The Mystery and Mastery of “Asking” for a Living

Maryn Wallace

By Maryn Wallace

When asked what I do for a living, I have typically answered “fundraiser.” Often times, people respond with a perplexed expression, inquiring if I do this on a volunteer (unpaid) basis, completely unaware of the need for such professional expertise, or that fundraising could even be a profession.

Once I would get past the clarification of what I do, the next comment is typically around the confidence, or should I say, uncomfortableness of making the ask. How many times have we each been told, “My biggest fear is having to ask someone for money. How can you do that for a living?”

So, how do we do it?

At least in my case, I feel tremendous appreciation and privilege for the opportunity to work with individuals and organizations who are committed to philanthropy. Whether it’s helping improve the lives of those who are in need, the environment, medical research or myriad of other worthy and essential causes.

I must say, however, the idea of making a cold call on a prospect, and asking them for a significant financial contribution (major gifts level) is something that I too feel uncomfortable with. But that’s why we approach this as a profession— to cultivate meaningful relationships with caring supporters, working to ensure that our organizational mandates align with their philanthropic interests, and to gauge at which point in the conversation a request for support is appropriate. The last thing we want to do is surprise a potential contributor with a solicitation, and conversely, we don’t want to miss the opportunity to seek investment.

So how do you become comfortable with making an ask? Here are my top 5 tips for becoming open to the idea of “asking for a living.”

  1. Transparency. Be clear with your prospective donor when you are there to speak with them about a significant financial contribution.  For example, if you seek their counsel on a volunteer role with the guise of making an ask, the donor will likely not be prepared to make a financial decision on the spot; nor will they appreciate being taken by surprise.
  2. Passion for your cause. In order to inspire a commitment to your organization, you must show passion for the project. Why would someone else invest if you are not excited about the project? Enthusiasm is infectious! Remember that.
  3. Put your money where your mouth is. Similar to the point above, it’s easy to inspire generosity for a project when you too are a contributor. Of course, you likely will not be able to give at the same level as the person you are seeking funding from; however, your contribution exemplifies your commitment and connection to the cause. I have always found it easy (and instinctual) to give to the projects I’m fundraising for. If this is not the case for you, then you may want to take a look at why that is.
  4. Understand and articulate impact. We all know that you must have a well-defined “case”. However, we sometimes forget to discuss the effect a gift will have on the donors themselves. Strive to understand their philanthropic goals; and how together, this investment can positively impact their interests and aspirations.
  5. Timing is everything! While we put a tremendous amount of preparation, strategy and thought into our meetings with donors, we have to remember that sometimes our donors just need time before making a commitment, and sometimes circumstances change and we have no control over that. There are a number of factors that go into a decision to make a significant investment, and while we have targets to meet and projects to get off the ground, we must always be respectful (and conscious) of the donor’s readiness to commit. It’s a fine line that we must walk in terms of negotiation, but respecting the donor’s state of mind and wishes must always be paramount.
Maryn Wallace has led and developed campaigns to engage and inspire action for change. Having spent five years with United Way of the Lower Mainland’s Philanthropy Department (Major Gifts), Maryn has a strong understanding of the power of collaboration and a firm belief that strategic partnerships and creative leadership can together, advance our society’s most pervasive issues. Her passion for philanthropy has helped to bring new and innovative solutions to market for various organizations ranging from universities, legal education, marine conservation and beyond.
In her current role as Manager, Advancement and Investor Relations for THNK School of Creative Leadership, Maryn applies her philanthropic spirit with impact investment strategies that will help to bring THNK’s mission to life: to develop the next generation of creative leaders at the intersection of business, public and social worlds, and catalyze breakthrough solutions to the world’s societal challenges.

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