Six Quarters, Three Steps: Your GenAI Roadmap For Success

You know what keeps me up at night?

Watching organizations lock themselves into 12-month plans that are really just budgets masquerading as strategy. Meanwhile, AI technologies are moving at supersonic speeds (just this past week, we saw new versions of Claude from Anthropic and SearchGPT from OpenAI!) 

This means that by the time those same organizations get to Q4, they have less and less runway to execute effectively.

So often, I hear something along the lines of, "We need a strategy that's forward-looking enough to create transformational impact, yet flexible enough to adapt to constant change." 

I’ve got you. Enter: The Six-Quarter Walk.⚡

Why (And How) The Six Quarter Walk Works 

Transformation doesn’t happen quickly—the bigger the change, the harder it is. We're not just turning on technology—we're changing people, culture, and ways of working. That takes time, and requires that delicate balance of structure and flexibility.

The six-quarter walk offers just that—it’s an 18-month rolling plan that creates a strategic buffer for unexpected developments, whether they're technology changes, competitive moves, or shifts in how quickly your organization adapts. Every quarter, you assess where you are, adjust the next five quarters based on what you've learned, and add another quarter to maintain your 18-month horizon.

This approach is different in that it allows: ▶️ Deep integration across your entire organization ▶️ Flexibility to accommodate rapid changes ▶️ Staged development of capabilities ▶️ Continuous adoption and adaptation

At a high level, here is how the journey typically unfolds:

Quarters 1+2 Here, you're laying down core capabilities and figuring out what you have to work with. What does your data look like? Where are the quick wins that can help you understand the technology better? What essential training needs to be in place? These early quarters focus on putting foundational initiatives in place that will enable your future success.

Quarters 3+4 With your foundation set, you can begin expanding your initiatives. This is where you take those early learnings and start refining your approach. You're not just running isolated pilots anymore— you're beginning to see how these initiatives can scale across different parts of your organization.

Quarters 5-6 Now you're ready to focus on the broader strategic implications. This is where organizations start optimizing their processes and ensuring alignment across departments. The focus shifts from individual successes to orchestrating a cohesive transformation.

But First, Clarity: 3 Areas to Assess 

Before diving into your six-quarter walk, you need clarity on three key areas: 

1️⃣ Value Creation. Think about how AI creates value through what I call the generative AI flywheel. Start with efficiency and productivity gains. Then look at enhancing customer engagement through AI-powered service and marketing. Finally, focus on transformation— where new capabilities create significant competitive advantage.

2️⃣Strategic Gaps. Where do you want to be in the future? Where do you want to play and how do you want to win? The reality of where you are today versus where you want to be helps identify the gaps that AI might help close. Then align your AI initiatives to close these strategic gaps.

3️⃣Capability Assessment. Assess your capabilities across five critical areas: Skills and workforce development, leadership and culture, processes and operational models, data readiness, and technology infrastructure. Be honest with yourself: If these aren't at least at an emerging level of maturity, you'll need to do foundational work early in your roadmap. Check out my recent livestream for assessing where you stand.

The Quarterly Check-In: Keeping Your Roadmap on Track

The Six-Quarter Walk isn't a "set it and forget it" plan. It requires consistent monitoring and adjustment, and that's where the quarterly review comes in. Here's a glimpse of what happens during this crucial checkpoint:

• Gather Feedback. Your AI Council (a cross-functional team leading your AI initiatives) gathers feedback from across the organization. What's working? What roadblocks are emerging? Are there exciting new opportunities on the horizon?
• Analyze Progress. The council reviews progress metrics, comparing them to the initial plan. Are you on track, ahead of schedule, or falling behind? What course corrections are needed?
• Assess the Landscape. The team scans the external environment for changes in technology, competitive moves, and regulations that could impact your roadmap.
• Realign and Adjust. Based on the gathered insights, the council adjusts the next five quarters of the plan, ensuring it remains aligned with your strategic goals and incorporates new opportunities. A fresh quarter is then added to maintain the 18-month horizon.
• Communicate Updates. The revised plan is clearly communicated across the organization, ensuring everyone understands the updated priorities and how their work contributes to the overall AI strategy.

This quarterly rhythm of assessment, adjustment, and communication is essential for maintaining momentum and ensuring your AI initiatives deliver maximum value.

Final Thoughts

In my work with organizations, I’ve come to see that success often comes down to a series of critical factors. (Of course, there are many at play, so be sure to to check out my most recent livestream for additional instructions and tips.) But when push comes to shove, the following four factors are particularly essential:

🔑 Synchronization: Success requires alignment across departments. Every team needs to understand how their priorities fit into the bigger picture

🔑 Adaptive Leadership: This is harder than it sounds. Many leaders struggle with plans that change quarterly—they prefer "lock and load" annual planning. Give them support and scaffolding to develop this new muscle.

🔑 Strategic Discipline: Remember, the art of focus is the art of saying no. You'll face many exciting opportunities, but success requires ruthless prioritization aligned with your strategic vision.

🔑 Clear Metrics: Use your existing business metrics to measure progress. If AI is truly supporting your strategy, it should move the needles that matter most to your business.

If this information was helpful, there’s plenty more! 

📌 Sign up for updates and early access to my upcoming book, co-authored by Katia Walsh, which is all about creating a winning generative AI strategy.

📌 Catch my most recent webinars:

• “Unlocking The Power of Generative AI.” I explain how to set up a generative AI “playground,” three ways to elevate your leadership with step-by-step instructions, and the broad outlines of creating a strategy. Get the recording and slides here.

• “Developing a Winning Generative AI Strategy for Competitive Advantage.” I walk through the steps needed to create a cohesive AI strategy that will last. Get the recording and slides here. 

Your Turn How did your organization pull together your GenAI roadmap?