AI Plans in Chicago, IL
AI strategy is only as good as its follow-through. In Chicago, I work with executive teams who have direction but need help turning that direction into action.
I help you translate AI ambition into real-world plans: clear initiatives with budgets, timelines, ownership, and built-in change-readiness. It’s not just about what to do. It’s about how to actually make it happen across your organization.
If your team is aligned on AI goals but unclear on execution, this is where clarity becomes progress.
When You’re Ready to Turn Strategy Into Action
If your leadership team in Chicago already sees where AI could move the needle, but you're stalled on how to make it real, that’s where I step in.
I help you turn rough outlines and good intentions into detailed, executable plans. Think business cases, defined workstreams, timelines, owners, decision checkpoints, and the real architecture of delivery.
We close the gap between “This sounds promising” and “This is how we move forward.”
A former COO. A planner at heart
I work with leaders in Chicago who are ready to stop talking about AI and start structuring it. Together, we define what gets done, who owns what, and how it gets resourced. We surface resistance. We get practical. We make it real.
Signs You’re Ready for Serious AI Planning
If any of this sounds familiar, we should talk:
You’ve identified AI priorities, but no one’s clearly responsible.
The tech team is experimenting, but everyone else is in “business as usual” mode.
Finance is asking tough ROI questions, and you don’t have the answers.
There’s excitement, but no working timeline. No numbers. No plan.
You’ve tried this before. It didn’t stick.
I’ve lived this. I know what it takes to turn potential into a repeatable, accountable plan. And in a city like Chicago, where speed and structure both matter, clear execution is your edge.
Turn AI Vision Into Accountability That Actually Happens
Big ideas don’t create change; follow-through does. I help Chicago leadership teams turn strong intentions into structured, shared commitments.
That’s where I come in.
As a certified coach and seasoned facilitator, I guide your team through the hard but necessary decisions: who owns what, what trade-offs are on the table, and what’s really going to move the needle. We design real-world AI plans grounded in accountability and results.
We don’t just sketch ideas. We build business cases you can stand behind, while tackling the human side of AI head-on: resistance, hesitation, and the old habits that stall progress.
When we’re done, you’ll have a clear, documented plan: who’s doing what, when it’s happening, and how you’ll know it’s working.
When Good Intentions Stop Being Enough
In AI planning, ideas are cheap. Execution is what matters.
Strategy without ownership? That’s wishful thinking. Skip change management? You’re setting yourself up to stall. That’s why I help leadership teams in Chicago build not just smart AI plans but sustainable ones.
Real planning means grappling with the truth:
Budgets aren’t unlimited.
Priorities pull in different directions.
Culture doesn’t shift just because you ask.
People don’t change behavior without clarity and support.
I’m not here to sell a vision. I’m here to help you build something that works and lasts.
Frequently Asked Questions
1. What’s the difference between an AI strategy and an AI plan?
Strategy sets the direction. Planning builds the map. If you already know your AI priorities but haven’t defined budgets, owners, timelines, or success measures, you need a plan. I help Chicago-based teams move from "we should do this" to "here’s exactly how we’ll get it done."
2. We’ve tried AI planning before, but nothing stuck. Can you still help?
Yes, and that’s actually common. Many plans fall apart because they don’t address culture, accountability, or change resistance. I work with executive teams to build AI plans that don’t just sound good; they hold up under real-world pressure.
3. What does an AI plan include, exactly?
A strong AI plan includes: defined objectives, business cases, budgets, timelines, ownership assignments, change-readiness strategies, and clear indicators of success. My job is to help your Chicago team build all of that without getting lost in the weeds or stuck in theory.
4. Who should be involved in creating an AI plan?
The most successful plans involve a cross-functional group: executive leaders, operations, finance, and yes, tech. But I guide the process so everyone contributes without the plan getting diluted or derailed. In Chicago, I often work directly with leadership teams to keep things tight and aligned.
5. How long does it take to build a real AI plan?
It depends on your team’s clarity and readiness, but most AI planning engagements take a few weeks to a few months. My goal is to create momentum fast while still designing a plan that’s durable, realistic, and aligned with your business rhythms.