#1: What important conversations are you continuing to postpone… and why?
#2: What concerns or issues are you tolerating – hoping they’ll fix themselves?
#3: Where have you confused being “nice” with being kind?
Meet Carrie, the newly appointed CEO of a family-held construction company. A year and a half into her role, she faced a situation that many leaders find themselves avoiding: a performance problem with family implications.
The challenge? A nephew serving as project manager whose performance and behavior weren’t aligned with company standards. His issues were causing team turnover, disrupting client relationships, and creating project delays. Despite Carrie’s coaching efforts and direct conversations, the problems persisted.
Adding complexity to an already difficult situation: the previous CEO—a direct family member who held the role for 25 years—remained as board chair with significant influence, creating constraints on Carrie’s leadership decisions.
When a leadership restructuring (unrelated to this specific issue) created an opportunity, Carrie chose kindness over niceness. Rather than continuing to postpone the difficult conversations and tolerate a situation that wasn’t serving anyone, she stopped avoiding the confrontation that had been brewing.
Throughout this process, Carrie responded with care, communicated with clarity, sought input from the board chair while maintaining clear boundaries about final decisions. She also documented her coaching conversations to ensure transparency, provided the nephew with additional resources and professional development opportunities before making the final call, and held regular check-ins with the affected team members to address their concerns and rebuild trust. She maintained healthy communication with clear boundaries with the board chair while making the tough decisions the organization needed.
The nephew eventually left on his own, but not quietly. He badmouthed Carrie and the organization, made false accusations of unfair treatment, and even said he wished the company would “go down in flames.”
But here’s where the story takes an unexpected turn.
Six months later, Carrie received a surprising message from the former employee. He was now teaching construction at a local vo-tech school and had never been happier in his career. The message included an apology for his behavior and words, and—perhaps most importantly—gratitude. He acknowledged that without that “push” out of his comfort zone, he never would have discovered what he was truly meant to do.
Sometimes being truly kind means making decisions that feel uncomfortable in the moment but serve everyone’s long-term good. Whether you’re a C-suite executive, managing front-line supervisors, or serving on a board, these principles apply universally.
So rather than continuing to hope problems will resolve themselves, consider these three questions:
#1: What important conversations are you continuing to postpone… and why?
You know the ones. They’re lurking in your mental “someday” folder, gathering dust while the situation quietly festers. That performance issue. That difficult family discussion. That strategic pivot your organization desperately needs.
#2: What concerns or issues are you tolerating – hoping they’ll fix themselves?
Spoiler alert: problems rarely resolve through benign neglect. Yet we keep crossing our fingers, as if the universe operates on wishful thinking alone.
#3: Where have you confused being “nice” with being kind?
This one hits different, doesn’t it? Sometimes the kindest thing we can do is have that uncomfortable conversation or make that difficult decision.
Don’t just survive the transition season – use it. Ask the hard questions. Have the difficult conversations. Choose kindness over niceness.
Onward, servant leaders.
