (like appreciation) is a bonus. There's no point in getting shirty because the writer doesn't love your crit. Years later they may, but right now they just hate you.
10. Do it properly
Nobody crits the critters. A well-written and penetrating critique takes time and effort. To analyse the story, identify problems, suggest improvements, and hardest of all, express these (potentially wrong) ideas in a way that's understandable and communicable to an audience that most likely doesn't want to hear them takes skill. Make the effort – it's not just the writer who'll benefit if you do it well. You'll learn about good writing from the analysis process and you'll also recognise your own weaknesses far more easily when you see them in the works of others.