• Rolando Damian Rodriguez

THE ART OF THE ASK





A tremendous amount of preparation typically goes into cultivating and engaging a generous donor.  But much too often – little thought is given to the actual “ask”. 

Yet the ask is the final and arguably the most important step in a long process of cultivation.   You need to be prepared . 


So what are some do’s and don’ts?  How do you increase your chances of success? 

Let's assume that before this critical moment, the following has already taken place:


  • You have identified relationships and connections

  • You have cultivated trust and interest

  • You have researched your donors’ interests and capacity

  • You know what you are going to ask for and why

  • You have prepared and tested your case for support


And now the moment of truth has arrived.  Let’s review a few pointers.


What exactly are you asking for?


The first step is to determine how much you are going to ask for.  And for what.  If you’ve done your homework, you have confidence about your donor’s interests and ability to give.  So be specific within reason. 


What does “within reason” mean?  Well how about - “Beth, I know you care about our cause and understand the need.  Would you help us with a pledge of $50,000 to make our new building happen?”  Or how about - “We need to meet our goal of $250,000, would you be one of the lead gifts to help us create our new outreach program”?


What you don’t say is “We trust in your generosity and hope you can help us with this important work”.  That’s just your anxiety at work, and not complete.

Think about the best possible outcome and the minimum acceptable outcome, and be prepared to have a discussion within these two endpoints. 


Don’t make the donor do the work.  Ask for the order.




Prepare for the Ask


Be Prepared!  You cannot ad hoc such an important conversation. 


Before the meeting, carefully review and practice your presentation, including the following key issues.



  • What are the key points to be covered?  It is critical to have a grasp of the facts.  This is not a time to be fumbling with papers.  You are making a personal request, look in your donor’s eyes, engage in a conversation. 

  • Who is attending?  Most often, a group of two sets the tone for such an important occasion.  Often it is a board member and a staff member, or even two board members together.  Ideally, the person making the ask has given a gift and can share how much and why.

  • Where is the meeting taking place?   The donor’s home or office is usually best, or perhaps at your facility.  Make sure it’s not a noisy and popular restaurant where you can hardly hear yourselves think, or where you get constantly interrupted. 

  • What are the specific outcomes that the donor can expect to achieve with his or her gift?  Don’t assume it’s understood.  “With your help, 25 wonderful children will receive college scholarships”.  Help clarify and motivate with clear outcome statements.

  • Are there benefits associated with the gift?  Recognition, honors or dedications should be clear and obvious.  While this may not be the main driver, it can answer questions that are on the donor’s mind. 

Again, don’t make the donor do the work!



Rehearse in advance.  Rehearse on the way.  Rehearse in your car. 


Practice is not memorization.


It’s knowing your materials and sharing with confidence and clarity.




Make the Ask.  If you prepared, and there are two of you, you already know WHO is going to ask.  Right?   There is nothing worse than two people meeting to request a gift, and each one waiting for the other to make the ask.  (I've been there!)


Make your presentation.  Develop the conversation.  Be composed.  Talk less, smile more (if you’ve seen Hamilton, I couldn’t help it).  Listen, listen, listen. 


Share stories, not a hodgepodge of facts and figures. 


Then Ask.




Be Quiet.


Silencio.  Do not keep talking.


Take a sip of water.  It can be awkward. 


Our culture hates silence.


Be quiet.  Let your prospect respond. 


Be prepared to listen.


This may be the hardest part. 


So practice it with colleagues and friends. If you talk you lose. 




Anticipate Questions


There will be questions.  But since you have carefully prepared, you have anticipated the questions that are most likely to come up.   


And if you don’t know the answer just say “that’s a great question,  I wish I would have thought of it.  I will get back to you within 48 hours with an answer”.




There’s a well-known saying in fundraising.  The ask is made by the right person, at the right time, for the right amount, for the right project.  All true, but also, “in the right way”!


Think positive, expect a yes and act like it.  Be confident but of course humble.  Listen.  Your organization is important, it does great work, you are asking a generous donor to invest in your mission.  Create a vision, help inspire.  By preparing and making a great ask, you are going to get a yes. 


You’ve just got to ask!

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        Rolando Damian Rodriguez  -  Crosspoint Philanthropy  - roland@Cpphilanthropy.com  -  (305) 726 -4904