7 Leadership Lessons Learned the Hard Way From Experience

Originally Published in Brainz Magazine - September 2025

The most important things you need to know about being a leader are usually learned the hard way. In this first of a two-part series, we explore seven essential lessons that can help you successfully lead a high-performing team — and hopefully avoid some of the toughest leadership challenges.

1. The more senior you are, the less likely you are to get the truth

As you move up, you’re no longer “one of the group” — you are the leader of the group. This means your influence grows, but those below you may provide less honest feedback. Even flawed ideas may receive support rather than challenge.

Action: Find people who will tell you the brutal truth and check in with them regularly. Create processes and safe spaces that encourage others to offer different opinions. For example, asking your team for contrary evidence to a proposed approach is a powerful way to expand thinking.

2. You can feel lonely, even when surrounded by people

Most leaders are constantly managing requests for their time, yet often lack space for deep, meaningful conversations. The mix of leadership relationships, confidentiality, and the constant need to appear “in control” can leave you feeling isolated, with few people you can speak openly with.   You can learn more about leader isolation here.

Action: Have at least a couple of trusted advisors — or even better, an independent coach — with whom you can speak freely.  Executive coaches provide a confidential, judgment-free space to work through challenges.

3. Mistakes are inevitable — and okay

Humans err. Your team will make mistakes, especially in fast-moving or growing teams.  Instead of fearing them, see them as part of learning and progress. What matters most is how you and your team respond.

Action: Implement systems to reduce avoidable errors but embrace the rest as opportunities to learn. Encourage openness to build a culture where mistakes fuel growth.

4. Don’t assume you know what your team wants

The higher you rise, the more distant your perspective becomes from your team’s day-to-day realities. What seems obvious to you may feel completely different to others.   This Forbes article explores 20 assumptions to avoid.

Action: Ask your team directly what matters to them. Don’t assume — you’re probably wrong if you think you already know.

5. You will always have more to do than is possible

Your list of projects and opportunities will always outpace your capacity. Waiting for things to “settle down” next month is an illusion.   Focused prioritisation and time management are critical for you to be highly effective.

Action: Identify your top 3–5 priorities and give them your full focus. Park the rest on a “later list” and return to it only when something truly becomes a priority. This keeps you effective and prevents overwhelm.

6. Uncertainty is part of leadership

Decision-making under uncertainty is part of the leadership job. The pace of change, limited resources, and complex challenges mean clarity is rarely complete.

Action: Build comfort with ambiguity. Experiment, learn, and adapt. Take calculated risks to grow your confidence and expand your skill set.

7. You shape the world for your team

Your capability sets the ceiling for your team’s performance. They will operate within the boundaries of your thinking and worldview. To serve them well, continuously expand your perspective and embrace continuous growth.

Action: Invest in your own leadership development, promote curiosity, and seek independent perspectives. Every step you take forward creates new opportunities for your team.

Leadership is a journey of ongoing learning. The lessons aren’t always easy, but embracing them helps you lead with confidence, authenticity, and impact. Stay tuned — next week I’ll share part two with nine more leadership lessons learned the hard way.