Leading with Empathy: Building a Workplace Where People Thrive
Oct 09, 2025
What separates good managers from truly exceptional leaders? After many conversations with business leaders on The Management Minute Podcast, one theme emerges consistently: empathy-driven leadership isn't just a nice-to-have—it's the foundation of high-performing teams.
In this week's episode, I sat down with Jason Elkins, marketing coach, digital media specialist, and founder of 100 Cups Consulting. Jason shared powerful insights about creating workplace cultures where people feel genuinely valued, supported, and empowered to bring their best selves to work every day.
Whether you're a new manager finding your leadership style or a seasoned executive looking to deepen team engagement, this conversation offers practical strategies you can implement immediately.
What Is Empathy-Driven Leadership?
Empathy-driven leadership goes beyond simply understanding your team members' perspectives. It's about actively adapting your management approach to meet each person's unique needs, communication preferences, and motivational drivers.
As Jason emphasizes in our conversation, culture isn't what you say in company meetings or write in your mission statement—culture is what you do. When leaders demonstrate genuine care through their daily actions, it creates a ripple effect throughout the entire organization.
The Business Case for Empathetic Management
Before diving into practical strategies, let's address the elephant in the room: Does empathy actually impact business results?
The research is clear:
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Employee retention: Workers who feel genuinely cared for are 3.2 times more likely to stay with their organization
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Performance: Team members who feel valued are 4.6 times more likely to feel empowered to perform their best work
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Engagement: Managers who practice consistent empathetic check-ins report 34% higher team engagement scores
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Innovation: Psychologically safe environments (built on empathy) generate 67% more creative ideas
The bottom line? Empathy isn't soft—it's strategic. When people feel valued and supported, they don't just work harder; they work smarter, collaborate better, and drive sustainable innovation.
Jason Elkins' Three Pillars of Empathetic Leadership
During our conversation, Jason outlined three essential practices that transform management from a transactional role into a meaningful connection:
1. Lead with Genuine Care
This doesn't mean blurring professional boundaries—it means recognizing that your team members are whole human beings with lives, challenges, and aspirations beyond their job descriptions.
Practical application:
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Start meetings by asking "How are you doing?" and actually waiting for a real answer
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Remember and acknowledge important personal events (not just work milestones)
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Create space for team members to share challenges without fear of judgment
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Model vulnerability by sharing your own learning moments and mistakes
2. Adapt Your Style to Each Individual
Not everyone on your team communicates the same way, processes information identically, or finds motivation through similar drivers. Cookie-cutter management approaches inevitably leave some team members underserved.
Practical application:
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Map your team members across communication preferences (direct vs. collaborative)
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Identify each person's primary motivation drivers (autonomy vs. structure, recognition vs. compensation, etc.)
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Adjust your feedback style based on individual receptivity
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Offer flexible work arrangements when possible to accommodate different working styles
3. Build Psychological Safety Through Consistent Actions
Jason emphasizes that trust isn't built through grand gestures—it's constructed through consistent, small actions that demonstrate your team can count on you.
Practical application:
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Follow through on commitments, no matter how small
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Respond to questions and concerns promptly
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Admit when you don't have answers instead of deflecting
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Celebrate failures that result from thoughtful risk-taking
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Address toxic behavior immediately, regardless of the person's performance metrics
The Culture Check-In Framework: A Weekly Practice
Here is a way to put this in practice.
Monday: Identify and Anticipate
Start your week by identifying one team member who might need extra support. Look for signs:
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Recent project setbacks or challenges
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Personal circumstances that might be affecting work
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Upcoming high-stress situations (presentations, deadlines, difficult conversations)
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Withdrawal from team interactions
Wednesday: Connect Authentically
Have a genuine check-in conversation—not about tasks, about the person. This isn't your standard status update meeting. Questions to guide the conversation:
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"What's energizing you right now?"
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"What's draining your energy?"
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"How can I better support you this week?"
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"What's one thing I could do differently as your manager?"
Friday: Reflect and Adapt
Take 10 minutes to reflect on what you learned and how you can better adapt your approach moving forward:
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What did I discover about this team member's needs?
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Did my support make a difference?
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What will I do differently next week?
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Are there patterns across my team I should address?
The key: This isn't a one-time exercise. Consistent practice transforms your leadership approach and builds deep trust over time.
The Adaptation Matrix: Tailoring Your Management Style
Generic management creates generic results. Understanding each team member's unique characteristics and adapting accordingly.
