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 answers. Experience taught me that the best leaders ask better questions, trust others with real responsibility, and create space for people to lead. That’s how ownership grows, innovation accelerates, and organizations become stronger than any one leader could ever make them. — Jean Accius, CHC: Creating Healthier Communities
4. STRENGTH AND VULNERABILITY AREN’T OPPOSITES
A hard lesson I learned is that leadership isn’t about authority, title, and having all the answers. The most effective leaders I’ve encountered are the ones who ask better questions, not the ones who dominate the room with answers. They understand that leadership is not a solo act. It’s built on the people around you and the culture you create together. There’s also a persistent belief that strength and vulnerability are opposites. They aren’t. Leaders who can admit what they don’t know and say, “I got that wrong,” earn far more credibility than those who project false certainty. Vulnerability, when paired with accountability, is a leadership superpower. — Meredith Rosenberg, NU Advisory Partners
5. REALITY TRUMPS STRATEGY
Reality is always right. Your strategy doesn’t matter if customers don’t care. A powerful, technically brilliant solution that doesn’t solve a real-world problem isn’t worth trying to sell. — Eric Simons, Bolt.new
6. LEADERS DON’T ALWAYS NEED TO HAVE ANSWERS
I used to think leadership meant having the answers. I’ve learned it’s much more about asking better questions, staying open to feedback, and continuing to learn. The strongest leaders create cultures where curiosity and growth never stop. We work every day to instill this mindset in the young people we serve. — Chris Moore, FIRST
7. LEADERSHIP REQUIRES A BESPOKE APPROACH
In my late 20s, I took my first proper leadership role. I thought that if I worked hard enough, I could inspire the team to my way of thinking. It failed. Leadership is hard work, but it’s really smart work. You can’t manage the team as a whole. You need a bespoke approach for each person, giving it thought rather than trying to force it. — James Greenfield, Koto
8. GOOD INTENTIONS AREN’T ENOUGH
One of the hardest lessons I learned is that good intentions aren’t enough. Strong systems matter. You can solve today’s problem. But if you don’t build a process others can sustain, you’ll be back solving the same problem tomorrow. That’s why I focus on creating solutions that outlast any one leader. — Michele Walsh, UNICEF USA
9. PROVIDE “AIRCOVER” FOR INNOVATION
Earlier in my career, when I was in the U.S. Coast Guard, I ran a high-profile effort to build network capability across high-cost, high-latency satellite systems. During weekend testing, despite what we thought were sufficient controls, an error left a connection open and ran out our budget. On Monday, I expected a high-intensity reckoning. Instead, the commanding officer calmly asked what went wrong, what I would do to fix it, and where I needed help. He taught me a lasting lesson about giving teams “aircover” to push the envelope on innovation. — Todd James, Aurora Insights LLC
10. CHANGE REQUIRES THE RIGHT CONDITIONS
Too often, leaders move too fast and assume people will just follow along. Without leadership alignment, resources, a clear plan, and the data that makes the case for change, transformation won’t stick. Build these elements and communicate the case for change before you move forward. The momentum will follow. — Jacqui Canney, ServiceNow
11. POOR PERFORMERS TAKE A TOLL ON HIGH PERFORMERS
I have always been awful at firing people. I tended to give them multiple chances to improve, not realizing the toll it took on the high performers. As sportscaster and former football coach Nick Saban says, “High achievers don’t want to be around mediocre people. And mediocre people don’t want to be around high achievers.” I eventually learned with the help of senior staff guidance that I wasn’t doing any favors for the poor performer by not letting them pursue other interests. — Ed Mitzen, The Business For Good Foundation
12. LEAN ORGANIZATIONS LIMIT GROWTH
I have always valued a lean organizational structure. There were no layers or depth to our organizational chart for the first decade or so. I tried to participate in all key aspects of our business, but doing so limited our team’s growth, creativity, and quality of output. Mine is a common tale in that regard. Creating roles for technical team leads and formalizing a leadership team was great for me, our company, and our clients. Our team has more freedom to create, experts focus on and excel in their area of expertise, and I have more time for strategic thinking and execution. — Brad Weber, InspiringApps
13. EXPECT WHAT YOU INSPECT
Early in my management career, I learned that good intentions don’t guarantee the right outcomes. Every day, people make tradeoffs between competing priorities, and without clear direction, important work can easily give way to urgent work. That experience taught me a leadership principle I still rely on today: You should expect what you inspect. If something truly matters, leaders must create regular touchpoints, measure progress, and hold themselves and others accountable throughout the year. Consistent attention—not year-end reviews—is what turns priorities into results. — Tony Bedard, Frontier Co-op
14. PROXIMITY TO PEOPLE WINS OVER PROXIMITY TO POWER
Early on, I believed the path to real influence ran through Washington. Chasing that conventional wisdom cost me time and momentum. Everything changed when I stopped following the crowd and bet on the South instead—building one of the country’s largest minority-owned government affairs firms right where I already stood. The lesson: Proximity to power matters far less than proximity to the people and clients you serve. Sometimes the market that others overlook is the one you were built to win. — Howard Franklin, Ohio River South
15. MONEY IS SPIRITUAL
DWP is a spiritual organization. As our work grew, people told us to be careful about how we talked about healing and collective thriving. They said, “Don’t be too woo-woo” or talk too much about healing. For a while we listened, choosing caution over conviction. I’ve come to understand that the caution was rooted in fear, not faith. And fear limits vision. The lesson: Trusting what you know, even when your industry is not ready for it, can be vulnerable. But leading from that place gives others permission to do the same. — Edgar Villanueva, Decolonizing Wealth Project