Dealing with Executive Resistance
Executive Engagement
Workshop Supplement
This supplemental guide to the Executive-Engagement workshop will equip you with practical strategies to navigate resistance with confidence and curiosity.
When facing pushback from senior stakeholders, remember: resistance is rarely about the words being spoken.
It's always about what hasn't been said.
The Core Four: Principles behind the Pushback
Embrace Objections
No one likes hearing no, but imagine if you heard a yes all the time. Sephora would become boring and stagnant overnight and lose their creative edge.
Expect Resistance
Instead of fearing pushback, expect it as an opportunity for meaningful dialogue and conversation. When we come to expect it, we can prepare for it.
Demonstrate Value
Pushback signals an opportunity to demonstrate value and engage in meaningful discussion.
Build Alignment
Pushback isn't adversarial; it's a chance to strengthen your position, clarify thinking, and build genuine alignment.
Your job is to uncover the deeper layer underneath
You'll often find that it's done to one of these three things, instead of the actual words:
The Three-Step Framework for Responding
1
Stay Grounded
Your natural first reaction may be to become defensive, over-explain, or justify your position. Resist this urge.
Instead, ground yourself physically: feel your feet on the floor, take a breath, and center your energy.
When you stay grounded, you can channel nervous energy into productive curiosity rather than reactive defensiveness.
You can then silence the inner critic or mental chit-chatter and move onto Step Two.
2
Get Curious
Shift from defending your position to genuinely exploring theirs.
This is the foundations of empathy. In a nutshell, we step into the other person's shoes and start seeing their worldview.
Some questions to ask yourself in the moment:
  • Where is this pushback coming from
  • What unspoken fear or misalignment is driving it?
  • What would need to be true for this to work from their perspective?
3
Redirect with Questions
Don't react to the resistance… Reframe it instead.
Transform disagreement into productive dialogue by redirecting the conversation toward areas of agreement.
When we focus on areas of agreement, instead of disagreement, the conversation will be much more fruitful and productive.
Use strategic questions to uncover common ground and move the conversation forward collaboratively rather than combatively.

Remember: Lawyers argue to win. Leaders ask questions to align. Your goal isn't to defeat the objection, and pummel them into the ground with arguments. Your objective is to understand what's driving their concerns and find common ground to move forward together.
Practical Response Playbook
Below are common executive objections you'll encounter, along with powerful reframing questions that shift the conversation from disagreement to collaboration.

Practice some of these or others before your next high-stakes meeting.
The Power of the Second Question
The real breakthrough in executive conversations rarely happens with your first question, it emerges from your second or third question. This is the beauty of genuine curiosity.
Each question peels back another layer, getting you closer to the true source of resistance. Here's an example:
Executive states:
"This isn't a priority."
Your First Question:
"What is taking priority?"
Their Answer:
"We're focused on customer retention right now."
Your Second Question:
"How might this initiative support customer retention efforts?" or "Where do you see potential overlap?"
This sequence does two powerful things, it:
01
Demonstrates that you're listening and genuinely interested in their perspective.
02
Creates space for them to discover alignment themselves rather than you forcing it on them. People support what they help create.
Quick Reference: Question Types
Clarifying:
"What specifically concerns you about this approach?"
Exploring:
"What would need to be true for this to work?"
Connecting:
"How does this relate to our Q3 priorities?"
Action-Oriented:
"What's the next step to test this?"
Timeline:
"When would be the right time to revisit this?"

Practice layering your questions. Don't settle for surface-level responses.
The deeper you go with genuine curiosity, the more likely you are to uncover the real concern and find common ground.
The quality of your questions determines the quality of your influence
Your Action Plan: From Training to Practice
Understanding these principles intellectually is different from executing them under pressure in a live executive meeting. The gap between knowing and doing is bridged through deliberate practice.
01
Identify Your Next High-Stakes Meeting
Choose an upcoming meeting where you anticipate resistance or need to influence senior stakeholders.
02
Prepare Your Reframing Questions
Based on what you know about the stakeholders, anticipate 3-4 likely objections and prepare your reframing questions in advance.
03
Practice with a Trusted Peer
Schedule 20 minutes with a colleague, mentor, or friend. Have them role-play as the resistant executive while you practice staying grounded and redirecting with curiosity.
04
Debrief and Refine
After your actual meeting, reflect on what worked and what didn't. What resistance emerged that you didn't anticipate? How effectively did you stay curious versus defensive?
The Leadership Shift
Every executive pushback offers you valuable data about business priorities, personal fears, and misalignments.
Individual Contributor vs. Leader
Shift your perspective from simply executing tasks to understanding and guiding the broader organizational vision.
React from Fear vs. Build Alignment
Instead of being defensive, use curiosity to uncover underlying concerns and build collaborative solutions.
Overcome Resistance vs. Transform to Momentum
Don't just diffuse objections; channel diverse perspectives and energy into powerful forward movement.
When you learn to decode that data through grounded curiosity, you don't just overcome resistance, you transform it into momentum.