It’s been 17 years since SI published its first major series on generic insider tips back in 2009 where we gave you a lot of advice that more-or-less still stands today if you want to safely acquire software. Yesterday we over-viewed what those 11 pieces of advice were then, and summarized the 6 major difference that affect how you apply that advice today so you can continue to make the right decisions when acquiring software in the age of AI Hype and exaggerated I2O claims. Starting today, we address the major points and what you look for.

Don’t Get Blind-Sided

There are two primary ways you’re going to get blind-sided with tech acquisitions in a modern Procurement organization. The first is still as it was 17 years ago — IT. In many organizations, IT still has too much power over software acquisition. Where the software is cross-department and enterprise core, it should have a considerable say, but for department/function specific apps or apps that sit on top of the core platforms, IT’s influence should be limited. But in organizations where IT still has too much sway, when IT decides it doesn’t like one of your choices, it can step in and, in a very public way say “we already have a product that can do that with extra licenses (and we just need to add one module)” or “it won’t work with our infrastructure, but this other product we’ve been looking at will” and, even if both of their suggestions definitely won’t do what you need them to do from a functionality requirement, it doesn’t matter, the damage is done, your selection (which might have undergone months of research and negotiation) is dead and it will be all you can do to prevent the bad choice from being mandated by the COO or CFO.

As we said before, this does happen but can often be easily prevented simply by taking the time to get IT on board before you present your suggestion and, preferably, before you even make the final selection. Find out day one any absolute and desired requirements they have, incorporate those that are truly absolute and relevant into your RFP, and be sure to convince IT up front that your process addresses your needs and theirs. Then get IT on board with the selection before going to the C-Suite.

Speaking of the C-Suite, this is the second primary way you’re likely to get blindsided. In the age of AI Hype, when every CXO is being convinced that, if they don’t have AI they’re going to fall behind, chances are they’re going to have their favourite overpriced Big X consultancy make a provider recommendation for whatever tech they think you need and then tell you after they’ve signed the deal that provider X with BS “AI” product Y is your new solution, and you better make it work because they just blew the software budget for the next 3 years.

This will generally be last generation junk with a bit of automation being sold as next gen AI or a hallucinatory Gen-AI LLM in a shiny wrapper with no real, solid, functionality, and neither will solve your problem.

The only way you can prevent this is to ensure you’re on top of all the major C-level consulting engagements and their purpose. That Procurement is seen as central in all services and consulting as a knowledgeable provider that can not only select the right Big X partner (event though the CXO’s favourite provider often isn’t the right one, you will never convince a CXO with a predetermined mindset otherwise) but ensure the organization gets the best deal possible. That Procurement should be kept apprised to ensure the invoices are accurate and the services delivered. That way you can understand what they’re looking for and monitor how the engagements are evolving, and once you see that the goal is to identify a product or service that will impact, or, even worse, be forced upon, Procurement, you can start educating the C suite as to what a true solution is, what the organization really needs, and how to weed out the charlatan solution providers from the real ones. You may still get stuck with a sub-optimal solution, because the C-Suite will insist on a big-name vendor with “AI” inside, but at least you’ll get one that at least partially solves the problem you have.

Watch Out for the Big Lies

Traditionally, the big lie was that many software vendor sales reps would lie and say “yes, we have that capability” when asked if their software could do something specific even if it couldn’t because, if asked to demonstrate it, they could say “it’s in beta and we can demo it next time ” (and assume their team could get it done, or at least enough fakery done, to convince you, by the next demo).

But now we have a new lie — and it’s the biggest lie of all. AI (or AGI) exists, it can do whatever you need it to, and its your new employee. And CEOs, supposed to be brilliant leaders, are falling for this BS left, right, and center. There’s no AI, Gen-AI hallucinates unpredictably on a regular basis, and it’s just as likely to bankrupt your business on a single buy than save you $1. As Joël Collin-Demers stated in his AI post (linked in this post), vendors with real AI (where AI stands for Augmented Intelligence, as that’s the best you can get)
tell you exactly what they do, in which sequence [to employ it], and [help you] understand how it solves your exact problem. They don’t sell just on AI hype, they show actual solutions.

There’s a reason I’ve advised you repeatedly to ban “AI” from your RFP responses and kick out any vendor that leads with AI, and that’s because those vendors are mostly, if not only, selling BS.