What I Learned From A Huge Leadership Failure

Your Leadership Classroom is Everywhere. Are You Paying Attention? Leadership isn’t about proving what you know—it’s about staying curious, observing, and learning from unexpected sources. Great leaders embrace a lifelong classroom mindset. In this episode I discuss: 

• One of my biggest leadership disasters
• Why you want to rethink your teachers
• The behaviors that make you a more intentional leader
• How to spot the lessons all around you

Chapters

• 0:00 Leadership as continuous learning
• 1:30 Learning from unexpected teachers
• 4:07 Observation over action in leadership
• 8:15 Embracing diverse perspectives
• 12:57 Creating your leadership learning practice
• 14:49 Final thoughts and invitation

Transcript

Speaker 1: 0:00

Hey, I'm Jill Griffin, leadership and career strategist and an executive coach, and I spent the last 15 years helping professionals elevate their careers and boost their workplace performance. I help leaders be intentional so that they can step up and be the leaders they want to be and also create capacity for the people they serve. When you know how to navigate change with real world solutions, you create a stronger leader, both in yourself and others. So today I want to talk a little bit more about leadership, and your classroom is everywhere. Are you paying attention? Leadership is often seen as a position of authority that comes with experience, expertise and confidence Okay, sure, that is all true, I'm down for that. And confidence Okay, sure, that is all true, I'm down for that. But I also believe that the best leaders aren't just experts, they're also students. Leadership isn't a destination. It's about a continuous learning process, and the best leaders cultivate a beginner's mind, the ability to approach every interaction and challenge and opportunity with curiosity and openness, and they recognize that everyone and everything and opportunity with curiosity and openness, and they recognize that everyone and everything and every experience around them has potential to teach them something. Let's dig in. One of the biggest mistakes that I see leaders often make is that they assume they can only learn from people at their own level or those that are above them on the credentialing chain. But in reality, wisdom exists in many unexpected places and leadership wisdom is one of the ways in which you're going to create capacity for yourself and others to create or achieve your goal. A junior employee may have fresh ideas and I know sometimes as leaders we sit there and we're like, no, you don't understand. I've been here. It doesn't work that way. But I would just say, is there an opportunity to pause and hear the person out? And it might be something as the way they're approaching the conversation and less about what they're actually saying. Is there an opportunity to learn there? Can you learn from a customer, a competitor? Sometimes even the simplicity and curiosity of a child or a younger person around you might create a pause and a way that you can approach something with a beginner's mindset. So I really feel that lessons come from unexpected sources. Feel that lessons come from unexpected sources.

Speaker 1: 2:28

I'll also offer that. You know I used to leave my New York City apartment and walk the same way every day and about a block away I would pass the landscaping crew that would be working on beautifying the front of this building and every day, unless it was pouring or like snowing, this man would say good morning, have a nice day. It did not matter if he sensed someone was walking by, he stopped what he was doing and said hello. And over years I mean it was years that this man said hello to me until he retired and over the years it really occurred to me like what an impact he had on me in such a small, profound way of just one letting me know that I mattered and I existed. And walking by and so much of leadership is displaying who it is that you want to be and therefore giving other people to be the same way. And what would be possible if we offered that level of kindness to the people that we're meeting with and the people that we are engaging with. Even if it is a tough negotiation Negotiations don't always have to be aggressive what if we came from kindness that authentic leadership isn't about proving what you know? And I understand sometimes it feels fearful or vulnerable to not be in the know. No, and I understand sometimes it feels fearful or vulnerable to not be in the no. But what if you create space for yourself to breathe and learn, and also for others and grow. I'll ask you who in your daily life might be an unexpected teacher and what insight might they offer you if you paid a little bit closer attention. Leadership is not about just doing action right. I offer you that leadership is about watching, in a world that values actions. Leaders often feel that they need to speak direct or like decide quickly, and some of our most valuable leadership insights come from simply observing.

