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  • Writer's pictureJenn Donahue

5 Lessons I've Learned in the Last Few Decades of Leadership

What have you learned from your past experiences that helped to shape who you are today?

It’s really important to me to learn from failure and use it as an opportunity to grow. That’s what I’ve been doing for the last few decades of my life. And now, it feels like time to share what I’ve learned so that I can help others.

If you go through life and don’t learn from your experiences, it can be really hard to move forward and keep growing.

I’ve spent the last few decades of my career in leadership (or rising into leadership) positions and I’ve learned a lot. My experiences and lessons learned are the stories I choose to share with my audiences because if just one person can learn from my past failures, mistakes, and successes, then I consider it a win.

Here are five lessons I've learned in the last few decades of leadership.

1.Understand How to Be Yourself

Authentic leadership is important to me. It’s a pillar of what I speak about and mentor others on. And while it didn’t happen overnight, I did eventually figure out how to be myself, even in a leadership position.

And trust me, I tried just about every other leadership style before I found what felt natural and good to me.

I tried leading like a man, being the demanding yeller, and even being the outgoing charismatic one (I had to take a nap for two days after that). Until eventually I became too overwhelmed, exhausted, and discouraged to keep leading in a way that didn’t feel true to me.

It wasn’t genuine or authentic and my team could see right through it. It didn’t build trust, respect, or inspire confidence in my team.

You have to figure out how to be yourself, even if it seems different, unprofessional, or vulnerable. I learned that I am an empathetic leader and I encourage others to do their best by really getting to know and understand your team on a personal level. Once we have that common ground built on trust, then the doors open to all kinds of possibilities and productivity.

I enjoy getting to know my team and building the confidence they need to go out and do great things. Being a great leader requires the courage to be YOU. It means letting go of who you think you need to be and instead accepting yourself exactly as you are.

From there, you will become a leader others want to follow.

2. It’s All About Your Team, Not You

Once you become a leader, it is no longer about you, it has to be about your team. I’ve seen so many people step into a leadership and think they are the sh*t! While it is impressive that you’ve gotten to where you are, you can’t let it overtake what you are there to do.

Being a leader isn’t just about climbing the ladder and always going for that next promotion, it’s about taking really good care of your team so that you, your people and the organization can be successful.

And, if you take really good care of your team, they will promote you and you won’t even need to promote yourself! You will get seen for creating and building an efficient and effective team, your people will praise you to others, and your boss will take notice of all of it. It’s a win-win-win!

3. Learn From the Bad Leaders, Too

I know what it’s like to have a horrible boss. When I was in Afghanistan our leader was truly terrible. He yelled and screamed at us, degraded me and my team, and made us feel like we were not good enough for the jobs we were hired to do.

While it was hard to show up to work during those days, later I’ve realized just how important that experience was for my growth and leadership development.

You can learn as much from a bad leader as you can a good leader. We’ve all had terrible bosses. I know you remember them. And oftentimes we think the only thing we gained from these bosses is stress, pain, and misery. However, it is these bosses that can help shape who you are as a leader.

If you can think, “How can I be better at this than that boss was?” you can open the door to endless possibilities for great leadership.

The bad boss becomes your guide post for who not to be as you discover your authentic leadership style.

So, pay attention to even the bosses that yell at you (like mine did) because they can still teach you something.

4. Learn How to Trust Your Team

True leaders have trust in their team. They are not micromanagers and they are able to let go of their own power so that others can do what they are good at.

Early in my career I had an “a-ha moment.” A 360 assessment was sent out to my bosses, peers, and subordinates and one of my subordinates wrote on the questionnaire, “she doesn’t trust us.”

After I felt a little bit of anger (ok, maybe more than a little bit) towards this anonymous person, I decided that maybe they were right. I did some self reflection and realized that when I got stressed out, I’d pull back on the trust and decide to just do everything myself.

Maybe you can relate. It is pretty typical for bosses, CEOs, and entrepreneurs to do this.

What is really happening when we do this is we are telling our team that they aren’t capable of doing their job well and that they aren’t worthy of being trusted to do what is asked of them.

I knew I needed to change.

Great leaders know the importance (and have seen the powerful results) of trusting their team. If you give your team the appropriate amount of training, instruction, and resources, then you have to step back and trust that they will do what you’ve asked.

I learned that without trust, you don’t have a team.

5. Be Decisive!

As a leader, people are waiting on your decisions in order to move forward, so it’s important to be decisive! Making decisions can be one of the hardest things to do and confidence is helpful when it comes to doing it.

There is a spectrum for decision making. It ranges from making impulsive, snap decisions to having what we called in the military, “paralysis by analysis.” It’s important to find your happy medium. Snap decisions can be harmful and well, indecision sinks the ship… as they say.

If you are not sure what type of decision maker you are, talk to your mentor, your peers, or your spouse and ask what your decision making style is. When you are aware of how you already make decisions, it’s easier to make decisions better.

Good decision-making is one of the best skills you can have as a leader. Take some time and effort to refine this skill and you’ll see how positively it affects your team and your business.

Learn Your Lessons!

If you truly want to become a great leader, you have to learn from your past experiences.

Learning from your mistakes, failures, and successes allows you to learn more about yourself and who you are as a leader. It helps you find your most authentic leadership style.

And the more you know who you are, the more your team will respect you and want to learn from you.

So, I challenge you to reflect on your past experiences and come up with your own five lessons you’ve learned in your career. How have these experiences shaped you? Are these stories worth sharing so that others can benefit from them?

If you’d like to hear more about the lessons I’ve learned and how each person’s experiences can contribute to becoming a better leader, reach out to me and let’s connect!


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