Letters to my sons

A collection of thoughts and lessons I've learned along the way for my little men, and anyone else that's interested.

Posts tagged with #Leadership

My sons,

From the moment of birth we are exposed to a vast array of environments. These environments have a wide range of variations. They can vary in formality, in size, in structure, in purpose. They can be professional environments of learning and productivity or personal environments of friendship and trust. They can be seasoned environments such as a childhood friendship that has aged well over time, or can be young and temporary environments like a hasty summer romance that burst into view only to fade from existence with the falling of the leaves.

Regardless of their variation, every environment we are in has the potential to be incredibly empowering and life-giving or to be terribly oppressive and stifling. Further, an environment can change drastically and quickly, sometimes without warning and seemingly without reason.

But there is always a reason. There is always a cause. Whether intentional or not, environments (or their modern, professional term “culture”) are shaped by a myriad of factors.

We’ve been discussing the concept of empowerment lately; today we’ll take a deeper look into empowering environments, their key ingredients, and how as leaders (official or otherwise) we can intentionally shape them.

What is an empowering environment?

There are many definitions out there of what empowering environments look like, and there are many contexts to which they apply. Each of these definitions has their uses and merits, and I’m not going to dispute any of them; rather, I’ll offer what I hope to be a useful generalization that applies across all walks of life.

An empowering environment is one in which every individual is free to express and to act in a respectable and appropriate manner without fear of retribution and unjust response. Said environment promotes the equality and equity of all its members, and creates space for meaningful dialogue and mutually beneficial encounters.

Said simply, an empowering environment is one where you can be yourself without fear of being judged unfairly.

Empowering environments have a number of things in common:

  1. They promote diversity of thought and opinion. Regardless of background or experience, empowering environments value the thoughts and actions of any individual objectively. They foster open and unbiased discussion and allow all ideas to be considered, regardless of their origin.
  2. They are supportive of mistakes. Empowering environments allow for mistakes to happen, and are built in such a way as to value mistakes with the knowledge that mistakes are a part of the learning process. There is no fear of retribution; rather there is praise for a chance taken, an idea investigated, and a calculated risk attempted.
  3. They are nonhierarchical. While there may be a physical hierarchy in place (for example manager/direct report relationship), those hierarchies are not leveraged as a value judgment, rather as a job description. Empowering environments allow for the truth that great ideas can come from anywhere in the organization or group.
  4. They allow for dissection to be expressed productively. Every group contain members who have differing opinions. Whether this is in the context of a family unit, a professional team, or a group of friends, there will be situations that arise in which members disagree. Empowering environments allow those disagreements to surface and to be discussed in a productive manner, and provide rules for tie breaking as needed.
  5. They foster and facilitate trust. Perhaps most importantly, empowering environments are one where trust is valued and nurtured. As a relational species, trust is one of the most important and valuable commodities we have. Empowering environments foster that trust, and readily promote and value the building of trust across its members.

What does an empowering environment do for its members?

Some of us may not have ever taken the opportunity to stop and think if we’re in an empowering environment, and as a result may not realize how drastically different and how immensely transformative such an environment can be. So let’s first take a look at a few symptoms of a truly empowering environment, with the understanding that this isn’t a black and white thing; there may be many environments and situations that we find ourselves in that are somewhere along the spectrum of “richly empowering” and “soul suckingly oppressive”.

A list (definitely not exhaustive) of ways to know one is in an empowering environment:

  1. One never has to question how their actions may be perceived. Now, I don’t mean the type of environment where one can be a jerk and not care about the consequences. I mean simply that if one takes a reasonable action that is well-intentioned and is intended for the good of the company/team, one never has to worry if that action will ruffle the wrong feathers, will come back to become personally detrimental, or will cause a chain of politically-focused events of which one will never know the details but will feel the impacts of their consequences. Empowering environments are psychologically safe environments where one can express themselves, can disagree, and can healthily move on regardless of the outcome.
  2. There is trust amongst the members. Trust is an underrated commodity in our professional and personal interactions these days, but it is the most important underlying fabric for any highly functional society. Without trust there can be no shared goals and wins. Without trust there can be no close relationship. Without trust there can be only marginal victories that are wrought with suspicion and underlying/hidden motives. Empowering environments not only value trust but actively seek to create trust amongst its constituents. This means that there are active actions taken to build trust, to reward those that earn trust well, and to constructively rehabilitate those that don’t. Trust is part of the leadership culture, and is an active action that leaders take steps to promote, grow, and cultivate in the group.
  3. One can spend 100% of their time on value-add for the organization. This one is nuanced, and may be controversial, but my belief is that in empowering organizations, one can spend all their time on what they do best without need of “managing up”, with the full trust that those in leadership positions recognize great impact and value to the group without the need for one to self-promote. This isn’t to say that communication of one’s efforts is unnecessary; rather this is to suggest that the communication is necessary for collaboration and effectiveness, and not for visibility and perception. We will expand on this concept in a later post, but for now suffice it to say that when one is in a truly empowering group, the term “managing up” disappears from view.
  4. The culture is one of abundance and not scarcity. It is true that scarcity breeds certain beneficial traits, but my opinion is that it breeds too many negative and undesirable traits that makes that view a dated and clearly insufficient view. (For more, Lazlo Bock writes a great exposition on this in his book, Work Rules. In contrast, a culture of abundance allows members to truly celebrate another’s successes and advancements without comparison or fear of one’s own opportunities. Leaders that own cultures of empowerment ensure that their members do not feel as though membership is a zero sum game.

