Asking the hard questions about your new landscape management software

Read Time5 minutes

PublishedSeptember 18, 2023

Any business investment requires research and patience. Many landscaping business management software platforms are available, and you don’t want to make the wrong choice.

Unfortunately, you can spend a lot of time researching your options and still come up with some blind spots.

Research only takes you so far; that’s why you need to take your investigation further. You need to ask the right questions to gain critical insight into a software solution. Questions that can help you understand how:

  • The software can transform your landscaping company

  • The functionality empowers growth

  • The management tools fit with your existing operations

This article offers strategies for landscape service business owners meeting with software sales reps and a downloadable list of 80 questions to ask.

Be precise

Remember, you’ll meet with sales reps for the software you’re investigating. Their goal is to only speak to the product's positives and how it can help a business in the lawn care and landscaping industry.

If you ask too broad or open-ended questions, you leave room for them to twist the answer into a positive perception.

Be precise about your concerns, needs, and the capabilities you’re looking for. 

Use examples

The best way to get direct answers is to have examples of what you’re looking to improve in your business, both in the office and for your crews on landscaping jobs.

These examples can derive from your daily operations and the common challenges you experience.

Or you can pull from examples of case studies and testimonials you researched before the meeting. Ask the software rep to expand on how other landscape contractors using their software achieved a specific goal, such as process automation.

Ask how you might achieve similar results in your business operations.

Be clear on costs and expected returns 

Every management software uses a different pricing model, and there’s even more variation in measuring the successful implementation of field service management software.

You can’t invest without fully understanding the potential return and the resources required to achieve it. Ask for data about how existing customers have improved profitability and timelines for growth.

Also, ask about other fees that may be involved with the platform. Some software claims to offer full functionality but keep critical features behind paywalls. This is your opportunity to ensure there are no curveballs after you sign a contract. 

Get personal

Investing in management software involves investing in a new partnership. Research a software’s reviews, considering customer experience, ongoing product investment, customizable features, and cloud-based functionality.

Follow up with the software provider about their lower ratings and how they’re addressing the weaker areas of their platform. Ask how their competitors perform by comparison.

Knowing you’re working with someone transparent about their areas for improvement will tell you a lot about the type of partnership you can expect from customer support as a user.

Assess integration capabilities

While it would be nice if you only needed one software platform for all your workflows, at the very least, you still need accounting software for your bookkeeping.

Software that forces you to do manual data entry isn’t living up to its potential to streamline and simplify.

Ask about the integration capabilities and consider how they could improve efficiency in your organization and landscaping projects. At the minimum, management software should sync data with a QuickBooks integration.

However, many providers partner with other platforms to improve how the green industry works, including employee payroll, customer credit card processing, GPS routing, and more.

Evaluate the scalability

You’ve probably already realized that finding landscaping business management software is a hassle. Not just the sales process but implementation and adoption by your team members. The fewer times you have to go through it, the better.

Ask a provider questions about the scalability potential of their platform, whether it’s cloud-based, offers a mobile app for the field, or has to run on a desktop. Do they charge per user or a flat fee?

Also, consider if the software provides functionality if you operate multiple branches, districts, or nationally across time zones. Fill your shortlist with software options that will be your forever software, no matter how large you grow.

Understand the post-purchase support

With some software providers, you will receive the most attention and support from the sales team.

Ask what customer support and resource are available to customers for education and training as well as troubleshooting problems and bugs in the software. Real-time responsiveness from a trained team of customer care representatives can make a difference in your experience using a platform.

Consider how user-friendly the management software is, especially if there’s a mobile device application your field team will need to use for time tracking and messaging.

Dig into the data security

Not only will a management platform house all of your business details, but it will also contain customer information in your CRM, potentially including credit card numbers or banking details for automated payments on recurring jobs.

You owe it to your current and future clients to perform due diligence in understanding the measures that your project management software takes to keep their data secure.

Providers should be able to explain their data encryption and user authentication methods.

Start with these 80 questions  

If you’re still not confident your questions are thorough enough, we’ve got you covered. Fill out the form to receive our list of 80 questions to ask a software provider before investing in your new management solution. These questions are pulled directly from our buyer’s guide and cover every aspect of forming a new relationship. 

If you’re need of more information, expand your search for a new management platform with these resources:

And when you’re ready to test them out, start with one of our representatives by booking a personalized demo of Aspire’s management software.


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