Need a ‘Do-Over?’ You Might or Might Not Get One in Advancement Work!

Bill Crouch

Mike Carter 


In the book, Start With Heart, (Crouch, 2020: 19-22) describes how hard work, preparation, and effective presentation of a significant giving opportunity led to a negative response from the individual being asked. After some time, a “do-over” was tried and it was immediately met with an enthusiastic “yes” which created a transformative gift for the college. 

What was the difference? In the first attempt, the cold facts and needs were outlined.  But, in the second, “do-over,” the donor’s heart was touched and connections were made between his family and the college. 

Because of the “do-over,” the donor and family realized that their gift would make an impact that would last for generations and be prominent in the college’s mission touching thousands of students. 

To begin, let’s define what a do-over is and how impactful it can be.

What is a ‘Do-Over?’

How many times has the thought, or even stark realization, that what was just experienced really needs a “do-over?” In other words, a chance to go back in time and re-create an experience that needed to turn out differently?

In advancement and development work, “do-over” opportunities present themselves in a variety of ways. Each advancement professional is striving for a desired outcome, normally a new viable relationship with a possible donor or the anticipation of a gift that will impact the mission of the organization. 

The experienced professional knows that when “forging new ground” whether it be for a new important relationship or sustaining a long-held donor close to the organization, sometimes the unexpected occurs and one is left with having to adapt to circumstances that were not anticipated.  

In our experience, we have made several thousand development calls at all levels, some to create new friends, others to sustain long-held cherished relationships. At times, these would net gifts that were noteworthy and, at other times, we would come away saying, “well that was a nice chat” but, no gift was secured! We learned to hope for a desired outcome, but emotionally be prepared for an underachieved result! This type of anticipation is important if one is to build a career in advancement and development.

Often, we would have the sensation when we were successful that we could repeat or have a “do-over” much like what we just experienced.  And, if we were not successful we needed a “do-over” to retrace our steps, move in different directions, and try to turn a less than positive donor experience into one that was positive and appreciated by all parties! The “do-over” worked as a form of self-assessment and allowed us to analyze and review what worked well and what did not.

One memorable experience occurred to one of us when making a call on a distinguished donor who loved a certain brand of expensive chocolates. This donor also appreciated fine crystals.   In preparation to make this development call, the specialty chocolates were bought and placed into a fine vase of crystal. We were ready to make the visit and sustain what had been a long and fruitful relationship with a very faithful donor. 

Upon arriving at the donor’s home, the vase was set on the porch in order to ring the doorbell.  When placing the glass vase down, it hit the concrete too hard and shattered with all the chocolates spreading across the porch. The door opened and the donor realized what had just happened. We were terribly embarrassed and we were searching for words.To our surprise and delight, the donor broke out in laughter and the visit turned out to be one of our most memorable. 

What did we learn? Glass and concrete don’t mix well. Furthermore, we learned that what appeared to be an embarrassing moment created an opportunity to connect with the donor in a way that still brings smiles to all.

Plan and Anticipate

We suggest that in preparing for visits, anticipate how the visit might go: from being turned away because it is not the right time, to a very successful visit that produces a mission-enhancing gift.  Engaging in preparation that includes “do-over” thinking can help you anticipate possible scenarios that could unfold during a visit!   

Adjust and Accommodate

Be prepared to make adjustments as human interaction can go in any number of ways during the course of development calls.  Circumstances can change, and when they do, be prepared to adjust your plans and accommodate the emerging dynamics. If you have anticipated a range of options, and used “do-over” thinking you will be more comfortable making on the spot changes.

Stay Humble and Appreciative

No matter what direction a new visit or even a well-established visit may go, remain humble and appreciative. The person or people you are seeing do not have to make time for you, but they are, so always be mindful that you are a guest and even when dynamics turn in a direction you don’t appreciate, stay humble and show appreciation. 

We can testify that when we used “do-over” exercises to prepare, we were able to handle sudden changes with a sense of humility and realize that what we were doing was in anticipation of a future visit and most likely a future ask for a gift.

Express Thanks at Every Opportunity

We all know that saying, “thank you,” needs to occur at the close of a conversation and/or visit.   We encourage you to express appreciation when it is natural and can flow appropriately into a conversation.  It is far better to say thank you one time more than necessary than to leave a donor feeling unappreciated.  Thanking and showing appreciation can pave the way for the next gift!

Do-Over Assessment Allows For On-Going Improvement

We suggest you use “do-over” thinking/assessment in anticipation and after making development calls. Use this simple form or self-examination to improve your skills in making development calls. Reviewing what has taken place and carefully considering the range of options can provide immediate confidence and move toward a successful development call.   

We at use techniques such as “do-over” exercises to improve the art of developing great donor relations.   Feel free to contact us if we can assist you in assessing and preparing for your next key donor encounter!

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