Cultivating empowerment

So as leaders (of organizations, teams, families, friend circles, or any other type of leading role) how do we cultivate an empowering environment?

The short answer is that this is hard, and that there are no definitive answers. The answers depend on the environment that you’re in, and the members (and future members) of that group.

As someone who has spent the majority of the past two decades building teams, let me share some of my thoughts and ideas that have worked well for me(always open for debate, and self-identified as a small set of data points of which I’ve sought to compare with the greats; Bill Gates, Sheryl Sandburg, Satya Nadella, Ray Dalio, Bob Iger, Bill Campbell, Kim Scott, and many, many others).

It starts with you

I cannot stress enough how much of building a culture starts with you as the leader. If you want to cultivate an environment of empowerment, you have to first be someone that empowers others. As Julius Campbell (played by Wood Harris) puts it in Remember the Titans, one of my all time favorite movies:

“Attitude reflects leadership, captain.”

To build an empowering group culture, you have to model that for your group. Be self-critical. Examine your actions, your motivations. Surround yourself with believable people who will challenge you, support you, and most importantly will call you out on your bullshit.

In order for us to empower others, we must truly internalize the belief that enabling their success is better than accomplishing our own. We as leaders must value the organization and the group more than we value our own progress. We must be happy to be made obsolete as our team grows and as future empowered leaders step forward.

But most of all, we must be transparent. We must own it. When we make mistakes - this is explicitly not an “if” but a “when” - we must own it. We must be accountable and transparent with our group that we’ve taken a misstep.

Empowering cultures enable autonomy, but also promote accountability. The more we demonstrate that to our groups the more readily that culture seeps into each member and solidifies.

Surround yourself with people that amplify that empowerment

Make sure that those you surround yourself with are bought in and also care about the culture that you’re creating, and are themselves empowering people. Remember that the company we keep not only is a reflection of ourselves but is also a reinforcement of our values. We become more like the people we engage with regularly.

Be quick to get rid of the bad eggs

It only takes one bad egg to spoil a dozen. Remember that as a leader, team and culture are your most important priorities. As hard as it is to make the call to remove an egg, it’s your responsibility to do so. Do so quickly, but do so fairly. Get a few validating perspectives from your believable people, and then act.

Often what seems rash or an overreaction at time in fact in hindsight seems painfully obvious. More often than not, leaders wait too long to get rid of the bad eggs, and by the time they do much of the rest of the batch has already spoiled. Act swiftly.

A final thought

There are many dramatically different looking empowering environments out there, so it is impossible to describe any recipe or archetype to which all will adhere. I suppose the best way to describe an empowering culture is a phrase blazoned in history by Supreme Court Justice Potter Stewart: “I know it when I see it”.


My sons,

We live in an age where leadership is a quality that is expected at every level. From an early age, children are engrained with the notion that they are all expected to be leaders. They are taught the qualities and characteristics of a leader, and are put in situations where they are expected to demonstrate leadership. Then they go to college and are told that leaders are to be esteemed, and that they are the leaders of tomorrow.

It’s quite clear that leadership - and the attributes and character traits that go along with it - is highly regarded. It behooves us, therefore, to dig in and learn about this topic; to consider, to study, to debate, and to discuss, and in so doing, deeply enhance our own understanding of what it means to be a leader.

It is said that the true measure of a man is not how he treats his equals or his superiors, but rather how he treats those who are inferior to him. This inferiority can come in many forms; an inferiority in status, station in life, accomplishment, or even ability. It could be the cashier at the checkout stand, or the bellman who takes your bags. It could be the new college hire on your team, or the person who restocks the snacks in the office pantry. It could even be the customer service agent you had to call because their company messed up your order.

The truth is that the way we treat these people speaks volumes to our character. Treating those who may be beneath us with dignity and respect says a few things, especially to those in our organizations.

  1. It says that we believe everyone has the same intrinsic value. We tell people who may be in our organization that regardless of their current role, we will treat them with respect and will distinguish evaluating their work from evaluating them.

  2. It says that we believe our current role as the manager is a job role and not a value judgment. As a manager, we are not worth more and are not valued more; rather, our role and responsibilities are simply different than theirs.

  3. It says that we will not judge a book by its cover, and will take the time and the care necessary to get to know people. It says that we will demonstrate the thoughtfulness and empathy needed as we evaluate them.

And if these aren’t enough, remember that as leaders we are examples to those we lead!

“Attitude reflects leadership, captain” ~ Remember the Titans

When we treat the least and the last with dignity and respect, we not only set ourselves up for success as leaders, but we influence those that we lead to do the same. And that, truly, is a mark of a great leader!


