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How to sell: Windows 11
The latest in the series that provides a handy sales pitch guide considers the message the channel should be giving to those users yet to make the jump away from Windows 10
In just a couple of weeks, support for Windows 10 will be switched off, leaving users vulnerable to security attacks on an unpatched system. But there are more reasons than just the risk element to encourage user operating system (OS) migration.
The channel has been warning customers of the need to migrate to avoid being left on an unsupported platform for months, but there continues to be a portion of users that have not yet made the move. That customer base is clearly a target for the channel, but pitching Windows 11 need not just be about emphasising the negatives of failing to do so. The OS offers other benefits, and some of those are highlighted here to provide a more rounded pitch that includes some carrot as well as the stick.
“Performance gains are a core advantage,” said James Young, head of infrastructure architecture at managed service provider (MSP) Ekco. “Windows 11 is designed to make better use of modern hardware, delivering faster startup times and more consistent performance even when handling demanding workloads. It also introduces tighter integration with cloud services, giving IT teams – and their MSP partners – more control over devices without adding administrative burden. For organisations, that means fewer performance-related issues and the ability to focus on strategic IT improvements rather than firefighting problems.”
Brian Sibley, virtual chief technology officer at Espria, stresses the security and improved management features from the OS.
“Windows 11 has enhanced security and manageability features, such as the requirement for secure trusted platform module (TPM) 2.0 hardware and the enhanced update cadence, reducing user impact,” he said. “Seamless integration with cloud services such as Microsoft 365 and Azure enhances the user experience, along with continued support for legacy applications where still necessary. Overall, it delivers significant advancements across key areas designed for the modern hybrid work environment.”
Anthony Dobson, UK and Ireland regional director at Arrow’s enterprise computing services business, also highlighted the benefits for the channel partner.
“For channel partners, the benefits of moving their end-customers to Windows 11 are twofold: it will secure the right licensing position for the future and open the door to the latest Microsoft capabilities,” he said. “Many end-customers don’t realise that they already have upgrade rights through Software Assurance or Microsoft 365 subscriptions. Acting on them now will help end-customers avoid the additional cost of Extended Security Updates when Windows 10 support ends in October this year.”
Who needs it?
The positive for the channel is the sheer size of the Windows base and the number of customers that will require migration.
“Any organisation still running Windows 10 should be planning its move,” said Young. “This is especially true for sectors under strict regulation, such as GDPR [General Data Protection Regulation] or NIS2 [Network and Information Security Directive 2], and for those that handle sensitive client information as part of their operations. For example, legal practices managing case files, healthcare providers holding patient records and retailers processing large volumes of payment data all face a heightened risk if they continue operating on unsupported systems. But in reality, every business has data worth protecting, which means the need to upgrade applies across the board.”
Dobson also advised a strategic focus on certain customers to begin with to ensure the channel gets the right targets before October’s deadline.
“Customers with perpetual Windows 10 licenses and no Software Assurance should be prioritised, as they will need to act before support ends,” he said. “Regulated industries, security-conscious organisations, and those managing distributed workforces have the most to gain from Windows 11’s compliance-ready security model and enhanced manageability. Even end-customers planning future hardware refreshes can benefit from acting now. Securing licensing early allows them to unlock Windows 11 capabilities immediately, without waiting for new devices.”
Liam Hardie, cloud programme manager at Infinigate Cloud, stressed the need for a partner to prepare the customer for the move to Windows 11 to ensure the foundations for a smoother migration are in place.
“It’s important to ensure that the entire organisation is prepared for the transition to Windows 11,” he said. “This includes verifying that all software is compatible with the new operating system. Most software is, but it is important to test applications, ensuring that any legacy software is made compatible and all software is documented so nothing gets lost in the move.
“Upgrading is a comprehensive process, so making sure you undertake the process correctly is vital,” said Hardie. “This involves assessing and upgrading each machine, as well as identifying devices that cannot be upgraded. On top of this, organisations will need to perform full backups to prevent data loss during the transition. Users may also require training on the new system, so organisations should be prepared to provide the necessary training and support to ensure a smooth adoption.”
How should you migrate to it?
