When Others Resist Your Redesign: Leading Through the Pushback
MONTHLY NEWSLETTER | October 2025
Last month, we explored redesigning your leadership architecture—creating new operating principles and structures to support your authentic authority. The response was overwhelming, but almost every message included the same question: "What do I do when people push back against my changes?" This month, we're diving into exactly that.
A senior director reached out last week: "I implemented several changes from your September newsletter. I started protecting my thinking time, stopped attending every meeting, and began making decisions based on my values rather than consensus. The work feels better, but my colleagues are... uncomfortable. One person said I'd 'changed' in a way that sounded like an accusation. Am I doing this wrong."
Here's what I told her: The pushback isn't a sign that you're doing it wrong. It's evidence you're doing it differently.
“Change always creates friction before it creates flow.”
Let’s talk more about that.
THE REALITY OF RESISTANCE
When you change how you lead, you disrupt an entire ecosystem of expectations and unspoken agreements. People have adapted to your loyal soldier's patterns. Your evolution requires them to evolve too, and most people will resist that.
This resistance shows up predictably:
Passive Resistance: People continue old patterns, scheduling meetings during your blocked time, bringing you problems they could solve themselves, hoping you'll revert to your old accommodating self.
Active Questioning: People may ask, "Why are you being so rigid? You used to be more of a team player." The implication is that your authentic leadership is somehow less legitimate than your people-pleasing performance.
Emotional Appeals: People may say, "I thought I could count on you. This isn't like you." These appeals target your loyal soldier, hoping to trigger old patterns of guilt and over-responsibility.
System Pressure: Your boss mentions you seem "less engaged." The organizational immune system kicks in, trying to push you back into your previous role.
Understanding the Psychology Behind Pushback
Your relationships were built partly on implicit agreements with your loyal soldier. Your boss got a leader who never pushed back. Your team got a manager who absorbed their anxiety. Your peers got a colleague who could always be counted on.
Now you're changing the terms without having explicitly renegotiated the original agreement. When you evolve, you hold up a mirror to everyone around you. Your boundaries highlight their difficulties in doing the same. Your authentic decision-making exposes their conflict avoidance.
Some people will be uncomfortable but ultimately supportive, these relationships will deepen. Others will be uncomfortable and unsupportive; these relationships will shift or end. And that's developmentally necessary.
The key is learning to distinguish between discomfort (temporary, adjustable) and incompatibility (permanent, fundamental).
THE CONVERSATIONS THAT HELP
You can't address resistance using your old people-pleasing playbook. Here are frameworks for the conversations that help others adjust.
The Boundary Conversation Framework
Name the change clearly: "I am being more intentional about how I spend my time and energy."
Acknowledge the adjustment: "I know this represents a shift from how I've operated in the past."
Explain the 'why' without over-justifying: "I've realized when I'm overextended, I can't bring my best thinking to the work that matters most."
State what you will/won't do going forward: "Going forward, I'll attend meetings where my presence adds unique value or where decisions affecting my team’s work are being made."
Notice this doesn't include an apology, asking for permission, or lengthy justification. You're informing—not requesting approval.
The "Let Me Think About It" Response
One of the most powerful tools for breaking the automatic "yes" pattern is creating space between the request and your response.
Scripts for creating space:
"That's an interesting opportunity. Let me look at my commitments and get back to you by [specific time]."
"I want to give this the consideration it deserves rather than answering reflexively. I’ll think about it and follow up with you."
"My instinct is to say yes, which is exactly why I want to pause and think it through."
The "I'm Not Available for That Anymore" Conversation
This is the conversation your loyal soldier most fears—and your authentic authority most needs.
How to remain warm while being firm: "I appreciate you thinking of me for this. In the past, I would have automatically said yes. I'm learning to be more deliberate about my commitments, and this isn't something I can take on right now while staying true to my priorities."
When someone reacts with disappointment or guilt-tripping:
Acknowledge their feelings without taking responsibility: "I can see you're disappointed."
Restate your boundary: "I understand, and my answer is still no."
Offer an alternative only if you genuinely want to: "I can't join the committee, but I'm happy to review the final recommendations."
NAVIGATING DIFFERENT SOURCES OF PUSHBACK
Different relationships, different resistance. The good news? The skills are transferable.
From Your Team
What's happening: Your team has become dependent on you to manage their uncertainty. Your boundaries require them to develop their own problem-solving capacity.
How to navigate: When team members bring you problems, ask: "What have you already tried? What do you think we should do? What would you do if I weren't available?" Distinguish between support (helping someone develop capability) and enabling (doing for someone what they can do themselves).
From Your Peers
What's happening: Your boundaries expose their lack of boundaries. Your authentic decision-making highlights their conflict avoidance.
How to navigate: Hold your ground without becoming defensive: "I appreciate your concern. I'm being more intentional about how I lead, and it's working well for me and my team." Find allies who support your evolution. Don't try to convince skeptics—you don't need everyone's approval.
From Leadership
What's happening: Leadership benefited from your loyal soldier's patterns. Your boundaries require them to be more realistic about workload and priorities.
