When an executive faces self-doubt in a strategic decision, remind them to reconnect with their vision and long-term goals. Break the decision into smaller steps, helping them build confidence by reflecting on past successes. Support their instincts with data to balance gut feelings with facts. Most importantly, reassure them that bold moves often involve risk, but it’s their ability to steer through uncertainty that makes them a great leader.

To guide an executive from self-doubt to bold action, I’d use The 10 Lenses of Agile Decision Mastery™, my decision-making framework. Start with Gut/Instinct Thinking to tap into instincts. Apply Emotional Thinking for deep empathy. Use Analytical Thinking to ground decisions with data. Leverage Big Picture Thinking for strategic opportunities, and Detailed Thinking for hidden insights. Apply Critical Thinking to weigh pros and cons. With Risk Management Thinking, manage potential risks first, then explore positive risks. Stimulate Creative Thinking for bold ideas, check Feasibility, and use Holistic Thinking to integrate all insights. Encourage brainstorming with the team and, ideally, an external consultant for an independent perspective.

Help them clarify the strategic decision’s purpose and potential impact. Encourage them to articulate the "why" behind the decision, connecting it to their larger vision and long-term goals, which can provide a foundation of confidence. Next, explore the specific fears or uncertainties fueling their self-doubt. This could involve a pros-and-cons analysis or examining worst-case scenarios to uncover practical ways to mitigate obstacles. Reinforce their strengths and past successes in similar situations, helping them see evidence of their capability to handle tough decisions. By shifting the focus to incremental progress and grounded confidence, you empower them to take decisive, impactful action aligned with their strategic goals.

They need to be helped through Reflective Inquiry: 1. What are your concerns about this decision? 2. What values or principles are guiding your thinking? 3. How does this decision align with the organization's goals? 4. What are the potential risks and consequences? 5. What would success look like? Then we must Explore Alternatives: 1. What other options have you considered? 2. What are the pros and cons of each option? 3. How do these alternatives align with your values and goals?

I'd begin by validating their concerns and acknowledging the complexity of the decision. By creating a safe space for reflection, I can help the executive identify their underlying fears and anxieties. Once these emotions are brought to light, we can work together to challenge negative thought patterns and replace them with more empowering beliefs. To further build their confidence and motivation, I'd suggest setting achievable goals. By breaking down the larger decision into smaller, more manageable steps, the executive can focus on making progress and celebrating small victories. This can help them build momentum and gradually overcome their self-doubt.