Letters to my sons
"The heart of a father is the masterpiece of nature."― Abbé Prévost
My sons,
I love to travel. Partly because I love the thrill of exploring a new city, of discovering a beautiful countryside, of experiencing a new culture, and of seeing the sun set over a different horizon. But also because these new experiences allow you to be surprised, to be caught off guard, to be vulnerable.
Perhaps it is the romantic in me that puts my heart and mind in a posture for inspiration, but it is in these moments of vulnerability that we find sparks of inspiration, of clarity, of perspective. These moments bring a much needed reprieve from our day to day, that allow us to see the world differently, to reflect and retrospect on life, and to wax poetic about our place in the cosmos. These moments give us glimpses into our purpose, our place, and our meaning.
For some, these moments are to be found in isolation, in quiet contemplation, and in enjoyment of their natural world surroundings. They may sneak up on you unexpectedly - a brief clearing in the middle of a hike, an opportune moment where there is not a single skier in sight as you cruise through the powder, or even a fleeting moment at a beach where you find yourself alone and reflective, gazing out into the vast ocean.
For others, these moments are found in the company of loved ones. Perhaps a warm revelation while catching a glimpse of one’s family happily chatting over a holiday meal, a quiet moment of realization as your children fall asleep before the movie has finished, or even a moment of grief shared with a loved one.
These beautiful moments, fleeting as they are, have the potential to bring clarity and focus to our lives if we let them. Their impact can be as small as a quick thought or as deeply impactful as changing our minds about something. They can be pensive and sombre or uplifting and inspiring. And the best part is, we can shape them.
Shaping your moments
Our subconscious minds are always at work. When we sleep, when we eat, when we’re engaged in active conversation, or when we’re pensive, our subconscious minds cannot be turned off. What they’re actively working on or thinking about is one thing, and whether we have the space and margin to listen to them is another. Let’s look at both of these.
It turns out our subconscious minds aren’t magical things. They’re simply (forgive the CS term here) background processes that are always running in our brain, processing and dealing with things that we encounter. Their inputs are what we give them - our experiences, our friends, our conversations, the things we read. This is our first hint as to how we can direct those moments.
We should note that our subconscious minds are slow. They take time to do their thing. And we’re usually not aware that anything is happening at all. But when they act, their impact is big.
When I was a wee lad I was happy, and hopeful, and generally pretty positive, as most little guys are. When I went through my teenage years though, I started becoming more judgmental of the world in general. Then when I graduated from university (I’m Canadian - we call it “university”, not “college” like our friends to the south call it, or “uni” like our friends across the pond do. Just “university”) and took a job at Microsoft, I discovered that I started becoming critical not just of the world at large but at those around me; my friends, my family, my loved ones. Then I became a manager, and then the doors just flew off the hinges.
I’ve since had to do a lot of work (and a lot of therapy, reading, learning, and reflecting) to get back to being a happy, hopeful, and generally positive (but not so wee anymore) person, but it’s worth thinking through how I got there in the first place.
Turns out a large influence in my youthful years was the Toronto Chinese Christian Church community at large. Yikes. I won’t hate on that whole community too much, as I’m sure it has changed over time, and I’m sure my experiences were… somewhat unique to me, but suffice it to say that I grew up being surrounded by a whole lot of immature adults vying for power, judging one another, and generally being nasty humans without caring that the youth of the time was paying close attention.
Fast forward to Microsoft culture circa 2008 and you’ll find an incredibly critical company, one that promotes “critical thinking” as applied to any and all problems. Including human engineering problems.
And my subconscious mind picked all of this stuff as regular inputs in my life, and acted accordingly. It assimilated those behaviors and attitudes, and slowly but surely changed my view of the world, my actions within it, and my reaction to it.
We are not the sum of our experiences, as has often been said, but rather we are the sum of the way we react and respond to those experiences. If we want to react differently, if we want to be inspired in those moments of clarity, then we must be thoughtful and forceful about controlling our inputs, about cultivating the garden of our mind.
Space to listen - a moment of clarity
Once we’ve reined in our thought process and have gotten a better handle on the inputs to our subconscious, how do we allow those insights to bubble up to our conscious minds? How do we put ourselves in a position where the fruits of the garden of our minds can have their moment of impact?