Speaker 1: 4:25

Ready for this one, I recall a time where I was newly promoted and then transferred into a different business unit in order to lead a new team, we'll say. And there was a huge client meeting and it was on my second day in the business unit. They did a completely different action and work than what my previous business unit had done. And the morning of this huge client meeting, the boss told me that he wasn't attending and that's a completely other story for another time. But he had prepared the presentation, and this is now again two days on. The job was not a reason to reschedule. He was like no, you're going and you're giving my presentation. I'll just tell you. I'd love to tell you a hero story here. It was an absolute disaster and, yes, I had barely time to review the presentation in the taxi on the way over to the meeting and I completely fumbled through it. But it was also the day that another teammate had started with the company, so their first experience was this disaster of a meeting and me witnessing my messiness and my failure. I never recovered with that employee and again, that's another podcast for another time.

Speaker 1: 5:45

But when I think back about my accountability and my role in this, is what if I went into that meeting with curiosity instead of someone else's script? Again, I was told under no uncircumstant turns that this is the presentation I'm to give and this is what is expected of me. And it's understandable that I would be nervous and I'd receive no training, no support. Again, I'm effectively two days into the job, even though it was a rotation within the company. And yeah, sometimes things are completely unfair and, as one of my mentors would say to me with one of the best Southern accents you could possibly muster up, would that be the state fair or the county fair, because there ain't no fair in business. There's been plenty of never been done before experiences.

Speaker 1: 6:36

It's called life Jill and the client was informed by my boss that he wasn't coming and that she was getting the new person. I could have used that time to build a relationship with her rather than talk at her. I could have asked her questions about the business challenges she was receiving or that she was going through. Based on the little bit of a brief I received. I could have had her talking and then used the presentation as a little bit of an outline and touch in and out or weave in and out of it versus oh, I was told to give this presentation, I have to give this presentation. I mean, it's just such a ridiculous amount of pressure that I put on myself to think that within what? 40 minutes of getting a presentation, knew on a job that I was going to go in and excel there. And yes, there was of course, the risk then of going back to my boss and saying I didn't give that presentation. But I feel like creating the win with the client would have been a better approach. But I feel like creating the win with the client would have been a better approach. But I couldn't see that in the time I could have tapped into my training of all my years, even as a certified meditation instructor. Right, I could have tapped into my years of intuition and noticed that I was presenting to her versus engaging with her.

Speaker 1: 7:55

I was so wrapped up in I'm in charge, I have to lead, and my desire to look good that it meant I lost my ability to see the situation differently or recognize patterns and look. Sometimes the most effective leaders need to say the least and notice the most. Great leadership isn't just about taking action or making moves. It's also about making the right moves at the right time, which comes when you slow down and start listening right. Two ears, one mouth use them proportionally. So you might be thinking God, jill, you're being very hard on yourself. All right, maybe I'm definitely Gen X, so I think we tend to be a little tougher on ourselves. But I like that. I strive for excellence. I like that. I strive to maximize efficiencies and create the best relationships. In all, how can I up-level a situation whenever I'm in it? I like that about myself, I tell you. The good news is I never made that mistake again.

Speaker 1: 9:00

I always went for building the relationship and the connection first, versus being like wall of information, like my friend Jay calls it. Let me be in thought leadership mode and be the wall of information, the expert with all the data and the points. I forgot who I was in the moment of being nervous, and again, that's the part of grace I do give myself. Of course, this would have happened, but now that I know in retrospect, building this in the rear view mirror, my top strengths are futuristic, intuitive empathy, the ability to spot patterns and trends and behaviors and reactions. That's my excellence, or one of my excellence. It's what has always made me an excellent strategist, but I tossed that all out the window because I had to look good and be the leader. So I'll offer you what do you notice and what might you have missed before?

Speaker 1: 9:55

Listen, you don't need to go back through all the archives of your experiences, but if you pulled out a couple of recent experiences that you didn't feel so great about and really looked at yourself and thought, how much in that experience was I listening and observing versus leading and doing the talking and part of observing, you could absolutely ask questions. That's what I'm saying Listening, observing, asking questions, being curious. So that would be one of the first things I would say. That, like in the classroom, is around you, everywhere. You can learn from everyone. So where are you finding those points?

