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Leadership Insights

By Trever Cartwright

Over the years, I’ve worked with many different clients with many different challenges. Along the way, I’ve been fortunate to learn and gain leadership insights from every matter I’ve had the opportunity to tackle. The insights below represent a few of my greatest takeaways.

 June 18, 2018
Leaving our Marks

I struggle with graffiti. Not street art, which aims connect and inspire us as a community—but the vandalism left behind by a misguided index finger and a can of spray paint. The mark it leaves is durable. It’s hard to ignore and it’s not easy to erase. So it got me thinking. Every day, as we do our best to journey the many twists and turns of our busy lives, we leave an enduring mark in the lives of others. We leave a mark on our families, our friends and our co-workers. We leave a mark on the myriad strangers we brush past each day as we rush to whatever’s next—do we nod and say hello? Or do we look right through them as though they were invisible? The marks we leave are uniquely our own and entirely ours to make. Whether we’re the vandal with a spray can or the stranger who says hello, our marks are durable. They’re hard to ignore. And they aren’t easy to erase. Knowing this, it makes sense that we leave them with care.


May 28, 2018
The bright, thin line

Each day, in our business and personal lives, we have many interactions with others. Some interactions are remarkable. Others are unremarkable. The remarkable interactions linger and leave a lasting impression. Sometimes we’re left stunned by what we just heard or observed. Other times we’re left uplifted and inspired by another’s grace and decency. Both experiences are remarkable, but for very different reasons. A bright, thin line separates one from the other. A friend of mine describes this unmistakable distinction as…too important to be good, or too good to be important. Let that roll round in your head for a moment! From time to time, each of us can find ourselves standing on the wrong side of the thin, bright line. The good news is, it’s up to us which side of the line we plant our feet.


May 23, 2018
It’s not a position. It’s a mindset
How do you define leadership? It seemed like a great place to start a two-day program I was facilitating called Leadership at All Levels. The response it drew from one participant was swift, heartfelt and direct: “I don’t know why I’m even here. I’m not a leader.” Then others in the group piled on with similar sentiments on the question. “I don’t make decisions–so how would I know what leadership is?” Only five minutes into the program and we were…in it…deep. The group’s pointed questions surfaced the core point of the whole program before I’d even turned the first page of my notes. Here it is: Leadership isn’t a position. It isn’t a title on a business card. It isn’t tenure in a company. It’s a mindset–a way of doing and a way of being. It happens at every level of an organization–not just at the top. We don’t need a corner office to prove we’re one and we don’t need anyone’s permission to call ourselves one. We lead when we take initiative. We lead when we make time for others. We lead when we listen.


May 21, 2018
The liberation of perspective
There is always a different perspective worthy of our time and consideration. When our minds are both willing and open, we’re able to escape our self-affirming stories, our comforting biases and many reasons why (or why not). When we make it a priority to seek it out, listen to it and give it an honest chance, the liberation of a different perspective makes our best decisions possible. Without the wisdom that comes from perspective, any good decision we make is nothing more than good luck.


April 29, 2018
Gradually, they become
Change is messy. Getting it to stick is packed with nuance. At the first hint of change, an organization’s culture can be a worthy opponent—one that should never be underestimated. Its job is to stand guard. To dutifully protect the way we’ve always done it, or the way that makes us feel safe, secure and comfortable. Though the headwinds of an organization’s culture are a powerful force for any leader who sees a different path and has the courage to take it, in time, it can be convinced. When a leader has the perseverance to lead the way, and the willingness to slog through the swamp with her people, the headwinds that initially seemed impossible gradually dissipate. The nuance: Cultures evolve. They don’t change. Gradually…they become…


April 24, 2018
Pay it Forward
It’s the second time it’s happened in the last 30 days. Somehow, I’m on a roll where I’m losing my wallet–I seem to be getting really good at it. Both times a good Samaritan went out of their way to reach me and let me know they found it on the ground outside my office. One even personally delivered it to my house. The other tracked me down through Facebook. The point is twofold. First: There are good people in the world (and it’s important to be one of them). Second: Gratitude feels good (and it’s a worthy virtue). Acts of kindness like these happen all around us, all the time, every day. Let’s not let them be overshadowed by the grind of our lives or the busyness of our days and be mindful that feeling grateful is a good reminder of how important it is to stop…and pay it forward.


