Delivering Constructive Criticism

Over the years I have been on both ends of constructive (and not so constructive) criticism.  Quite frankly, I still struggle with doing this flawlessly every time, but I've put together some guiding principles that I try to work under and thought might be helpful to you:
Be timely – Providing feedback as close to the event as possible is always the best approach, because the event is fresh in minds and can be related to more easily.  However, make sure you’re not providing feedback out of emotion and positioning yourself for an emotional argument.  Go out for a walk or sleep on it first then give the feedback.  Try not to wait longer than a day or so as the effectiveness of the feedback will go down the longer you wait.
Amazon.com Widgets Get some coaching if necessary before giving feedback – Consider running your feedback by a trusted colleague, friend, or spouse before giving it to the recipient.  Ensure that you don’t make it a griping session or an attempt to get support for your position.  Heed your coach’s feedback and incorporate it into your feedback for your recipient.  Another benefit of using a coach is it helps build your confidence in delivering the feedback and enforces some accountability on you to do it. 
Don’t offer feedback if your emotions aren’t in check – If you can’t seem to get over any anger or frustration don’t offer the feedback, even if a couple of days have passed.  If you can’t be factual and unemotional about your feedback it won’t come across as feedback; it will sound more like you’re picking on the recipient.  Get over your emotions then give the feedback.
Talk face to face if at all possible – You’re likely to get better results if you are able to discuss face to face and not only hear the verbal but see the non-verbal reactions, such as crossed arms (signifies an unwillingness to cooperate) or facial expressions.  I’ve tried to give feedback through e-mail or over the phone and have not been nearly as successful as giving it face-to-face.  If you can talk face to face, do it.   
Jot down the behaviors you want to give feedback on ahead of time – Know the specific situation and behaviors that raised your eyebrows and write them out ahead of time.  Ensure the behaviors are factual and easily understandable and not laden with emotion.  If you feel you may not be able to judge the emotional content of the feedback, ask a colleague to review whether your feedback is factually driven and not emotionally-charged.
If something was done well, say so – If your recipient did something well, start your feedback session off with the things that were done well.   Don’t worry that you may be dampening the effect of the constructive feedback because you also gave positive feedback.  Mixing positive and constructive feedback tells the recipient you are being objective and balanced and will make your feedback more effective.
Avoid emotional attacks – Statements like “You idiot!” or “Your ideas are stupid!” are very general, have no constructive value and don’t belong in a feedback session (or anywhere else for that matter).  Your feedback should focus on fact and some unemotional assessment, such as “The joke you told in the meeting today could have been offensive to some of the attendees.” 
Let them know how the behavior affected you or others – For example, let’s say you are giving feedback to your recipient on his inability to meet deadlines.  The feedback could be, “You have not met the last three deadlines assigned to you.  Your colleagues need to take on additional work that was to be assigned to you because you are not meeting assigned deadlines.”  Helping the recipient understand the impact of the behavior assists in helping to understand the need to change the behavior.
Establish an understanding on desired behavior – Clearly outline for the recipient what behavior is desired.  Using our deadline example above, the desired behavior would be as follows: “The team needs you to meet each deadline given to you to keep the project on schedule.”  Even though this may seem unnecessary at times, you’re better off to ensure that desired behavior is clear with the recipient, and that he agrees to the desired behavior.