The obvious one is to prioritize margin, to accommodate it, and to plan for it. Many successful executives do this. Bill Gates used to have his infamous Think Weeks where he would spend an entire week away from all distractions so that he could think and give his mind time to speak back to him. Oprah has popularized the silent retreat. John Rockefeller scheduled hours on his calendar to just sit and stare out the window.
In his book ~Stolen Focus~, Johann Hari expounds on the plethora of studies that show that the kid in the back corner staring out the window daydreaming was much more likely to be successful, learn better, and even reason better. There is much research in recent years that shows how giving ourselves space to play, margin to relax, and time to daydream is incredibly beneficial for us.
One way to orchestrate these moments is to take our vacations. Many years ago my mentor told me that if I ever worked for a company or a person that asked me not to take my vacation or asked me to work during it that I should immediately start looking for a new job. I agree. Corporate America has created a model set to squeeze every last drop of productivity from a person without realizing that leaving people as husks of their former selves is only the secondary problem. The primary is that in doing so, we deprive people of growth, of learning, and as a result get less out of them.
Make sure you prioritize taking your vacations, and for the love of God, turn off your devices and don’t check email while you’re there.
It is in these disconnected moments that life can take you by surprise. I recently took a train ride to Portland with my little dude and during that 4 hour disconnected journey, I happened to be staring out the window at a steady stream of trees rolling by when suddenly we hit a picturesque clearing. The sun was shining just right and the beautifully manicured acres of lawn sloped gently down to a turn of the century farm house painted a deep royal blue. The house stood nobly at the foot of a hill that created gorgeous backdrop, its white picket fence encircling a luscious garden on one side, and a row of 30 foot trees on the other. A lone horse stood beneath the tree, topping off that quaint, beautiful scene from a different life and a different time.
That moment, combined with my mind’s lingering thoughts from the novel I had just finished, elevated my perspective and transported me, causing me to think about the beauty of the human spirit, of the longevity and resiliency of our species, and of our ability to build noble things that can stand the test of time.
And then the whole scene was gone, covered by the steady rows of bushes lining the tracks. But not before leaving yet another breadcrumb of clarity and perspective for me to chew on for the rest of the trip.
And so my encouragement to you is to put yourselves in places where you too can allow the thoughts marinating in your subconsciousness to surface, where you can be inspired, and where you can be taken by surprise.
My sons,
All of us have dreams. From a young age, we learned that the sky’s the limit for human ingenuity. We were told that we could be anything, do anything. But over time, those dreams start to fade, and our belief in our ability to achieve them (nay, whether we even deserve to achieve them) starts to fade. Most of us have lost sight of those adolescent dreams and have settled into the mediocrity that is adulthood. We are content in living the life that we’re supposed to live - a life that plods along slowly but surely, doing all the things that our culture tells us area part of a properly lived life.
Sounds pretty dull doesn’t it?
How do we snap out of that? How do we move back into a space where our lives are exciting, where we’re passionately running towards some big, lofty dream, and where inspiration comes and drives us to our limit and pushes us beyond where we ever thought we could go?
The answer is simple, and comes in the form of all sorts of cliches. Take your pick of them:
- Less is more
- Gotta take two steps back in order to set up three steps forward
- It’s not quantity, it’s quality
The truth of the matter is, our lives are so jam packed full of stuff, filled with noise, and overflowing with the seemingly urgent that we have no margin, no time, no mental space to allow ourselves to listen. It has been said that inspiration is very polite. She knocks softly and then goes away if we don’t answer the door. She does not force her way in, does not make a big fuss, does not cause a scene.
We cannot shove inspiration down someone’s throat. We knock softly, and if they’re not ready to answer, that’s okay, we can come back some other time. Similarly, we cannot be inspired if we are not paying attention to the knocking on our own doors. If we are too caught up in ourselves, too focused on our own worlds, or have too much noise drowning our ears, we will miss the gentle whisper that inspires and elevates.
If we want to hear the gentle whisper of inspiration we must first learn to listen, and to have the margin and mental space for her.
Learning to listen
An unfortunate reality of our modern world is that we are driven by noise. We praise great orators, admire the outspoken leaders, and aspire ourselves to have that type of impact. As a result, we focus much of our learning and our development on how to speak, how to convey an idea, and how to be heard.
