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“I’m new to AI and unsure how it can help me. Interview me by asking one question at a time to identify how you can help me.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“The questions we ask shape our future.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Becoming an AI-driven leader means shifting from playing at a tactical level to leading with strategic clarity. Your ability to ask the right questions is a valuable skill. It will elevate your leadership by helping you overcome biases and assumptions, drive greater growth, and unlock new levels of value as you use AI as your Thought Partner.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“How will you address the potential gap between perceived confidence and actual competence in strategic decision-making? How will you ensure the training translates into measurable improvement in performance?”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Here’s the situation. Here’s what I think we should do. Coach me on that.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“The first step to becoming an AI-driven leader is changing your limiting beliefs around AI. You need to believe that AI will enhance you, not replace you.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“As an AI-driven leader, you embrace the dual role of both composer and conductor. You create strategies that pave the way for competitive advantage and lead the performance of these strategies with the finesse of a maestro. Using the tools and talents at your disposal, you bring your vision to reality. As your business continues to change, it is you as the AI-driven leader who is best equipped to navigate both the challenges and opportunities that lie ahead.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“my job as a leader is to teach you how to think. What do you think the answer is?”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“We are prone to various biases that can impede our ability to adapt to change.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“It’s not about the gap between where you are and where you want to be. It’s about celebrating who you are becoming along the way.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“I need to make an important decision. Here is the situation: (describe the situation). Here are the solutions I have identified so far: (list the solutions you’ve identified). I want you to act as an expert in identifying risk by asking me one question at a time to help me see the second-order consequences of these solutions.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Question every requirement. Delete any part of the process you can. Simplify and optimize. Accelerate. Automate.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“The more you ask, the more thinking leverage your people will bring you.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“the success of your communication is determined by the way it is received, not your intention. If your stakeholders can’t understand the value you intend to deliver, then you will fail.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“I need to make a decision for our business and want to be strategic about involving the right people in the process. Acting as my Thought Partner, I want you to interview me by asking one question at a time to help me answer the following questions: 1. Who are the decision-makers who can approve or reject this decision? 2. Who are the influencers who can sway the thinking of the decision-makers I need to engage?”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“If you don’t understand your business problem, your business challenge, the market forces, and customer demand, then asking ‘How do we use AI?’ is the wrong question. —Chris Winton”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“The sunk cost fallacy leads us to continue investing in failing initiatives, while the status quo bias makes us prefer the current state of affairs.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Resist the temptation to outsource your thinking to AI. Use it as your Thought Partner, but always maintain your role as the Thought Leader, providing context and judgment to shape the final output.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Their job is not to do everything on their job description. It’s to deliver results in alignment with your culture. That will only happen when they focus on the 20% that drives the majority of the results.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Nokia’s flagship N95, which came out before the iPhone 2G, had fourteen of those fifteen features, plus many extras that the iPhone lacked. The problem? No one knew! The difference-maker wasn’t the product itself but the strategic thinking and decisions of the leadership team. Steve Jobs recognized that strategy meant building an advantage in the long term through the actions taken in the short term. He crafted compelling stories as if Apple’s future depended on it—and it worked!”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“What we do know is that decisions you make determine your company’s fate and define its future. When done well, they help your company leapfrog the competition and build a sustainable competitive advantage. When done poorly, they can lead to bankruptcy.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Once a leader believes in AI’s potential, then they can drive it through their company. This would not come from showing them how to write a better email. That is not what drives business value. But enhancing their strategic thinking and decision-making? Now, that’s a game changer!”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Our thinking drives our actions, which drives our results.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“need to make an important decision. I’m considering these two options. Your task is to evaluate the upside and downside of each potential solution and explain which you’d recommend and why.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“people are often unaware of their biases and assumptions. If you ask AI to build on flawed foundations, it will simply magnify the mistakes.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Attached is our strategic plan. I want you to act as my AI Thought Partner™ by asking me one question at a time to challenge my biases and the assumptions we have made. I also want you to challenge if our plan has the sufficiency to achieve our goal. Once you have enough information”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Don’t base your goals on what you think you can do. Instead, think big and launch yourself onto a completely new trajectory.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Take a look at our strategic plan for our upcoming fiscal year. Acting as an executive coach, I need you to challenge our assumptions. Start by questioning our goals: are we really pushing the envelope, or are we playing it safe? Then assess the structure of our plan: is it robust enough to achieve our goals even when things don’t go as planned, or are we too reliant on ideal conditions? After our discussion, I’d appreciate your feedback on the strengths of our plan, areas for improvement, and actionable advice to ensure we’re set up for success.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“The true purpose of a goal is to act as a compass, guiding you toward who you can become.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions
“Instead of using AI for the 80% of tasks that drive only 20% of your results, harness it for the 20% of priorities that drive 80% of your success.”
Geoff Woods, The AI-Driven Leader: Harnessing AI to Make Faster, Smarter Decisions

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