7 Questions to Ask During a Software Demo to Get the Most Out of It

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7 Questions to Ask During a Software Demo to Get the Most Out of It

Software demos are essential for understanding how a software solution can meet your specific needs. However, simply attending a demo is not sufficient. Asking the right questions can make the difference between making informed decisions and wasting time.

This article provides you with 7 crucial questions to ask during a software demo, enabling you to select the software that best meets your requirements and drives your business forward.

Pre-Demo Preparation: Laying the Groundwork for Success

Before diving into the live demo, take a step back to understand your needs and the software you are considering.

List Your Requirements

Understanding your current pain points, desired outcomes, and workflow is vital. This clarity allows you to tailor your questions during the demo, ensuring they directly address your business needs.

Also, focus on any current software or hardware with which the new solution will have to interact. Make sure you know what version you have.

Get a Head Start with Video Demos

Preparation is crucial. Knowing what to look for beforehand will save time and ensure you cover all critical aspects.

Before the live demo, check if there are any video demos available:

  • Video demos offer a preliminary understanding of the software’s capabilities.
  • They can help frame your questions and refine your focus during the live session.

Find the provider's YouTube channel or ask about demo videos when booking the live demo.

At Connecting Software, we always recommend that our potential customers watch the relevant demo videos in the Connecting Software in Action series. These videos provide detailed insights and real-world use cases of our software, making them an excellent starting point.

By prepping with this type of video, you’ll ensure your live demo is efficient and targeted, addressing your most pressing needs.

7 Essential Questions to Ask During a Software Demo

1. Where does this fit? Seamless Connection with Existing Systems

A software solution that integrates seamlessly with your existing systems is key to maximizing efficiency and minimizing disruption. During the demo, ask:

  • Can I install this in the environment I want? Specify if it is self-hosted or SaaS and if you have any operating system constraints.
  • How does this software integrate with our current ERP, DMS, or other relevant systems? Be specific and indicate the versions you use.
  • Can you demonstrate real-world examples of successful integrations?

2. What Will We Need for Onboarding and Training?

Understanding the onboarding and training process offered by the vendor ensures a smooth transition for your team. First, determine if training is required and for whom. Some systems run in the background, and the user workflow remains unchanged, which eliminates the need for training.

If training is required, inquire about:

  • What training materials and support are included?
  • Are there dedicated onboarding specialists to assist our team? Where are these specialists located (for time zone and language concerns)?

3. How Can We Tailor the Software to Our Needs?

Ideally, you would be able to customize the software to fit your unique needs and workflows rather than have a one-size-fits-all solution. Find out:

  • To what extent can the software be customized to fit our unique needs and workflows?
  • Can we customize the software and its reports ourselves?
    • If yes, can you demonstrate how we can do it?
    • If not, who can do it? Can we estimate the time and cost for this?

4. What About Data Security? Protecting Your Crown Jewels

Data security should always be a top-of-mind concern when thinking about questions to ask during a software demo. During the demo, explain exactly what your security concerns are and ask:

  • How does this software safeguard our sensitive information?
  • Does the software comply with relevant privacy regulations?

5. Cost Transparency: Understanding the Bottom Line

Get a clear picture of the total cost of ownership. Ask:

  • What is the pricing structure for this software?
  • What different pricing plans exist? Is there a price plan for SaaS and another for self-hosted?
  • Are there maintenance costs?
  • Are there any other fees? For example, for storage, traffic, or support?
  • Are there ways to cut costs? Just make sure you cut costs and not corners!

6. Scalability: Is the Solution Future-Proof?

Your business is bound to evolve. Choose a software solution that can keep pace. Ask the vendor:

  • Can this software scale to accommodate our projected growth in users and data?
  • Can you demonstrate real-world examples in which the software had to handle increased processing demands?

7. Where Can I Find Social Proof? Success Stories Matter

Learning from the experiences of others is invaluable. Ask the vendor:

  • Can you share testimonials or case studies from customers in our industry?
  • How can we learn more about how other companies have used this software to achieve success?

For example, at Connecting Software, we always provide potential customers attending our live demos with the Success Stories that we feel are more relevant to them. Beside that, on our site, we organize the stories by topic, so we can also direct them to the Dynamics 365 success stories, for example.

If you can find success stories still when preparing for the demo, that is even better. Learning what others did can give you insights into the questions to ask during the software demo.

After the Demo: Making an Informed Decision

Reviewing the Information Gathered:

Once the demo concludes, take time to analyze the information you gathered. Compare features, functionalities, and pricing plans. Prioritize features that directly address your most pressing needs.

Decision-Making Tips:

Beyond the software itself, consider the vendor's responsiveness and support structure. A reliable vendor with a proven track record of customer success is a valuable asset.

Key Points

By thoroughly preparing for your software demos and asking the right questions, you empower yourself to make informed decisions. Software demos are more than just a presentation—they are an opportunity to ensure that the solution aligns with your specific needs, integrates seamlessly with your existing systems, and supports your long-term goals.

Remember to take advantage of pre-demo resources like video demos to streamline the process. For example, we always recommend that our potential customers watch the relevant demo videos in the Connecting Software in Action series. These videos provide detailed insights and real-world use cases of our software, making them an excellent starting point.

If you find our solutions intriguing and want a personalized walkthrough, don't hesitate to book a live demo with Connecting Software's experts. Our team is ready to answer your questions, demonstrate the capabilities of our software, and help you understand how it can be tailored to meet your business needs.

Schedule a Live Demo Button


Ana Neto - Connecting SoftwareBy Ana Neto


Software engineer since 1997, she is now a technical advisor for Connecting Software.

Connecting Software is a producer of integration and synchronization software solutions since 2004. We operate globally and we are also a proud “Top Member” and "Top Blogger" at CRMSoftwareBlog.

Further Reading

Dynamics 365 Success Stories

Dynamics 365 articles


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