Unless your Small or Medium-Sized Business (SMB) is brand new, every strategic decision you make today is influenced by the “baggage” of past choices: existing organizational structures, current staffing, previous technology investments, and established brand positioning. This baggage is real and creates constraints. But if you allow these past decisions to control your future direction, you risk mediocrity and, at best, incremental growth.

The “Technology Debt” Drag

Consider the common challenge of “technology debt.” This is the cumulative gap between tactical or less-than-ideal IT decisions made over time and what an optimal, modern solution would look like. In many established businesses, this results in a complex “ball of yarn”; a mix of legacy systems, newer platforms, and multiple “middleware” layers struggling to keep pace with today’s business demands. In such an environment, it often feels like you’re running your fastest just to stay one step behind the competition. The de facto strategy becomes being a “fast follower,” not by choice, but by constraint.

The Problem with Chasing the Puck

The issue with solely focusing on current parity and reacting to existing market conditions is that it condemns you to a perpetual game of catch-up. You’ll never have the resources or focus left to truly innovate and win. The answer to this puzzle comes from a perhaps unlikely source, hockey legend Wayne Gretzky, who famously said:

“A good hockey player plays where the puck is. A great hockey player plays where the puck is going to be.”

If your SMB constantly accepts the constraints of the past (where your business is on the ice right now) and focuses only on matching industry parity (where the puck is now), you’re destined to chase the play rather than dictate it.

Breaking the Cycle: Choosing to Skate to the Future

It’s true that existing technology debt, organizational inertia, or other legacy factors limit the resources available for new initiatives. However, these constraints primarily affect the amount of resources, not what initiatives and ideas you can strategically pursue. You can continue to chase the current puck, or you can make a conscious decision to skate to where it’s going.

The only way to break the reactive cycle is to deliberately direct your primary attention and a strategic portion of your resources towards where your market, your customers, and technology are heading. This might mean accepting a temporary gap in parity on some current, less critical fronts to free up resources to leapfrog to a future advantage. As your fractional CIO, a key part of my role is to help you make these tough but necessary strategic choices regarding your IT investments and roadmap.

Becoming a “Student of the Game” for Your Industry

How do you know where the puck is headed? It’s not luck. Like Gretzky, who was a brilliant student of hockey, you need to become a deep student of your “game”:

• Understand Your Market: Dedicate significant time to researching and understanding the trends, disruptions, and emerging opportunities affecting your industry.
• Observe Your Customers: Intensely observe how customers use your current products/services and those of adjacent players. What are their unmet needs? What future problems will they face?
• Seek External Perspectives: Actively consume insights from analysts, thought leaders, industry bloggers, and trusted advisors who view your market from different angles.

You don’t need to be the Wayne Gretzky of your industry to succeed with this approach. But applying a similar dedication to understanding your landscape will enable you to anticipate future needs and position your SMB on the “open ice” more consistently.

What’s Next

Stop spending all your energy worrying about where the puck is right now. Instead, dedicate strategic focus and resources to skating where you anticipate it will be. This proactive, future-oriented approach, especially in leveraging technology, is how your SMB can move from playing catch-up to leading the way and “Succeed Sooner.”

Is your SMB burdened by “technology debt” or past decisions that hinder its ability to innovate and skate to where the puck is going? If you’re looking for a strategic partner to help you develop a forward-looking IT strategy that balances current needs with future opportunities, let’s connect with Succeed Sooner Consulting.