Speaker 1: 10:26

Next is the thirst for knowledge. A lot of times leaders feel that they're in charge and that they've got to keep doing and practicing what they know and like doubling down on that. Great leaders never stop learning. You are actively seeking new ideas, challenges, want to challenge your own assumption and continually refine your skills. Some of my best insights came from gospel choir practice or botanical formulation and yes, I have very diverse hobbies. But reading business books, exploring psychology, philosophy, art, history. I used to take my team once a quarter to a museum where we had a day where we were just going to wander through a section of a museum to get inspiration and that was part of our time to be in possibility and inspiration.

Speaker 1: 11:18

Can you surround yourself with more diverse thinkers? Right, diversity is amazing. It's diversity of thought as much as it is representative diversity. You are going to learn from other people's lived experiences. If, again, you be quiet and actually start observing or asking them questions and being curious, can you build a network of people who think differently than you but you have an agreed level of respect that we're not here to antagonize each other and to have disagreements. We're here to sort of be in a philosophic conversation and a debate. It's not about winning or someone being right or wrong. It's about opening your mind to different possibilities, because I often find it's when you step away from those conversations and marinate on them is when you find new insight. Can you include new or younger employees or less experienced employers, or even those from outside your core industry into your set of diverse thinking?

Speaker 1: 12:19

And then also asking for feedback. I mean, sometimes you probably have heard the expression feedback is a gift, even if you want to punch yourself or the person. You don't have to agree with the feedback. You don't have to implement it, but hearing from your team, your peers or, again, even competitors, can reveal blind spots and spur innovative thinking. You need to be intentional and make learning part of your practice and ensuring that in order for your leadership to continue to evolve in the high velocity of business that you need to be also evolving with the world around you, and the only way you do that is by bringing in diversity of thought. Then I also want you to think about applying what you learn.

Speaker 1: 13:01

I keep what I call a leadership log and I've created it in Notion. It's basically a repository that helps me remember all that I've absorbed. Sometimes I have a gut feeling that something is significant, but I don't know why and I don't know how I'll use it. This can be a quote, it can be a concept, it can be a book, it can be really anything. This has served me incredibly well and, yes, this information potentially could be searchable, meaning I could go Google and try to find that quote again, but it's not going to have my thought around it, my IP around it, and I certainly can't tag it in the way that I want to in order to bring it back up for a later date.

Speaker 1: 13:43

For the last 20 or so years, I've evaluated myself weekly. I learned from my own brilliant brain that has created multi-millions of dollars for brands and businesses and people. And how can I learn from my brain and show that I can apply what I'm learning? In order to scale my career, I have to scale my brain and show that I can apply what I'm learning. In order to scale my career, I have to scale my brain. So, in addition to an evaluation, which is like what worked, what didn't work, what would I do differently, I'd also offer having some sort of weekly reflection where you ask yourself what did I learn about leadership this week? How can I apply this lesson in the work or the project or whatever initiative is in front of me, and then who else might benefit from this? Or can I bring this concept to my diverse thinking group and we can stretch and pull on it a little bit?

Speaker 1: 14:35

Your classroom is everywhere. Are you paying attention? The best leaders in the world do not just lead, they are continuous learners. Their education never stops. You can get it from your colleagues, your team, your competitor, your challenges, your neighbors, your gospel choir groups. All of it is a constant classroom.

Speaker 1: 14:56

Every conversation, experience or setback is an opportunity to reflect and refine who you want to be as an intentional leader in this world. Friends, who you getting your coaching from? I would love to be your executive coach and your leadership strategist. You can find all my information in the show notes. You can also check out my website, where I list everything and explain to you how I work, and I'd love to meet with you. If you have any thoughts or feedback on this particular conversation, email me at hello at jillgriffincoachingcom. I want to hear what is the most unlikely source. You've heard a leadership insight or a bit of wisdom from. Makes it fun. Share your story with me. I'd love to hear it Again. Hello at jillgriffincoachingcom. All right, friends, have a great week, be intentional, reflect. Learning is everywhere and be kind. I'll see you soon.