The way you han­dle your re­quest makes all the dif­fer­ence

Inc. (USA) - - CONTENTS -

“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. — KATE ROCKWOOD


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.


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.


“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.


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.”


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.

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