Software Acquisition Insider Tips 2026 – The Terms Have Changed But the Game Remains The Same

SI has been giving you best practice advice on acquiring software to solve your extended sourcing and procurement (related) needs since the beginning, with deep dives into every major technology you might need, and deep exposes on (fake) tech that didn’t work.

However, it’s first major series on generic insider tips on software acquisition was back in 2009 when it published a seven-part series on the seven-shards of software acquisition that gave you a lot of advice that more-or-less still stands today. In a nutshell that advice was:

  • don’t get blindsided by IT
  • watch out for the big lie
  • chuck the checklist
  • wait for the blush to leave the rose
  • read the contract
  • forego the escrow
  • draft a real unbiased RFP
  • … streamlined for performance, not wokeness
  • separate software from service
  • monitor the market
  • skip the mind games

And it more or less stands today. The main differences are where the sideswipes come from, what the big lie is, what you have to look for in the contract, what you really need in place of the escrow, how software and services are blurring in new ways, and what to look for in the market. The rest remains the same. So to ensure you know what to look for and that you continue to get the best deals on your software (because, regardless of what new fangled terms are used to describe it, or the delivery mechanisms, it’s all still software), we’re going to revisit these series and make the necessary updates.