A charitable fundraiser turned startup founder offers seven questions entrepreneurs should consider themselves before they ask tough questions of others.  

By Layne Gray (Founder, VivaDressUp)

Entrepreneurs are constantly faced with the challenge of asking tough questions – of vendors, potential employees, and contacts that may be able to help in some way. But sometimes we need to ask ourselves the questions in order to get where we want to go.

In my work as an entrepreneur and as a charitable fundraiser, I’ve learned that the things that stop potential customers from buying into your business or service are often very similar to the things that stop donors from giving to worthy causes. Understanding those challenges and issues is the first step in doing something about them and turning disengagement into participation.

To increase your chances of getting others involved in your mission, whether that’s a company or a great cause or (as is the case with my most recent venture, VivaDressUp) a mixture of both, start with the following questions drawn from my experience in charitable fundraising, as well as an entrepreneur.

Can Your Prospects Afford It?

If you’re offering a product your donors cannot afford, i.e. too high of a ticket price to a fundraising event, you have to find a new audience or charge less. From an entrepreneurial perspective, we have to make sure we’re delivering something meaningful to a target audience who can afford what we’re selling. For example, VivaDressUp’s customer spans the range of socioeconomic classes, so we have to offer products that offer quality, but at affordable prices.

How Do You Plan to Ignite Passion in Others?

It’s your responsibility to instill a sense of excitement in your teams to get them motivated to really come through for you. This is especially true for volunteers, who are doing what they do because they want to give back, but the same can be true with employees despite the fact they’re being paid. If they leave at 5:01 p.m., it may be time to reenergize their dedication by leading by example.

Are Those You’re Asking for Money From Fully Engaged?

When fundraising or building a company, someone may verbally agree to something, such as a corporate sponsorship or partnership, yet never come through. If your customers, vendors and partners do not fully comprehend your vision at first, they may too embarrassed or too busy to understand it better. Because of that, getting it down to an elevator pitch, is vital. Once you are able to do that, you are much more likely to be able to get them on board,

Have You Thanked Them Adequately?

Most donors are put off if the only time they hear from a charity is when they are being asked for money. The same is increasingly true for customers. It is important to thank any individual or company properly and often. For example, VivaDressUp has launched with corporate partners, including Procter and Gamble and Newell Rubbermaid. They’ve taken notice of the effort we’ve put forth to thank them through social media.

Can You Rally Your Constituents So You Are All Marching in the Same Direction?

Rather than pinpoint one singular path, which can lead to frustration and setbacks when things go awry, concentrate on moving forward. If you guide your team in the right direction without being married to one path, you will have the flexibility to adapt to inevitable change and be closer to the goal. I often say that instead of trying to chart an exact course to the North Pole, just keep the team moving north.

Have You Set Realistic Expectations…

… as to what you can achieve within a given period of time? Anyone can say they are going to achieve off-the-charts profits. Analyzing past fundraisers or other companies within the same space can provide a reality check on those goals.

There Are Many Worthy Ideas. What’s Special About Yours?

The good news is that an entrepreneur doesn’t have to answer that question by having a first-of-its-kind product idea; it’s often the second or third iteration that realizes the most success. In fundraising it is the rare case that a first-time charity event even breaks even. The risks are high and if you have a sense of what has been done well, or even poorly, you can improve upon it and make your mark as something truly special.

Sepia - LayneAbout the guest blogger: Layne Gray is the founder of VivaDressUp, an ecommerce consignment platform that helps charities fundraise. A seasoned fundraiser, she has generated millions of dollars for charity. Before starting VivaDressUp, she created Vivanista, founded LKE Productions, and was an early employee at Oracle.