Choosing the right software for your business is as important as hiring the right employees—it should fit in with your team, contribute to your growth, and help you achieve long-term success. With so many options available, this guide will help you narrow down what to look for and how to make a confident decision.
Here are 10 questions to consider before making your purchase, along with actionable tips to ensure you make the best choice.
1. What problems am I trying to solve?
Before you start researching software, take a moment to evaluate your business challenges and goals. By framing your search through the lens of the specific issues you’re trying to solve, you’ll ensure the tools you choose to address your needs directly. Are you aiming to streamline operations, enhance customer experience, or improve team collaboration?
Identify pain points like:
- Time-consuming manual data entry
- Difficulty meeting customer demand promptly
- Inefficiencies in team workflows and miscommunication
- Lack of actionable data for decision-making or reporting
Look for solutions that are specifically tailored to your business type or industry to ensure they’re the right fit.
2. What is a must-have vs. a nice-to-have feature?
Not every shiny feature is a must-have. Define the essentials that align with your priorities, and separate them from optional features that would be nice but aren’t critical.
Create a two-column list of the must-haves and nice-to-haves. Here’s an example:
Must-Haves | Nice-to-Haves |
---|---|
CRM integration | Advanced analytics |
Mobile app access | Gamification capabilities |
User-friendly interface | Predictive AI features |
Robust security and data privacy | Pre-built templates for customization |
Scalability | Integration with niche third-party apps |
Use this list to evaluate potential tools.
3. Will this connect with my tech stack?
Software doesn’t work in isolation. It needs to integrate seamlessly with your existing tools, like CRM, ERP, or payroll systems, and the way it integrates is just as important to understand.
- Native Integrations (Direct Integrations): These are pre-built integrations offered directly by the software. They are usually seamless, with data being exchanged in real time without requiring third-party platforms. Native integrations are the most reliable and secure, but they are often limited in scope to specific systems and may not support all tools or workflows.
- Third-Party Integrations (via Platforms like Zapier, Integromat, etc.): These solutions connect different tools by acting as intermediaries. They can be simple to set up and cover a broader range of systems, but they often suffer from limitations such as slower data exchange or added dependency on third-party services. Security risks may also arise as there is an extra layer involved, and troubleshooting issues might require involving a third party.
- API-based Integrations (Deep Integrations): Custom integrations that allow direct data exchange between systems, typically through the use of APIs. APIs offer deep functionality, flexibility, and scalability, allowing for real-time communication and highly tailored integrations. Because they involve fewer intermediaries, API-based integrations tend to be more secure and less prone to disruptions. However, they often require more technical expertise, upfront configuration, and ongoing maintenance.
- Webhooks: A specific type of API-based integration, webhooks send data from one system to another automatically as soon as an event occurs, in real-time. Unlike APIs, which can require polling for data at intervals, webhooks notify and send data when a specific action happens, reducing latency and improving system responsiveness. Webhooks can be a lightweight way to achieve real-time integration without relying on complex systems. They can be part of deep integrations and are very efficient in pushing small, event-based data in real time. However, they are best suited for specific tasks or events and may not be the best solution for managing complex data workflows.
When evaluating integrations, think through how they would connect to your workflows and what steps would need to take place. Ask vendors for a demo of the integration to see how it would connect to your current systems.
4. Will this scale as we grow?
Your business today may look very different a year from now. As your team expands, customer demands increase, or new opportunities arise, the software you choose must be able to adapt to these changes. Scalability ensures that your solution can support both short-term needs and long-term growth without requiring a costly or complicated transition to another tool.
Scalable software allows you to gradually increase your usage and capacity in line with your growth, whether that means adding more users, upgrading storage, or tapping into new features. Without scalability, you may face constraints that impact your productivity or force you to invest in additional systems to fill the gaps.
When evaluating scalability, think about both your current needs and where you envision your business in the next few years. Will the software still meet your requirements as your company grows? Is it flexible enough to handle changes in how you work or the volume of data you’re managing?
Ask vendors these important questions:
- What’s the maximum user capacity? Ensure the software can handle an increase in users or licenses without issues. Some tools are limited by their pricing tiers, so it’s important to know if and when you’ll need to upgrade as your team grows.
