As a senior executive, your ability to influence, align, and mobilize others towards strategic goals is crucial for your success. However, misalignment often occurs at the highest levels due to differing motivations among your peers, board members, or senior team. To truly understand what is driving those around you, it is essential to engage in meaningful conversations that reveal their goals, ambitions, and fears. Developing your questioning skills is key to uncovering these motivations.
When it comes to asking questions, the type of questions you ask can make a significant impact. While “Why” questions may seem direct, they often lead to justifications rather than insights, anchoring discussions in the past rather than focusing on forward-looking solutions. Instead, high-performing executives use “What” questions to unlock deeper insights, uncover hidden risks, and align stakeholders effectively.
By reshaping “Why” questions into “What” questions, executives can shift conversations from resistance to resolution, ensuring that discussions are strategic, action-oriented, and productive. Through my 25 years of executive coaching experience, I have observed that nearly any “Why” question can be reframed as a question starting with “What.”
Here are ten “What” questions that senior executives can ask to surface motivations and drive alignment within their teams:
1. What are your biggest strategic priorities in this situation?
2. What risks or unintended consequences do you see if we move forward with this approach?
3. What would success look like not just for you, but for the business as a whole?
4. What underlying factors or constraints are shaping your perspective on this issue?
5. What past experiences—good or bad—are informing your thinking on this decision?
6. What are the biggest misalignment risks you see between leadership, employees, customers, the board, and other key stakeholders?
7. What does this decision look like from a competitor’s perspective?
8. What would need to be true for you to feel fully confident in this decision?
9. What blind spots might we have in our current thinking?
10. What’s the best way to ensure alignment and execution at scale?
Next time you are in a leadership team meeting, choose one of these questions to uncover a perspective you may not have fully considered. See how it shifts the conversation and impacts the outcomes. Share your experiences, perspectives, or lessons learned in the comments on LinkedIn.
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