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of others offering help. That’s because those contemplating making a request of another tend to focus on the costs others will incur complying with their request, and don’t emphasize sufficiently the costs of saying no. Rejecting an appeal for help violates an implicit and socially desirable norm of being “benevolent.” Would you rather be known as generous or stingy? In addition, turning down a request made in person is awkward. We are taught from childhood to be generous, so we are inclined to grant the requests of others almost automatically. Furthermore, saying yes to a request for assistance reinforces the grantor’s position of power. To offer mentoring or to open doors for another not only causes someone to depend on you and reciprocate the favor, perhaps by becoming a loyal supporter in the future; it also signifies that you can do something for someone else and that you therefore have power.

Business school professor Frank Flynn and a former doctoral student, Vanessa Lake, studied how much people underestimate others’ compliance with requests for assistance in a series of studies that illustrate how uncomfortable asking for help can be. In one study, participants were asked to estimate how many strangers they would need to approach in order to get 5 people to fill out a short questionnaire. The average estimate was about 20 people. When the participants actually tried to get people to fill out the short questionnaire, they only needed to approach about 10 people on average to get 5 to comply with the request. Asking for some small help from strangers was apparently so uncomfortable that about one in five of the study participants did not complete the task. This dropout rate is much higher than typical in experiments where almost everyone finishes once they agree to participate.

In another study, people estimated they would need to approach 10 strangers to let them borrow their cell phone to make a short call—the actual number approached to reach the target of 3 acceptances was 6.2. And people also overestimated the number of strangers they would need to approach to get someone to walk them to the Columbia University gymnasium about three blocks away. They thought it would take 7 asks, but it took just 2.3 on average. Once again, asking people to walk with the participant to show them the gym was apparently very uncomfortable, as more than 25 percent of the participants did not complete the task after agreeing to do so. The Flynn and Lake research demonstrates that people are pretty bad at predicting the behavior of others. It is hard for us to take the other’s perspective and see the world from his or her point of view. Their research also shows that asking people for small favors makes the requesters very uncomfortable.4

Asking Is Flattering

One reason why asking works is that we are flattered to be asked for advice or help—few things are more self-affirming and ego-enhancing than to have others, particularly talented others, seek our aid. When Barack Obama arrived in the U.S. Senate, he built relationships by asking for help. He asked about one-third of the senators for advice and forged mentoring relationships with Tom Daschle, the party’s former Senate leader who had just lost his reelection bid, as well as with Ted Kennedy and Republican senator Richard Lugar. As an article about Obama in the New York Times noted, “His role as a good student earned him the affection of some fellow lawmakers.”5 If you make your request as flattering as possible, compliance is even more likely.

Ishan Gupta is a young man on the move. He cofounded Appin Knowledge Solutions, a technology training institution in India. I met him when he was in business school, which he attended after he lost a power struggle at Appin. He was still in his twenties and about to graduate into the difficult labor market in the recession of 2009 with multiple offers. Gupta had done a great job building networks and branding himself as an up-and-coming talent, particularly in India, and he did it by writing a book on entrepreneurship.6 Although India