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This is a blog post I made recently that I thought I would repost here.

I have gotten a couple of questions recently about the best way to go about getting feedback from professionals. Here are some tips I have gathered.
Remember: you may not (and likely will not) get a reply every time. Many artists are very busy and are swamped with requests for feedback. Please go into this process without expectation and do not feel like it’s a personal failure if you don’t get responses right away.
Send an email, not a social media message. Social media messages get lost in sea of feedback. Emails have no character length requirements, are more professional, and (most importantly) are more often accessed from a computer rather than a phone. You’re going to get a lot more in-depth feedback when someone has access to a real keyboard.
Be concise, polite, and don’t be demanding. Many professional artists are very busy. If your email looks like a daunting wall of text, there may be a lower chance of getting a response. Keep your email to 10 sentences or less if you can. If you have questions for the artist, write the questions in the email rather than asking if you can ask the questions. If you want a review of your work, link directly to your portfolio website, not to a landing page or blog.
When showing work, link to a website gallery with 10-15 carefully curated pieces. Show your best work, and display it with as much professionalism as you can. Many professionals get swamped with requests for feedback. Stand out from the crowd of WIP images, low-res photos, and poorly designed websites. Keep your design clean, simple, and fresh. Don’t include autoplaying music or a distracting background. Make sure the images are clickable. I advise against any sort of auto-scrolling slideshow (and honestly, against slideshows in general).
Ask specific, unique questions. Try not to ask a question that is likely to appear in an FAQ, such as “what program should I use?” In fact, search the artist’s website and social media for any answered questions first to make sure you aren’t repeating commonly answered questions.
Have someone proofread your email. If you are adept at sending professional emails, you can likely skip this step. If you are unfamiliar with the format, have someone take a look over it first. Use a subject line that is eye-catching but polite. Begin with something like “Hello, my name is ____ and I am studying to be an illustrator(/concept artist/etc)”. Include a sentence that explains quickly why you are looking to this specific artist for advice and what you are hoping they can help you with. Make sure your body text is free of typos (there are plenty of online editing tools to help with this). End with a signature.
Patreon Patrons tend to get priority. In the current social media climate, many independent artists are on Patreon. If you are a Patron, even at a $1 or $2 tier, an artist may recognize your name more easily. Many artists also have higher level tiers for feedback, which is a fantastic way to ensure you will receive high quality feedback while supporting an artist.
Be active on the artist’s social media feed. Again, if the artist recognizes your name, you may be more likely to get a reply. This also helps an artist feel like they are giving back to someone who has given to them.
Attend conventions or events. If you go out to see an artist at a gallery event or convention, you have the opportunity to ask for feedback in person. If the event is incredibly busy, I would recommend waiting for the end of the day when the masses have left. Wait for a time when there aren’t other people there who may be looking to buy. Structure your question the same way you would your email. Introduce yourself, explain why you like the artist’s work, and ask if they have time for a quick portfolio review. If you have an iPad or tablet, that tends to be the best way to show your work in person. If not, 10-12 small 8x12-ish prints in a folder is just fine. Try to get your work printed professionally. I would recommend against showing your work on a smart phone screen. If you are able to, perhaps buy something from the artist while you are there. If the artist says they aren’t able to, politely thank them for their time anyway and remember that it is not personal; it’s likely they are tired, busy, or overwhelmed.
Ask the right artists the right questions. If you are looking to get work as a character designer, specifically approach character designers.
Know what information you want, specifically. Broad questions are a lot harder to answer. Specific questions, such as “how can I make the shape language of my weapon designs more appealing to target Blizzard?” is much easier to answer than “can you give me some tips on designing?”
Overall; show that you are putting effort and care into your request for feedback. Show that you are serious, professional, and polite. Remember that a lack of reply isn’t personal. Hone in on the specific information you need as you go along.