How To Cut Through the Sales Pitch During Software Demos: Questions to Ask a Software Vendor Before You Buy

Avoid costly software mistakes: Ask targeted demo questions about functionality, pricing, integrations, and support before making a purchase.

You've reached a critical juncture in your software selection process. After weeks of research and vendor comparisons, you've narrowed your options down to one or two vendors, and it's time for live demonstrations.

But this moment is just as critical for the vendor. For them, it's about closing the sale. For you, it's about vendor vetting to avoid a costly mistake. According to Software Advice's 2026 Software Buying Trends Survey*:

• 45% of decision-makers have regretted one or more software purchases made by their firm in the last 18 months. 

• Not only that, more than a third of software buyers removed a vendor from their shortlist after a sales pitch or presentation. Plus, half of the respondents decided not to go with a vendor after trialling the software.

• Over a quarter of those who regret a purchase say the product's performance didn't meet their expectations, while 21% cite issues with integrating the product into existing systems. 

Why this matters: Picking software isn’t just a checkbox—it’s a decision that can make or break your team’s workflow.

This guide serves as your software buying checklist for what to do before, during, and after your demo. You'll find a list of helpful, comprehensive questions to ask software vendors about functionality, software pricing transparency, implementation support, and technical compatibility.

Before the software sales demo: Set yourself up for success

Software demo preparation separates successful adopters from disappointed buyers. Your vendor outreach strategy should include requesting specific demo formats and providing detailed requirements in advance. Following demo scheduling best practices means giving vendors sufficient lead time to tailor their presentations to your specific needs.

Ask the vendor for two different product demos

Here’s what to ask for and why:

1. A business process demo. This session should focus on how the software supports your daily operations. Include the managers and team members who will use the system on a day-to-day basis to view workflows, intake forms, dashboards, and mobile views. This matters because 26% of buyers who regret a purchase say the product's performance didn't meet their expectations.

2. A technical deep dive. Your IT team should meet the vendor's technical representatives to discuss system compatibility, data storage locations, expected downtime for upgrades, and integration requirements. This step is critical, since integration issues are the number-one cause of purchase regret among software buyers.

Give the vendor at least two use cases that the software should support

Prepare detailed use cases that reflect real scenarios your team faces. Present at least one for the daily user showing the complete workflow, and another for an executive who needs approval capabilities and high-level reporting. Here are a couple of examples, for reference:

• For project management software, you might say: "As a project manager, I need to review progress across five simultaneous projects from a single dashboard and generate weekly status reports for each one, including budget variance and resource allocation."

• For accounting software, try: "As an accounts payable manager, I need to review and approve 50-75 purchase orders in bulk each week, with the ability to reassign batches to processors when I find errors that need correction."

Plus, if customers will interact with the software directly, ask to see a walkthrough from their perspective.

Let the vendor know what features you'd like to see customized

Some features fall outside a platform's standard functionality and require customization. Flag them in advance so the vendor can prepare.

For instance, you're evaluating customer relationship management (CRM) software, and you want the system to send automatic text messages confirming phone numbers. If that particular CRM needs a third-party plugin, you'll want to see how the integration works.

Get detailed cost information for any customizations or plugins. 

Why this matters: Nearly a quarter of regretful buyers cite unexpected costs as a primary factor leading to disappointment.

Ask for time to showcase the software’s top strengths

Allow the sales team to showcase what makes their product stand out; you might discover functionality you didn't know existed.

For example, when evaluating property management software, the vendor may demonstrate how they utilize artificial intelligence (AI) to enhance property asset discovery and search capabilities. 

Why this matters: The top reason businesses increase software spending is to add functionality, such as AI features.

During the demo: Questions you need to ask

When researchers asked buyers what they'd change about their software selection process to avoid future regret, 43% of disappointed buyers said they'd perform a needs assessment to determine the processes they need the tool to perform. 

Here are some questions that can help you get that clarity during your demo:

Functionality and fit

• Can I see these features in action on the mobile app? If the software offers a mobile application, you should review what intake forms, dashboards, and workflows look like on smaller screens. Ask the vendor to demo the actual mobile interface, not just screenshots.

• Is there an alternative way to perform this function? Instead of forcing the software to replicate your current process exactly, ask how the vendor recommends accomplishing a particular task. You could save time and money by adapting your process rather than customizing the software.

• What happens if we need to make changes to these workflows later? Find out whether you can modify workflows yourself or if you'll need to pay for developer support every time you want to adjust something.

