The Dying Art of Asking Questions

By nature, I am a curious person — annoyingly so. My parents never complained about it, though I was definitely the “why?” child. While I’m sure this can be outwardly irritating, as an adult this practice keeps me well-informed on things of immediate or peripheral importance; a valued skill in nonprofits.

In recent years, however, I have noticed a downward slope with regard to asking questions, and this comes on all sides. Board members who express little interest in knowing what’s happening; staff who miss opportunities to learn more about the organization’s direction; “leaders” who make decisions based on internal feelings rather than seeking input. While not attempting to break this down on a systematic or psychological level, from my direct experience I’ve surmised a few roads which lead to lack of questioning:

  1. Time. “There are only so many hours in the day; I don’t have time to seek feedback and input when things just need to get done.”
  2. Fear. “Gosh… what if I get an answer I don’t want, or don’t like?”
  3. Ignorance. “Oh, wait, was I supposed to ask someone about this?”
  4. Ego. “I know better than everyone, so why would I waste my time asking questions to which I already know the answer?”

Those things all read badly, though not all of them come from a bad place. How many of us enter a situation where — sorry for using this phrase, but — we don’t know what we don’t know. The people before us didn’t keep running records or manuals, the staff has 100% turnover so there’s no institutional knowledge, and the Board are nowhere to be found for inquiries.

For whatever reason, we are losing the drive to be curious. Lack of creativity and inquisition are an issue in schools with children, but gosh, it’s an atrophying skill in adulthood too. In organizations, some of this is a top-down issue. Years ago I worked in places where questions were frowned upon, because how dare you question the all-knowing executive director.

I am, however, finding pockets of hope. I very recently joined the Board of a scrappy (their word, not mine) creative nonprofit, which has been enlightening. At each meeting, I talk with the team about fundraising, future planning, etc., and to my surprise… they ask a lot of questions. There are things about which they don’t know, and they want to know. As a volunteer, it’s kind of amazing to see the lightbulbs go off, but that really only happens when people ask genuine questions, and genuinely want to know the answers.


This is creepy but cute, right?

As a fundraiser, I believe there is an art to asking questions. Some of the best visits I’ve had with donors and prospects end with the people saying things like, “Gosh, it was so nice learning about you!” In reality, I’m simply asking questions about them (some guided, some open-ended), which get conversations moving. It’s not simply “What are you interested in supporting and can we have your money so we can do that?” Rather, it’s asking about their experiences, what interests them, what organizations they believe are doing great work, where they see philanthropy making a difference, and so forth. Little of that is about “me” or “my work,” yet at the end of a good conversation, you can paint a nice little picture, simply by asking questions.

So ask away, friends! Ask genuinely and honestly. People want to share, and sometimes it simply takes a little prompting. “The smart ones ask when they don’t know,” mused Malcolm Forbes, “…and sometimes when they do.”


Be On Time, Leave On Time

I like to think I’m unique, though there are so many ways in which I’m not. I’m not the shortest man on the planet, I don’t have the tallest hair. However, many professional experiences are solely mine, and where I find the latter most comically true is in some of my experiences in nonprofit fundraising.

Those in development (fundraising) may be familiar with the idea of the “reverse ask.” Picture it — you’re out with a donor, having a great talk, enjoying your coffee, then right as you’re about to shift into solicitation mode… the tables turn.


I hilariously remember once, a colleague and I visited a prospect at her home to discuss supporting a cultural initiative. After about one hour, my colleague gave me the look, implying, “alright, let’s do this, let’s get ‘dat money.” Misreading the room, I changed the subject — and took the donor up on her offer for cookies — which extended the visit another hour.

So there we were, entering hour three, and just as we’re about to make our ask, the donor pulls out some papers and flat out reversed the conversation — she asked us for financial support of a project she was producing. It was truly artful.

The colleague and I no longer work together, but we’re dear friends, and to this day we joke about that experience. We shake our heads in jest and say:

“Never take the cookie.”

But really what I mean is: in any given situation, know when your time expires. As nonprofiteers, I find this is something we do exceedingly poorly. Time as a gift, or at least a non-renewable resource, and it helps to fully know how much you want to offer any person or situation. It’s as respectful to leave on time as it is to be on time. When I feel something stretching longer than it should, I like to say, “So-and-so, please allow me to give you back as much of your day as I can,” which is usually understood and acknowledged.

So, folks, unless the purpose of your donor visit is to talk about pastry philanthropy, take it from me and don’t take the cookie.