"Can I pick your brain?" The question makes Derek Andersen cringe. "So many founders use the same zombie-sounding ask, but it's generic and ambiguous," he says. "No one wants to have their brain picked." Andersen should know: As the founder of Startup Grind, a 200-chapter community for entrepreneurs, he has approached thousands of people for intel. And as his Redwood City, California-based organization has grown, Andersen himself has been subjected to an onslaught of clumsy insight requests. "As entrepreneurs, we get so wrapped up in our own thing we often put zero thought into the ask," he says. "If you're thoughtful, you'll immediately rise above 95 percent of the others asking for this person's time." He breaks down how to float to the top.
Quiet your qualms
Is asking for insight annoying? Does it make you seem like an amateur? Will it forever mark you as incompetent in this person's eyes? Shhhh. Time to tamp down any doubts you might have about tapping someone else's expertise. Not only is advice a daily currency for entrepreneurs, but research shows that being on the asking end can actually make you look more competent. And a study from researchers at Cornell and Stanford found that people tend to underestimate--by as much as 50 percent--how willing others are to help when asked.
Think haiku, not novel
Guess what? No one is reading the eighth paragraph in your email asking for advice. If you want real insight (and not just a yes or no answer or radio silence), don't look for a pen pal. You're after a quick meeting or phone call, and to get there you need to keep your ask shorter than you think is humanly possible. "I might spend three hours writing a five-sentence email," says Andersen.
Sweat the subject line
"Quick Q" won't cut it when you're trying to get your email noticed in a jam-packed inbox. "But the good news is that email is generally so boring, anyone who creates any disruption in the pattern can get an opening," says Andersen. When he sent a cold email with a speaking invitation to Vinod Khosla, the founder of Khosla Ventures, he spent hours brainstorming a subject line that would stand out--minus annoying emojis or exclamation points. His final draft (Vinod + Startup Grind = Awesome Sauce?) got a reply from an investor who receives hundreds of emails every day.
Bring it down a notch
We'd all love to have Marc Andreessen on speed dial for advice. But before you start chasing the über-elusive, size up your more accessible peers. "The best advice might be from someone who's on the ground, who's more hungry and less withdrawn from the actual day-to-day problems you're facing," says Andersen. "And then, if you click and you're both hustling, maybe you rise up in the ranks together." He points to Tagged founder Greg Tseng, who reached out to (a not-yet-famous) Reid Hoffman more than a decade ago. Hoffman wound up investing in Tagged, and later, when Hoffman launched LinkedIn, Tseng helped supercharge membership. "Don't get wrapped up in a brand name," Andersen points out. "The founder sitting next to you at a conference could be the next Evan Spiegel."
Make it convenient
You'd be surprised by how many people ask for a meeting and then suggest a coffee shop near their own office, says Andersen. Don't make the rookie mistake of assuming everyone's commute is created equal. If you're reaching out for help, get ready to meet people wherever is easiest--for them. Andersen once flew to Los Angeles to chat with Keith Ferrazzi, author of Never Eat Alone, while they sweated side by side in a boot-camp-style class. "I'm not in shape at all, so I was sore for weeks afterward," he says. "It was brutal." When Andersen reached out to Steve Blank for advice, the serial entrepreneur suggested a 9 a.m. meeting the next day at his ranch--two hours away. "It's not super convenient, but if you're asking for help, you have to be willing to work for it," says Andersen. (Fast-forward a few years, and Blank is now an adviser to Startup Grind.)
This wasn't a job interview, but you still have to send a thank-you note. Even if the person's intel was ho-hum, "you can find some bit of good or useful info to thank them for," says Andersen. He recommends a brief, same-day email of appreciation. Then, if you wind up using any of that person's tactical advice, consider it an opportunity to circle back and thank him or her again. It might kick-start a second conversation--or something bigger.