Pricing and contracts

• Of the features I've asked for, which require custom code? Custom code is expensive and creates complications during upgrades. Ask for specific cost estimates for each customization.

• Are there any hidden costs I should be aware of? Some vendors charge setup fees, integration fees, data migration costs, or premium support fees that are not included in the base pricing. 

• What's included in the annual licensing fee? Clarify whether the base license includes customer support, software updates, security patches, and standard integrations, or whether you need to pay extra for them.

• What are your contract terms and cancellation policies? Understand the length of the commitment, whether the vendor locks in your pricing, and what happens if you need to cancel. Successful software adopters are more likely than disappointed buyers to include contract negotiation as a formal step of their selection process.

Implementation and support

• Are the integrations I'm requesting ready to use, or will your team need to develop them? Some vendors advertise integrations that aren't actually plug-and-play. Get details about which integrations are compatible out of the box and which require additional development work. This matters because 61% of surveyed organizations experienced disruptions during software implementations in the past 18 months.

• What does your implementation timeline look like? Ask about the typical duration from contract signing to go-live. The most common implementation disruptions are integration issues (40%), data migration problems (38%), and delays (38%).

• What level of support do you provide after implementation? Clarify response times for different severity levels, whether you'll have a dedicated support contact, and how their team delivers training.

• How do you handle data migration? Given that 38% of implementation disruptions involve data migration problems, you need to know exactly how the vendor will move your existing data into the new system.

Security and compliance

• Where is our data stored, and who can access it? Understand the physical location of data centers, whether data is encrypted at rest and in transit, and what access controls are in place. If you operate in a regulated industry, verify that the vendor can meet your compliance requirements.

• What security certifications do you maintain? Look for relevant certifications, such as SOC 2, ISO 27001, or industry-specific compliance standards that are applicable to your organization.

• How are APIs and endpoint integration vulnerabilities managed and secured? Ask about the vendor's approach to application programming interface (API) security, including authentication methods, rate limiting, and how they handle security patches for integration points. This is important because integrations create potential entry points that can be vulnerable to security threats.

• What's your disaster recovery plan? Find out how frequently data is backed up, where backups are stored, and how quickly the vendor can restore service if something goes wrong.

After the product demo: Get everything in writing

Don't commit yet. Request formal documentation outlining the implementation details.

This documentation often takes the form of a request for proposal (RFP). At a minimum, ensure it includes:

An itemized list of costs

You should ask for separate line items for licensing fees, implementation costs, ongoing support, training, customizations, and any third-party integrations or plugins. This breakdown lets you verify previously stated prices and negotiate effectively. It also protects you from the unexpected costs that plague 24% of disappointed buyers.

Clearly defined roles and responsibilities

The vendor will likely expect your team to handle specific tasks during implementation. The documentation should clearly outline who is responsible for what. This prevents overcharges and ensures critical tasks don't fall through the cracks. 

A detailed implementation timeline

The timeline should include major milestones, dependencies, and the necessary actions and assigned stakeholders at each stage.

Integration specifications

For each integration, obtain documentation on how it works, the data flow between systems, and whether it's a standard integration or requires custom development. This addresses the integration issues that cause 40% of implementation disruptions.

Training and support details

Understand what training consists of, how it's delivered, and what ongoing support looks like after go-live.

If your instincts tell you something's wrong or the vendor is glossing over concerns, speak up. How they respond to your questions now indicates how they'll handle your needs in the future. This is about vendor accountability and setting clear expectations for vendor partnerships from the outset.

Successful software adopters are more likely to define their budget and identify must-have features during the software selection process than those who do not. They're also more likely to involve IT professionals in the decision.

Navigate the software selection process with confidence

You now know how to prepare for demos, what software demo questions to ask during presentations, and how to document everything afterwards. These steps help you avoid the regret that 45% of decision-makers experience with software purchases.

The key takeaway here is to be thorough at every stage. Define your budget and must-have features upfront. Involve your IT professionals in technical discussions, perform a comprehensive needs assessment, and negotiate your contract carefully.

Ready to continue your software selection journey? Check out these additional resources:

• The Ultimate Software Vendor Evaluation Guide

• How To Evaluate New Software in 5 Steps

• How To Write a Business Case for New Software [Template Included]

• 5 Critical Steps to a Successful Software Implementation Plan

You can also explore software categories to compare options for your specific needs. Our software advisors have helped hundreds of thousands of buyers find the right match for their business. Schedule a call or click here to chat with an advisor now.