My son,

God created us to be in community. He designed us to live with others, to experience life with others, and to share our journeys with others. And with that shared journey comes the ability to be inspired by, and to inspire. To be challenged by, and to challenge. To be loved, and to love. To be taught, and to learn.

That's what mentoring is about.

It's about sharing the things that you've learned with others, and in turn learning from the experiences of others. It's an acknowledgement that you can't learn everything there is to learn in life on your own.

It's a commitment to another person saying that I will walk this next part of my journey with you. I will share things that may be uncomfortable or even unpleasant with you for the sake of our mutual trust and learning.

It's about building a bond of trust to allow someone else to see into your soul and to allow them to speak into it. It's about having the grace to look into the heart of another and treat it with care. It's about truly embodying the statement that together, we are better than the sum of our parts, and that "as iron sharpens iron, so one man sharpens another".

I've been blessed in my life to have a small number of phenomenal mentors over the years. These men have poured into my life, have relentlessly pushed me to be better, and have shared with me pieces of their lives and their faith that have helped reveal to me the type of man that I want to become. And I am eternally grateful for their faithfulness.

In turn, I try to do that with others, and try to pour my time, care, and effort into their lives as well. As your mother has helped me discover, the legacy I want to leave is to be known as a person who inspires others to be the best that they can be.

And so my prayer for you is that not only do you find good mentors that will help you through the journeys that you'll go through, but that you too will walk alongside someone else and aid them in their adventures and be a guiding post for them as well.


My son,

Your namesake is one of independent action, intentional living, and transformative thinking. My prayer is that you would be a man that is kind hearted, who wants to help others, and can lead them to be better.

Leadership is something that is the birthright of every man. God created you to lead your household, just like Jesus leads the church. It is not something you can shirk away from, and so my hope is that you will willingly step into that role, deliberately and intentionally.

There are many books on leadership out there, but over the years, I've been able to boil those thoughts down into 5 key learnings.

Leaders motivate those they lead to action by providing a compelling mission and vision.
Leaders have the tenacity to drive outcomes and to overcome adversity and resistence.
Leaders build relationships that create trust and promote honesty.
Leaders are stewards of even the least of those that they lead.
Leaders leave no one behind.

I'm sure there are many other nuggets of wisdom that you will pick up over the years, but these are just a few that I've found to be timeless truths. I hope they can serve you well, as they have done so for me.


My son,

Hopefully you will have grown up having built strong relationships; relationships built on trust, mutual respect and admiration. If so, you may find yourself entrusted with another's secret.

I cannot stress the importance that you keep that secret.

Any relationship that matters values honesty and trust. Divulging another's secret proves a person unworthy of that trust. No matter what the cost, no matter what fire your feet are set to, honor that secret, for it is not yours to share.

When you keep that secret, you prove yourself trustworthy and honorable. When you keep that secret in light of personal suffering, you prove your character, and you prove yourself worthy of respect. In one of my favorite movies, Scent of a Woman, Al Pacino puts it superbly in his final speech:

"I don't know if Charlie's silence here today is right or wrong. I'm not a judge or jury, but I can tell you this: He won't sell anybody out to buy his future! And that, my friends, is called integrity. That's called courage. Now that's the stuff leaders should be made of."

And that's my hope for you, that you would be a leader of men, a great leader that builds strong relationships, fosters long-lasting bonds, encourages others, and builds others up. In order to do that, you have to be a man of integrity, who knows how to keep confidences, and who doesn't have a loose tongue.


My son,

By now you should know that the two movies that have influenced me the most are Top Gun and Gladiator, and hopefully you'll recognize the title of this post as a pivotal line from the latter. The message I want to convey to you today is that while Commodus spits out this phrase facetiously, mercy is absolutely a critical characteristic for us to develop.

While Grace is the act of blessing someone with something undeserved, Mercy is the act of withholding judgment or retribution from someone that deserves it. Both of these are demonstrated by Jesus for us. His Mercy withholds the consequence of our sin, and His Grace gives us the opportunity to know and have a relationship with God.

As you know, the legacy that I want to leave behind is that I'm a person that inspires others, that motivates them, that instills passion and drive in those that are around me. To do this, we need to able to see people not for who they are, but for the best that they can be.

The capacity to consistently bring out the best in people is called leadership, and the ability to see people not as they are but as they were created to be requires the attribute of mercy.

Leadership requires not just an openness and intuition to see the best in people, but the corresponding amount of Mercy to allow people to make and learn from mistakes as they get there. Great leaders are able to focus on the accomplishments and successes while taking hold of failures and errors and using them as learning opportunities.

So how do we develop our ability to have mercy?

We develop our ability to show mercy when we are able to see how much we ourselves need mercy shown to us. When we humbly recognize our own position and understand the amount of mercy God has demonstrated for us, we are able to see how we should in turn extend mercy to our contemporaries, and we begin to model the characteristics that God desires for us.

My prayer for you then is that in light of your confidence in knowing who you are and what you are capable of, that you would be humbled by the knowledge of who God is and what He created you for, and from that posture of humility be able to show grace and mercy to those around you.


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