What I’ve Learned About Leadership and Collaboration

Lessons That Hurt When Ignored

Mar 22, 2025

After decades in business, leading complex teams, and building companies, there are some undeniable lessons that keep resurfacing. Sometimes hard, sometimes confronting, but always valuable. These are insights that don’t come from books or theories, but from reality — the moments when you’re faced with decisions that determine whether something grows or falls apart.

1. Trust without confrontation is not trust

Trust is the result of honest conversations, even when they’re uncomfortable. Without confrontation, there’s no depth. The art of leadership is embracing discomfort and confronting issues when unspoken tensions or concerns arise. Trust without confrontation is mere illusion.

2. Vague agreements are the death of any project

Vague roles, unclear responsibilities, and avoiding tough choices always lead to confusion and delay. Good leaders always establish clear boundaries. They know when and how to take the reins to provide direction and ensure clarity. A team without clear agreements is like a ship without a compass: it drifts aimlessly.

3. Good leadership is not about being nice, but about providing direction

Your job is not to be liked, but to provide clarity and direction. Leadership requires courage — the courage to make unpopular decisions when necessary. Leaders who leave everything open for debate without clear direction create chaos, not involvement.

4. The ‘soft’ side is critically important

The ‘soft’ aspects of leadership — like empathy, open communication, and psychological safety — are the hard prerequisites for success. If you don’t know what’s going on in the minds and hearts of your team, you can’t lead effectively. Ignoring these puts you at risk of miscommunication, mistrust, and demotivation.

5. You don’t have to carry it if it’s not being carried

Leadership doesn’t mean you have to carry everything on your own. A team that isn’t working with you is not a team worth holding onto. Letting go — whether it’s a project, a task, or even a team member — is not a weakness, but an act of strength and wisdom.

6. Giftedness makes you sharp, but also vulnerable

Giftedness allows you to think quickly and analyze deeply, but it can also lead to miscommunication or isolation. Leadership requires not just strategic insight, but the wisdom to place your own abilities in service to others — without losing the human connection.