Leadership

From AI Hesitation to Confidence: 4 Simple Strategies for Senior Leaders

From AI Hesitation to Confidence: 4 Simple Strategies for Senior Leaders
Editorial Team
February 3, 2025
From AI Hesitation to Confidence: 4 Simple Strategies for Senior Leaders

During our recent "AI for Senior Leaders" live learning event, Geoff Woods, the bestselling author of The AI-Driven Leader, captured a crucial paradox in AI implementation:

"I literally interviewed over 200 execs one-on-one for my book. 100% of them said AI was the future and that they would adopt it, but less than 5% had taken any action."

At Learnit, we've been helping organizations navigate technological change for over two decades. Through our work with thousands of teams and their leaders, we've learned that success with new technology isn't about having all the answers – it's about expertise guiding curiosity, learning by doing, and goal-directed practice.

So, we brought three widely respected experts working on the front lines of AI adoption together with one of our most popular instructors to address this critical question:

We know AI is no longer optional—but where and how do we start?  

The good news? AI is a leadership tool, not just a tech upgrade. And you don't need to be technical to make it work for you.

Breaking Through the AI Adoption Barrier

Three renowned AI experts joined Learnit's Mickey Fitch-Collins to share their transformative insights on how senior leaders can start using AI more effectively.

  • Thiago Dasta, a pioneering technology entrepreneur whose groundbreaking 3D mechanical CAD platform was acquired by Autodesk
  • Gabe Keading, founder of OneWave AI and former director of Enterprise sales at GovSpend
  • Geoff Woods, whose strategic guidance helped grow Jindal Steel's marketcap from $750M to $12B

Our experts identified three key barriers to AI adoption:

  • Time and Priority Challenges: Senior leaders are already overwhelmed with daily operations and delivering immediate results. While they recognize AI's importance, finding time to learn and implement new technology often takes a back seat to pressing business demands.
  • Value Implementation Gap: Many executives experiment with AI for basic tasks like asking questions or simple automation but miss opportunities for strategic implementation where AI could drive significant business value, particularly at the executive level.
  • The Foundation Mindset: Organizations frequently view AI tools as mere add-ons to existing processes rather than seeing them as foundational technology that could transform their business model. This perspective, similar to early skepticism about cloud computing, can prevent leaders from recognizing AI's full potential for creating new business opportunities.

AI as Thought Partner

The experts shared a game-changing framework for senior leaders that transforms AI from a simple query tool into a strategic thought partner: the Context-Role-Interview-Task (CRIT) method.

Context: Provide rich background about your situation and goals

I’m the CEO of a manufacturing company that’s leased equipment from a company in Japan and we’ll go bankrupt if we can’t restructure our debt.

Role: Assign AI a specific persona (e.g., investment banker, board member)

Your role is to act as an investment banker with deep expertise in restructuring debt.

Interview: Let AI ask targeted questions one at a time

Ask me up to three questions one at a time to deepen your understanding of the situation.

Task: Direct AI toward specific, strategic outcomes

Give me the top 5 non-obvious strategies I should deploy to get the board to restructure our debt.

Real World Impact

The panel illustrated the power of this approach with two more compelling case studies: a CEO facing a hostile board who used AI to analyze the directors’ personalities and predict meeting dynamics leading to "the best board meetings we've ever had," and a sales team that transformed their reporting process from hours of manual work into an interactive, real-time dashboard. Additionally, each of our experts provided a demonstration of real-world ways senior leaders can use AI as a thought partner.  

Strategic Planning Reviews with AI

(Demonstrated by Geoff Woods)

1. Create a new chat in ChatGPT

2. Structure your prompt with:

Context: "I'm reviewing a strategic plan for [specific goal]"

Role: "Act as an aggressive growth-minded board member"

Interview: "Ask me one question at a time, up to 4 questions"

Task: "Analyze strengths and weaknesses, and provide specific recommendations"

3. Upload relevant documents (e.g., strategic plans, reports)

4. Let AI interview you about the plan

5. Review AI's analysis of strengths, weaknesses, and recommendations

Custom GPT Clusters for Business Intelligence

(Demonstrated by Gabe Keading)

1. Create a central "brain" GPT with your company's core knowledge

2. Build specialized GPTs for specific functions (email, support, sales)

3. Use the "@" command to collaborate between GPTs

4. For sales analysis:

Upload sales data files to Projects

Request specific charts (e.g., "Make me a chart on ROI for sales reps")

Ask, "What data am I missing?"

Use Claude to convert insights into a React-based visual report

Agentic AI for Data Integration

(Demonstrated by Thiago Dasta)

1. Connect data sources (CRM, documentation, transcripts)

2. Let AI analyze patterns across all connected data

3. Ask specific questions (e.g., about pricing discussions)

4. Use insights to automate content creation and analysis

5. Apply findings to improve business operations 

The Path Forward

Thiago Dasta predicts 2025 will be the year of "agentic AI" - AI systems that can autonomously work toward specified outcomes. The time for senior leaders to build their AI foundation is now. Or, as Geoff Woods so eloquently put it, "Your questions create awareness of use cases. Taking action builds proficiency. Good communication delivers results."  

Take Action Today

The leaders who take action now will shape the future of their organizations. But success with AI isn't just about technology – it's about bringing your team along on the journey and creating a culture of practical innovation.

Ready to move from insight to action? Join our hands-on workshop, Lead AI Adoption for Your Team. This practical skill-building session helps managers and leaders:  

  • Navigate the human side of AI adoption, including addressing employee concerns and managing change
  • Establish clear guidelines for how AI and team members can work together effectively
  • Create space for more strategic work by thoughtfully integrating AI into daily operations
  • Build a framework for successful AI implementation that puts people first 

The workshop is specifically designed for leaders who want to move beyond the hype and create real, practical value with AI while keeping their teams engaged and confident.

Want to dive deeper into the insights from our expert panel? Watch the full recording of this engaging session here.

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The leaders who take action now will shape the future of their industries. Will your organization be ready?