How To Spot A Secure Leader

The title leader can be given to anyone.

But the term leader and manager are worlds apart.

Most managers were promoted because of seniority or selected because of their technical prowess. Two of the many wrong reasons to become a manager.

Micromanagers are so rampant because the wrong skill sets are glorified. Individual performance isn’t a clear indicator of potential leadership. Using a sports analogy, the best player on a team isn’t automatically the MVP.

The difference between a secure leader and an insecure manager is encapsulated in the following statement:

How willing are they to implement other’s ideas?

Working with youth was my first introduction to leadership development. I remember planning a 6-week summer camp. I came prepared to share the weekly topics I felt were best, but then it hit me, “in order for the youth to feel empowered I should choose their agenda (ideas) over mine.”

At the time I thought it was a subtle gesture, but it turned out to be the difference between recruiting teenagers and developing young leaders. Because I let them choose the topics, they put way more effort, creativity and were much more motivated to run a great program.

Back to the sports analogy. Imagine you’re the coach of an individually talented team. You’d think your job is to throw your team out there and just let them figure it out. Although that’s not a bad strategy, the better one is to identify the strengths of each player, then put them in a system that allows them to shine in a customized role. The coach’s job is less about managing talent and more about governing egos. Leaders allow their people to thrive because they’re focused on eliminating distractions so they can maximize performance.

A manager’s role isn’t to puff his/her chest out trying to be the best. It’s about serving the people under them by trusting their ability to make the best decisions. In the age of infinite information what gets lost is people are your greatest asset, not data.

The simple act of hearing your team out and choosing their ideas over yours will increase morale and retention tremendously.

Why is this act so powerful?

Because it takes a secure leader to know he/she doesn’t need to be the smartest person in the room, only smart enough to empower the ones who make you look good.

Why Coaching Trees Don’t Work


There’s a belief out there that leadership can be taught. Skills yes, but replicating no.

Take for instance two all-time basketball coaching greats: Phil Jackson & Mike Krzyzewski.

Both have disciples trained under them, yet given head coaching duties the success rate isn’t nearly as high. Why is that?

First of all, people can’t be scaled. You can have a mentor, but the goal of the mentee should never be to clone their model. Leadership is grounded in self-awareness so your style needs to be conducive to your personal strengths. You can’t be anything you want. You can only be the best version of you.

Second, there’s an art of leadership that is instinctual. Almost impossible to teach. Both Jackson and eventual Coach K successors have huge shoes to fill. Their replacements will be forever compared to their career success. Unfair as it is, each leader has to create their own legacy. Leaders are less focused on who came before them and more locked into where they want to go. As technology improves so does the sharpening of people skills. In sports the truly great coaches have a sound strategy, but what sets them apart is their ability to manage superstar egos. No book, online resource or manual can teach you that. You learn best through experience and since each individual is unique there’s no formula for optimal results.

Third, confidence in vision. Many would argue charisma, but that comes from a strong belief in self. The confidence in vision needs to be strong enough to take the team to a level even the leader hasn’t reached before. A leader’s vision should be bigger than themselves which further defends the idea of focusing on the future instead of looking back. Vision casting can be taught, but the size of the goal is directly tied to the confidence of the leader. Most successors aim to maintain past standards, but that’s peering in the rear view mirror. Beyond prior records, data and research, leaders must push on regardless of the struggle. That type of perseverance is a character trait developed over time.

Leadership development is real, but not as simple as following a set number of rules. Great coaches create a legacy that can’t be caught. Besides observing and having a deep appreciation for great leaders, it’s about identifying your greatest strengths and leveraging those on a daily basis for maximum results. Coaching trees don’t work because humans are too dynamic to be simplified down to a system. Train up leaders, but give them autonomy to spread their wings in the way they choose. That’s how a tree really blossoms.


The Future Of Leadership


You may think this is about a new type of leadership, but it’s not.

The future of leadership has more to do with “where” than “how.”

It’s remote.

Flex-time or working from home is here to stay for many reasons: less distractions, no commute and becoming new parents. But the heart of remote leadership lies in trust.

Think about it. What people hate is being micromanaged. That usually happens when your boss is “looking over your shoulder” expecting you to do the work a certain way.

Working remotely completely diminishes that. Responsibility and self-discipline becomes a two-way street. Bosses need to be clear about what needs to be done. Workers need to make sure tasks are accomplished.

Being stuck to a location limits your talent community and allows for two extremes: micromanaging and hands-off leadership. Neither are beneficial for the company.

Not being in the same physical space forces both sides to focus on what matters: finishing the work while leaving out what doesn’t: how it’s being done.

A great way to test out remote leadership is at your office before you make the transition. Working remotely saves time and money, but most of all it provides what we all want more of: autonomy.

Are you a part of the future?

Why Artists Make Terrible Producers


Listen up aspiring/current entrepreneurs.

Imagine you’re a singer. You don’t write the songs or create the music, you just sing the song. The producer on the other hand never performs on stage, but they definitely run to the bank every time you open your mouth.

Neither is better. Just different.

For some reason 9 years ago when I took the leap from working for a boss to being my own, I thought I had to be an artist. The irony is while being employed I was a much better conductor than performer. Why did I make the shift: ego, naivety, achievement-oriented? All of the above.

Most of us do one role really well and the other one not so much. In my case I love coaching individuals, I’ve gotten much better at speaking and heck I even wrote a book. But I got away from what I do best and makes the biggest impact.

The latter matters more than the former. I’m a huge believer in strengths. Figure out what you’re great at and do more of that. The artist in me strayed away from the advice I’ve been giving, but the producer is aiming to get it back.