April 17, 2018
Try Something Different

Think about the last few meetings you were in. At any time, were you inspired? Were you curious? Were you even interested? If the answer is no, no and no. Then it’s fair to say something needs to change. Your time is too valuable to waste. The next time you find yourself in a meeting struggling to mask that nagging, ever-present yawn or wiggling yourself awake while silently pleading for it to finally end, try something different. Rather than placing all the responsibility for a great meeting on its leader, take responsibility for asking an interesting question. In an instant, that glacially paced meeting won’t seem so bad. You might even leave inspired.


April 5, 2018
When the Mood Strikes
Today it’s funny. Yesterday, nothing was funny. Have you ever been in a lousy mood, but weren’t quite sure why? That was me. After the mood from hell became apparent–to just about everyone–I tried to fake a good mood–I made small talk, acted interested in conversation, became overly agreeable. All this did was make matters worse. I just felt..frustrated AND moody… and kept demanding of myself to make a darn decision: am I in a good mood or a bad mood? This self-imposed ultimatum got me thinking. Who would actually choose a bad mood? We work with people and their moods all day long. I bring mine. You bring yours. We toss our collective moods into the ring and, more often than not, they mix well and it all works. When they don’t, it’s not the end of the world.  With some perspective, we’re able to see them for what they are–they’re just moods. The good news is that, tomorrow, yesterday’s bad mood will likely give everyone a good laugh, including yourself. The next time the mood strikes, give yourself some space…and choose it. Good or bad, we’re all human. Whatever your mood, it will pass.


 March 31, 2018
The Price We Pay
The world doesn’t work like it used to anymore. At 53, I’m reminded of this every day. Whenever I reach for my reading glasses, grab hold of anything solid for help to stand, or brace to cushion the force of a sneeze, I know the world is…different. Not bad. Just…different…than it once was when such precautions weren’t necessary. Despite the annoying aches and pains and the need to work harder and harder at the gym just to maintain, the good news is that, with age, a new world emerges–one that works if we let it. Life brings with it valuable experiences each day. When added together over time (and when we put our glasses on to see them for what they are), these experiences become the insight, perspective and clarity we need to show up with unique confidence and ease.  We’re able to accomplish things we weren’t capable of before. We relate to the world and the people in it in a different way than we once could. If age is the price we pay to earn this level of thinking and being, I’m happy to brace myself…and pay it.


March 26, 2018
The Reward
Cedric Porter was an Episcopalian minister in Nevada City, California. He was also my grandfather. Though I didn’t know him well—I was four when he passed—family lore has made him a familiar presence throughout my life. A few years ago, I read through several of his sermons. Some he had handwritten with his impeccable penmanship, others he painstakingly typed with a typewriter that had a faulty “t” key. Though each was remarkable, one in particular, written in August of 1957, caught my attention. I committed a portion of it to memory and have since inscribed it on the entryway wall of our office. In his own words: “The strength of any organization is but the strength of the ideals that motivate it. Its influence is only as great as the constancy with which its members endeavor to uphold those ideals and to make them a part of their daily living.” He packed a lot into these two sentences. For me, three words rise high above all the others: Ideals. Strength. Influence. In that order. Gradually, organizations earn their strength and influence. Neither comes easily. And neither can be taken for granted. In fact, both are fragile. Yet, with enduring ideals, an organization that is both strong and influential becomes the reward. If you ask me, that’s a reward worth striving for.


March 21, 2018
A Wake Up Call
I had a wake up call today. It was one of those cringe-worthy moments many of us as leaders have had when the truth of how we show up floods in like a tidal wave. I approached one of my team members and quietly said, “I’d like give you some feedback.” Her reaction told whole story. Without hesitating, she picked up a pen, took out a pad and, and with a look of dread and disappointment, said, “Uh-Oh.” She was certain she had done something…wrong. Why else would I give her feedback? The twist in all of this was that she hadn’t done anything wrong at all. In fact, she had done everything…right and I wanted her to know. This wake up call had me reflecting on how I spend my time as a leader–more specifically–the quality of the time I spend. As leaders, we’re afforded only so much time in a day to make a difference. Wake up calls–in whatever form they take and within whatever context they occur–are welcome reminders of how important it is to make it a priority to spend the time we have more wisely.


