Most of the SMBs we talk to honestly believe that they’ve “got security sorted.” They’ve paid for Microsoft 365 licences, they’ve got antivirus, maybe even some backups in the cloud. But then something happens — a supplier security questionnaire lands in their inbox, a phishing email gets through, or a staff member clicks on a fake invoice that siphons thousands — and it’s clear there was never a real strategy. Just technology scattered across departments, and a lot of misplaced confidence.
Over the years I’ve spent making cyber accessible to non-technical leaders through clear strategy, strong execution, and market-driven innovation, I’ve learned that most cyber security failures have very little to do with the technology itself. They come down to how people (outside of the IT team) think about security: what they prioritise, who they involve, and how clearly they define ownership. Time and again, it’s leadership alignment, culture, and consistency that make or break the entire effort.
In this article, I’ll walk you through the seven biggest reasons we see cyber security strategies fail, using real examples from the businesses we’ve worked with. More importantly, I’ll show you exactly how to fix each one — without the jargon, the fear-mongering, or a six-figure budget. Because the truth is, when it comes to keeping your business safe, you don’t need a bigger spend, you need a clearer strategy.
When our team asks, “Do you have a written security strategy?”, we often get blank looks. Some say, “Our MSP handles that”. But when we dig deeper, it’s clear there’s no plan. Just a handful of tools and assumptions. So when incidents happen, chaos follows. No one knows who’s responsible for what, or even which systems are affected. Security then becomes reactive and a constant (and very stressful) game of catch-up.
Start small and practical:
Anybody in the cyber space will tell you that security isn’t an IT cost: it’s a business risk that should be a priority for every single person in the organisation. That’s because if your leadership team sees cyber security as “an IT problem,” your strategy will fail. I get it, when you’re not in the industry, it can be difficult to wrap your mind around the technical side of security, which makes it that much harder to understand the ROI.
We’ve seen countless IT teams working their socks off to keep things secure — applying patches, reviewing alerts, training staff — only for it to stall at the board level because the decision-makers don’t see the ROI or understand the value. The language is often the barrier: IT talks about vulnerabilities, but leadership thinks about revenue, contracts, and operations. Until something goes wrong, whatever the IT team says feels abstract and “techie”.
We saw this play out when I worked with a manufacturing client that failed a supplier questionnaire for a major contract because they couldn’t provide evidence of their security controls. It wasn’t that they were insecure; they just couldn’t prove it. That single miss cost them a six-figure deal.
Get security onto the leadership agenda:
Before I go any further, let me clarify that Microsoft 365 has fantastic security tools and is investing heavily in cyber protection. However, as Philip Connor mentioned in this article, having a Microsoft 365 licence doesn’t mean you’re protected. This is one of the most dangerous misconceptions: businesses assume Microsoft takes care of everything, so they don’t monitor or manage what’s happening inside their tenant.
One client thought Defender for Office was blocking all phishing emails. When we checked, the alerts were going somewhere — but nowhere anyone was actually looking. Hundreds of security alerts were sitting in a shared inbox, completely ignored. It was only when an account was compromised that they realised the gap had been open for months.
Buying security isn’t the same as managing it. I know some vendors have “got you covered”, but security is a shared responsibility. The provider gives you the tools, and you’re responsible for using them properly.
Identify who owns what:
No matter how advanced your systems are, your people will always be your biggest risk, or your best line of defence. While user awareness training is effective, it isn’t enough on its own. Most programmes are one-off, boring and forgettable. Real learning happens through repetition and context: people need to have a deep understanding of their role in keeping the business safe.
We once helped a company recover after a WhatsApp scam cost them thousands. The finance manager received a message that appeared to be from their CEO, asking for an urgent payment. This bad actor was spot on with the user impersonation: the tone, photo and language used were all perfect. So, nothing was questioned, and the money was gone in minutes.
Make cyber awareness part of your culture, not an annual box-tick:
This one sounds obvious, but it’s something that catches many businesses out. I’m talking about patching, MFA, backups, and end-of-life systems. We still see servers running outdated operating systems, unpatched vulnerabilities, and backups that haven’t been tested in months. Covering the basics might not be at the top of your to-do list because “everything still works”. Until it doesn’t.
Make the basics your first KPI:
The threat landscape never sleeps, so neither can your strategy. But most internal IT teams are stretched thin: juggling helpdesk tickets, onboarding and hardware refreshes. They simply don’t have the time or resources for proactive risk management, tracking emerging threats or updating controls fast enough. So, while attackers evolve, defences fall behind – and over time, complacency creeps in.
Another client was hit by a business email compromise (BEC) attack. Their finance team received a real-looking email from a supplier asking to update bank details. The payment went through — straight to the attacker. When we investigated, it wasn’t a hack or breach, but a lapse in verification. They’d never updated their supplier payment process.
Schedule quarterly control reviews:
We worked with a business that suffered a ransomware attack. They had backups, but no process for restoration. To make matters worse, the IT provider and internal team disagreed on priorities. It took three days just to get everyone aligned, and those three days cost them hundreds of thousands in downtime.
Write a simple incident response playbook:
The failures I’ve walked you through and the customer stories I’ve mentioned aren’t theoretical — they’re real, and they cost real money. I’m talking lost revenue from failed deals, reputational damage after public breaches, staff burnout (and potential turnover) from constant firefighting, and landing in hot water when you can’t prove compliance to regulators.
Every major cyber incident we’ve helped a business recover from had the same origin: no strategy, no ownership, and no rhythm of review. As Babble’s Cyber Security Product Manager, it’s my job to help SMBs like yours build practical, no-nonsense cyber strategies that actually work — not just look good on paper.
Ready to see where you stand? Book a free Cyber Security Risk Assessment and benchmark your current setup. You’ll know exactly where to focus next — before someone else finds your weak spot for you.