Your Summer IT Health Check

10 Questions Every Business Should Ask Before September

Summer offers something that's often in short supply during the rest of the year: time to think.

With colleagues taking annual leave and business activity naturally slowing down, it's the ideal opportunity to step back and review whether your technology is supporting your organisation as effectively as it could.

Too often, technology is only reviewed when something forces the issue. A security incident. A major project. A growing team. A system that's no longer fit for purpose.

A better approach is to review your technology before those challenges arise.

Whether you're responsible for IT, operations or the wider business, taking time to ask the right questions now can help you identify opportunities to improve productivity, strengthen security and ensure your technology is ready to support your organisation through the months ahead.

At a Glance

In this guide, we'll explore:

• How to get more value from Microsoft 365
• Ways to simplify your technology environment
• Practical steps to strengthen cyber security
• Questions to test your business resilience
• Why reviewing your IT strategy before September matters

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Are You Getting the Most from Your Technology?

Before investing in new technology, it's worth making sure you're getting the maximum value from the tools you already have.

Question 1: Are you getting the most from your Microsoft 365 investment?

Microsoft 365 has become the foundation of the modern workplace, yet many organisations only use a fraction of its capabilities.

It's common to find businesses paying for licences that no longer reflect employees' roles, or overlooking security and productivity features that are already included within their subscription.

Consider:

• Are you regularly reviewing unused or underutilised Microsoft 365 licences and services?

OR

• Has your Microsoft 365 environment been reviewed within the last 12 months?
• Does each employee have the right licence for the way they work?
• Are you making full use of the security and productivity features included in your subscription?
• Could you optimise licensing without compromising user experience?
• Are Microsoft 365 licences assigned and removed promptly when employees join, change roles or leave?

Reviewing Microsoft 365 isn't simply about reducing costs. It's about ensuring your investment delivers the greatest possible value.

Question 2: Are your teams making full use of Microsoft 365?

Technology only creates value when people know how to use it.

Many organisations continue to rely on familiar ways of working, despite having access to tools that can improve collaboration, simplify processes and save valuable time.

Think about how your teams use:

• Microsoft Teams
• SharePoint
• OneDrive
• Planner
• Microsoft Lists
• Loop
• Microsoft Copilot, where appropriate

Small improvements in adoption often have a much greater impact than introducing new software.

Question 3: Could you simplify your technology environment?

Technology naturally evolves over time.

Applications are introduced, legacy systems remain in place and departments adopt different solutions to meet their needs. Before long, complexity starts to increase.

Now is a good opportunity to review:

• Duplicate software
• Unused applications
• Legacy systems
• Multiple suppliers providing similar services
• Licences that are no longer required
• Are you paying for overlapping tools that provide similar capabilities?

A simpler technology environment is easier to manage, easier to secure and often more cost effective.

Health Check Tip: Before investing in something new, make sure you're getting the most from what you already have.

Is Your Business Secure?

Strong cyber security isn't achieved through a single project. It's built by regularly reviewing the fundamentals.

Question 4: Do you know exactly who has access to your systems?

People join, leave and move roles throughout the year.

Without regular reviews, user accounts and permissions can quickly become outdated, increasing unnecessary risk.

Ask yourself:

• Have all leavers been removed from your systems?
• Does everyone have the appropriate level of access?
• Is Multi-Factor Authentication enabled for all users?
• Are privileged accounts reviewed regularly?
• Do you have visibility and control over which AI tools employees can access and what information they can use?

Managing user access remains one of the most effective ways to strengthen your security posture.

Question 5: Are your devices fully up to date?

Laptops, desktops and mobile devices are often overlooked during busy periods.

The quieter summer months provide the perfect opportunity to complete essential housekeeping.

Review whether:

• Operating systems are fully patched
• Devices are encrypted
• Endpoint protection is current
• Older hardware should be replaced
• Unused devices have been removed
• Are your device management and monitoring tools providing the visibility, control and automation your organisation needs?

Small maintenance tasks completed now can help prevent larger issues later.

Question 6: Is your cyber security keeping pace with your business?

Businesses evolve constantly.

New employees join. Hybrid working becomes the norm. Cloud services expand. As your organisation changes, your approach to cyber security should change with it.

Consider:

• Is Multi-Factor Authentication enabled across the organisation?
• Are employees receiving regular cyber security awareness training?
• Are vulnerabilities identified and addressed promptly?
• Have security policies been reviewed recently?
• Does your security approach still reflect the way your business operates today?
• How well does your organisation align with the latest Cyber Essentials requirements and NCSC guidance?
• Have you assessed the security, access and data protection implications of introducing AI agents?

Cyber security is an ongoing discipline, not a one-off exercise.

Health Check Tip: Small improvements made today can significantly reduce risk tomorrow.

Could Your Business Cope with the Unexpected?

Business resilience isn't about predicting disruption. It's about being prepared when it happens.

Question 7: If your systems failed tomorrow, how quickly could you recover?

Most organisations have backups.

Far fewer know how quickly they could restore critical systems if something went wrong.

Consider:

• When was your last successful restore test?
• Are recovery tests automated or scheduled regularly?
• How long would recovery realistically take?
• Which systems are business critical?
• Could employees continue working during an outage?

Recovery should be tested regularly, not assumed.

Question 8: Could your business continue operating during an unexpected disruption?

Power outages, internet failures, cyber-attacks and severe weather can all disrupt business operations.

Business continuity is about ensuring your organisation can continue operating, whatever the circumstances.

Ask yourself:

• Could employees work securely from another location?
• Are key business processes documented?
• Does everyone know what to do during an incident?
• Are communication plans in place?

Preparation doesn't prevent disruption, but it can reduce its impact.

Health Check Tip: A business continuity plan is only valuable if it's been reviewed and tested.

Are You Ready for What's Next?

Technology should support your future ambitions, not simply your day-to-day operations.

Question 9: When did you last review your IT strategy?

Technology changes quickly.

Business priorities change even faster.

If your IT strategy hasn't been reviewed recently, there's a good chance it no longer reflects where your organisation is heading.

Consider:

• Your business objectives
• Planned growth
• Technology investments
• Security priorities
• Budget planning
• Opportunities to improve efficiency
• Your approach to AI adoption, including governance, security, legal and data protection considerations

A strategic review now can help avoid reactive decisions later.

Question 10: Does your technology strategy support where your business is going?

Technology decisions should always support wider business objectives.

Whether you're planning growth, improving efficiency or strengthening resilience, your technology should enable those ambitions, not hold them back.

Ask yourself:

• Is your technology aligned with your business goals?
• Are you investing in the right areas?
• Are there opportunities to simplify or modernise?
• Are you confident your technology will support future growth?
• Is your organisation adopting AI with a clear strategy, appropriate governance and defined business outcomes?

Sometimes, asking the right questions is the first step towards making better decisions.

Health Check Tip: The best time to prepare for September is before it arrives.

Ready for September?

A summer IT health check isn't about creating unnecessary projects or finding problems where none exist.

It's about taking advantage of a quieter period to step back, challenge assumptions and make sure your technology is supporting your organisation as effectively as possible.

For some organisations, that might mean getting more value from Microsoft 365. For others, it could involve strengthening cyber security, reviewing business resilience or ensuring technology investment is aligned with future business goals.

Whatever stage your organisation is at, taking time to review your technology today can help you start September with greater confidence.

What's next?

We've turned these ten questions into a practical Summer IT Health Scorecard, designed to help you benchmark your organisation and identify areas that may benefit from further review.

Download the Summer IT Health Scorecard and see how your organisation measures up before September.

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