What a Bad Boss Can Teach You About Leadership
You remember your losses more than your wins. That’s just how it goes.
I don’t mind, because that’s where I’ve found the fire in my belly and the discipline to focus like never before.
Of course, I want to win, but I also want to grow. And that’s where things get tricky.
Winning often leads to stagnation. While everyone’s fighting to get in the winner’s column, you could argue that losing is actually more valuable.
Winning doesn’t produce the need for adjustments, skill improvements, or resilience that losing does.
It’s a bit like having a good boss versus a bad one.
We’d all prefer a leader who inspires us to be our best, but looking back, it’s crazy how much I learned from the bosses I loathed. Those times were far from ideal, yet the lessons in what not to do have been priceless.
Here are some traits of a bad leader
No awareness on the team pulse & needs
Makes decisions based on impulses
Never take responsibility
Aiming to use team to further their own career
It’s twisted, right?
Those toxic bosses showed me exactly what I never wanted to become. I knew firsthand how demoralizing it felt to work in an environment like that, so committing to never be that kind of leader became second nature.
Here’s where my mind twists into a pretzel: I’m striving to create an environment where everyone on my team thrives, grows, and feels fulfilled.
But if they never experience bad leadership, are they missing out on those priceless lessons?
I don’t know.
For now, I’m focused on being the best leader I can be. While I hope no one has to experience a bad boss, I also wonder—can we sustainably create a world without bad leaders if there are no bad leaders to learn from?
Maybe we’re in fact dependent on the “bad guys.”
Maybe it’s naive to think we can eliminate bad leadership altogether.
Honestly, I'm not sure.
As I ponder this and give myself a headache, let’s agree on one thing: at some point, there will be loss, and it will be painful. How you respond to that pain is a reflection of your character and will largely dictate the happiness you seek.
I’ve learned from personal experience that this is true.
In the spirit of Halloween, here’s a slightly dark assignment for you:
Reflect on some of the toughest moments in your life. Think about what you took from those experiences—how you responded to the pain and how it shaped you. The purpose is to prepare yourself for future losses.
Whether it’s a struggling experience with your boss or a detrimental life event.
1. Reflect on Your Losses
Identify Key Moments: Think back on a few major setbacks or tough moments in your life. Write them down to clearly define what they were and why they were significant.
Extract Lessons: For each instance, consider what the experience taught you. What did it reveal about your strengths, weaknesses, or response under pressure? This builds self-awareness, which is key to personal and professional growth.
2. Assess Your Responses to Challenges
Analyze Your Actions: Look at how you responded during those difficult times. Were your actions constructive or reactive? Did they help or hinder your progress?
Set Intentional Responses: Use this knowledge to build a strategy for how you’d like to respond to future challenges. Setting these intentions helps reinforce resilience and gives you a more proactive, steady mindset in high-stakes situations.
3. Learn from Both Good and Bad Leadership
Take Notes on Good Leadership: When you’re working with a strong, supportive leader, observe their approach to decision-making, communication, and team dynamics. Document what makes them effective and what you want to emulate.
Recognize Lessons from Negative Leaders: If you’ve encountered poor leadership, reflect on what didn’t work, how it affected you and your team, and the specific behaviors you want to avoid. This helps reinforce the kind of leader you don’t want to be, which is invaluable for your own growth.
4. Prepare for Future Losses
Identify Triggers and Patterns: Reflect on the types of challenges you’ve faced. Are there patterns? Recognizing these can prepare you mentally and emotionally for similar situations.
Develop Coping Strategies: Consider actions that can keep you grounded during losses—a supportive conversation, a workout, or revisiting your goals. Having these tools at hand enables you to respond constructively to new challenges.
5. Commit to Growth, Not Just Winning
Prioritize Continuous Improvement: Recognize that growth often comes more from losses than wins. Make a habit of seeking improvement, regardless of the outcome.
Track Your Progress: Document both wins and losses, focusing on what each taught you. By reviewing these periodically, you reinforce a mindset focused on growth and learning, rather than solely on winning.
6. Apply What You’ve Learned to Your Team
Foster a Growth-Oriented Culture: Share stories of your own wins and losses with your team, highlighting the lessons they brought. This encourages open discussion and a culture where growth is prioritized over perfection.
Model the Behavior You Want to See: Lead by example. Whether in handling setbacks gracefully, admitting mistakes, or celebrating learning moments, demonstrate the resilience and focus you want your team to adopt.
