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IT Strategy Tune-Up: A Framework for Annual Reviews with Your IT Services Provider
Your IT strategy isn’t something you can set and forget. Technology changes, and so do the needs of your organization. Without regular check-ins, even the best-laid IT plans can fall out of alignment with your business objectives, leaving your operations vulnerable to inefficiencies, compliance risks, and missed opportunities for growth.
That’s why conducting an annual review of your IT strategy is a healthy habit. These reviews provide a structured opportunity to evaluate how well your current IT systems and services are performing, ensure alignment with your organizational goals, and identify areas for improvement or innovation.
In this post, we’ll outline a practical framework to help you conduct a productive annual IT strategy review with your managed IT service provider (MSP), getting into:
- Why annual IT strategy reviews matter
- Preparing for your annual IT strategy review
- Defining an IT strategy review framework
- Conducting the review meeting with your IT service provider
- Defining your IT roadmap
From conducting the review meeting to keeping your team accountable throughout the year, this guide is designed to give you the tools you need to make sure your IT investments are working for you—not the other way around. Let’s dive in.
Why Annual IT Strategy Reviews Matter
In one way or another, your business is always facing shifting priorities, evolving risks, and continuous innovation. Without regular check-ins, it’s easy for your IT roadmap to fall out of sync with your goals. An annual review ensures your IT strategy stays proactive, aligned, and prepared for what’s ahead. Here’s how.
It Helps You Keep Pace With Change
Nearly two-thirds (64%) of organizations plan to increase their IT budgets in 2025, with greater investments into generative AI (54%) and security (52%). These statistics show IT and business leaders are committed to adapting to stay ahead. An annual IT strategy review helps your organization keep pace, ensuring your tech investments support emerging opportunities and mitigate evolving risks.
It Helps You Stay Aligned with Business Goals
Your IT strategy is about more than keeping the lights on—it should drive your business forward. Annual reviews give you the chance to step back, evaluate whether your IT initiatives are truly meeting your goals, and recalibrate where needed. Whether you’re focused on cutting costs, improving customer experience, or scaling operations, this is your moment to make sure your IT is pulling its weight.
It Helps You Protect Against Risk
The barriers to entry for cybercriminals are eroding as advanced tools, phishing kits, and “as-a-service” resources become more accessible. This shift enables less sophisticated threat actors to carry out operations with greater efficiency and impact, posing an increasing risk to businesses of all sizes. Regular IT reviews provide a necessary opportunity to consider these risks and formulate a plan to address them, protecting your business from costly disruptions.
It Helps You Evaluate Your IT Managed Services Provider
An annual IT strategy review is the perfect time to evaluate your managed IT service providers. With 37% of businesses planning to reevaluate their IT vendors and contracts in 2025 as part of an IT cost optimization initiative, this process ensures your IT service provider is delivering value and aligning with your business goals. By analyzing their performance, responsiveness, and contributions to your roadmap, you can make informed decisions about whether to continue, renegotiate, or explore other options.
Preparing for Your Annual IT Strategy Review
Taking the time to audit your organization’s needs and assess your current IT state before your strategic review ensures that the discussion with your IT Managed Services Provider is focused and data-informed. Here’s what to do before your review.
- Audit Your Organization’s Needs
Begin by gathering feedback from key internal stakeholders across departments. What’s working well with your IT services? Where are the pain points? Understanding these perspectives provides a clearer picture of your organization’s evolving requirements.
- Assess Your Current State
Review performance metrics and outcomes from the past year. Metrics like service-level agreements (SLAs), response times, and resolution rates can offer valuable insights into the effectiveness of your IT systems and your managed IT service provider’s performance.
- Identify Your Strategic Priorities
What’s happening in your business? Consider upcoming organizational goals and challenges. Are you planning to scale operations, adopt new technologies, or address emerging security threats? Pinpointing these priorities will guide the review and ensure your IT roadmap aligns with your business direction.
Defining the IT Strategy Review Framework
A well-defined framework will help you hold a productive and focused IT strategy review. This framework can act as a roadmap for your discussion, ensuring that you and your IT service provider evaluate the right areas, use relevant data, and uncover actionable insights.
