When you’re a senior executive, your success depends on influencing, aligning, and mobilizing others toward strategic goals. Yet, even at the highest levels, misalignment often arises due to differing motivations. How well do you truly understand the priorities driving your peers, board members, or senior team? And are your assumptions accurate?
The best way to understand what’s motivating someone is to engage them in a conversation that surfaces their goals, their ambitions, and their fears. To do that well you need to develop your questioning muscles.
At the executive level, the key to influence isn’t just asking questions—it’s asking the right questions. While “Why” questions might seem direct, they often lead to justifications rather than insights. They tend to anchor discussions in the past—why something happened, why someone holds a certain belief—rather than surfacing forward-looking solutions.
Instead, high-performing executives use “What” questions to unlock deeper insights, uncover hidden risks, and align stakeholders. Here are a couple of examples of the impact of reshaping “Why” questions into “What” questions:
❌ Why do you think that? → Prompts defensiveness.
✅ What factors have most influenced your thinking? → Surfaces the underlying logic.
❌ Why are you against this approach? → Can feel like a challenge.
✅ What concerns do you have about this approach? → Encourages constructive dialogue.
This subtle but powerful shift helps executives move conversations from resistance to resolution, ensuring discussions are strategic, action-oriented, and productive.
What I’ve learned in 25 years of executive coaching is that just about any “Why” question can be reframed as a question that starts with the word, “What.” With that observation in mind, here are:
Ten “What” Questions Senior Executives Can Ask to Surface Motivations and Drive Alignment
- What are your biggest strategic priorities in this situation?
→ Surfaces overarching objectives that may be driving their stance. - What risks or unintended consequences do you see if we move forward with this approach?
→ Uncovers hidden concerns that could derail execution later. - What would success look like not just for you, but for the business as a whole?
→ Expands the conversation beyond personal or functional priorities to enterprise impact. - What underlying factors or constraints are shaping your perspective on this issue?
→ Reveals external pressures (e.g., regulatory, competitive, investor-driven). - What past experiences—good or bad—are informing your thinking on this decision?
→ Helps understand whether prior failures or successes are influencing current risk tolerance. - What are the biggest misalignment risks you see between leadership, employees, customers, the board, and other key stakeholders?
→ Identifies potential friction points that could slow or block progress. - What does this decision look like from a competitor’s perspective?
→ Encourages a thinking shift from inside-out to outside-in. - What would need to be true for you to feel fully confident in this decision?
→ Surfaces conditions for buy-in and signals potential areas of compromise. - What blind spots might we have in our current thinking?
→ Encourages executives to challenge assumptions and stress-test decisions. - What’s the best way to ensure alignment and execution at scale?
→ Moves the conversation beyond decision-making into implementation and accountability.
In your next leadership team meeting, pick just one of these questions and use it to uncover a perspective you hadn’t fully considered. See what shifts. Then, let’s compare notes—what impact did it have?
Share your story, perspective, or lessons learned with me in a comment on LinkedIn.
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