There is a moment in every leader’s career when the job changes.
Not the title. Not the scope. The responsibility. For me, that moment came when I realized I had been confusing empathy with tolerance, and popularity with leadership.
Early on, I believed that being a good leader meant being understanding, patient, and generous with second chances. I prided myself on giving people room to grow. I told myself that development takes time, that potential deserves investment, and that loyalty is built through compassion.
All of that is true. But what I learned, often the hard way, is that empathy without boundaries becomes tolerance of misalignment. And tolerance of misalignment slowly erodes culture.
The advice to “hire slow, fire fast” is often delivered as a sharp, almost cold leadership mantra. In reality, it is neither harsh nor transactional. It is about stewardship.
When you hire slowly, you are not being indecisive. You are being deliberate. You are recognizing that every person you bring into an organization shapes its standards, its energy, and its trajectory. Skills can be developed. Experience can be accelerated. But values, integrity, and ownership rarely transform under pressure.
In fast-moving environments, especially in media and tech where I have spent most of my career, the temptation to hire quickly is real. The pressure to deliver is constant. When the workload increases and the team feels stretched, adding capacity feels like relief. But hiring under pressure often leads to compromised judgment. And compromised judgment rarely compounds well.
Still, hiring carefully is only half the equation. The more difficult half is knowing when something is not working, and acting decisively.
There were times when I delayed a hard decision because I wanted to be fair. Because I believed more coaching would change the outcome. Because I did not want to be seen as impatient or unsupportive. I told myself that empathy required endurance.
What I failed to see at first was the broader cost.
While I was extending timelines and offering additional chances, my highest performers were carrying the weight. They were absorbing missed deadlines. They were compensating for inconsistent standards. They were watching carefully to see whether the values we spoke about were truly enforced.
Culture is not defined by what leaders say in meetings. It is defined by what they tolerate.
That realization shifted my understanding of leadership. I stopped viewing it as a popularity exercise and started seeing it as stewardship. A leader is not there to win votes. A leader is there to protect the long-term health of the organization.
Empathy remains essential. It means having honest conversations early. It means providing clear feedback. It means offering real support and a fair opportunity to improve.
Tolerance, however, is something different. It is the prolonged acceptance of behavior that undermines the collective standard. And when tolerance replaces accountability, the entire team feels it.
Hiring slowly protects the future.
Acting decisively when necessary protects the present.
Neither decision is easy. Both require courage. But over time, I have learned that avoiding discomfort rarely leads to stronger culture. Facing it, thoughtfully and respectfully, almost always does.
That is why Lesson 37 is not about being ruthless. It is about being responsible.And once you understand leadership as stewardship rather than popularity, the decisions, while still difficult, become clearer.
For those who lead teams:
Where have you drawn the line between empathy and tolerance?
And when did you realize the job was bigger than being liked?