Teens: How to Write Two Important E-mails

Last week at the Adventure Semester, I showed the teens how to write two important types of e-mail—and then challenged them to hit “send” six times before the day was over. They were:

  1. How to write a request for a letter of recommendation
  2. How to introduce yourself to an interesting stranger (and make a small request)

Below are my workshop notes for your perusal, along with example emails that were written and sent by Adventure Semester teens.

How to Request a Letter of Recommendation

  1. Write to someone with whom you’ve had a strong working relationship: the longer and more recent the relationship, the better. Parents don’t count!
  2. Begin by clearly stating that you’re requesting a letter of recommendation. (Don’t bury the lead.)
  3. Explain what the letter is for: A specific college application? The Common App? A job? A general letter of recommendation that you’ll use for various purposes in the future? An endorsement to post on your website? Clearly answering this question will help the writer address the letter to a specific audience.
  4. Explain the guidelines:
    1. How long should it be? (Give a specific target range in terms of number of paragraphs or word count. For a general letter of recommendation, think 3-5 paragraphs.)
    2. When do you need it? (Provide a firm date whenever possible. 2-4 weeks notice is respectful.)
    3. Who should I send it to? (Most professional letters of recommendation for college or jobs go straight from the author to the organization; they don’t pass through the hands of the person being recommended. A general letter of recc can be sent straight to you.)
  5. Help me write the letter. This means:
    1. Tell me what our professional relationship means to you.
    2. Tell me what aspects of our work together you want me to highlight in the letter: your perseverance, team spirit, creativity, or a specific accomplishment?
    3. Is there a specific story you want me to recount? This is not a weird or manipulative thing to do. Rather, it jogs my writer’s memory and helps them write a better, more authentic letter.
    4. Include a list of your recent significant activities and accomplishments (i.e. other stuff you’ve been up to) so that the writer can have a better sense of context and possibly reference your other activities in the letter.
  6. If you don’t hear back within 5 days, write a gentle follow-up email that displays respect for the fact that this person is probably busy (which you should always assume). For example: “Hi Tabi, just checking in to see if you receiving my request for a letter of recommendation. The deadline is 3 weeks from now. If you have the time to work on this, that’s awesome, and If not, I totally understand! Let me know and I’ll find someone else to write a letter for me.”
  7. After the person writes you the letter, send a thank-you email. Some people even send thank-you cards or gifts. (This is appropriate after receiving a letter, not before! That’s called bribery.)

Example written by Adventure Semester participant:

Hi Barb!

I am emailing you to ask if you would write me a general letter of recommendation. This would be very helpful for me as I apply to more educational travel programs in the future. I have worked with you and Katie since I was in the 8th grade (almost 5 years now) and have loved every minute of it!

It has been a joy learning from you as a student and then having the opportunities to turn around and teach those same skills to the younger kids as their mentor and director. Being able to take over a full cast for Alice in Wonderland this summer definitely was a huge learning experience for me, and I consider it a total success.

It would be fantastic if you could talk about the different higher roles I’ve held through the company (ie. assistant director and director), and how I’ve handled them. I would love it if you would highlight on my leadership skills and my high energy and enthusiasm in a sometimes stressful working environment as well.

The guidelines for the letter are:

  • 3 paragraphs
  • Sent to me at [email address]
  • I need it by November 30th, 2015

Obviously you are very busy with Winnie the Pooh and Guys and Dolls show weekends in the immediate future, so I will follow up in 2 weeks once you’ve had a few days to recuperate.

I appreciate your time and effort, and hope you are doing well. I can’t wait to see you all when I return home this winter!

Katie Mitchell

How to Connect With an Interesting Stranger (and Make a Request)

In the case of our Adventure Semester participants, the challenge was to connect with someone in Denver who they’d actually try to meet when our group arrived there a few weeks later.

During this challenge we spent a lot of time just figuring out just who to email in the first place and what to ask them. It’s tricky! I encouraged them to contact someone who (1) has an interesting job that the teen might want to do and ask a few questions about it, (2) could provide feedback on an idea or project the teen is working on, or (3) would let the teen briefly shadow them at work.

  1. First, find the person’s email. Sometimes they have it listed on their own website. Sometimes you can find it by googling “[name] email” or “[name] [city] email”. Sometimes you’ll have to resort to sending it to a generic organization email (like info@coolcompany.com)—but you can still address to the email to a specific individual. And sometimes you’re stuck with using a web contact form.
  2. Keep it short! 4-6 sentences is appropriate. There are many ways to scare off a stranger receiving an email from you, and sharing your life story is a classic one.
  3. Start with “why”: Who are you? Why are you contacting this person? Why did you choose them instead of someone else? And why should this person care about you?
  4. Share any credibility indicators you might have. For example, if you’re contacting a writer or artist, do you have published work or photos of your own art or writing online? Link to them! Do you have any names you can drop that will indicate your experience in this person’s field, like… “I worked with [person] at Sunnyvale Martial Arts for 3 years” or “I’ve volunteered at Mister Meow Cafe, a cat café just like yours, for 3 months”? Drop them!
  5. Do your homework, a.k.a. Googlestalk for the win. Research this person and their work for 5 minutes online, and then mention something that you learned about them in the email. If you’re writing a university professor, mention one of their classes or published papers. If you can find someone’s bio, mention something about their past that piqued your curiosity. This shows the person that you’re a self-directed learner who values their time and won’t ask questions you can easily google yourself.
  6. pick your brainMake a clear, specific, reasonable request. Typically 30 minutes or less is a good timespan for a first request and shows that you respect that they’re busy (even if they’re not). If you want to ask them some questions, mention one or two of them in the email. Be specific and never say “I want to pick your brain” (or something similarly vague); to me, that indicates that you’re not really sure what you want to get out of our conversation.
  7. If you’re trying to meet someone face-to-face, make it convenient for them. Tell them exactly which dates and times you’re available, offering multiple options. Offer to meet them at their place of work, a nearby coffee shop (where you’ll buy their coffee), or wherever else might be convenient. (For safety, only agree to meet in public or semi-public places like an office where lots of other people are around.)
  8. Follow up gently if you don’t get a response in 3-5 days.
  9. If you don’t get a response, don’t take it personally. People are busy!
  10. If you do get a response—and it’s in your favor—send a brief follow-up thank-you email. And consider turning lemons into lemonade by asking them to refer you to someone else who might be able to answer the same questions or fulfill the same request.

Example written by Adventure Semester participant:

Hi Eve,

My name is Catherine Canann and I am a 15 year old vocalist who will be visiting Denver briefly in mid-November. I discovered you when I was researching opera singers in Denver. I am really passionate about voice; here’s a link to to my entry video for the Hal Leonard Musical Theatre online competition.

I am interested in opera as a potential career, and I’d love to hear the story of how you got started, your journey with opera, and what brought you to where you are today. May I request 30 minutes of your time on November 17th or 18th? I’m available to travel anywhere in Denver and can meet at a time and place of your convenience before 5pm.

Let me know if you’re available. All the best,


[Catherine received a positive response from this email! Both emails were used with permission.]



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