Kate Jefferyes, EMEA Microsoft lead at Tanium, noted the importance of taking a migration in stages to ensure it delivers the right result and experience for the customer.
“The first step is understanding your IT environment,” she said. “That means assessing hardware and application compatibility, backing up critical data and budgeting for new devices where needed. Creating a full picture of endpoints, including legacy systems, allows IT teams to prioritise effectively.
“Once migration begins, visibility and automation are key,” added Jefferyes. “Real-time insights across all endpoints help IT teams make informed decisions, while automating repetitive tasks like provisioning and monitoring keeps the roll-out on track and reduces pressure on staff.
“Migration doesn’t end once devices are upgraded,” she said. “Ongoing monitoring, automated alerts and clear reporting are essential for maintaining compliance and security. These practices also ensure organisations are better prepared for the next cycle of technology change.”
Ben Lee, head nerd at N-able, listed the steps that start with backup, then checking compatibility using Windows Update or turning to the Windows 11 Upgrade Assistant tool if further guidance is needed.
“If your computer is managed by an IT team, leverage the tools and technologies for staging and deploying the Windows 11 upgrade at scale,” he said. “After the upgrade has completed, re-run Windows Update to catch any feature, driver and BIOS [basic input/output system] updates.”
How can the channel support that process?
One of the key aspects the channel needs to encourage is a conversation that starts with the hardware. A migration plan can be agreed, but if the PC fleet cannot support Windows 11, there are going to be problems.
“The largest barrier for upgrading is hardware compatibility,” said Lee. “Microsoft had to make deliberate trade-offs building Windows 11, prioritising security improvements that require newer chipsets and central processing units [CPUs] such as trusted platform modules [TPMs] at the cost of older hardware compatibility.
“The requirements for Windows 11 are well documented and easily checked in advance. Some devices can be made compatible with BIOS updates or configuration changes, but unfortunately not all. Again, Microsoft provides many different tools and mechanisms to help minimise the upgrade risks.”
For IT service providers, the opportunity is in guiding customers through readiness. That means assessing hardware estates for compatibility, helping plan pilots and test phases, and building migration roadmaps that minimise downtime. Where hardware falls short, they can advise on upgrades or replacements. The real value is helping customers see migration not as a disruption, but as a chance to modernise and secure their IT environment, he added.
What are the prospects for those who stick with Windows 10?
Lee shared the view of many in the channel regarding the real risks of delaying migration.
“Organisations that choose to remain on Windows 10 must weigh the risks carefully,” he said. “While the OS won’t suddenly fail, it will gradually become more exposed to security gaps and compatibility issues. Microsoft has occasionally released emergency patches for out-of-support systems, but this is the exception, not the rule. Extended Security Updates may be an option, but they come at a cost and only delay the inevitable. IT service providers should help customers make informed decisions, either by planning a managed migration now or by being clear on the risks of standing still.
“Upgrading to Windows 11 isn’t about chasing the latest version, it’s about staying secure, supported and ready for the future,” added Lee. “The sooner organisations plan their move, the smoother and safer the transition will be.”
Jefferyes also had a word of warning for those customers opting to continue paying for support.
“Microsoft’s Extended Security Updates provide a short-term safety net by continuing critical patches for Windows 10 devices,” she said. “It ensures that enrolled devices will continue receiving security updates, helping protect against vulnerabilities and exploits that could otherwise leave systems exposed. However, this extended support does not include new features, feature updates, customer-requested non-security Windows updates, or design change requests. It also comes at a rising cost, and at its core, it’s a temporary measure and not a long-term solution.
“Ultimately, the Extended Security Updates program buys time, but it doesn’t solve the underlying problem,” added Jefferyes. “Organisations should plan to move to Windows 11 or another supported operating system well before the deadline to ensure security, compliance and resilience in the years ahead. Making that move is a crucial step in mitigating risk across the entire environment.”
Customers are migrating: the evidence has been seen in PC sale figures, and the need for the channel to support migrations will continue. The pitch is a balancing act between warning of risks and security vulnerabilities, and promoting the efficiency and performance gains from investing in Windows 11.
