Procuring a freely licensed photo in order to complement an article can be a daunting task for the uninitiated. Outlined below are (roughly speaking) the steps I took to obtain a photo/portrait for Glenn Greenwald in order to add it to his article on Wikipedia. In this case, I've contacted Greenwald himself but note that doing this (asking the article subject) does not always guarantee a free image. The copyright holder is the person who has taken the photo. Thus, the article subject is usually not the copyright holder and may or may not possess any photos which they can give permission for. Nevertheless, doing this may still be useful as they can provide information regarding their photographer's contact information.

One thing to keep in mind when trying to get any photo to add to Wikipedia is the Wikipedia:Image use policy. While there are other things to consider, this is official policy which means that every effort should be made to familiarize oneself with it. You should also read through Wikipedia:Requesting copyright permission.

Before trying to obtain a picture, first make sure there isn't one already freely licensed over at Commons. Though if there was one, it would probably already be in the article somewhere, still, it never hurts to check. One may also make a Picture request over at WikiCommons, though my experience has been that this may take from 'a while' to 'forever.' Also, though I've never asked myself, Flickr sometimes has photos, and has been suggested as a way to obtain relevant images (but you still have to get the licenses!) and you can even search for images by license category. Uploading images that are free to Commons will have their license screened, and even if the Flickr user later changes the license, we can still keep the image. This screening does not occur on Wikipedia.

The next step for me was to request a photo from Glenn Greenwald. . .I found his email address where he regularly writes, but what to email him? Well of course there is a Wiki page devoted to this and it can be found at Wikipedia:Boilerplate request for permission. The email I sent was modeled from the first example and was as follows:

With an affirmative response to the initial email send a 2nd email which includes the declaration of consent form and ask that they send back the form with the photo as an attachment. At this point you can either suggest the licenses to fill in or go ahead and fill them in yourself. My recommendation is to go ahead and fill out the form completely so that they just have to copy and paste. I also think that it is probably a good idea to get dual free use licenses GFDL and CC-by-sa-3.0 (as they are both useful down the line, depending on the situation). So the 2nd email might look like this: (be sure to link the text of the licenses in the email)

Note: only complete this step if you plan to immediately follow up with an email to WP:OTRS permissions. Otherwise your uploaded image will be deleted.

To be able to upload to WikiCommons you have to be registered (If you are not go here [1]). Once you are registered, log in and upload the image (from the menu on this page, select "It is from somewhere else"). In the Summary, be sure to write a good concise description of the image. Also, next to "permission=", add "{{Otrs pending}}". Finally select "GNU Free Documentation License" from the Licensing selection box (assuming you obtained both GFDL and CC-by-sa-3.0; you can add the other license after the image is uploaded).

Once the image is uploaded, email "permissions-commons AT wikimedia DOT org" with the relevant email thread showing that you obtained the 'declaration of consent' for the photo (the email correspondence resulting from steps 2 and 3). Be sure to link the uploaded image at WikiCommons in the email, so that it is easy for them to check and add the appropriate information to the permission section of the summary.

If you haven't already, make sure to add the other license (for example, type "{{GFDL-en}}" or "{{cc-by-sa-3.0}}" below license sub-heading) to the image, below the license information used to upload the photo. Once OTRS has reviewed and added the permission information, then add it to the appropriate article on Wikipedia. Also look around on Commons to see if there are appropriate categories for the uploaded image. Done!