Dimension 1: Communication Preference Spectrum
Direct Communicators prefer:
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Clear, concise messages
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Bottom-line-first conversations
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Minimal small talk
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Explicit expectations and feedback
Collaborative Communicators prefer:
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Context and background information
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Thinking out loud together
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Relationship-building conversations
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Feedback embedded in dialogue
Dimension 2: Motivation Driver Spectrum
Autonomy-Driven Team Members thrive with:
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Freedom to determine their own approach
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Minimal oversight once expectations are clear
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Opportunities to pioneer new initiatives
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Trust to manage their own schedules
Structure-Driven Team Members thrive with:
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Clear processes and expectations
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Regular check-ins and feedback
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Defined roles and responsibilities
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Predictable routines and workflows
Creating Your Team Adaptation Map
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Plot each team member across these two dimensions (this isn't about labeling people—it's about understanding preferences)
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Identify mismatches between your natural style and their preferences
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Create adaptation strategies for each person
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Check your assumptions by having open conversations about working preferences
Example scenario:If you're a naturally collaborative communicator managing a direct communicator who thrives on autonomy, you'll need to consciously:
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Front-load the key point in every conversation
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Resist your urge to provide excessive context
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Set clear expectations and step back
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Schedule regular (but brief) check-ins rather than impromptu conversations
Building a Culture of Care: Small Actions, Big Impact
Jason's insights remind us that the strongest teams are built on foundations of genuine care and support. But how do you create that culture when you're managing competing priorities, tight deadlines, and organizational pressures?
Replace Transactional Questions with Human Ones
Instead of: "How's that project coming?" Ask: "How are you doing with everything on your plate right now?"
Instead of: "Why haven't you finished this yet?" Ask: "What obstacles are you encountering? How can I help clear the path?"
Instead of: "Any updates for me?" Ask: "What's something interesting you've discovered or learned recently?"
Create Space for Vulnerability
Psychological safety—the belief that you can take interpersonal risks without fear of negative consequences—is the foundation of high-performing teams. As a leader, you set the tone:
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Share your own challenges and learning moments
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Acknowledge when you don't have all the answers
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Ask for feedback on your leadership and actually incorporate it
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Celebrate intelligent failures that resulted from thoughtful experimentation
Celebrate the Whole Person
Work is just one dimension of your team members' lives. Recognizing achievements and milestones outside the office demonstrates that you value them as complete human beings:
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Acknowledge personal wins (running a marathon, child's graduation, volunteer work)
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Respect personal time and boundaries
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Offer flexibility when life circumstances require it
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Remember important dates and events
The Empathy Paradox: Why Caring Leaders Get Better Results
There's a common misconception that empathetic leadership means lowering standards or avoiding difficult conversations. Jason's experience—and research—proves the opposite is true.
Empathy Enables Accountability
When team members trust that you genuinely care about their success and wellbeing, they're more receptive to:
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Honest feedback about performance gaps
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Challenging stretch assignments
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Difficult conversations about behavior or results
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Course corrections and pivots
Why? Because they know the feedback comes from a place of support, not judgment. They trust that you're invested in their growth, not just checking boxes on a performance review.
Empathy Drives Innovation
Teams operating in psychologically safe environments generate significantly more innovative ideas. When people aren't worried about looking foolish or making mistakes, they're willing to:
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Propose unconventional solutions
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Challenge existing processes
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Experiment with new approaches
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Share half-formed ideas that spark breakthrough thinking
Empathy Attracts and Retains Top Talent
In today's competitive talent market, skilled professionals have options. The organizations that win the war for talent are those where:
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People feel genuinely valued
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Individual strengths are recognized and leveraged
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Personal growth is prioritized alongside business results
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Culture aligns with stated values
Common Empathy Leadership Pitfalls (And How to Avoid Them)
Even well-intentioned leaders can stumble when implementing empathy-driven approaches. Here are common mistakes to avoid:
Pitfall 1: Confusing Empathy with Sympathy
Sympathy feels bad for someone: "I'm sorry you're struggling with this deadline."
Empathy understands their perspective and helps problem-solve: "Tight deadlines are stressful. What's making this one particularly challenging? Let's figure out what we can adjust."
Pitfall 2: Being Empathetic Only When It's Convenient
Selective empathy—being understanding when business is good but reverting to command-and-control when pressure increases—destroys trust faster than having no empathy at all.
Solution: Recognize that empathy matters most during high-stress situations. Your consistency during challenging times defines your leadership.
