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The Insider’s Guide to Buying Enterprise Software

Business women holding posts in ENTERPRISE.

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.

Let’s face it, it’s easy to build some requirements that you need and then glide along the sales process – sitting through the vendor sales presentations, seeing the demos, reading the success stories, getting a few references, and then signing the quote. But the best buyers really get inside the process – and follow seven key ground rules.

1. Never EVER buy on futures.

The first golden rule of buying software is 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 pinch 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. Many vendors are going to be most aggressive and “blue sky” about promises on their roadmap when they really want your business – but don’t fall into the futures trap.

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

This is your opportunity to really do your diligence and mitigate your risk. Find out what other customers are really like you, or have achieved the same results, in a similar operating environment as you. Are they using the same ERP or CRM system as you? Did they do a similar integration? Are they the same size and in the same industry? Which partners did they use to make themselves successful? Don’t just limit it to similar industry – 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. You don’t want to be the one pushing the functional and scalability boundaries of the software as you grow. If you are, you’ll be spending a lot of time submitting tickets to the vendor. You want the software already to have been there, done that. So don’t just check references for customers similar to you or check for customers that are in your industry and your current size – check the ones that are where your company/project wants to be in 3-5 years’ time.

4. Use your network and social to do your research.

In the old days, you’d have to rely on that customer success story that’s been polished by the vendor, or participate on that carefully prepped reference call that the vendor sets up for you. Or perhaps you had to network at expensive conferences, seminars or work through your contact list to get some advice. 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, which help financial professionals network around financial management software and best practices. Better yet, get plugged into LinkedIn groups and see what your peers have to say, or even use Quora to ask the questions. If a vendor has no reviews or mixed reviews on these sites, ask why is that? Are you buying PR hype or real software that delivers value? As a buyer, you’re more empowered than ever before with these tools, but it surprises me how few people use them to drive their decisions.

5. Know the meaning behind the buzzwords before you are influenced by them.  

 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? Do you care? 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. First can mean many different things – maybe you’re the first customer that the vendor has on their new solution. Or perhaps you’re the first with 1,000 users. Or maybe you’re first using a brand new feature. There’s a plus side of being first – you’ll get more attention from the vendor, 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 and see how sausage is being made – otherwise that shiny demo you saw could be only that, a slick demo from an ever-slicker pre-sales guy. Instead of seeing that report you asked for in your requirements, try and build it yourself. Nothing beats going to a workshop, or asking for a free trial, and playing with the product – it’s the only way you’ll get the real perspective.

Use these ground-rules, and you’ll have a solid foundation for success for your next decision.

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

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