How to Buy the
Right Software

Practical Help for
Companies of Every Size


Welcome to the step-by-step guide on how to buy the best cloud software for your business. This series provides the collective wisdom of many people who over decades of work life have been involved in every aspect of software for business needs—from identifying requirements, selecting, purchasing, implementing, using, and expanding software installations, to selling software, and even killing failed software projects. We’ve written the guide we wish someone had given us for our early software search projects.

This guide does use specific business needs or software solutions as examples because we do sell software for specific needs. However, the guide is designed to help you buy the right software for any business need—from product development and quality processes to manufacturing operations, finance, design, and digital marketing.

We recommend you use the guide sequentially from start to finish; your search process will go smoother and your degree of success higher. However, you can also jump to any chapter for immediate help at your particular software search step.

Examples: Throughout this guide, you’ll find examples based on what we’ve learned in our own software space. These composite examples represent our collective experiences as both the teams and leadership selecting software and as the vendor participating in selection processes, as well as input from our customers through interviews and surveys.

Jump to the Resources: This guide has many templates. If you want to jump to the resources, you’ll find all of them within the master software search project template. This is a Trello template board you can use to create a board for your team. It has links to all the other resources we mention in the guide.