March 7, 2018
The Value of Hope
It’s been a while, but the conversation still rattles around in my head. A friend and I somehow landed on the topic of beliefs. She asked me what I believed in. I began sharing some of my beliefs. I shared that I believe in being a decent person. I believe there aren’t important people and unimportant people. I believe we often sell ourselves short when it comes to embracing what we’re really capable of. The next belief I shared brought her to a full stop. I said I believed in hope. She was floored. HOPE? REALLY? YOU BELIEVE IN HOPE???!!! THAT IS SOOO WEAK! The conversation didn’t last long after this. I was surprised by her reaction. And she was surprised by mine. Was I really getting into an argument about hope? Yes–I do believe in hope. I believe without hope the world is truly and literally hopeless. As a business owner, I can tell you, having hope from time to time has served me well. As a human being, hope has been a welcomed companion in my life’s journey. I have hope for my friends. I have hope for people I don’t know. I have hope that my next meeting will go well….Yes. I do believe in hope! I believe in its humility. I recognize, though, that hope alone is not enough. Hope, mixed with personal will and accountability, in my opinion, is a good combination.


February 28, 2018
Take a Stand
When was the last time you took a stand on a matter that had some risk associated with it? We saw evidence of this today when Edward Stack, the CEO of Dick’s Sporting Goods–one of the nation’s largest sports retailers–immediately ended sales of all assault-style rifles in its stores. Arguably, this decision demonstrated personal courage and conviction–whether you’re for guns or against them. There’s a bigger lesson here for each of us who aspire to be strong leaders–it has to do with having the fortitude to make a hard decision and the courage to take action on that decision. No waiting periods. No floating the idea to assess the potential penalty to be paid. No handwringing over certain blowback.  In our own organizations, being willing to take a stand and hold your ground is not always easy–but, at times, necessary. It’s easy to confuse being unmovable on a particular matter with being unmovable as a leader. Think about it–there is a difference. Sometimes, you just have to say…this is where I stand…and be okay with it.


February 25, 2018
Find Your Grit 
Got Grit? It’s one of the most important characteristics any leader or entrepreneur needs in order to cause their vision to come to life. One step forward may often be followed by two steps back…or even three. But, for the leader with grit, two or three steps back isn’t seen as a reason to quit. Two or three steps back is simply a welcomed opportunity to better prepare for the big leap forward.


February 22, 2018
Shake Things up a bit
Five-year-olds are among the most hopeful, bold and visionary beings I’ve ever been around. Ask a five-year-old what he wants to be when he grows up…”an Astronaut.” Ask another and she’ll tell you with absolute resolve…”the President.” How is it that these incredible young minds can be so clear? So intentional? So unreasonable? So unconstrained? How can we not respond with anything less than our total assurance and belief that, he WILL become an Astronaut? Or that she WILL become president? As leaders, we would do well by taking a lesson from a five-year-old’s playbook. Shake things up a bit! Ask yourself what you (and your organization) might accomplish if you risked being truly bold and visionary.


February 16, 2018
Office Politics
Think for a moment about the office politics at play in your organization. Every organization has some level of politicking going on–it’s a byproduct of any human system. We play the part of office politician whenever we get that feeling in our gut that something needs to be said–when the words teeter at the tip of our tongue–when we clear our throat and begin to say the words, but stop ourselves just in time–and say…nothing. Instead we choose to stoke the fires of the stories we tell ourselves, or the stories we tell our coworkers.  Think of it this way: Office politics is an individual choice. Your choice. The next time you get that feeling in your gut, rather than hold back, say the words. Create the space for your words to be heard in a constructive way. Don’t use your words as weapons. Say the words because you care more about the team than you do about being a politician.