But we don’t spend time learning to listen.
Active listening is a skill just like any other - it can be learned, can be practiced, and can be improved upon. It has nuances like every other skill does. It has its masters and its novices. Some are born with more of it, some with less. And like every other skill, where we start doesn’t matter. We can all learn to actively listen so that we are more attuned to what is going on around us.
Creating space
One of my most cherished habits is my nightly thinking and processing time. I use a modified version of Zettelkasten to support my growth and learning, and one of the disciplines I’ve picked up from it is creating space every night to process my thoughts from the day and to synthesize my notes into my own system. This process requires me to first sit and clear the thoughts in my head and then to pick up each thought that I’ve recorded throughout the day and to consider it, process it, and synthesize it into a long form paragraph or two.
Which system you use is less important. What matters is that you have a system, and you have a method by which you nurture and care for your thought life. The daily nurturing of your mind allows you to create space to listen, to be attuned to your surroundings, and to see where your thoughts lead you. This is gonna sound cheesy, but I’m going to say it anyway - your mind is like your sacred garden that needs to be tended to and taken care of. Cultivating a healthy and strong thought life will provide benefits to every other area of your life.
Cultivating our inputs
We must therefore be intentional about our inputs. Tending to the garden of our mind means we are thoughtful and careful about what we let into it. This should be an obvious one, and despite the fact that we’ve all definitely seen the effects of not guarding our minds well, most of us could use some improvement in the things we let in.
We’ve all done this and all have first hand experience with this. Remember that friend who was constantly negative and could (and would) complain about anything and everything under the sun? Prolonged periods hanging out with them probably made us more negative as well.
It works in the opposite too. When I was younger I had a great friend who was super passionate about technology and about the product that we were working together on at the time. We spent countless hours discussing the work we were passionate and excited about, and would even discuss some of the technical details of our work while on the chairlift at the slopes. It’s no surprise then that this period of my life was characterized by strong technical thinking and development, as well as a high amount of professional productivity.
I in turn was very much into motorcycles and would openly drool over the latest super sport bikes that were released each year. It’s also no surprise that my friend ended up getting a motorcycle as well.
Great inputs have the power to lift up a life, to change our mind, and to enrich our thought processes and passions. Bad inputs have the power to pollute our mind, to destroy our sense of self, and to turn a once-productive mind into a destructive one.
The gentle whisper of inspiration
Inspiration comes in many forms, and may sound different to different people. She may take different approaches, may speak through different people and events, and may look different each time she tries to visit us. She may speak to us through listening to a stranger’s story on the plane, or through the sight of a bird soaring high with “god rays” bursting through the clouds. She may nudge us when we’re dozing off watching the trees roll by on our commute, or may give us a glimpse of something greater as we’re playing with our kids.
One thing is certain though - she always whispers.
There is no sure fire way to guarantee that we will hear her every time. But if create space, if we spend the time to be mindful and attentive, if we learn to follow the little inklings that begin like whispers in the wind of our minds, then we may learn to distinguish her voice and pay more attention when she speaks. But we’ve got to be ready to listen to what she says! Remember that there is no confirmation bias for inspiration. She may often say things that make us think twice - that is a good thing! An inspired life is an elevated one, and we can surely use more of those in our world!
My sons,
A characteristic of the modern world that we live in is that we always seem to be short on time. We never seem to quite have enough time for all the things that we want to do, and the time we do have seems to slip through our fingers in a manner that leaves us not remembering what we’ve been up to, and wondering where all our time actually goes.
Whether we’re talking about our professional life (there never seems to be quite enough time to finish all our features, to fix all the bugs, to polish all the user experiences, or to ensure we’ve got the right metrics) or our personal life (how many of us are happy with the amount of time we spend on social engagements, with family, and with loved ones?), we never seem to quite have a handle on our time. The older we get, the busier life gets and the more problematic this becomes.
When time was a luxury
When we were younger, we had what felt like an abundance of time, especially when compared to the lack of other resources (such as money) and minimal commitments and responsibilities that demanded our time. We could therefore trade off time for other things. I distinctly remember in my college years standing at the corner of Albert and Columbia where I lived, and contemplating walking the 45 minutes to Conestoga Mall or spending the 3$ to take the bus. I walked. Yikes.
