Part one: Requesting endorsements
1. Endorse them first.
Asking someone to endorse you is akin to asking for a letter of recommendation. Although the means of drafting the endorsement are less cumbersome than an old-fashioned letter, the task of authoring a thoughtful and sincere commendation is no less work. If you know and respect the person well enough to expect her to provide a positive assessment of your abilities, you should show that respect by endorsing her first. This expression of good will reminds your colleague of your positive attributes and feels good to do. It may very well inspire your colleague to draft your endorsement in return, without you even having to ask.
2. Personalize the request.
LinkedIn provides template emails for requesting endorsements, but graduates of the finishing school should know better than to simply send the boiler plate request. Doing so could send the message that you couldn't be bothered to type a few personal lines, yet you are requesting that they compose an original tribute to your abilities. The message you send should be customized to suit the tone of your relationship and the purpose for your request.
3. Explain the need.
While you are personalizing the message you should explain why you are seeking this endorsement. This gives your request some significance, a sense of timing or urgency, and may also provide your colleague with an opportunity to assist you beyond the endorsement request. Whether you are seeking a specific job opportunity, branching out into your own business, or looking to generally enhance your profile, these details can help your colleague form the content of their endorsement and prioritize your request among their other tasks. Your colleague may even have some good leads for you now that he/she knows what you are looking to do.
4. Make it easy for them.
Writing an endorsement can be a difficult to begin. Writing is not a strength for everyone, and it may have been a while since you two last worked together. Remind your colleague of the projects you worked on and what went well. (This is another good reason to endorse your colleague first). You may even suggest some skills or accomplishments you would like them to highlight, specific to the purpose of the endorsement. For example: "Since I'm seeking a project management position, it would be great if you could mention anything you felt I was particularly good at such as delegating tasks, multi-tasking and keeping the project team on schedule.")
5. Don't forget to thank them.
Always follow up with a note of thanks. Your colleague has taken time out of her busy schedule to help you in your career efforts. A quick note or a phone call to thank her will always be appreciated.