As I’ve progressed through my career and into technology leadership, one challenge has remained constant: aligning IT initiatives with business strategy. This isn’t just about supporting the business—it’s about becoming a true strategic partner that drives value. Today, I will share my approach to bridging this critical gap, especially for those aspiring to or currently in IT leadership positions.

The Misalignment Problem

Misalignment is a common problem and it can be present regardless of company culture, size or industry. Over the years I have witnessed countless well-intentioned IT projects fail because they weren’t properly connected to business objectives. The common pitfalls I’ve observed include:

• Technology for technology’s sake: Implementing new solutions because they’re cutting-edge, not because they solve business problems, AKA shining penny (or I guess nickel’s now - RIP the Penny) syndrome
• Communication barriers: Business leaders speaking in terms of employee impact, market share and customer acquisition while IT discusses infrastructure and technical specifications
• Mismatched timelines: Business needs quick wins while IT plans multi-year transformations
• Isolated planning: IT developing roadmaps without substantial business input
• Undefined success metrics: Launching projects without clear KPIs tied to business outcomes and lack of measurement throughout the project and after

These misalignments don’t just waste resources—they erode trust between IT and business stakeholders, creating a cycle that’s difficult to break.

At their core, these misalignments often stem from organizational structures that have historically treated IT as a service provider rather than a strategic partner. Different career paths and educational backgrounds between business and IT professionals create distinct professional languages and priorities. Business leaders are trained to focus on market dynamics and financial outcomes, while IT professionals are rewarded for technical excellence, seamless launches and system stability. Without intentional effort to bridge these divides, the gap tends to widen over time as each group reinforces its own culture and practices.

Becoming a Business-Minded IT Leader

So how do we go from being a technologist to being a business-minded IT Leader? Early in my career, I made a pivotal realization: to be effective in IT leadership, I needed to think like a business leader first and a technologist second. Here are a few ways that I developed this mindset:

Get out of the IT bubble. I make it a point to attend business leadership meetings even when technology isn’t on the agenda. This exposure helps me understand the pressures, priorities, and perspectives driving business decisions.

Build meaningful relationships with business unit leaders. Beyond formal meetings, I schedule regular one-on-ones with business stakeholders. These conversations usually are not about IT—they are about understanding their challenges, desired outcomes or goals, and how they measure success.

Learn the financial language. I took the time to understand financial statements, margin calculations, and how business units measure performance. I also learned how to read SEC documents because many of the companies I have worked for have been publicly traded. This allows me to frame IT initiatives in terms of financial impact rather than technical specifications.

Experience frontline operations. Some of my most valuable insights came from spending time with customer service teams, visiting warehouses, observing sales calls, or working on the front lines in retail. This firsthand experience revealed operational pain points that technology could address. It also showcases where well intended technology is getting in the way of business success.

From Strategy to Execution: A Practical Framework

Once armed with this deeper business understanding, the next challenge becomes translating that knowledge into actionable IT initiatives. The business-minded perspective you’ve cultivated becomes the foundation for effectively mapping technology solutions to strategic needs. Over the years, I have gathered a few different techniques to do just that. These come from different areas, such as ITIL, Lean, Agile, PMP, ADKAR and many others which I cobble into a framework I call the “Strategy Cascade,” and it works as follows:

1. Strategy Immersion: Deeply understand the business strategy, including market positioning, competitive advantage, and growth targets. Knowing exactly what the business really going after in this particular period or cycle.
2. Capability Mapping: Identify the business capabilities needed to execute the strategy.
3. Gap Analysis: Understand what technical underpinnings are required to bring the business capabilities to life in support of the strategy. Assess where the current technological capabilities may fall short.
4. Initiative Development: Create targeted IT initiatives to close the most critical gaps.
5. Portfolio Optimization: Prioritize initiatives based on business impact, financial impact and feasibility.
6. Delivery Alignment: Structure delivery timelines to match business needs and showcase quick wins. Look for opportunities to prototype rapidly and test with the areas of the business where the greatest impact will be felt to learn/check, and adjust so that you can iterate until you reach the desired outcomes.

Let me illustrate this with a real example from my experience:

At the time, our company strategy was to increase throughput from our factories. As the SAP Service Owner I needed to understand what we meant when we said increase throughput. I took two pathways in order to better understand the company strategy. First I connected with our customer support team who allowed me to tag along on a customer visit where I saw first hand the impacts of our slow and delayed deliveries had on the next layer of the manufacturing process. Since our company made products that were components in other companies products slow delivery on our side meant their delivery was also slow. They were not able to fulfill orders as fast as they were capable because they could not get parts from us.

Now that I had an understanding of the impact our factory output had on our customers, I took the second pathway and walked the shop floor in one of our factories. During the shop visit I gained an understanding of the processing our products go through, the role technology plays and where there were challenges.

I then pulled our team together to map out our current capabilities and identify any gaps. We found several areas of opportunity and improvement. Rather than proposing a massive transformation project, we developed a portfolio of initiatives with varying timelines and impact levels—some delivering value within weeks such as updating the process step sequencing to improve the speed of delivery, others building toward longer-term capabilities such as migrating from on-premise SAP ERP to SAP HANA to increase system performance.

Measuring What Matters

A critical part of bridging the strategy-execution gap is establishing the right metrics. I’ve found that effective measurement requires:

Dual metrics: Tracking both technical success (uptime, performance) and business impact (business outcomes, revenue influence, cost reduction, customer satisfaction)

Leading indicators: Identifying early signals that an initiative is on the right track, not just waiting for final outcomes

Transparent reporting: Creating simple status and dashboards that business leaders can understand without technical translation

For example, when we were migrating to a new point of sale system, we tracked traditional metrics like system performance, and data quality, but also monitored changes in transaction speed, items per transaction, and return customer visits—the actual business outcomes the technology was meant to influence.

The sun is setting on the days of the IT leader as a purely technical role. Today’s successful IT leaders function as business strategists who happen to specialize in technology. We must be bilingual—fluent in both business and technology languages—and serve as translators between both worlds. It’s not enough to execute well on defined projects; we must actively shape which projects should be pursued in the first place. As you develop in your leadership journey, continuously ask yourself: “Can I tie this initiative directly to our strategic goals?”’ and “How does this technology decision advance our business strategy?” When these questions becomes automatic for both you and your team, you’ll know you’ve truly bridged the gap.