Not only were there fewer taxes on our time back then, but there were fewer things for us to do with that time. For the majority of us, the only real available options were hanging out with friends, studying, playing sports, playing video games, or eating. Or sleeping I suppose, but that’s one thing college students never feel like they need to do much of. Maybe give or take a few more things. But realistically, there were not that many options for us to balance between, and so we had plenty of time at our disposal.
Subservient to the system
Fast forward a number of years, and we find ourselves with more things to do than we can mentally keep track of. Things ranging from replacing dead lightbulbs to remembering kid birthday parties, from scheduling a follow up dental appointment to remembering to congratulate a friend on their promotion. Everywhere we look there is something we need to be doing, something we need to remember.
And that’s just the things we have to do. What about the things that we want to do?
What about finding time to have a heart to heart with a loved one, or to read that self-help book that’s been so highly recommended for you, or to try that new restaurant, or to simply sit and think? With all the taxes on our time, is it a surprise that most of our wants and desires go unfulfilled and unsatisfied?
60% of Americans feel they are too busy to enjoy their lives most of the time, while 12% feel they are too busy all of the time. That means that one in ten of us feels that we never have the time to enjoy our lives, that we are always too stressed to make forward progress in the things that we desire to do.
If this isn’t subservient to the system, I don’t know what is.
The important over the urgent
It is universally accepted that when push comes to shove and our time constraints squeeze more tightly, the things we trade off are the non-urgent but important things. This is the tyranny of the urgent, and happens in both our life and in our work.
In life, how many of us have traded off our personal reading and development time because we’re too busy? How many of us have told our kids to come back later when mommy or daddy isn’t working on something urgent that came up? How many of us have showed up late to a friends’ gathering and left early to rush home for that work call instead of showing up early to support and build that relationship? What about healthy eating and home cooked meals? What about daily exercise and meditation?
In work, how often do we make the short term fix instead of the right long term architecture? How many times have we swarmed to some urgent and tactical problem rather than spending the time to develop the right long term team and skill sets? How about burning a bridge with a partner team by escalating and effectively forcing them to get what you need done? How often do we focus on the transactional rather than spending the time to build ~non-transactional relationships~?
Managing the time you’ve got
It is true that much of our time is not our own. Time is a networked resource and gains value expressly because there are others that can make demands on it. As we grow in our lives and in our careers, there become more demands of our time that truly are outside of our control. How we manage the demands, and most importantly, how we manage the remaining time we have left is crucially important.
So how do we do this effectively?
1. Ruthlessly prioritize what you need to be in top shape
Perhaps the hardest one to do, it is also the most important. We need to take the time to thoughtfully determine what the daily requirements are for us to be in top shape. Have you ever shown up to a meeting fully prepared but not feeling your best self? You know your stuff, but it just doesn’t come out right. That’s because you’re not at your best self.
Take the time to figure out what that means, and be unapologetic about it.
Personally, I never leave my bedroom in the morning without having showered, groomed, dressed well, and made my bed. I spend at least 30 minutes a day reading, and spend as much if not more time than that thinking. With a few allowed exceptions, I also need to eat healthy. I need to exercise daily (this one’s been a struggle… but I’m working on it). I need to have quality sleep for at least 7 hours a night.
I am uncompromising in these, as without them for prolonged periods I am not able to be my best, and everything else suffers as a result.
2. Dedicate time to thinking
Another characterization of an overloaded life is that things are frantic, frenetic, and unorganized. We jump from urgent thing to urgent thing and run at a break neck pace for as long as we’re able. We spend all our time doing, and as a result end up decreasing our effectiveness by not thinking enough.
Most of us live reactionary lives. We react to the incoming torrent of tasks, demands, and requests made of us. We don’t spend the time to deeply think about what, and more importantly why we are doing what we’re doing.
Thinking deeply requires time. It requires dedicated, uninterrupted time. Our brains are bad at multitasking, and can easily get distracted. In order to be our best selves and to be the most effective and efficient in our endeavors, we need to spend time thinking. Whether we’re thinking about our intentions, our options, the possible alternatives, how to develop our staff, or our strategic advantages, we need the time to thoughtfully pore over our thoughts, data, and inputs.
