16 Leadership Lessons I Learned the Hard Way

by Charles Smith July 22, 2019

Normal teenagers don’t read leadership books. They play baseball, chase girls, and wait on their budding mustache to bloom into all its glory. But as my wife continually reminds me, other than my sweet mustache, I wasn’t normal.

In my defense, I came by it naturally. Our home was filled with leadership books. They were left on bedside tables, stuffed in briefcases, and alphabetized near the theology section of our home library. As a young businessman and civic leader, Dad devoured anything that helped him wrap his mind around his growing responsibilities. As his only son and namesake, I followed suit. By the time I graduated high school, I could quote John Maxwell and Peter Drucker like a seasoned executive.

But it was all theory. As I soon found out, leadership in the real world is complicated, contextual, and hard. To grow beyond my theories, I had to immerse them into real organizations with real people and real problems.

Here are several leadership lessons I’ve learned the hard way.

1. Believe the Best

A mentor once told me he works to “believe the best about someone until they make it impossible to do so.” Get in the habit of assuming the best when things go wrong. When that frustrating email lands in your inbox, assume you misunderstood it. When a staffer fails to complete a task, assume he was busy doing something else.

Almost without exception, when I’ve been tempted to scold a staffer or sulk in frustration, I’ve later learned I misunderstood the situation. For the most part, people are trying hard and want to please you. Assume the best and give lots of grace.

2. Prioritize People Over Process

It is so easy for me to get this wrong. I’m naturally wired to prioritize results over relationships and processes over people. That’s not to say I don’t value people—quite the opposite. But if I’m not careful, I can appear to care more about the finish line than the people who helped get us there.

Ask God to help you avoid even the appearance of this mistake. Good leaders love their people. Good leaders work to encourage their people. Good leaders develop their people. Good leaders prioritize their people.

3. Build a Team of Truth-Tellers

Leaders naturally drift toward isolation and echo chambers. As they do, they increasingly risk making poor decisions, and often they lack self-awareness and end up harming themselves and others.

Avoid this by cultivating a team who will tell you the truth and hold you accountable. Continually invite your team to say hard things and challenge your opinions. Not only will your organization be stronger for it, it might just save your soul.

4. Listen to Your Team 

Confident and decisive leaders often have a bad habit of not listening. Sadly, few things dampen creativity and collaboration like a leader with all the answers.

Cultivate the assumption that someone else probably has the best idea. Learn to ask probing questions and actively listen to the answers. Doing so not only exposes you to great ideas; it also makes your team more likely to support your final decision.

5. Listen to Your Critics

Learning to see criticism as a means of grace is crucial to a leader’s long-term effectiveness and health. God often uses our critics to correct us, strengthen us, humble us, and ultimately to sustain us.

Before you delete that angry email or disregard that recent complaint, assume it may contain some element of truth. What might God be showing you? Ask friends and trusted colleagues to evaluate the criticism with you. Then rejoice that God graciously brought this to your attention.

6. Be Patient

Nothing happens as fast as you’d like. People quit. Strategies change. Vendors go out of business. All of these disruptions are part of life, and a failure to anticipate them can leave you and your team feeling like they’re always behind the proverbial 8 ball.

A patient leader sets realistic timeframes and sticks to them.

7. Know Your Environment

Leadership never happens in a vacuum, but in a particular context with particular needs. The leader’s role, then, is to understand and assess that context so he or she can discern what needs to happen next.

So get to know your environment by asking questions, reading old reports and meeting minutes, and developing a general curiosity about the organization. It takes time, but the tortoise usually wins.

8. Manage Expectations

One vital thing a leader does is set and manage expectations. People are pretty flexible with things they knew upfront. It’s the surprises that get us in trouble.

Give yourself more time than you need. Assume the final bid will come in a little higher than you hoped. Work to consistently underpromise and overdeliver. If you do, organizational stress will decline, and your credibility will rise.

9. Execution Is King

“Execution is everything,” actor Jeff Bridges famously quipped. Execution may not be everything, but it’s certainly where the men are separated from the boys.

Ideas, vision, and strategy are equally important, of course, but they remain abstract concepts until someone does the hard work of execution. Build a team culture that rewards faithful execution.

10. Define Your Values and Protect Your Culture

Develop key values, and reward and reinforce them often. I do my best to underscore our values at most staff meetings and to give recent examples of how folks in the room are living those out.

This small thing can go a long way toward establishing and maintaining a healthy culture.

11. Simon Sinek Was Right

In his book Start With Why, Simon Sinek argues that great leaders inspire action by starting with why it’s needed.

Learn to incorporate context and “the why” in daily conversations with staff. It will both anchor tasks in the vision and also inspire deeper commitment and effort.

12. Overcommunicate

I’m convinced it’s impossible to overcommunicate within an organizational context. Develop a clear vision, mission, and strategy—and convey it until you are blue in the face. Talk about it in meetings; integrate it into discussions and whiteboard sessions.

Relentlessly remind your team why your organization exists. It’s the rudder of your ship.

13. Know and Protect Your Priorities

Limitations force leaders to make choices. Whether you lead a team of two or 2,000, you cannot, and should not, do everything. Refer to your vision, values, and strategy. What is central to the mission? Memorize and protect those things.

Don’t let the good eat the great. Rehearse and guard your priorities.

14. To Lead Is to Be Misunderstood

Despite your best efforts to communicate clearly, some will be confused. Despite having sought advice and moved slowly, some will call you a reckless maverick. Despite your pure intentions, some will question your motivation.

Ultimately, it’s impossible to lead without sometimes being misunderstood. Listen for legitimate concerns, make necessary adjustments and clarifications, and trust Jesus with the rest.

15. Keep Calm and Carry On

For good or bad, leaders set the emotional tone within an organization. The good news is that your optimism will soon become their optimism. The bad news is that your cynicism will also become their cynicism.

Do your best to keep your cool, laugh at honest mistakes, and keep the team moving forward. Hope is the most powerful tool in your arsenal.

16. Anchor Your Worth and Identity in Christ

As important as leadership is, basing your identity on how people respond not only robs Christ of glory, it also renders you incapable of authentic leadership. In the end, we simply cannot lead what we worship.

Pray for a deep and growing sense of who you are in Christ. Ask God to continually remind you that you are far more than the sum of your gifts and contributions; you are a son or daughter of the eternal Father. Leading from that reality, not for it, is the name of the game.

Editor's Note: This originally published at The Gospel Coalition.