In an episode of The 4-Hour Workweek, author Tim Ferriss’ podcast, Evan Goldberg, Seth Rogen’s creative partner behind hits like “Superbad” and “Pineapple Express,” told Ferriss that he’s become aware of how important it is to confidently reach out to people you admire.
Goldberg acknowledged that he’s in an advantageous position to make professional connections now that he’s established a successful career, but he mentioned how a connection who now works at Funny or Die once approached him on the street and turned that conversation into a regular correspondence that works in both of their favor.
“Sometimes people just drop their guards and agree to s— they shouldn’t,” Goldberg said, half-jokingly.
One of the best ways to initiate a conversation with someone you admire — whether they’re in your industry or someone with an interesting career — is through a cold email.
Determine who you would like to reach out to
Aim high, but be realistic.
In a 2014 podcast interview with Sethi, Ferriss suggested finding someone who may be famous but is currently out of the limelight, since their inbox — or their assistant’s inbox — is likely less flooded with media requests.
He said that, for example, if you’re a competitive swimmer looking for advice, you may not be able to reach Michael Phelps, but you have a shot at connecting with a less well-known Olympic medalist.
Entice them with your subject lines
If you’re being referred by someone in their inner circle, mention their name in the subject. Levy likes the subject line “Quick Question.” It signals to the reader that they can open the email and remain on a path to a cleaner inbox by deciding quickly whether they will respond or not.
Craft a clear, concise message
Sethi said the best format to follow is introduce yourself, reach a commonality, and then ask a question. Whether you do this in a single line or short paragraph depends on the recipient.
You’ll want to have them take a look at your message and be able to give an adequate response, even if it takes them 30 seconds on their smartphone. When Levy emails a high-demand person like a celebrity, he keeps his email down to one sentence that cuts out any trace of filler.
If he emails an executive, who makes decisions based on available information, he’ll limit his message to three to five sentences and include some links they can click if they’d like to learn more about him and his organization.
Sethi and Ferriss also said that the most important thing to remember is to be respectful of the power dynamic between you and your recipient. Don’t resent them for their saturated schedule, and be grateful if their reply is even a few words long.
Be polite and don’t sound like a salesman
“I don’t try to convince them of anything in my message,” Levy said. “It’s not, ‘Oh, I think it would be really good to do this because of X, Y, and Z.'”
Instead, it’s “‘This is what I do … I think what you’re doing is fascinating, and I’d like to sit down with you and talk about what you’re up to.'”
Sethi also made the point that it comes across as awkward if you set up a conversation as transactional, as if you’ll help your recipient if they help you.
Make sure, however, to offer a clear next step, such as scheduling a phone call or grabbing a coffee, that they can respond to.
Sethi said that if you are lucky enough to interact with this person, it’s essential that you reconnect with them in a natural way.
That means expressing genuine appreciation for their time. Don’t, however, follow up a coffee meeting with a bulleted list of seven more questions or start a habit of bothering them with pointless emails because you feel like you need to stay in touch.
Sethi says that he’s found that refined networking skills separate the mediocre from the successful, and that the best $100 you can spend in a year will be on grabbing coffee with those who can help you advance your career.
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