7 Reasons Cyber Security Strategies Fail (and How to Fix Them)

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.

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What This Blog Covers:

• There’s No Written Strategy
• Leadership Doesn’t Buy In
• Relying on One Vendor to Do Everything (Yes, Even Microsoft)
• The Human Factor: Still the Weakest Link
• Ignoring the Basics
• Failing to Adapt to a Changing Threat Landscape
• No Trusted Partner or Incident Playbook
• Turning Strategy into Action

1. There's No Written Strategy

Not documenting your cyber security strategy is by far the most common failure we see, because it’s arguably the easiest trap to fall in. It’s not that businesses are negligent or don’t care – that couldn’t be farther from the case. The issue is that they’re incredibly busy and get tied up in other profit-driving initiatives, and they think the basics are enough. Smaller businesses in particular tend to view cyber security as a technical problem rather than a business risk. They delegate it entirely to IT without defining outcomes or accountability.

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.

How to Get it Right:

Start small and practical:

• Write a one-page document that covers your biggest risks, your key objectives, and who owns each area.
• Add timelines for review — quarterly is ideal.
• The goal isn’t a 40-page policy that collects dust, but creating a living document that drives action.

2. Leadership Doesn’t Buy In

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.

How to Get it Right:

Get security onto the leadership agenda:

• Report it like any other business risk — with KPIs tied to outcomes leaders care about: uptime, compliance, reputation, and deal retention.
• Hold quarterly reviews and give executives visibility of where the business stands — red, amber, green. That visual accountability changes everything.

3. Relying on One Vendor to Do Everything (Yes, Even Microsoft)

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.

How to Get it Right:

Identify who owns what:

• Document which alerts you’re monitoring, who’s responsible for actioning them, and how quickly they’re expected to respond.
• Ask your providers to demonstrate what they’re monitoring — and hold them accountable. No assumptions, no grey areas.

4. The Human Factor: Still the Weakest Link

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.

How to Get it Right:

Make cyber awareness part of your culture, not an annual box-tick:

• Run monthly micro-trainings, gamify phishing tests, and celebrate people who spot and report scams.
• For high-risk processes like payments, use what I call human MFA: always verify through a second channel — phone call, Teams message, or face-to-face — before acting.

5. Ignoring the Basics

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.

A client once discovered that their backups had been failing silently for three months. It was only when they needed a restore and nothing worked that the issue was flagged. They were lucky the incident wasn’t ransomware — otherwise, that would’ve been the end of the business.

How to Get it Right:

Make the basics your first KPI:

• Patching is done monthly.
• Backups are tested quarterly.
• MFA is enforced across every user, system, and app.
• If you haven’t done so already, plan your migration away from Windows 10 Microsoft already ended support for Windows 10 in October, which opens the door for bad actors.

6. Failing to Adapt to a Changing Threat Landscape

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.

How to Get it Right:

Schedule quarterly control reviews:

• Review configurations, update training, and refresh playbooks.
• If you can’t do it internally, partner with a Managed Detection & Response (MDR) provider who can. Security isn’t a set-and-forget function: it’s a continuous process.

7. No Trusted Partner or Incident Playbook

This is the final — and often most painful — failure point because it’s so easily avoidable. When an incident happens, businesses panic. Who do we call? Who has the passwords? What should we tell customers? Without a playbook that holds the answers to all of these questions, the entire organisation is in complete disarray. Most SMBs have never rehearsed a cyber incident, and are perfectly fine with ‘crossing that bridge when they get to it’. But trying to improvise when you’re under pressure and no one can access the company data is next to impossible.

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.

How to Get it Right:

Write a simple incident response playbook:

• List contacts (internal and external), define communication roles, and run tabletop exercises twice a year.
• If you work with external partners, involve them in those rehearsals so everyone knows their role before a crisis hits.

Turning Strategy into Action

Mitigating these common cyber security strategy failures is not dependent on the technology, but on having the right processes and ownership in place. Luckily, the fix is pretty straightforward: simply requiring clarity, consistency, and communication.

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.