What I love most is: leadership development. Most of the time it happens through an organized program. As much as I love being directly involved, the biggest impact happens when the effort is multiplied through other leaders (think Uber driver vs. Uber, the company).

In a society where personal branding is mainstream it’s hard to step behind-the-scenes. But if you’re truly a producer, want to scale your idea and desire greater impact the shift from artist to producer must happen.

So choose the role that better fits you: artist or producer. Then proceed and make sure to stay in your lane.

3 Ways Leaders Are Willing, Not Ready


Are leaders born or made? That’s a debate this article can’t cover (in under a 1000 words) so I won’t go there. Everybody wants to be a leader, but if you knew what it really entails you might change your mind. In previous positions I’ve held, I learned over time that leadership isn’t as glamorous as advertised. In order to be an effective leader you have to be willing to absorb the following 3 things:

1) Willing to Take The Blame – If you want to lead, you have to accept being the goat. Not the “greatest of all time,” but pointing the finger at yourself when your team fails. It may not be your fault, but when something goes wrong people usually point “up.” I remember a time one of my staff members said something insensitive during a presentation and one of the audience members expressed their displeasure to me immediately. It wasn’t my mouth that this inappropriate comment came from, but after discussing it with my colleague, I decided to publicly apologize to the crowd. I wasn’t thrilled about it, because it wasn’t my “fault,” but it was under my watch so I took the fall for my team.

2) Willing To Deflect Praise – If you love getting credit for success, get out of leadership. Books, media and social networks paint a different picture, but rarely do leaders get praised when things go well. In fact, the better you get at leading and the longer you do it, it becomes an expectation (not appreciation). It’s like the obedient, older brother who gets overlooked by the prodigal son by his father. “Hey, I’ve been doing great all this time, but now this delinquent boy comes home and you give him a party?” Thanks for noticing. Not only do you have to take responsibility for your team’s blunders, but you also don’t get rewarded for achievements. Leadership isn’t all what it’s cracked up to be.

3) Willing To Follow – Maybe the hardest lesson to learn as a leader is managing your ego, not the egos of others. I learned this as a coach. Sometimes you’re right and they’re wrong, but you still go with their decision even when it turns our bad. Why? Because leadership is about developing people. If you make all the decisions, followers become dependent on the leader and never learn to soar on their own. When you delegate responsibility/let your team make decisions and live with the outcomes, they become leaders during the process. It’s not about telling people what to do and enforcing it. That’s called dictatorship. It’s why we hate micromanagers. The best way to illustrate this concept is an inverted triangle. The leader is at the bottom and his/her job is to support the people “above” them. Serve up and you’ll never fall down.

The better question to ask when it comes to leadership is: are you willing? Leadership is not for everyone and that’s okay. There can only be so many chefs in the kitchen, then it becomes too chaotic. Leaders are thrown into situations where they aren’t prepared all the time. It’s about knowing yourself, knowing your values and knowing your role. You don’t need an official position to lead, you just have to be willing to do the tough things and not get applauded for it.

Winsight Episode 44: Developing Potential

nba draft lottery


With the NBA Trade Deadline passed and the Draft ahead of us for all major sports what’s our fascination with young, untapped potential?

In this episode, we’ll talk about developing potential and how to do it through the following example:

When does potential get realized? Is there a time limit?

Potential is based on expectations, but you can also change the trajectory by your work ethic & teaching

During the recession in late 2008 the first thing to go was training & development. What was the long-lasting effect of this decision?

When it comes to developing our own potential, how much responsibility is our own?

For the answers to the above questions, listen to the podcast! After you do, we’d love for you to leave your thoughts below!

Winsight Episode 42: Succession Plan

succession plan, leadership development, pass the baton



Have you thought about who your “replacement” is? It doesn’t matter if it’s a formal position or just someone you see potential in. What matters is that you want to invest in someone.

In this episode about succession planning, here are the points covered:

– In sports, teams are always rebuilding with new talent

– Similar to the corporate world, building your talent pipeline is crucial because the knowledge will eventually “leave the room”

– At the heart of leadership development, who will take your place?

– This is bigger than you, so who are you investing in?

Think about who is your successor. What will you do this week to engage that relationship further?

Winsight Episode 26: Leading the Current Generation

millennials, gen y, talent development and retention, entitled, startup generation, emotionally reactive



Millennials. A single word can conjure up varying descriptions and emotions. Some of the stereotypes about this generation are true, yet others are not. Instead of sitting here and complaining about the shortcomings of this group, I prefer to point out how to lead them effectively.

In this episode the following points will be discussed:

  • Why teaching isn’t about being the “best in your field
  • How body language is a warning sign for motivation
  • The two types of vision that need to align
  • What Baby Boomers and Millennials have in common

Does this change your thoughts on Millennials? What adjustments will you make dealing with Millennials going forward?

Winsight Episode 7: Developing Leaders



Leadership is a buzz word and everyone wants to be a leader. The truth is a small percentage of people are actually leaders. Now you can learn leadership skills, but that doesn’t make you a leader. You can hold positions, but that doesn’t make you a leader. Personally I fall much more on the side that a leader is born not made, but today’s episode isn’t going to tackle that dispute. Today, I’d like to share my personal thoughts on the difference between leadership and leadership development.

Through personal examples and stories I’ll share:

  • The second tier of leadership
  • The inverted triangle and how it changed my leadership style
  • How deferring on a hiking trip won a popularity contest
  • How leadership math works

As a leader what type of legacy do you want to leave? How does your style affect others? Share your positive and negative examples below so others can learn from your example!

developing leaders, leadership development, coaching, winsight podcast, coaching leaders, lead by example, managing vs. leading