Bill Gates used to have Think Weeks where he would go off himself to a secluded place with no interruptions and dedicate the week to reading, learning, and thinking about the business. While we may not all have the luxury of clearing out a full week like Bill could, we can certainly block off time throughout our week to think, and to remove the distractions and notifications while we’re doing it.
3. Learn
Above all things, we need to make sure we are learning. As our world evolves around us, we too must grow and evolve with it. Our thinking needs to adapt and mature. Our reactions need to consider new inputs and alternatives. Our plans have to accommodate the shifts in technological advances that are underway.
As such, we need to ensure that we are carving out time to learn. Whether it is a weekly time block, a quarterly retreat, or an annual reading goal, it is imperative that we dedicate time to our own learning and enhancement.
Putting it all together
As a manager, I need to get better about creating time and space for my teams to do these things. I can help by sharing more context, reducing meetings, and empowering more decisions to be made lower in the organization. As an employee, I need to be willing to take responsibility for the immediate outputs that I have balanced against the long term growth that we’ve been discussing. As a person I need to think about the big picture not only of what I’m accomplishing, but more importantly who I am becoming.
And above all, I have to have the patience to see this through, knowing that the tweaks I make in my life won’t produce results overnight, but will set me up for a lifetime of greater success and happiness.
My sons,
Human beings are wired for play. In our earliest years, life basically consisted of eating, sleeping, and learning through play and exploration. If you walk into homes with young infants or toddlers, you will commonly hear the sound of laughter, of bubbly little voices excited about the brand new discovery that squishing the plastic giraffe causes it to emit a squeaking sound (both of my children grew up with Sophie the giraffe teething toys).
But something strange happens in elementary schools all around the world. We begin to change the daily environment of our children from one dominated with play and exploration to one filled with learning, memorizing, and study. Once they hit middle school, daily scheduled play time (aka recess in America) gets eliminated altogether. Free play time at home after school gets replaced with extracurricular activities and more homework. Even volunteering, which used to be a self-initiated activity stemming from the goodwill of one’s heart has become a required prerequisite by our educational systems.
By the time that child graduates from college, free play, which used to consume the majority of their days, has been transformed into something that we relegate to our 3 weeks of vacation a year if we’re lucky. That child now lives in a culture that serves the god of progress and achievement, a god which happily will take any and all time that we do not fight to hold onto. They are told that excessive play is immature, and are in an environment that regularly reinforces that their only purpose in life is to make progress.
The benefits of progress
Let’s be clear - I’m not advocating for us to play constantly and to ignore our responsibilities in favor of that play. Our world is increasingly complex and requires increasingly dedicated, educated, and creative people to continue to make it better for us all. And let’s make no mistake about it - our world is infinitely better than the one previous generations lived in, across any and every measurable metric.
Average lifespans worldwide are longer. Many deadly diseases have been either eradicated or made treatable and non-fatal. More people are being educated. There is greater (although not perfect) gender equality. There is less violence and crime. The number of people in the world who have electricity has increased from 70% in 1990 to 90% in 2022.
I know there will be some that argue that the world is a more dangerous and terrible place than our past - to those I will highly recommend two books: Steven Pinker’s ~The better angels of our nature~ and the late Dr Hans Rosling’s ~Factfulness~.
On a more local scale, we have persistent access to the internet. We have a plethora of options of electric cars and carbon-zero household products. We have the ability to say goodnight to our home assistant and have her turn off all the lights, close all the garage doors, lock all the doors, lower all the shades, and turn off the bed warmer that was keeping our bed at a balmy 80 degrees for us to climb in. (Okay, maybe that last one was just princess Sam in action).
No matter how you dice it, that progress has many benefits.
The evolving conditions for progress
Unfortunately, our conveyor belt approach to equipping our children to carry on that mantle of success is in need of an update. While it is true that decades ago our assembly line approach to education produced workers skilled enough to work the machines of the day that propelled our world forward, our world has evolved, and the needs and conditions for that progress have changed.
As our world continues to move from physical and manual work to knowledge work enhanced by greater automation, the need for creativity, imagination, and ingenuity have become the new baselines for advancing our world forward. And as it turns out, creativity cannot be taught, it must be fostered and nurtured.
