"The Kindest Thing You Can Do Is Have That Hard Conversation"
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Higher education leaders are told to lead with empathy and compassion -- and we should. But we're also responsible for standards, accountability, and results. Sometimes those two things seem at war.
I wrote about leading from the heart in , where I shared how a grad school friend -- let's call her Sarah -- used that approach as a department chair to improve her department's climate.
She was happy that her Heart First approach was working, but then she faced a new challenge.
"I've been more empathetic, but I think one of my administrative staff may be taking advantage of it," she told me. "He's been given an important project, but he's missing deadlines and ignoring my requests. I can't let this continue, but I don't want to be a dictator. How do I be compassionate without being a pushover?"
I recognized that feeling immediately -- I'd faced the same dilemma.
I told Sarah what I wish someone had told me years ago: Heart First leadership isn't about saying yes to everything. It's about caring enough to have hard conversations. As one of my favorite yoga teachers likes to say, we must have a "soft front and a strong back."
Early in my career, I confused kindness with avoiding conflict. But I learned that endless accommodation isn't kind -- to the struggling employee who needed clear expectations, to the high performers watching standards erode, to the students who deserved better, or to yourself when you have to account for results.
The Misconception About Leading from the Heart
I understand why leaders fear that leading with empathy means losing authority. You show vulnerability, lead with heart, and suddenly worry: Have I given away my power?
The answer is no -- but only if you understand that Heart First leadership actually requires backbone. Mary Beth O'Neill explained it simply in her book "Executive Coaching with Backbone and Heart":
"Backbone means knowing and clearly stating your position, whether it is popular or not," she wrote. "Heart is staying engaged in the relationship and reaching out even when that relationship is mired in conflict."
Compassion without accountability isn't kindness -- it's avoidance that hurts everyone: the struggling employee, their colleagues, students, and the mission you're all trying to serve.
Strengthening Your Spine
Backbone isn't about being harsh or cold. It comes from clarity about what matters, courage to address issues directly, consistency in maintaining standards, and care for people's growth. Research consistently shows that the best leaders combine warmth with high standards -- they listen with empathy and expect excellence. They stay connected with their team while being clear about expectations.
When you need to have a backbone conversation, use what I call the Clear Consequences approach:
- Name the issue as specific, observable behaviors, not vague judgments. "You've missed three deadlines this month" works better than "you're slacking off."
- Explain the impact on students, colleagues, and the shared mission -- help them see the ripple effects and why their work matters.
- Set clear expectations about specifically what needs to change and by when, giving them space to figure out how to get there rather than rescuing them with solutions.
- Be honest about consequences. Explain what happens next if the behavior continues, framing consequences as the logical destination of staying on this path, not as threats.
- Offer genuine support by asking what they need and how you can help.
The key insight: you can be compassionate about someone's struggles while holding them accountable for performance. These aren't contradictory -- they're complementary.
Real Leadership in Practice
Sarah used this framework with her struggling employee. She started with empathy, really listening when she asked if he was okay. Then she added backbone by naming the missed deadlines and their impact. The conversation was hard -- her hands were shaking -- but she stayed calm, clear, and compassionate.
The result surprised her. "He actually seemed relieved," she told me. "He said, 'I appreciate that you noticed I was struggling and that you care that I succeed.'"
But that wasn't the end of it.
Three weeks later, Sarah called again. Her voice was tired. "Things got better for about ten days," she said. "Then he slipped back. Different excuse, same pattern. I need to talk to him again, don't I?"
Yes. And that's the part about backbone nobody warns you about. One clear conversation rarely fixes chronic performance issues. You're not failing if you have to revisit the same topic -- you're doing your job as a manager.
Sustained backbone means referencing the previous conversation and noticing patterns rather than treating each incident as isolated. It means escalating consequences appropriately, moving from setting clear expectations and offering support, to adding closer monitoring, to formal documentation, and sometimes to discipline. Throughout, you stay compassionate about struggles while remaining clear about standards: "I hear that this is difficult. And the work still needs to get done on time. Both things can be true."
Sarah had two more conversations over the next six weeks. Each was harder, not because she was doing it wrong, but because the pattern wasn't changing. Eventually, she moved to a formal improvement plan. "I feel like I failed him," she told me.
"You didn't fail him," I said. "You gave him multiple clear chances. He chose not to take them."
She was quiet. Then: "I guess caring about someone doesn't mean I can make their choices for them."
Exactly. And sometimes the kindest thing is helping someone who cannot or will not meet expectations to see that this role isn't a good fit.
Managing Your Own Emotions
Something nobody talks about: backbone conversations are hard on you, too. Your heart races. Your stomach knots. You rehearse the conversation at 2 a.m..
I've been there. I've had my voice shake during accountability conversations. I've felt my face flush when someone makes the same excuse for the third time.
Before the conversation, ground yourself physically -- take five deep breaths, feel your feet on the floor, relax your jaw. Get clear on your intention by writing it down: "I want to help this person succeed." Acknowledge your feelings by naming them to yourself, which reduces their power.
During the conversation, notice when your heart starts to race or your face gets hot -- that's your signal to slow down, breathe, and pause before responding. Having your key points written down keeps you centered when emotions spike.
After the conversation, debrief with someone you trust, then let the energy flow through and out. Don't keep ruminating. Recognize that you won't handle every conversation perfectly. You're learning.
Sarah told me something powerful after her fourth conversation: "I was dreading it so much I almost cancelled. But then I realized: if I'm this stressed about having the conversation, imagine how stressed he must be living in limbo -- knowing he's falling short and waiting for the other shoe to drop. Having the conversation was actually the kinder choice."
Your discomfort during a backbone conversation is temporary. The harm from avoiding it lasts much longer.
Your Action Step
As a yoga teacher, I know that regular practice is the key to creating a strong spine and an open heart. So, this week, I invite you to identify and address one situation where you need more backbone -- a performance issue you've been avoiding, a boundary that's been crossed, or standards that aren't being met.
Prepare for the conversation by getting clear on the issue and impact, deciding on consequences, and identifying support you can offer. Write your intention on a note card and keep it in front of you when you're having the conversation. Notice the other person's reactions in the moment, and over the next several days, pay attention to whether they're taking corrective action. Follow up to provide feedback on what you're seeing.
The harder part: be ready to have the conversation again, if needed. One clear conversation is progress, but backbone means sustaining that clarity over time, even when it's exhausting. Track what you said and when, document improvements and setbacks, and be consistent and patient. But don't be endlessly tolerant of the same behavior.
Remember: Having backbone isn't about being mean. It's about caring enough to have hard conversations -- as many times as necessary.
The Heart of Leadership
Looking back many months later, Sarah shared the outcome: "It didn't work out with that colleague. He left for another position. But our relationship ended on good terms. He thanked me for being honest about his performance. He said other supervisors had let him slide for years, and he wished someone had been clearer earlier."
Being honest built respect between them, even though the ending wasn't what she'd hoped for.
Heart First leadership works because it's built on genuine care. But genuine care includes holding people accountable over time, maintaining standards consistently, and having candid conversations -- again and again, if necessary.
I'm still working on this myself. Some days I lean too far toward empathy. Other days I lean too hard into accountability. Some weeks, I'm just tired of having the same conversation for the third time. But I'm getting better at the dance.
In a time when higher education is facing unprecedented pressures and our people are exhausted, we need more leaders who can hold a soft front and a strong back -- not just once, but for as long as it takes.
