Askers and Guessers in philanthropy

I’ve been thinking a lot about a concept I saw linked on MR that’s been making the rounds of the blogosphere: the distinction between “Askers” and “Guessers.”

This terminology comes from a brilliant web posting by Andrea Donderi that’s achieved minor cult status online. We are raised, the theory runs, in one of two cultures. In Ask culture, people grow up believing they can ask for anything – a favour, a pay rise– fully realising the answer may be no. In Guess culture, by contrast, you avoid “putting a request into words unless you’re pretty sure the answer will be yes… A key skill is putting out delicate feelers. If you do this with enough subtlety, you won’t have to make the request directly; you’ll get an offer. Even then, the offer may be genuine or pro forma; it takes yet more skill and delicacy to discern whether you should accept.”

Neither’s “wrong”, but when an Asker meets a Guesser, unpleasantness results. An Asker won’t think it’s rude to request two weeks in your spare room, but a Guess culture person will hear it as presumptuous and resent the agony involved in saying no. Your boss, asking for a project to be finished early, may be an overdemanding boor – or just an Asker, who’s assuming you might decline. If you’re a Guesser, you’ll hear it as an expectation. This is a spectrum, not a dichotomy, and it explains cross-cultural awkwardnesses, too: Brits and Americans get discombobulated doing business in Japan, because it’s a Guess culture, yet experience Russians as rude, because they’re diehard Askers.

At an individual level, what kind of family you’re raised in makes a difference in whether you’re an “Asker” or a “Guesser.” But there are situations that structurally place people into those roles, whether they’re personally compatible with them or not, and the funder-nonprofit grant relationship is one of those. Program officers are incentivized to be Askers by their position, particularly when it comes to offers of technical assistance or other non-grant activities. Grantees, due to the opaque nature of almost all foundation decision-making, are conditioned to be Guessers, putting out feelers tentatively to try to get at what the funder might actually want, but not necessarily wanting to risk a full-on ask that might get declined. Good fundraising practice says that nonprofits should be willing to risk rejection in pursuit of a grant relationship that’s a strong fit, and that if that happens, they should go back and ask for feedback about their application they can try again. But that follow-up question so rarely comes. With technical assistance, funders offer a resource they think will be useful to a grantee (hopefully based on some assessment) and would probably not be psyched if the grantee turned it down, but wouldn’t necessarily hold it against them. It’s an Ask that could be refused, but that’s OK for the funder. The grantee, put into the role of Guesser, instead may “hear it as an expectation” and “resent the agony involved in saying no.”

This is what makes both fundraising and providing grantees with technical assistance hard: it’s a situation structurally set up to have the funder be an Asker and the grantee be a Guesser. Is naming this dynamic a way to start overcoming it?


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