Intentionally unproductive
As a child, I found myself constantly bored. Whether it was sitting in a boring Canadian history class (I must have read about Vimy Ridge, the one important thing Canada did in WWI a thousand times) or sitting at home after school with no access to video games and on-demand TV/movies, I was constantly bored. I strongly believe that that boredom played a huge part in helping me achieve much of what I have accomplished in my life.
That boredom was the fertile ground that enabled my brother and I to invent games to play. It gave me the time and space to dream up worlds and explore them in my mind’s eye. It gave me impetus to read, to imagine, and to dream. It allowed my mind to wander into all sorts of places and situations.
Granted, there were down sides as well. I got myself into a lot of trouble because of that boredom (my mom and my principal were on a first name basis…), and I found myself more often then not finding creative ways to be mischievous. While running around with a can of WD-40 and a lighter lighting spiderwebs on fire and flushing out ant hills wasn’t particularly useful (or safe, really), that time of non-productivity was a launch pad for all sorts of creativity.
It turns out that our subconscious minds are much more capable than our conscious ones. It also turns out that our conscious minds are much louder than our subconscious ones, so if we’re constantly engaged, our subconscious minds have little time to be active and to make connections on our behalf.
DaVinci knew this. Excerpts from his recovered notebooks showed that not only did the grand master paint and create timeless works of art, but he allowed his mind to wander to all sorts of unrelated and fanciful topics. In 1485 for example, he imagined the first parachute three centuries before an actual parachute was made and deployed successfully, and he detailed out specifications for it in one of his notebooks. It was constructed in 2000 and demonstrated to work successfully at 10,000 feet! He also imagined a submarine, a helicopter, and solar power among many other things.
How did he do all this?
He had intentional unproductive time. He knew that his mind needed rest, space, and margin to do its best work, and he actively created time to daydream. He would often go for walks with nothing on his mind and nothing in his hand but a pencil and a notebook and presently realize that he had filled many pages with seemingly unrelated thoughts. In 1994, Bill Gates bought one of DaVinci’s notebooks for $30M. Other notebooks have gone for $5M or more.
Creating margin
I will never be a DaVinci or a Gates. Neither will you. But that doesn’t mean we can’t learn from the greats of our world and integrate some of their practices into our lives. It turns out there are many studies that show a plethora of benefits of having margin and allowing ourselves to daydream. A few benefits:
- We become more creative. When we daydream, our subconscious minds make connections between seemingly unrelated topics, letting us maximize the learning and benefits we get from our experiences.
- We can build better relationships. Something my college advisor told me that has stayed will me to this day is the truth that if you want to make connections with people, you have to make space. People don’t have crisis moments when it is convenient for you to show up for them. They don’t have breakdowns, epiphanies, or life changing events happen to them on your schedule. If you don’t have space for them, they will find someone else that does.
- We become more interesting. By giving ourselves margin to daydream, to pursue hobbies and interests, and to explore and experience without agenda or purpose, we become more interesting! No one is interested in a cookie cutter person that just eats, sleeps, and works. People are intrigued by those who go off the beaten path and explore!
My sons, I know that there is great pressure for you to be always productive. I know you’ve been told that the stakes are high. I know that without a doubt those things were told to you with the best intentions. But they don’t tell the whole story. Be productive, yes. But also make sure you spend time to be intentionally unproductive - I guarantee you won’t regret it!
My sons,
Lately I’ve been thinking a lot about culture - team culture, family culture, friend group culture - and how much it impacts our lives. In his book Wanting, Luke Burgis explains how much of what we think we want is not actually intrinsic to us but is rather a product of us mimicking those around us, mimicking the culture we have. If that’s the case, culture is an incredibly important thing for us to think through.
What is culture?
Culture is not what we desire to do. It is not a set of principles or values that we print out and put on the walls to inspire our teams. It is not “the way we’ve always done things”, nor is it what our founders had in mind.
Culture simply put, is the way we do things today.
That means culture changes with each new day, with each new person that joins the team, with each new adjustment to the daily norms that we introduce. It means that culture shifts and grows as we do.
