[Guest Post] Got Technology Blind Spots? Ask These 8 Questions Before the Demo!

ByGrassroots Unwired

[Guest Post] Got Technology Blind Spots? Ask These 8 Questions Before the Demo!

[Guest Post] Got Technology Blind Spots? Ask These 8 Questions Before the Demo!

Choosing a new software platform for your nonprofit can cause lots of stress. But, in my experience, there’s one part of the process that especially makes nonprofit accidental techies freak out a little bit.

There are three key phases to choosing a new software platform:

  • Name the problem you’re trying to solve. You may not need a new system to fix it.
  • Define your requirements. And think beyond tool functionality.
  • Manage the demo process. Ask the right questions.

It’s that third section – managing the demo process – that makes most people feel very squirmy. That’s because they believe that their nonprofit accidental techie status may be about to bite them in the butt. They probably know a lot of things about their needs but making sure you’ve asked the vendor all the right questions is a different matter entirely. It can be a real blind spot.

I frequently offer a workshop on this topic, teaching nonprofit staffers how to evaluate and buy the right nonprofit fundraising and communications software. No matter how many times I’ve given this workshop I always notice the same pattern.

Folks start off relaxed and attentive – until we start talking about the demo process. Then… something changes about the vibe. Attendees sit up in their chairs and lean forward. Hands are waved in the air. People seem stressed out.

But why is this so hard?

What I Don’t Know Drives Me Crazy

We all have blind spots. It’s not always easy to figure out how to deal with them.

Take Sue – she’s the executive director at a nonprofit that provides shelter to homeless women and their children. Great mission, smart staff, thriving supporter base.

The organization is growing rapidly, and her current mix of CRM and engagement software is more than just a pain. It’s holding the organization back.

Sue felt completely reliant on the software vendors to lead her team through the demo and selection process. That worried her, so she called me for a little advice on the demo process.

“I can get answers to the questions that I already have, but I’m sure there are lots of questions that I won’t even know to ask”, she said. “And to make this investment confidently, I have to be sure that I’m not missing anything.”

She was putting so much pressure on herself that making a final software choice was going to be really difficult for her.

There are SO MANY things that just don’t spring to mind when you’re dealing with nonprofit technology, and that makes the stakes feel high.

If it makes you feel any better, I guarantee that we’ve all been surprised by one or more blind spots as we navigate the complexities of today’s array of software platforms. But if you’re like Sue, you need something (or someone) to point out as many potential pitfalls as possible. And the vendor, try though they may, is not always going to be able to do that. So it’s on you.

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8 Questions to Ask Your Software Vendor Before the Demo

First, a pro-tip.

Use open-ended questions for the best results. When you’re investing tens of thousands of dollars (and often more) on new systems, the devil is truly in the details. A simple yes or no answer just doesn’t give you the context that you need to know whether something will work for you and your organization.

Here’s one example:

You: Do you provide training?
Vendor: Yes, we do.

You need specifics! When do you get the training? How is it delivered? Is there documentation? Is the training specific to your configuration, or are you trained in a vanilla version? How many people can be trained?

The best way to get those details is to ask questions in a way that they can’t be answered with a yes or no. Open-ended questions also help to turn this into a conversation rather than just running through a checklist. Conversations provide information, which can trigger new questions.

Here’s that same training question phrased just a bit differently:

You: How will my team be trained?
Vendor: We offer two hours of classroom training and on demand video training, etc. etc.

You’re going to get a much more comprehensive answer by using open-ended questions!

Here are the big eight questions with some context for each one:

  1. How often do you add new features to your system? There may be functionality you need ‘on the road map’, but that could mean anywhere from 2 months to 2 years before it’s released. Get a sense of how the vendor rolls out new functionality.
  2. Which merchant accounts can we use? Changing merchant account providers can be time-consuming and may cause changes to your reconciliation processes. Sometimes you can keep your current provider – good to know in advance.
  3. How long will our implementation take? Very generally, system set up can take anywhere from two months to a year. Make sure you find out what a realistic time frame is for your specific migration. Do you need to go faster or slower?
  4. How does our legacy data move into the new system? Every organization’s data schema and requirements are just different enough that no two migrations are the same. Getting the new system set up to receive your data is the first step. Creating the import files, pushing them in, and testing the import may fall to your team to manage.
  5. How will our team be trained? I used this as an example because getting a good ROI on the new system is directly related to the quality of the training, and most organizations have a need for ongoing learning as their use expands over time. If you think you’ll need custom training on on-site sessions, ask for them.
  6. What makes an organization a good fit for your system and company? There’s no perfect system out there, so you need to know whether your organization has characteristics and requirements like the organizations that are happy using the software.
  7. Who will manage our account during (and after) the implementation project? Vendors offer a variety of account management models– sometimes you have a dedicated person, and sometimes you don’t. Learning about the vendor’s structure will help you know whether their model will provide you with a satisfying business relationship.
  8. How do we access support? Here’s another place where you’ll find a bunch of different approaches. Ticketing systems, live chat, phone, and email are all in the mix. Be sure you understand whether only one person can contact support or if any user can ask for help.

If you’re feeling nervous about your nonprofit technology blind spots, start with these eight questions. They’ll help to expand your understanding of elements that are as important as functionality and cost, and you’ll be more likely to find a system that’s a great match for your needs.


This post is republished with permission from Maureen Wallbeoff’s blog. Maureen is a nonprofit digital strategist and technology coach. If you are drowning in data or your systems aren’t working efficiently together, she’s got practical wisdom to share! In addition to her work with clients, she has authored two guides on nonprofit engagement software, blogs at her website, and answers questions live every Friday afternoon on her Facebook page. A regular contributor to nonprofit industry media channels, Maureen has led workshops all over the U.S. and Canada and is one of Idealware’s expert trainers. Contact Maureen: maureen@meetmaureen.com | 508-744-3366

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