Morning Brew - 🥶 Dang, that’s cold

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What’s top of mind at the water cooler.

Chances are you’ve sent or received a cringy cold email. From sketchy coffee chat invites and requests from strangers to pick your brain, it’s safe to say that most of us could use a lesson or two in the fine art of crafting the cold outreach. And while your cold email probably won’t land you a million dollar investment from Mark Cuban, getting it into the right inbox could lead to career growth and valuable connections.

To get some insight into what it really takes to become an outreach aficionado, Sidekick tapped LinkedIn career expert Andrew McCaskill and cold email copywriter Elyse Savaki. They shared these tips:

• Cold email must-haves: “You need to communicate why the person who’s receiving this email should care,” Savaki told Sidekick. McCaskill recommends being as specific as possible. “What is it that you want them to do?...Make it clear, keep it simple, and give them something to respond to.”
• Know who you’re talking to: “Tailor your message to the person you’re reaching out to. Finding common ground not only makes you more memorable, but it also shows that you did your research,” McCaskill said. “You want to make it safe for them to take whatever [next] step you’d like them to take. So if you’re asking somebody who doesn’t know you very well at all to make an introduction for you, you want to give them a few reasons why that’s a safe thing to do,” Savaki advised.
• Get to the point: “Be succinct [and] sincere,” Savaki said. Your best bet for getting people’s attention is keeping your email at or under 100 words. She also recommends getting creative with your questions: “If what you're really looking for is guidance and advice from them…don’t just ask an open-ended question…ask better questions and you’ll get better answers,” she explained.
• Whatever you do, don’t do this: Don’t “send the same general, template-y note to everyone you reach out to,” McCaskill said. “Being too persistent in your outreach is also a no-no. Send the initial touchpoint, then give them some time to read and respond before following up.” And do proofread your email for formatting errors, wrong names, and spelling and grammatical mistakes before hitting Send.
• Consider skipping the offer for coffee or drinks: “Offering a favor out of the gate can seem a bit sketchy to a new contact—and in some industries, might even be seen as a red flag. There’s a fine line between a friendly request for help and coming off as transactional or insincere,” McCaskill explained. Savaki also recommends avoiding favors “unless you actually truly have something you can do for them in return.”

If you need a push in the right direction, Savaki strongly recommends checking out this doc from author and entrepreneur Ramit Sethi, which is filled with templates for each and every kind of cold email situation.—MW

Your punch list for when you punch out.

Watch: The life and creative process of Jean-Michel Basquiat remain shrouded in mystery. In this video, his sisters share what it was really like growing up with the artist, and the ways his impact continues through his artwork.

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Pearls of career wisdom.

What career advice would you give your younger self?

“When you’re young, you’re hungry, with this ‘climb to the top as fast as possible’ mentality. And while you shouldn’t lose that hunger, you need to know when to toggle between persistence and patience. Persistence is tenacity and hustle. It’s raising your hand, learning as much as possible and working hard to master a craft or set of skills.

“Patience is recognizing that success doesn’t happen overnight. Patience is also giving yourself the grace to learn and make mistakes and letting the experiences shape you into the professional you will become. Both can help—and hurt—your career trajectory if not toggled appropriately.

“Start with persistence. Pursue your passions and get as much experience as possible. But be patient in seeing each experience through, reflecting on what you’ve learned, [so you can] determine the next step to pursue and be persistent about.”—Meredith Klein, head of consumer and product comms at Pinterest