Once your photos have been taken, your photographer will usually send you a link to all the photos taken – maybe a hundred or more. This is both the curse and the blessing of digital photography. Rather than the photographer carefully curating the best photos to show you as proofs to choose from (and that was difficult enough!) you now get them all because there’s no cost to doing so.
I’ve seen a number of people get stuck here, so overwhelmed that they never do choose the photo they want to use or else wait for a long time. Please don’t do that. Here are a few suggestions to help.
1) Scan through the entire collection and get all the self-criticism out of your system (you won’t be able to help yourself so I’m not going to tell you not to do that.) Just get it out of the way! Make a note of any that you immediately like (it can happen!)
2) Go through the photos and note if there are any with a collar askew or a necklace slightly off-center – anything that’s an obvious flaw that your photographer couldn’t easily correct with Photoshop. Don’t worry about some stray hairs sticking out – the photographer can fix that. Depending on the site where your photos are stored, you should be able to mark favorites or somehow sort them. If not, just make a note of the numbers – it’s likely that the “flaw” appears in a series of them.
3) You probably had at least a couple of “looks” – perhaps two different jackets or shirts. See if there is a look you prefer and if so, mark the others off your list. Remember this is your professional image/brand. The conservative dark suit jacket may be perfect for the corporate shareholders brochure but perhaps a professional but more approachable look would be better for people you want to connect to you on LinkedIn.
4) You probably had at least a couple of different backgrounds. See if there’s one or some that you prefer. Discard the ones with backgrounds you just don’t like for this professional image.
5) Go through the photos now and look for anything that is a look that you don’t care for – perhaps a squint or a smile that sometimes shows one snaggle tooth touching the top of your lip. Maybe one eye sometimes droops. Maybe that double chin is worse in some photos. I can’t tell you what your self-criticism is likely to be. I haven’t met anyone without any! This is not about beating up on yourself – just ruthlessly discard those photos.
6) Go through once more and look for a smile that seems more natural. It’s likely that some photos will show a stiffer smile. Discard those.
7) Now, and only now, you can share the remaining photos in your “favorites” folder with 2-3 close friends or family members (not more) whom you trust to give honest feedback. Too many disparate opinions will only confuse you more. Do not and I repeat DO NOT share the entire portfolio with your friends or family members and ask them to choose from them all. I’m sorry but nobody loves you that much! And, if they do, you’ll hear “Oh – they’re all beautiful.” Ask them to pick their top 5 poses of you and also tell you why if possible. They may say something like it’s just a more natural smile or that something just looks more like the you they know and love. Ideally all of you will have an overlap of at least 1 or 2 photos you agree on. If not, it should still help to narrow your choices down.
The trick of this is to do it quickly – like ripping off a band aid. Your gut instincts are usually pretty good. 
Once you’ve got your choices narrowed down have a conversation with your photographer. They may have some excellent feedback about the photos that they like best. Talk with them about what corrections you’d like fixed (errant hairs/a flower in the background that looks like it’s coming out of your head/wrinkles or acne scars minimized/whatever.) Don’t ask for too many changes to what you really look like. You don’t want someone to meet you for the first time after seeing your photo on LI and saying they would never have recognized you! The photographer wants you to look good and be happy. Talk to them about what’s best.
Note: Don’t choose a photo that’s been cropped too tightly in the actual taking of the picture. You need some background to be able to crop it correctly for LinkedIn. I’ll write about that next time.