After being in the software industry for nearly 20 years—having sold software, demoed it, implemented it, developed it, and marketed it—and bought quite a bit of it too, I’m still surprised by how many buyers don’t follow some basic ground rules when they’re making such a big decision.

Asking some basic questions and doing some key research yourself can make all the difference between success and failure. The best buyers follow seven ground rules to really get inside the process.

1. Never, EVER buy on futures.

The first rule of buying enterprise software is to always structure your buying decision on what functionality the vendor provides today based on your current needs. And always take what vendors promise you’ll get in the future with a very large grain of salt. Product roadmaps come and go, new product leadership arrives, business priorities change, and those plans are often notorious for fluctuating too—all the more important to buy what’s shipping today.

2. Ask “Do you have customers like me?”

This is your opportunity to really do your diligence and mitigate your risk. Find out which other customers are really like you, or have achieved the same results, in a similar operating environment as you. Did they do a similar software integration? Are they the same size and in the same industry? Which partners did they use to make themselves successful? Get granular: You’ll learn the pitfalls, but you’ll also sleep better at night knowing that you’re not an “edge case” customer.

3. Ensure there’s headroom to grow—right now.

Ensure that there are other customers like you who have scaled higher, or are doing more today. Don’t be the one pushing the functional and scalability boundaries of the software as you grow. You want the software already to have been there, done that. Check references for customers that are in your industry and are where you want to be in 3-5 years’ time.

4. Research through your network and social media.

Things have changed dramatically in the last few years. Review sites like provide much more direct feedback than you’ll ever get from a vendor-provided reference. Or use professional communities like Proformative, which help financial professionals network around financial management software and best practices. Better yet, get plugged into LinkedIn groups. If a vendor has no reviews or mixed reviews on these sites, ask why. Are you buying PR hype or real software that delivers value?

5. Go beyond the jargon.

There’s a whole industry around tech buzzwords—cloud, multi-tenancy, in-memory, big data, etc. The hype is driven from everywhere—analysts, media, and vendors who all have an interest in talking about the next big thing. Now, don’t get me wrong, as a former engineer, I love technology—but as a prospective customer you really need to understand the technology if you’re making a purchasing decision based on it. For example, if you’re buying a cloud solution you need to know the differences. Is it built for the cloud, or is it on-premise software that’s hosted? Is the difference important to you? Is the product really a “big data” solution—or is the vendor just jumping on the bandwagon? The lesson here is to get the facts behind the buzz before buying into it.

6. Understand the pros and cons of being one of the first.

There always has to be a first customer of any solution. There’s a plus side of being first—you’ll get more attention from the vendor or you might get a break on the quote, because they want to make you successful. The downside is that you’ll get more than the typical share of frustration. So you have to ask yourself how strong of a position you are in with your anticipated project to absorb those kinds of obstacles as they come up, and how much faith do you have in the provider to support you as you push the boundaries of their software.

7. Get hands-on with what you’re buying.

Sure, the vendor provides experts who will demo the product, and perhaps build a customized demo based on your requirements. But you really need to know what’s going on behind the curtain. Instead of seeing that report you asked for in your requirements, try to build it yourself. Nothing beats going to a workshop, or asking for a free trial so you can play with the product. It’s the only way you’ll get the real perspective on the product.

Use these ground-rules, and you’ll have a solid foundation for success on which to base your all of your future software purchasing decisions.

What’s your perspective on other questions buyers should ask?

A version of this post originally appeared on the Adaptive Insights blog.