Leading with Empathy: Building Trust in Teams
By Karry Kleeman
3x SaaS Exited CRO | Board Member | Investor | Advisor | GTM Executive
In business, trust is the foundation of high-performing teams. Without it, collaboration suffers, engagement declines, and productivity stagnates. But how do leaders build trust in an environment that demands results, rapid decision-making, and constant adaptation? The answer lies in leading with empathy.
Empathy isn’t just about being kind—it’s about understanding the perspectives, emotions, and challenges of those you lead. When leaders prioritize empathy, they create teams that feel valued, supported, and motivated to do their best work.
Why Empathy is a Leadership Superpower
For years, leadership was often associated with authority, strategy, and execution. But in today’s evolving workplace, leaders who cultivate emotional intelligence and empathy outperform those who rely solely on command-and-control tactics. Research shows that empathetic leaders drive greater employee engagement, reduce turnover, and foster more innovative and resilient teams.
Empathy enhances leadership in several key ways:
- Strengthens relationships: Employees who feel heard and understood are more likely to trust and respect their leaders.
- Encourages open communication: When leaders create a safe space for dialogue, teams become more transparent and collaborative.
- Boosts morale and motivation: Employees who know their leader cares about their well-being are more engaged and productive.
- Fosters adaptability: Teams with high psychological safety are more willing to take risks and innovate.
How to Lead with Empathy and Build Trust
Empathy isn’t an innate trait—it’s a skill that can be developed. Here’s how leaders can cultivate an empathetic leadership style that builds trust and enhances team performance.
1. Listen More, Talk Less
Empathetic leadership starts with active listening—not just hearing words but truly understanding what’s being said (and what’s left unsaid). Ask open-ended questions, be fully present, and resist the urge to immediately offer solutions.
Practical Tip: In meetings, practice reflective listening by summarizing what you’ve heard before responding. This reassures employees that their voices matter.
2. Recognize Individual Challenges
No two employees are the same. Some may be juggling personal challenges, mental health struggles, or professional roadblocks that impact their work. Leaders who take the time to understand these challenges can provide tailored support.
Practical Tip: Check in with team members regularly—not just about work but about how they’re doing personally.
3. Encourage Psychological Safety
Trust is built when employees feel safe to voice concerns, admit mistakes, and share new ideas without fear of retaliation. The best teams are those where people feel secure enough to take risks.
Practical Tip: Normalize failure by sharing your own mistakes and what you learned from them. This creates a culture where growth, rather than perfection, is valued.
4. Show Vulnerability and Authenticity
Leaders don’t have to have all the answers. Showing vulnerability—whether it’s admitting when you’re wrong or sharing your own struggles—helps humanize leadership and fosters deeper connections.
Practical Tip: Share personal stories about challenges you’ve faced and how you overcame them. This builds relatability and trust.
5. Support Work-Life Balance and Well-Being
Employees perform at their best when they’re not burned out. Leaders who support work-life balance—by respecting boundaries, encouraging time off, and offering flexibility—build trust and long-term commitment.
Practical Tip: Lead by example—log off at a reasonable hour, take breaks, and encourage your team to do the same.
Real-World Impact of Empathetic Leadership
At LogicGate, where we scaled from $1M to $50M in ARR, fostering a culture of empathy and trust was just as critical as our business strategy. High-growth environments are demanding, but we prioritized open communication and employee well-being to sustain motivation and morale.
Similarly, at SpringCM, leading up to its $270M acquisition by DocuSign, the most successful teams weren’t just those with the best technical skills—they were the ones where trust and collaboration thrived. Empathy in leadership was a differentiator that fueled both performance and retention.
Final Thoughts
Empathy isn’t a soft skill—it’s a leadership necessity. When leaders prioritize understanding, active listening, and authenticity, they build stronger, more resilient teams. In today’s fast-changing world, where uncertainty is the norm, leading with empathy isn’t just the right thing to do—it’s the smart thing to do.
So ask yourself: Are you leading with empathy, or are you just managing? Because in the end, the best leaders aren’t those who demand trust—they’re the ones who earn it.
About Karry Kleeman
Karry Kleeman is a seasoned software executive, go-to-market strategist, and revenue leader. He thrives at the intersection of business growth and human connection, blending a sharp instinct for scaling companies with a deep passion for people and a commitment to infusing a human touch into the process. He is known for bringing energy and clarity to organizations—rallying teams around a common mission, driving execution, and creating momentum that fuels growth.
With a career spanning decades in enterprise software, Karry has built and led high-performing revenue organizations from early-stage startups to IPOs and strategic acquisitions. He has played a pivotal role in scaling multiple companies to successful exits, generating well over $1 billion in enterprise value. At LogicGate, he architected a go-to-market strategy that propelled the company from $1M to $50M in ARR. At SpringCM, he led the revenue function through its $270M acquisition by DocuSign. And at Mobius he helped scale the business from $3M to over $100M, culminating in a successful IPO.
Karry’s ability to inspire and energize teams is a core part of his leadership. Just as he commands attention and engagement when performing live music, he brings the same presence and intensity to leading teams—aligning them around a shared vision, setting the pace, and ensuring everyone is moving in rhythm toward ambitious goals. When he’s not driving business growth, you’ll find him performing classic rock hits anywhere he can find a live mic.