February 13, 2018
No Leader is a Finished Product
When it comes to leadership, none of us is a finished product.  Learning to lead is a lifelong journey with no destination or end point–just lots of twists and turns along a winding road. If we keep our minds open and approach the practice of leadership with a spirit of curiosity and a desire to make a difference in the lives of those we work with…eventually we get better at it. If you’re the type of person who believes being the best leader you can be is important, then you’re well on your way to becoming an even better leader tomorrow than you were today. The journey is worth it.


February 8, 2018
Old School Industrialist vs. Iconic Ingenuity 
What an accomplishment this week achieved by SpaceX. The successful Falcon Heavy launch and its safe return represents an exceptional milestone and, perhaps, the beginning of a new era in space exploration. What a contrast to watch this amazing display of iconic ingenuity and determination along side what, sadly, continues to unravel at Amtrak. I don’t know Richard Anderson, Amtrak’s new CEO. I do know he has his hands full–and I can only imagine the pressure he’s under.  Last summer, during an interview on CNBC, he was asked about Elon Musk’s Hyperloop plans–the system that would make travel between LA and SF possible in 30 minutes. Anderson shared that, while he didn’t think it (the Hyperloop) was possible, he was glad there were people who dreamed about things like this. He went on to describe himself as more of an old school industrialist who is more concerned about cashflow and return on invested capital.  This is a critical leadership moment for Anderson. The future of Amtrak is in a free fall. Great leaders become great because they’re willing (and able) to dream. Spreadsheets won’t help Amtrak. A leader with a vision and the courage to set that vision into motion will.


February 6, 2018
When Leaders Drive Hard, Then Drive Off
Years ago, a good friend and colleague shared a point of view I thought was compelling. He said, “…Leaders often drive hard, then drive off…” Over the years, I’ve shared this thinking likely hundreds of times with clients of my own. It paints a vivid picture of what often happens in organizations going through change or simply working hard to implement their strategic plans. One of the most important responsibilities a leader has is to co-imagine (emphasis on “co-“) the future and then endeavor to inspire the collective heart and mind of his or her organization–to enthusiastically tell the story of the important role their organization will play in the world or in their community. As leaders, it’s easy to get wrapped up in our own stories of what’s possible. It’s a lot harder to take the time to actually bring our people with us on the journey forward. It’s okay to drive hard–in fact it’s a good thing. While we’re driving, we just have to remember not to leave our team behind, lest we risk arriving alone.


January 30, 2018
If Your Challenge had a Voice and Could Talk
Every leader faces tough decisions. Some are big and the stakes are high. Others maybe not so big, but still important. The next time you find yourself struggling to make an important decision, or you find yourself staring at the ceiling at 2AM wondering what to do, ask yourself this simple question, “If this (situation or challenge) had a voice and could talk, what would it say it needs most from me right now?” The answer this perspective-building question reveals will likely come quickly and clearly.


January 24, 2018
Should I ask or Should I Tell?
One of the most important things a leader needs to ask themselves at any given moment is this: Should I ask, or should I tell? Knowing the difference between the two and which would be most effective given the dynamics of the moment or the challenge at hand is often what separates a good leader from a great leader. Many times, the right question well-timed is tenfold more valuable than the right answer too soon.


January 17, 2018
A Sliver Bullet
It’s not uncommon to have some tension with a co-worker. Maybe they said something that triggered a reaction in you. Maybe you said something that triggered a reaction in them. Sometimes the tension lingers on and on…for months or even years. In our work with organizations, we’ve found there’s a tool that can fix useless, energy-draining drama like this. With practice and when used with good intentions, it’s a silver bullet for cutting through layers of organizational muck–a way to squash it once and for all. And everyone, even you, has this amazing tool at their disposal. This miracle tool is communication. Nothing gets fixed without it. All it takes is the will to use it.


January 13, 2018
Two Cultures
In every organization there are always at least two cultures at play: the leadership culture and the employee culture. The most effective organizations are those led by leaders who recognize this universal truth and make it a priority to understand the composition of their gap and then work to keep it as narrow as possible. Take some time to reflect on what’s contributing to the leadership/employee gap in your organization–those gap-creating dynamics that are keeping it from realizing its full potential. Get clear on the range of steps you can take to narrow the gap. Get focused on right ones to take.  Then get moving. Lastly–your goal is not to eliminate the gap because there will always be one. Your goal is to keep it as narrow as possible.