08-03-2026IMPACT COUNCIL

15 leadership lessons that leaders learned the hard way

Crash courses in trust, delegation, judgment, and growth.

[Photo: Getty Images]

The Fast Company Impact Council is an invitation-only membership community of top leaders and experts who pay dues for access to peer learning, thought leadership, and more.

BY Fast Company Impact Council

Leadership positions may be the stuff of envy. From the outside, it can look like the person in charge has it all figured out. But leaders are human, too. And that means bumping up against some harsh realities as they ascend to roles with increasing responsibility. Great leaders take the lessons they learn along the way and make it part of the way they do business.

We asked members of the Fast Company Impact Council what’s one leadership lesson they learned the hard way? Fifteen of them shared the leadership wisdom they earned in the school of hard knocks.

1. YOU MUST SELL YOUR VISION

I used to think if the strategy was right, people would just follow it. What I learned the hard way is that isn’t true. You must sell the vision internally as hard as you sell the product externally, and keep selling it, not just announce it once. It takes far longer than expected for people to internalize a new direction and make it their own. Leadership isn’t setting direction. It’s the slow, repeated work of getting people to own that direction as much as you do. — Blake Brannon, OneTrust

2. GO FAST TO GO SLOW

Slow is smooth and smooth is fast. You can typically individually do most things very quickly and efficiently but that does not scale. Instead go slow to explain the “why” behind how you think about a problem, the “what” behind how you approach solving the problem, and the “how” you plan to execute. Coach and provide feedback, letting others try, fail, try again, and then succeed. This is how you maximize your impact on an organization and maximize total operating leverage. — Alex Triplett, You.com

3. LEADERSHIP DOESN’T GO IT ALONE

The hardest leadership lesson I learned was that carrying the weight alone isn’t leadership—it’s a bottleneck. Early in my career, I believed great leaders had the best........

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