How to navigate: Demonstrate the value through results. Frame your changes in terms of organizational values. Know when to compromise versus when to hold firm. Be prepared to make difficult choices if your organization fundamentally cannot accommodate authentic leadership.
From Family
What's happening: Your professional evolution is affecting your personal life. You're renegotiating family patterns too.
How to navigate: Bring them into the conversation about why you're changing. Show them the benefits, like being home for dinner more often. Recognize that you can't be authentic at work and inauthentic at home.
RED FLAGS: WHEN PUSHBACK SIGNALS SOMETHING DEEPER
Most pushback is temporary discomfort. But sometimes resistance reveals fundamental incompatibility.
Recognize when the environment is toxic:
Your boundaries are consistently violated despite clear communication.
You're punished professionally for authentic leadership.
The culture fundamentally requires people-pleasing to succeed.
Your values are incompatible with how the organization actually operates.
Sometimes our development outpaces our environment's capacity to accommodate it. If you've done the work and the organization still cannot accommodate your authentic leadership, you haven't failed. You've outgrown this context.
The question isn't "What's wrong with me?" It's "Is this environment aligned with who I'm becoming?".
Perhaps this transition will pave the road to a new chapter.
STAYING CENTERED IN THE STORM
Practical ways to stay centered in the messy middle:
Commit to essential practices:
Daily check-ins: Morning—"What matters most today?" / Evening—"Did I lead in alignment with my values?"
Boundary journaling: Track when you hold boundaries and when you don't
Support systems: You cannot do this work in isolation. You need a coach, therapist, or mentor who understands this transition, plus peers on similar journeys
Practice self-compassion when you slip: You will have moments when you revert to people-pleasing. This isn't failure—it's practice. Your loyal soldier served you for decades. She won't disappear overnight. When you notice yourself reverting, practice curiosity instead of shame: "What triggered the old pattern? What can I do differently next time?"
Celebrate small wins: Every boundary you hold is a micro-act of courage that rewires how you lead.
THE TRANSFORMATION ON THE OTHER SIDE
Unfortunately, some people will not adjust and embrace your authentic leadership. Some relationships will end. But when you hold steady through the resistance, something remarkable happens.
The people invested in you, not in what you do for them, adjust to your new way of operating. These relationships become more reciprocal and energizing. The relationships that fade were never really meant to go the distance.
When you stop trying to please everyone and start leading from your values, you attract different people and new opportunities. You become a magnet for people and work that actually align with who you are.
A real example: A VP I worked with spent six months navigating intense pushback. Her peers called her "difficult." Her boss worried she wasn't a "team player."
But she held steady and communicated her vision. A year later, her team had the highest engagement scores in the company. Her boss nominated her for senior leadership development, noting, "She's developed the courage to lead from conviction rather than consensus, which is exactly what we need at the next level."
The pushback transformed from resistance into respect.
YOUR PUSHBACK RESPONSE PLAN
Pre-write responses: Think about the pushback you're most likely to encounter. Write out your responses using the frameworks above. Practice saying them out loud.
Identify your support team: Who can you call when you're questioning whether you're doing this right? Write down three names. Reach out proactively.
Monthly check-in questions:
Where did I hold my boundaries this month? Where did I struggle?
What pushback did I encounter? How did I navigate it?
What relationships shifted? In what direction?
Am I becoming more authentic or just more rigid?
That last question is critical. Authentic authority isn't about becoming inflexible. It's about being grounded enough in your values so you can be genuinely flexible without losing yourself.
THE FINAL TEST
Navigating pushback is the crucible that tests your commitment to authentic leadership. Your loyal soldier will whisper that it's not worth it, that you should just go back to being who everyone expects.
Thank her for her concern and keep moving forward.
The leader who can stay centered while disappointing others is the leader who can create lasting change. The leader who can hold boundaries while remaining connected is the leader who builds cultures where everyone can be authentic.
So hold steady.
Trust your compass.
You are not behind—you are becoming.
And as you hold your ground, you’ll notice something extraordinary: What once felt like resistance begins to feel like alignment. That’s when you’ll realize—this isn’t the storm before the calm .
This is the calm you created.
THIS MONTH'S REFLECTION QUESTIONS
Where are you already experiencing pushback against your redesigned leadership? What form is it taking?
Which relationships feel most challenging as you evolve? Are people uncomfortable or unsupportive?
What would it mean to stay true to yourself even when others are uncomfortable with your choices?
Who is in your support system as you navigate this transition?
When are you most tempted to revert to people-pleasing? What triggers your loyal soldier?
COMING NEXT MONTH
The Compounding Effect: How Authentic Authority Creates Organizational Transformation
You've done the internal work, redesigned your architecture, and navigated the pushback. Now what?
In November, we explore how your individual evolution creates ripple effects throughout your organization—and how to leverage your authentic authority to create systemic change that outlasts your tenure.
"Of course there is always resistance, always a drag on movement toward better things. The dead hand of the past clutches us by way of living people who are too frightened to accept change."
—Kim Stanley Robinson, The Ministry for the Future
