There used to be a solicitation strategy commonly used by annual giving programs that went like this: “If you make a gift now, we won’t ask you again this year!”

That’s not a very good strategy.

For one thing, it implies that asking someone for their financial support is annoying or bothersome. More importantly, though, it suggests (incorrectly) that gifts are only needed once a year. The truth is that very successful annual giving programs try to secure individual gifts at least once each year – not at the most once each year. In fact, the best programs strive to give donors the opportunity to give how, when, and however often they choose to support current operations at your institution.

And that’s where “second asks” come in.

What is a second ask? Simply put, it’s a request to someone who has already made a gift to make an additional donation before the end of the fiscal year. This could be to the same fund or a different fund.

Due to the increasing popularity of Giving Days and time-bound challenge campaigns, donors today are frequently invited to make more than one gift in an effort to help institutions meet their philanthropic goals.

Some programs may be reluctant to ask donors for more than one gift a year for fear of offending them or hurting future retention rates. Understanding the benefits and limitations of second asks can help you decide whether incorporating this strategy is right for your institution.

One of the primary reasons that institutions incorporate second asks is to upgrade donors. For example, if a donor has been consistently contributing $750, a second ask for $250 can serve to increase the donor’s total giving to $1,000 and welcome them as a member of a leadership gift society. In addition, second asks can help highlight the urgency of a particular aspect of your case for support—or enable you to focus on a special interest, such as a department or an athletic team—after the donor has already made an unrestricted gift.

Second gifts from donors also tend to lead to better stewardship, helping them form deeper connections with the institution. This in turn leads to increased engagement and sustained giving. Studies have shown that donors who give multiple gifts in the same year are more likely to renew their giving than donors who give one gift annually for three consecutive years.

Despite the many advantages of asking for a second gift in one year, some limitations must be acknowledged. These include appreciating that more dollars from one donor does not equate to more donors. If participation rate is a key performance indicator for your program, second asks will not make a difference. In addition, some philanthropic cultures may be hesitant to embrace the idea of multiple asks. It is important for annual giving staff to be prepared to address these concerns and articulate the reason why the program is using this particular tactic.

Finally, the timing of a second ask must be carefully considered. Spring can be an advantageous time for the institution to ask for a second gift, because many annual giving program deadlines are linked to the end of the fiscal year. A springtime gift may not be the best fit for your donor, however – who is likely more motivated by calendar-year-end and tax-based considerations.

Despite the trickiness of timing, asking a donor for a second gift can have a huge impact on the overall trajectory of your annual giving program. Regular donors who make multiple gifts a year are more likely to respond to a gift officer’s request for a visit, make their first-ever gift of over $1,000, and consider a planned gift to your institution.

If you have’t incorporated second asks into your annual giving strategy yet, then give them a try. A simple A/B test could help you (and others at your organization) get comfortable with the idea and see the impact it can have. You may be pleasantly surprised at the results.