Below is an example framework that outlines key conversation pillars, provides context for each focus area, and suggests metrics and KPIs to measure success. While this is just an example, you can use this as a guide to structure your review and tailor it to your organization’s needs.
| Review Pillar | Description | Metrics and KPIs |
|---|---|---|
| IT Cost Optimization | Evaluate whether IT spending aligns with the budget and delivers ROI. | Cost savings from optimizations Variance from last year’s IT budget |
| Security | Assess the effectiveness of cybersecurity measures and compliance efforts. | Number of incidents resolved Time to detect/respond Penetration test scores |
| Operational Efficiency | Measure the performance of IT systems and processes in supporting business needs. | Uptime percentage SLA adherence Response and resolution times |
| User Satisfaction | Gauge employee and customer satisfaction with IT services. | Net Promoter Score (NPS) Survey feedback Support ticket satisfaction ratings |
| Scalability | Determine if IT systems can support future growth and changes. | Resource utilization Readiness for new tech or users |
Conducting the Review Meeting With Your Managed IT Service Providers
Once you’ve prepared and defined your review framework, it’s time to bring everything together in the annual IT strategy review meeting. This meeting is an opportunity to reflect on the past year, analyze performance, and set a clear direction for the year ahead. Here’s how to structure an effective discussion:
Revisit Last Year’s Goals
Start by reviewing the priorities outlined in last year’s IT roadmap. Evaluate successes, identify shortfalls, and discuss your lessons learned. This step sets the stage for a transparent and constructive conversation about progress.
Walk Through Metrics and KPIs
Present the data you’ve collected based on your framework. Highlight areas where performance met or exceeded expectations, as well as any metrics that show opportunities for improvement.
For example, you might analyze your cybersecurity incident resolution times to assess how quickly threats are being mitigated, or evaluate resource utilization to determine if your infrastructure can handle projected growth. If gaps are found, you can use these insights to drive improvement in the upcoming year.
Explore Emerging Technologies and Trends
Your IT Managed Services Provider should be using this time to discuss changes on the horizon—whether that be new automation tools, AI capabilities, or security measures that could enhance your IT infrastructure. This is the time to work collaboratively with your IT service provider and evaluate whether these technologies: a) align with your business goals, and b) fit into your IT plan.
Establish Priorities
With data in hand and productive conversations on the table, now’s the time to discuss gaps in your current systems, security concerns, IT cost optimization, or opportunities to improve efficiency. With your IT service provider, define improvement areas and establish clear priorities to address in the upcoming IT roadmap.
By structuring the meeting around these steps, you’ll ensure the conversation is productive, actionable, and aligned with your long-term objectives.
Defining Your IT Roadmap for the Year Ahead
A strong annual IT roadmap bridges your strategic goals with actionable steps to achieve them. After evaluating past performance and setting priorities, it’s time to develop a plan that aligns with your business’s objectives. First, define key initiatives that will drive your IT strategy forward. These might include upgrading outdated infrastructure, implementing new technologies, enhancing security measures, or improving user experience. It’s good practice to prioritize these based on their potential impact and alignment with your overarching goals.
Next, align your budget and resources with the roadmap. Review costs to determine whether additional investments are required for technology, training, or staffing. Work closely with your IT service provider to explore cost-effective solutions and ensure everyone is aligned on resource allocation—and come up with a game plan to secure executive buy-in, if needed.
Finally, define success criteria for each initiative. For example, success might be reducing downtime, improving incident resolution times, or increasing user satisfaction scores. Clear benchmarks will help you evaluate the roadmap’s impact so you can pivot as needed.
Keeping the Plan Moving
An annual IT strategy review is just the starting point—keeping it moving throughout the year is another story. Here’s are a few ways to stay on track:
- Establish timelines and responsibilities, breaking each initiative into actionable steps (like quarterly initiatives) with clear deadlines.
- Assign clear roles within your organization and your IT service provider to ensure accountability for each initiative.
- Monitor success and share updates by using dashboards or reports to check in on key metrics, keeping everyone aligned and focused.
- Schedule regular check-ins with your IT service provider to track progress, address challenges, and adjust priorities as needed.
Need help defining your IT strategy?
An annual IT strategy review is a welcome opportunity to ensure you’re prepared for the future. But achieving that requires a trusted IT partner who truly supports your success.
At Convverge, we go beyond the basics of a typical provider to deliver strategic IT support tailored to your business. Whether it’s collaborating on an IT strategy as your Managed IT Service Provider or helping you execute on it with a Professional Services engagement, we have you covered. When you’re ready to take your IT strategy to the next level—explore our Managed Services to see how we can support your business vision with our tech expertise.
