The Role of AI in Strategic Planning for Chiefs of Staff
Five practical ways to use AI for more effective strategic planning and execution
Following our recent workshop with the Ask a Chief of Staff community, Abby Parker, Co-Founder & COO at Elate, shares key takeaways on how AI is transforming strategic planning and execution.
If there’s one thing every Chief of Staff knows, it’s that strategic planning never goes as planned. Teams move fast, priorities shift, and before long, the carefully crafted strategy you started the quarter with looks nothing like the one you’re executing.
This sentiment echoed throughout our recent Ask a Chief of Staff workshop on The Role of AI in Strategic Planning with Brooks Busch, my Co-Founder and Elate’s CEO, and Shannon Keedy, Elate’s Director of Solutions Consulting.
As Chiefs of Staff shared their experiences, one theme came through loud and clear: AI is not replacing strategy leaders. It’s helping them lead more effectively.
AI is becoming the bridge between strategy and execution. It’s giving Chiefs of Staff the ability to see what’s coming before it happens, communicate more clearly, and free up time for the kind of work that moves the business forward.
Here are the biggest lessons and practical takeaways from our discussion with the Ask a Chief of Staff community.
1. AI is a Strategic Enabler, Not a Replacement
The misconception that AI will replace human decision-making misses the point. Strategy will always require judgment, alignment, and leadership. What AI can do is eliminate the manual lift that slows those things down.
Most Chiefs of Staff spend countless hours collecting updates, reformatting slides, and chasing data that should already be visible. AI helps change that equation.
As Shannon shared in the workshop, “AI isn’t here to take the wheel. It’s here to help you steer faster and with more confidence.”
Strategy-specific AI tools like Strategy Advisor are designed to work alongside you, not ahead of you. It summarize updates, highlights what’s off track, and helps you turn noise into direction so you can focus on what matters most.
2. Real-Time Insight Replaces After-the-Fact Reporting
If there’s one place Chiefs of Staff can feel AI’s impact immediately, it’s in reporting.
Every leader has faced the late-night scramble to pull together updates for the executive team. The process is manual, slow, and often outdated by the time the slides hit the boardroom.
AI is turning that into a thing of the past. With systems that generate first drafts for reports and summaries automatically, your meetings no longer need to be status readouts. They can be decision sessions.
The most effective teams are now sending AI-generated pre-reads before leadership meetings, freeing time to focus on what matters: making choices, solving problems, and aligning around action.
If you want to see this in action, explore how Reporting Assistant turns strategy updates and risks into clear, executive-ready reports in minutes.
3. Early Warning Signs Prevent Strategic Surprises
Strategy doesn’t break overnight. It unravels slowly through early warning signs that are easy to miss until it’s too late.
AI changes that. It can monitor signals across teams, metrics, and even sentiment in written updates to flag risks before they escalate.
One of my favorite moments from the session came when Brooks said, “The most valuable signal is often the one you never thought to look for.” That’s the essence of AI-powered foresight.
By catching issues early, Chiefs of Staff can move from reaction to prevention. You can identify the dependencies or teams that are quietly falling behind before the metrics show it.
Risk Navigator is one example of how this can work in practice, helping leaders go from problem found to problem solved faster.
4. The Right Questions Matter More Than Perfect Answers
AI doesn’t replace the need for strong strategic thinking. It amplifies it.
The future Chief of Staff will not be defined by how well they manage updates or compile reports, but by how well they ask the right questions.
Great leaders are using AI to expand perspective, not outsource it. They’re using it to test ideas, model scenarios, and communicate strategy in ways that connect to every level of the business.
As we discussed in the workshop, “AI helps you find the right question faster. But the human still provides the answer.”
That’s the mindset that separates teams who use AI for efficiency from those who use it for real strategic advantage.
5. How Chiefs of Staff Turn AI Insights into Strategic Action
If you’re looking to apply these lessons inside your organization, here are five simple ways to get started:
1. Shift from pre-reads to readouts.
Send a short, AI-generated summary to your leadership team before meetings. Use your time together to make decisions, not review slides.
2. Run a weekly risk radar.
Spend ten minutes reviewing leading indicators and AI summaries to identify where your plan may be slipping. Address issues before they become surprises.
3. Analyze past plans.
Upload last quarter’s decks or spreadsheets into tools that can identify patterns and gaps before you start your next planning cycle. Elate's Plan Analyzer was built for exactly this kind of work.
4. Standardize your language.
Agree on consistent definitions for objectives, outcomes, and initiatives so AI can read and interpret your strategy accurately.
5. Track decisions, not just progress.
Start documenting “what changed and why” after every leadership meeting. It will help you measure impact and continuously refine your strategy.
The Real Shift
The real story here isn’t about technology. It’s about time.
Chiefs of Staff spend too much of it gathering information and not enough using it. AI gives you that time back.
By turning static plans into living systems, it helps you lead with more clarity, more foresight, and more confidence in every decision.
If you’re ready to see what this looks like in practice, we’d love to show you. Connect with our team and see how we’re helping Chiefs of Staff turn vision into execution faster than ever before.
