Compassionate Leaders Make People Feel Good—and Perform Better

Legal departments and corporate teams are navigating a perfect storm: evolving client expectations, rapid transformation cycles, and prolonged uncertainty.

As pressure mounts to deliver—build more, sell more, solve more—traditional managerial training suggests narrowing focus, increase controls, and identify areas to reduce risk. But in my experience as a design thinker, this narrowing effect works against what organizations need in times of sustained turbulence.

Creative problem solving requires openness, flexibility, and trust, which are often the most endangered qualities in high-pressure moments. And that’s where compassionate leadership plays a defining role.

Compassionate leadership is a strategic capability, not a soft skill. One must know how to navigate volatility while keeping teams engaged and aligned, building trust across the enterprise, and surfacing adaptable solutions in unpredictable times.

Compassion Reframed

Compassion isn’t about lowering expectations; it’s about understanding context and actively engaging with all factors of a team member’s performance. At its core, compassionate leadership focuses on setting people up for success.

Leaders still need to execute, but the challenge is to do so while acknowledging the weight employees carry rather than just the goals they must meet. Compassionate leadership doesn’t negate the need to make hard decisions—it simply acknowledges the human impact and seeks a more deliberate thoughtful path.

In one of my experiences in rapid change management, one high-performing individual began missing deadlines. Traditionally, the assumption might be that performance was beginning to slip, or they were quietly quitting. But through a check-in (“What’s helping or hindering your work right now?”), I learned the employee was juggling additional responsibilities outside the team due to a staff departure.

With this understanding, we could adjust workflows and priorities. I could also formally recognize work performed that hadn’t been captured by the legal department. Performance bounced back, and trust deepened.

This kind of framing mirrors a principle in design thinking: What are all the factors we need to understand for the problem we’re trying to solve?

Compassion as Metric

Compassion can also be a measurable metric and doesn’t need to just be seen as intangible. Quarterly wellness check-ins and self-evaluation metrics can provide a composite picture of team health.

When analyzed alongside retention data, particularly during pressure periods such as mergers, reviews, or leadership transitions, these indicators can help leaders see hidden burnout. Serving as a compassionate leader can be a leading indicator, not just a reactive tool.

For example, in one team facing intense corporate challenges, we asked during self-evaluation: “What percentage of your work time last quarter felt sustainable?” This provided a chance for leadership to proactively intervene. And when the team says it’s stretched too thin, a leader can be better equipped to prioritize resources.

Read More: Amy Yeung shares how GCs should also harness empathy and teams’ diversity of experience.

Delivery Matters

In moments of internal restructuring, the way leaders share information matters as much as what they share. A compassionate response weighs the operational goals alongside human ones.

When a team receives a Friday email titled “Important Updates” detailing immediate team changes, team members have little context and warning. Traditional management techniques dictate that this Friday afternoon approach would provide time for individuals to internalize the news over the weekend. But it can fuel rumors and side conversations, anxiety, and disengagement.

Contrast this with a compassionate approach:

• An early-week message that includes not just the update, but also a Q&A anticipating questions.
• The message’s tone acknowledges uncertainty rather than denying it.
• Managers are prepared ahead of time to hold individual follow-ups.

Though the content remains challenging, the experience becomes one of dignity and transparency. Rather than adding value to grapevine communications, leaders can create a foundation for trust and long-term performance.

Timing matters in other moments as well. When planning a difficult exit process, a compassionate manager considers personal observances, such as birthdays, religious holidays, or events such as Mother’s Day, adjusting notifications accordingly. Avoiding the traditional dates also acknowledges the managerial time needed to attend to team needs and the realistic likelihood that family events and vacations are often scheduled around these dates.

These aren’t grand gestures, but they minimize additional emotional disruption for the terminated team member and the rest of the team as well, preserving dignity and psychological safety. While these gestures are small, they send a big signal: You matter.

Making Space Amid Constraint

Implementing technology changes, such as incorporating artificial intelligence into department work processes, can raise a team’s anxiety, including about whether the technology will eliminate roles. This often-described “necessary game changer” has been projected as a method to further automate company processes but hasn’t always been projected as an elevation tool for individuals to practice at their peak.

Also, building technology use skills has often been “on one’s own time,” and organizations may not have projected (or incorporated in their current planning) educational training and learning moments for individuals to skill up. Trying to pin down how the company will implement AI to identifying learning resources, and setting aside time and financial resources to do so, can be a significant hurdle.

Compassionate leadership recognizes the full set of requirements needed for an individual to achieve AI fluency, identifies the corporate resourcing and externalities, and seeks understanding to help bridge the gaps.

One leader, introducing a contract management tool, was asked to do so with urgency and speed. They paused, gathered feedback on workflow fears, and ensured that team members were part of the pilot and implementation process.

This was about designing durable change rather than an intent to delay. Management was aligned with the pacing, and this extra time to create space for understanding and a greater breadth of and interest in training.

Consequently, we saw higher team adoption and technology fluency. Compassionate leadership was a force multiplier; it gave employees permission to problem solve and to stretch instead of to live in fear.

More Durable Workplace

Capability, not just culture, is an outcome of compassionate leadership. Individuals are willing to reach across the aisle and work together to achieve goals. People feel seen—and they also feel supported in the ways that help them do their best work or recover more quickly when they can’t.

In an era when uncertainty and speed may seem like the only inevitability, the most decisive leaders are those who go beyond seeing the strategy and foster a team who can carry it forward.

This article does not necessarily reflect the opinion of Bloomberg Industry Group, Inc., the publisher of Bloomberg Law, Bloomberg Tax, and Bloomberg Government, or its owners.

Author Information

Amy Yeung has served in senior and executive legal leadership, counseling fast-growth private and Fortune 1000 public companies. Yeung has also served in leadership capacities in legal operations, DEI, and innovative leadership, including in her current positions as past chair of the Law Department Management Network of the Association of Corporate Counsel and a fellow of the College of Law Practice Management.

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