If you’re a kid making a PowerPoint to get a puppy, or at work going through procurement for a tech vendor — we’re always evaluating. We think about price, value, time and benefit, but not necessarily in any order. We can end up abandoning our cart because building a mental business case is too hard, or we end up buying the wrong thing.

When we’re afraid of making the wrong choice we spend too much time analysing every possibility. When we’re convinced we know with our gut what the right answer is, we don’t consider all the alternatives.

We have to avoid the analysis paralysis and the best way to do this is by keeping it simple. ‘The business case’ can be as easy as writing a list of pros and cons, but it’s important to recognise which features are red herrings!

I’m fairly good at buying things, which makes it sound like I’m constantly on a shopping spree, but the truth is I don’t like wasting my money, or my company’s. Usually, I’m buying technology, so I try to think about the whole service offered and if any of that is actually useful to me:

1 - Support

Firstly, do you need it? If you know you’ll need zero support, there’s no need to be paying a premium. Secondly, are they skilled enough to give support? You might be comparing a customer service department to a user forum. The key here is to question it, understand what the support looks like and what the support is like elsewhere.

2 - Flexibility

Sometimes you don’t want to subscribe to a 5-year contract. I’ve always been a buy-once type of person for hardware, favouring subscription models for software. When it comes to work this can be a little different, think about how your need might grow. If you think you might need to upgrade in future, make sure this is an option.

3 - Free trials

My advice here isn’t to do a free trial, it’s to do a free trial seriously. Use the hell out of it! The problem with free trials or pilots is that it’s going to be difficult to show value. This is because of two things: 1) you won’t use it in the same way as if you had paid for it. If you spend a small fortune on a video game, you’re sure as heck going to play it. If you get a free game, you won’t feel bad if it gathers dust; 2) you’re only invested for a limited time. If you know you’ve got the tool for life, you’re already thinking of how to integrate it into your workflow and really make it work. It’s unlikely you’ll fall in love within 30 days as you did with Netflix.

4 - Added Extras

If you’re not going to use it, it’s not an added extra. You might see a bunch of features on a providers website and think “great, copy and paste that to the pros list”. But more features doesn’t mean better business case.

5 - Beware of the upgrades

I always take it as a good sign when a provider will let you use a downgraded version of their tool, especially when you’re just figuring things out. I’m thinking of Charles Proxy and OBS here. I use their Lite versions because I have everything I need, and the rest is just excess for now.

6 - Do more than Google

Unboxing videos are great on Youtube, and if you’re able to, find demos or user-guides. Try to see how you’d use it as if you were an expert. Try not to rely on social media too much, there’s a lot of sponsored content out there. Look for independent user reviews, it might sound shallow but well-written criticism is super helpful.

So, putting this into practice I’ll tell you about a recent personal purchase. Internet (expecting groans here). I went with a provider that was a reasonable price but I could upgrade if I need to, no smoke and mirror bolt-ons I’d never use, and had great reviews online. Buuut, then it stopped working.

Nowadays we shop around because there are providers willing to compete on customer service, price, and frankly, being decent human beings. They’re helping us to build the list of pros and cons, we just need to select what to use for our business case.

The more simple we make it, the easier it is to part with our money and not feel like we’ve been done over