Amy Cheetham grew up in rural Maine and didn’t go to the kind of college that investment banks aggressively recruit from. She didn’t have family connections to banking or a meticulously curated undergraduate resume to help her break into the business.
What she did have was an email address and a willingness to reach out to strangers.
After 150 or so emails, Cheetham—a graduate of Connecticut College, a tiny liberal arts school in New London, Connecticut—landed a coveted summer internship at J.P. Morgan. Along the way, she learned how to effectively use email as a tool of persuasion.
“It can be really easy to write a long meandering email that isn’t direct and to the point,” she says. Writing an email that leads to your desired outcome is something else entirely.
“As soon as someone opens an email they should know what it’s about and what they’re supposed to do,” said Miriam Dumaine, vice president of client solutions at the Ariel Group, a consultancy focused on helping people communicate better in professional settings.
Getting to that point isn’t always easy, especially when you’re asking for help.
“Don’t beat around the bush,” said Cheetham, who is now a principal investor at Costanoa Ventures, a San Francisco-based early-stage VC firm. “You’re reaching out because you want help. Being honest about that is totally fine.”
Be strategic with your subject line
Before you can get someone to act on your email, you have to get them to open it.
If an email requires immediate attention, reflect that urgency through its subject, recommends Erica Dhawan, the author of Digital Body Language. “Thinking about the what and a when in a subject line can go very far in helping people set priorities,” she says.
Keep subject lines short and remember email apps may not display them in full. If something truly is urgent, say so early on. The productivity app Boomerang found that subject lines of three to four words in length received the most responses, but Cheetham says she found keeping between six and eight words to be the sweet spot.
However short you decide to go with your subject line, you’ll need to include enough detail to entice your reader to click for more. If you’re asking for something specific, Cheetham recommends referencing that request in the subject line.
Slow down and be deliberate
You’re not the only one quickly skimming your inbox nowadays. Everyone does it.
“We tend to skim and search,” says Dhawan. “What that can cause us to do is not read a message clearly or respond clearly to what was being asked.”
Before you hit send on that hastily-drafted email, give it one more read. There’s no need to obsess over every word, but you should ensure your message—and any specific asks you’re making—are crystal clear.
Avoid firing off quick messages—especially if you’re angry—and don’t force recipients to read between the lines. “It’s not okay to be sloppy in email anymore,” Dhawan says. “Take the time to understand when it’s okay to be brief and when it’s important to have a more thoughtful reply.”
To minimize endless email chains, consider a meeting or phone call instead to talk through issues that are complex, sensitive, or likely to generate confusion.
“A phone call can be worth 1,000 emails,” she says.
Make it easy for the reader
The best emails make it as easy as possible for the recipient to take the desired action. They’re direct, convey a professional tone, and clearly articulate their goal.
If you don’t already know the recipient, start by introducing yourself and highlighting a common bond—like a shared alumni affiliation—to create a more personal connection. “You’ll want to include words that create an emotional connection,” says Dumaine of the Ariel Group.
For Cheetham, one of those words was camel, Connecticut College’s mascot.
If you’re asking to set up a phone call, include a calendar link with your availability. If you’re asking for a recommendation letter, offer a template or provide details to make it easier for your reader to draft their own.
Author Dhawan recommends keeping emails to just a few paragraphs and incorporating headings or bullets to improve readability. “Get to the point quickly and people will be more appreciative,” she says.
Boomerang found that emails between 50 and 125 words were more likely to receive a response. Don’t cut back too much, though. Boomerang found emails under 10 words elicited lower response rates.
If you know the recipient well, you can skip a formal sign off and end with your name or signature. Otherwise, Sincerely, Cheers, Best Wishes, and Thanks could work depending on the tone you’re looking to strike.
“My general rule of thumb here is be yourself and be professional,” says Dhawan.
Strike the right tone
An email to a boss or prospective client should be more formal than a quick note to your work spouse about where to have lunch or a happy hour cocktail.
“We often change our emails based on power levels,” says Dhawan, explaining a natural tendency people have to take a more formal tone with people they perceive to be their superiors.
She describes it as a trust and power matrix. It’s about “who has more or less power and how much do we trust each other,” she said. The more power, equity, and trust you have in a relationship, the more informally you can communicate.
In some situations, an emoji may be enough to professionally convey a message. In others, seemingly curt responses like “K” or Thx” could make a recipient wonder if you really value their time or contribution.
If you’re looking to persuade someone to do something or change their thinking, choose your words with care and use them to create a strong argument for your case. “Persuasion is about language,” says Dumaine. “It’s about the words that you use.”
Follow up—but don’t be annoying
If your email hasn’t received a response at all, wait at least a few days to follow up. “When you’re the junior, you’re hanging on every word,” says Cheetham. “People are super busy.”
She recommends being polite but persistent, but also knowing when to give up. If a first email hasn’t gotten a response, try sending a follow-up at a different time when an inbox may be lighter or consider a new subject line.
If you haven’t received a response after three emails, stop. “At the end of the day, you have cut your losses and move on at a certain point,” she says.
Once you’ve made a connection, consider following up to share updates on your progress. “People love it when you follow up and let them know if they were helpful,” Cheetham said.
Sometimes, it’s the follow-up that ultimately accomplishes the goal. It wasn’t until her third or fourth conversation with one fellow Connecticut College alum that Cheetham was referred to the person—his spouse—who ultimately helped her land at J.P. Morgan.