Pitfall 3: Avoiding Necessary Difficult Conversations
Empathy doesn't mean avoiding accountability. In fact, letting poor performance or problematic behavior slide is not empathetic to:
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The underperforming employee (who isn't getting feedback they need to grow)
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Their teammates (who end up carrying extra weight)
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Your customers (who receive subpar results)
Solution: Combine empathy with clarity. Address issues promptly and directly, while maintaining respect and offering support.
Pitfall 4: Burning Yourself Out Through Over-Extension
You cannot pour from an empty cup. Leaders who constantly sacrifice their own wellbeing "for the team" inevitably burn out, creating gaps in leadership when their people need them most.
Solution: Model healthy boundaries. Taking care of yourself isn't selfish—it's essential for sustainable leadership.
Measuring the Impact of Empathy-Driven Leadership
How do you know if your empathy-driven approach is working? Look for both quantitative and qualitative indicators:
Quantitative Metrics
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Employee retention rates (particularly among high performers)
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Engagement survey scores (especially questions about feeling valued and supported)
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Voluntary turnover rates (are people leaving for other opportunities or leaving you?)
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Time-to-productivity for new hires (strong cultures accelerate onboarding)
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Internal promotion rates (are you developing future leaders?)
Qualitative Indicators
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Team members voluntarily share personal challenges and ask for support
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People speak up with concerns and ideas more frequently
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Conflicts are addressed directly rather than avoided or gossiped about
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Team members support each other without being asked
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Exit interviews cite reasons other than culture or management
Key Takeaways: Leading with Empathy in Action
As I reflect on my conversation with Jason Elkins and the insights he shared, several core principles emerge:
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Culture is defined by consistent actions, not aspirational statements. What you do every day matters more than what you say in annual meetings.
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Adaptation is the hallmark of skilled leadership. One-size-fits-all management inevitably leaves team members underserved.
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Empathy and accountability are partners, not opposites. Caring deeply about your team means caring enough to help them grow through honest feedback.
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Small, consistent practices create transformative results. You don't need grand gestures—you need to show up with genuine care day after day.
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The strongest leaders lead from humanity first. Your team members are whole people, not just resources to be optimized.
Listen to the Full Conversation
Want to hear more of Jason's wisdom on empathy-driven leadership? Listen to our full 15-minute conversation on The Management Minute Podcast:
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Apple Podcasts: http://apple.co/3IqYxzq
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Spotify: https://bit.ly/3XvUmq4
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Amazon Music: http://bit.ly/3K9jj7V
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iHeart Radio: https://bit.ly/3Iq2VOW
Resources for Empathy-Driven Leaders
Free Download: Grab my High-Performer's Clarity Journal designed to help you find hidden gifts in challenging leadership days. Studies show that journaling about difficult experiences for just 5 minutes can reduce stress hormones by 23%.
Text-Based Leadership Coaching: Imagine having a coach in your pocket, ready to guide you through crucial moments without waiting for a scheduled session. My text-based habit coaching delivers real-time support, strategic guidance, and accountability that fits your busy schedule.
Schedule a discovery call: https://app.usemotion.com/meet/donita-brown/meeting
Join the Conversation
How are you implementing empathy-driven leadership in your organization? What challenges are you facing? What's working well?
Share your experiences in the comments below, or connect with me on LinkedIn to continue the conversation. Leadership is a journey we're all navigating together.
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Final Thoughts: The Ripple Effect of Empathetic Leadership
Maya Angelou famously said: "People will forget what you said, people will forget what you did, but people will never forget how you made them feel."
This truth sits at the heart of empathy-driven leadership. The meetings you conduct, the projects you oversee, the strategies you implement—these will all fade into organizational history. But the way you made your team members feel? That impact reverberates through their careers, their personal lives, and eventually, through the way they lead others.
When you lead with genuine empathy, you're not just building a better team—you're creating a ripple effect that extends far beyond your immediate sphere of influence. You're modeling a form of leadership that the business world desperately needs more of.
Jason Elkins reminded me of this truth during our conversation, and I'm grateful for leaders like him who are doing the daily work of creating cultures where people truly thrive.
The question isn't whether you have time for empathy-driven leadership. The question is: can you afford not to?
Your next leadership breakthrough starts with a single conversation, a moment of genuine connection, an adaptation to meet someone where they are.
Start today. Your team—and your organization—will thank you.
Dr. Donita Brown is the host of The Management Minute Podcast, helping busy managers develop values-based leadership practices in just 15 minutes every other week. With a background in organizational leadership and a passion for practical, actionable wisdom, she interviews business leaders from diverse industries to distill their insights into immediately applicable strategies.
Copyright © 2025 Donita Brown. All rights reserved.