Culture is the way you spend an extra 10 seconds to say “hi” to everyone on your way in. It is the way we gather everyone on the team to go to lunch everyday. It is our willingness to speak up in meetings, our courage to express our opinions, and our trust knowing that those opinions won’t be slammed down by our peers. It is how we utilize documents or presentations, what our expectations are of instant messaging and email, and how much information we share with or withhold from our partner teams.
And it is what every new person gravitates toward when they join us.
An intentional culture
The thing with culture is that it can happen “naturally” (aka accidentally) or it can happen intentionally. Intentionality is better.
I’ve had the privilege of seeing many different types of leaders at work, each with a wide variety of skills and competencies. I’ve seen leaders that are hyper intentional about the culture of their teams, and I’ve seen leaders who simply accept whatever culture their team has as long as the leader is able to work in the manner that they prefer.
The leaders who had a firm understanding of the type of culture they wanted to cultivate on the team were not only more well-liked (turns out people like it when their leaders care about their experience), but their teams had more longevity. Regretted attrition rates were lower, team loyalty and ownership was stronger, and willingness to collaborate was noticeably higher.
Some of this is obvious - a leader that cares about culture naturally values people who care about culture as well, thereby building a virtuous cycle of people who are intentional about the environment, habits, and practices of the team.
Less obvious for instance, is the reality that leaders that cared about culture typically cared to see the impact of the culture they’ve created. They engaged themselves in inclusive behaviors, in learning from the team what’s working and what isn’t, in getting feedback, and in having dialogue and discussions with the team. These leaders cared about culture, and spent time actively crafting, refining, and sharing. They led by example, both in their communications and in their behaviors.
What makes a good culture?
There are a number of dysfunctional behaviors and norms that have permeated themselves into our world, with some much less obvious than others. Unfortunately for our world, there are still some very overtly dysfunctional cultural habits in the workplace today. Things such as blatant disrespectful and discriminatory behaviors towards women or clear minority groups unfortunately still happens today. Less obvious are things like CYA (cover your ass) cultures, cultures where bosses take credit for their team’s work, or hierarchical cultures where subordinates don’t speak up unless spoken to.
Healthy cultures on the other hand tend to balance productivity with fulfillment. Healthy cultures are ones where people can come as their authentic selves and do their best work together. They are cultures which enable and empower while keeping strong expectations and a high bar. They are cultures that elevate people and stretch people, allowing them to grow and develop, not just as workers but as people.
My SVP says it incredibly well. He says he builds teams of passionate and relentless people. I love that.
We want to create a culture where passionate and relentless people thrive. People who are incredibly passionate about what they do, about the mission that they’re on, about the impact that they have on the world, and about their craft and their role in achieving that impact, but at the same time are relentless in their pursuit of excellence, in their dedication to their craft and their learning, and in their desire to build the best thing for their customers, whoever those customers may be.
There are a few things that are essential to create a culture that fosters these behaviors.
- Open communication. The most critical ingredient required for great teams is open communication. Any culture where a diverse set of passionate and relentless people can thrive deeply requires open communication. This is because people are different. When you’ve got a lot of strong people together with poor communication, inevitably one person ends up steamrolling the rest without listening to others and you end up with an adversarial and mistrusting culture.
- Strong opinions, weakly held. Another key part of great team cultures is the ability to have weakly held opinions, to be convincible. The world is big. The amount of information, knowledge, and wisdom out there is astronomical. To think that one individual has it all, is always right, and knows best is not only improbable and naive, but just down right stupid. We therefore need to build a culture that recognizes that great ideas can come from anyone, anywhere. Have opinions, yes, but be willing to be convinced of other viewpoints as well.
- Regularly revisiting cultural norms. Great teams need to regularly revisit their cultural norms and reevaluate whether adjustments need to be made. Our world changes - new technologies develop, the business landscape changes, societal trends shift - and if our teams wants to stay relevant, we need to change along with it. In order to ensure we do that well we’ve got to regularly revisit our norms to decide if the patterns and practices that have served us well in the past will continue to allow us to excel in the future.
Whether we like it or not, whether we’re conscious of it or not, and whether we have input into it or not, culture affects each and every one of us. It is the set of norms that we automatically take on whenever we enter the sphere of any group that we’re a part of, whether that’s work, friends, church, or even family. The more awareness and thoughtfulness we have the more we’ll be able to help craft and shape our cultures to be healthy and empowering places for all of us.