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Play the Odds, Swing for the Fences

Long before I began my own consulting business I learned to play the odds. I knew which donors had a higher likelihood of committing in a particular period and who was less likely to want to be involved. I knew what every good development officer knows, if you don’t ask, you stand to gain nothing. I will argue that for many donors who are not yet ready to participate, you even stand to lose future involvement if you have not engaged them at all.

I also knew when to cut my losses. To step back and wait until a prospect was really ready or more inspired or in an improved financial situation. Much of the time, I liked to swing for the fences with prospects who wanted to make a significant difference.

Gamblers, risk takers and forward thinkers—today’s mavericks (innovators, entrepreneurs, venture capitalists)—understand the importance of making safe bets. In planning their work, development officers need to weight their own portfolios with different types of prospects and donors—those who you think will be safe bets based on previous conversations, those who you hope to convert to be donors (at least some day within the foreseeable future) and those who have not shown any inclination to this stage, but surely may in the future. A risk reducing mix will help you reach your annual goal.

But do you want to just reach your goal? Many development officers are content to do only that. I knew someone who was very talented very engaging. He could have raised significant funds every year, but as he approached a number that he had in mind, I know that he thought that was enough so he didn’t really exert himself for the remainder of the year. Nothing seemed to be able to motivate him to change that.

But there are some development officers who would like to take a major leap and secure a few outstanding contributions year after year—their competition was purely with themselves, not others.

Risk takers realize that big wins come from playing the long shots that smaller, smarter wagers subsidize. If you don’t swing for the fences, it’s hard to hit home runs. Venture capitalists feel the same worries as the rest of us, but they are able to set aside emotion and objectively scrutinize challenges and opportunities. Then they intelligently gauge the odds, manage a portfolio of risks and make decisive bets…given enough time and tries, these “bets” inevitably pay off for the individual and the organization. Think about the progression of Fore Systems or FreeMarkets in Pittsburgh--these startups became very successful companies. And there are many whose names are unknown to most people, startups that were much smaller and less notable or those that didn't emerge at all..

For example in fundraising, an individual contacts the institution and has seen something on TV that looked a bit like a miracle for the disorder or illness that he/she has. The individual has decided to try and get involved and determine if more money invested could actually make a serious impact on the research and improve the quality of life.

I have met multiple development officers who do not want to field such prospects, in fact, instead of carefully pursuing this (since it often requires a very different and more determined approach than an already engaged patient might), the development officer passes this on to someone else who may be able to help. Perhaps that someone has more experience, or, I would argue, more patience and confidence and hope in the situation. Sometimes these opportunities work out and become very meaningful and sometimes they don't. I have been on both sides of such experiences. Sometimes nothing emerges and sometimes swinging for the fences is a great strategy.

Well, the willingness to be flexible and selectively aggressive are among the most crucial talents that an outstanding development officer can have.

What steps should you take when thinking through your portfolio?

1. Get to know the odds. Once you know the odds, make smarter and smaller bets on your prospects listing.

2. Always be taking calculated risks. Again, nothing ventured, nothing gained. However, if the risks are too high or the cost-benefit ratio is not in your favor, find another opportunity. (For example, a prospect who keeps promising, but always finds an objection to the plan the institution proposes. Don’t turn your back. Just exercise patience and don’t over-commit to the time you allocate for discussions.)

3. Be prepared to take a winding route to success. This may mean circling around obstacles and doubling back when necessary. (For example a donor who you never thought would give, but you always kept their needs in mind…then several years later you encounter the answer to what they are asking—call them.)

4. Chart your own course in business, life and career. Don’t let others chart it for you. Always keep in mind that your portfolio of prospects and work opportunities has to grow and diversify.

5. Create more opportunities to win. Thus, the greater your chances of winning. This really requires careful work every day.

6. Solve problems. Forget fear and consistently focus on making the right calls needed to produce meaningful results for the prospects and for your mission.

Remember: As a development officer or a consultant, the game is always in progress.

With recognition to Make Change Work for You, by Scott Steinberg, 2015.


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