- Is there an option to upgrade features or storage? Many software solutions allow you to add more storage or premium features, but not all of them are built to scale efficiently. Look for options that offer easy and cost-effective upgrades to keep your business running smoothly as it expands.
- If your team size doubles, will the software still work for you? Growth isn’t just about increasing users—it’s also about how the software can handle that growth in terms of data processing, speed, and feature flexibility. Be sure the software can support an increase in user load, data volume, and overall system usage.
- Look for unlimited or flexible solutions. Some tools may impose limits once you hit a certain threshold, whether it’s related to user licenses, workflows, or the number of submissions. Choose solutions that won’t penalize you for growth, so you can scale without the worry of hitting a cap.
In addition to adding users and features, scalable software should also be adaptable in terms of workflow customization and integration. As your needs evolve, your software should be flexible enough to accommodate new processes, integrations with additional platforms, and expanded functionality. By choosing a scalable solution, you future-proof your software investments and avoid interruptions as your company expands.
5. Will my team be able to use it?
The best tool is useless if your team can’t figure out how to use it. Complicated software leads to frustration and low adoption rates. Ask about the onboarding support available for the tool.
- Seek out clean, simple interfaces with intuitive navigation.
- Choose tools that provide strong training resources, like tutorials or access to customer success teams, to ensure smooth onboarding.
- Look for software with customizable features to adapt to your team’s unique workflows and preferences.
6. How much will it *really* cost me?
Pricing isn’t just about the subscription fee. Beyond the upfront cost, consider training, maintenance, and other hidden expenses that could arise. Sometimes, low-cost or “freemium” software with pay-per-feature pricing ends up being more expensive in the long run than solutions with a higher initial cost.
Create a cost breakdown including:
- License fees
- Overage costs or usage costs
- Add-on fees
- Implementation costs
- Ongoing support or upgrades
This gives you a clearer picture of the software’s total cost over time. Here’s Here’s a clearer breakdown of the software’s total cost over time. For example, consider these additional features that come with a FormAssembly subscription—beyond the monthly cost—that could make all the difference.

7. What is their reputation?
A software company’s track record matters. Look for vendors with proven reliability and excellent customer reviews.
- Check third-party review sites like the Salesforce AppExchange and community spaces like Reddit for unbiased opinions.
- Ask vendors for references or case studies from businesses like yours.
- See how they stack up in G2, Gartner, Forrester, and other quadrant ranking services.
8. How secure is this software?
Data breaches are costly and damaging. Make sure your software provider prioritizes security and compliance with industry standards.
- Ask about encryption and data storage practices.
- Confirm compliance with regulations like GDPR or HIPAA if applicable.
Check out this on-demand webinar on Vetting your Vendors: How to Choose Secure Software.
9. Can I drive it before I buy it?
Never commit to software without thoroughly testing it first. A demo, trial period, or proof of concept can help you determine if the tool truly fits your needs and integrates well with your workflows.
- Set clear evaluation criteria before testing to assess functionality, user-friendliness, and scalability.
- Involve key team members to ensure the solution meets everyone’s requirements.
- Consider requesting a proof of concept to see how the software performs in real-world scenarios specific to your business.
10. How are we doing?
Purchasing software is just the first step. To ensure you’re getting the most value, actively monitor usage and performance.
Key areas to assess:
- Is the software being used effectively across the team?
- Are there any technical issues or outstanding bug tickets?
- Are there features we’re not using or underutilized because they need more training or better integration?
Regular team feedback allows you to quickly address pain points, optimize workflows, and make sure the software continues to meet your changing business needs.
Bonus Tips for Success
Create Your Own Buyers Guide
Build a side-by-side comparison chart of features to evaluate how each vendor stacks up in key areas. This will give you a clear visual representation of strengths and weaknesses.
Leverage ROI Calculators
Look for vendors that provide an ROI Calculator to help you estimate the total cost of ownership and potential return on investment more accurately.
Request a Product Roadmap
Ask the vendor for a product roadmap to understand what features are being developed for the future. This will help ensure the software will continue to evolve and meet your needs as your business grows.
Avoid the sting of buyer’s remorse—follow these steps to choose software that aligns with your needs and drives your business forward.
Still on the hunt for the right tools? Check out this blog on how to evaluate data storage and access management in data collection tools.