You’re reading The SME Security Brief, practical IT, cyber security and technology advice for Irish and UK businesses. No jargon. No scare tactics. Just what you need to know, every week.
If someone forwarded this to you, you can subscribe at thesmesecuritybrief.com.
THIS WEEK’S THREAT 🔴
The most expensive IT mistake most small businesses make has nothing to do with security.
Ask most small business owners how they ended up with their current software and you will hear a variation of the same story. Someone recommended it. A salesperson gave a compelling demo. The owner of a similar business was using it. There was a good deal on at the time. The person who made the decision has since left.
Very rarely does the answer involve a clear understanding of what the business actually needed before anyone spoke to a vendor.
This matters more than most people realise. The software a business runs on shapes everything. It determines how work gets done, how data is stored, what can be reported on, how staff are trained, and how easy or difficult it is to make changes in the future. When the wrong software gets chosen, or when the right software gets bought from the wrong vendor, the consequences play out slowly over years. Licences creep upward. Customisations pile up until nobody fully understands the system anymore. The original vendor becomes the only people who can touch it. Switching becomes so painful it gets postponed indefinitely. The business becomes dependent on a system it never fully owned.
This is not just an inconvenience. It is a genuine business risk. Heavily customised systems are harder to update, which creates security vulnerabilities. Vendor lock in means you have no negotiating power when prices go up or support quality drops. And the time and money spent maintaining a poorly chosen system is time and money not being spent on growth.
The good news is that most of this is avoidable with a small amount of work done before any vendor conversation begins.
What you should do this week,
Think about the most important software your business currently runs on. Do you know when it was chosen, who chose it, and whether those requirements still apply today?
If you are considering any new software in the next six months, read the tip and tool sections below before you take a single demo call.
If you are already locked into a system that is causing problems, the checklist section will help you understand your options.
THIS WEEK’S TIP 💡
Write your requirements before you talk to any vendor.
This is the single most valuable thing you can do before embarking on any business system change, and almost nobody does it. The moment you sit in a demo, you start evaluating the vendor’s solution rather than your own needs. The salesperson controls the conversation. You end up asking whether their system can do certain things rather than asking whether their system is the right fit for what you actually need to do.
The fix is simple. Before any vendor conversation, write down what you need. Not what looks impressive in a demo. What your business actually requires to function.
Start with the problem, not the solution
The most common mistake is starting with “we need a CRM” or “we need a new accounting system.” Start instead with “we need to track customer interactions across our sales team” or “we need to produce management accounts monthly without spending two days gathering data.” Describe the problem. The solution comes later.
Separate your must haves from your nice to haves
Every requirement should be categorised as either essential or desirable. An essential requirement is something the system must do for it to work for your business at all. A desirable requirement is something that would be useful but that you could live without. When you are evaluating vendors, a system that meets all your essential requirements and some of your desirable ones is almost always better than a system that dazzles you with features you did not know you wanted.
Think about who will use it and how
A system that looks elegant to a technically confident person can be a daily source of frustration for someone who just needs to get their work done quickly. Think about your least technical user. Will they be able to use this without significant training? What happens when someone new joins and needs to get up to speed? The best software for a small business is usually the one the whole team will actually use, not the one with the most features.
Think about where your data lives
When you move to a new system, your existing data needs to come with you. Before you commit to anything, ask how data is imported, how it is exported if you ever want to leave, and who owns it. A vendor who makes it easy to get your data out is a vendor who is confident enough in their product to compete on merit. A vendor who makes data portability difficult is one you should think carefully about before committing to.
Think about total cost, not just the licence fee
The monthly or annual licence cost is rarely the full story. What does implementation cost? What does training cost? What does support cost when something goes wrong? Are there fees for additional users, additional storage, or access to certain features? Get a full picture of what this system will cost in year one, year two, and year three before you make any decision.
THIS WEEK’S TOOL 🛠️
How to evaluate a vendor properly and spot the ones to avoid.
Once you have your requirements written down, evaluating vendors becomes much more straightforward. You are no longer watching a demo and hoping something impressive appears. You are working through a list and checking boxes.
Insist on a site visit to a similar customer
Ask the vendor to arrange a visit to a customer of similar size and type to your business so you can see the system running in a live environment. This is the single best way to evaluate whether a system will genuinely work for you. Watch how staff actually interact with it day to day. Ask them what they wish they had known before going live. Ask what slows them down. A vendor confident in their product will welcome this. As an example, a site visit to review a warehouse management system once revealed that the way the system was set up by design would slow down picking and despatch to a point where it simply would not work for the volume of orders being processed. That discovery in a live environment saved a costly and disruptive implementation. You will never learn that from a demo.
Ask for references from businesses like yours
Not testimonials on a website. Actual contacts at actual businesses of a similar size and type to yours that you can call and ask real questions. How long did implementation take? What went wrong? How responsive is support? Would they choose the same vendor again? A vendor who cannot or will not provide this is a vendor without confident customers.
Red flags in the sales process
Pressure to decide quickly, especially around an offer that is about to expire. Reluctance to put anything in writing before you sign. Vague answers to specific questions about support, data ownership, or exit terms. A contract that is significantly longer or more complex than the product seems to warrant. Any of these should slow you down, not speed you up.
Read the contract before you sign it
This sounds obvious and almost nobody does it. Pay particular attention to the notice period required to cancel, what happens to your data if you stop paying, what the vendor’s liability is if something goes wrong, and whether the pricing is fixed or subject to increase. If you are signing a contract worth more than a few thousand euros or pounds per year, it is worth having a solicitor look at it.
Think about the relationship, not just the product
You are not just buying software. You are entering a relationship with the vendor that may last for years. Are they easy to communicate with? Do they respond quickly? Do they listen to feedback and improve the product? Do they have a clear roadmap for where the system is going? A good product from a vendor who goes quiet after you sign is not a good purchase.
QUICK COMPLIANCE CHECKLIST
Five questions to ask before committing to any new software,
Have you written down what your business actually needs before looking at any vendor options?
Do you have a clear list of essential requirements and desirable requirements that you will use to evaluate every option consistently?
Have you asked for a site visit, not just a vendor demo?
Have you spoken to at least two existing customers of the vendor and asked them direct questions about their experience?
Have you read the full contract, including the cancellation terms, data ownership clauses, and pricing change provisions?
BEFORE YOU GO
Choosing business software is one of the decisions that feels low stakes in the moment and high stakes in hindsight. It is easy to be swayed by a polished demo, a confident salesperson, or the fact that everyone else in your industry seems to be using a particular system. None of those things are a substitute for understanding what you actually need.
The businesses that get this right spend more time on requirements and less time on demos. They ask harder questions and take longer to decide. They are harder to sell to, which means they end up with systems that genuinely fit how they work rather than systems that looked good on a Tuesday afternoon in a conference room.
Take the time to do it properly. The cost of getting it wrong compounds for years.
See you next week.
The SME Security Brief
Found this useful? Forward it to a business owner who would benefit. It takes two seconds and could save them a serious headache.
You’re receiving this because you subscribed at thesmesecuritybrief.com. To unsubscribe, click here.
If you find this newsletter useful and want to show your support, you can buy me a coffee. It genuinely means a lot and keeps this going.
