Do you know what is hard about working in technology? For me it’s that most people don’t know what they want, or it is very difficult for them to say what it is they actually want. Malcolm Gladwell in a 2004 TEDTalk on spaghetti sauce illustrated this problem so well, that I’m just going to quote him:

If I asked all of you, for example, in this room, what you want in a coffee, you know what you’d say? Every one of you would say, “I want a dark, rich, hearty roast.” It’s what people always say when you ask them what they want in a coffee. What do you like? Dark, rich, hearty roast! What percentage of you actually like a dark, rich, hearty roast? According to Howard, somewhere between 25 and 27 percent of you. Most of you like milky, weak coffee. But you will never, ever say to someone who asks you what you want that “I want a milky, weak coffee.”

This can be a real problem for me, because a major part of my job is to figure out what each nonprofit wants or needs from their database, and then to build to those needs. What I have found is that it can be very difficult for an organization to put together an accurate technology assessment. Then, because the organization hasn’t started with a good picture of what they need, the likelihood of purchasing or building technology that truly works for that organization is significantly decreased.

Over the past seven and a half years, I’ve worked hard at asking organizations the types of questions that get at what they really need. Today I want to share some of those questions so that you can get an accurate picture of what sort of technology your organization needs.

What does your organization do [mission] and how will this database fit into that mission?

This is almost always my first question, even though I’ve usually researched the organization before sitting down with them. The genius of this question is that it frames the rest of the discussion. It’s easy, when looking at purchasing new technology, to be sidetracked into wanting “all the latest features” or to become obligated to a list of features that “all nonprofits need” (based on a reputable and well-intentioned blog, tip sheet, or article). Then organizations run the risk of paying for more software than they need, and missing key features that are particular to their specific mission.

What is annoying/difficult about your current way of doing things? Why?

While it’s hard for people to describe what they think is good coffee, they are usually pretty good at identifying bad coffee. Similarly, the things that people find difficult in their current way of doing things can point towards what they need in a new system. The key to this question is to probe the whys. Different organizations, or even different parts of one organization, might have problems with the same part of their current process, but for very different reasons.

Imagine that this technology project is a complete success, what will be different for your organization or the way you work? What’s your dream scenario?

This is a good question for two reasons: First, if we have multiple departments represented in the room (and we should always have multiple departments represented in the room), this question can bring out the different ways the technology in question affects each department. Second, it allows the organization to talk about their needs in terms of what they need, not how this need should be accomplished. What I find is the most common failure of RFPs is that they focus on how things should be done, instead of what should be done. The truth is, the organization is the expert on the what, and the technology firm, if you’ve chosen a good one, is the expert on the how.

What else?

These three questions should give you a good starting place as you figure out what questions you need to ask of your organization. I won’t pretend that three questions will get you a perfect picture of your organization’s needs – there are lots of other questions that you could and should ask, and there are times when questions are the wrong tactics for assessment. On April 4th, I will be leading a session at NTEN’s NonProfit Technology Conference where we will talk about the best ways to assess your organization’s technology needs. If you are going to be at the conference, I’d love to have you in the room; if you’re not going to be at the conference, you can listen in and join the conversation by using the hashtag #12NTCask.

In the meantime, let me know what questions you’ve found useful as you do your own technology assessments.