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 #Hospitality

My sons,

We’ve been discussing the concept of hospitality, first generally and then as it applies to work. We shift our focus now to how it applies in life.

I’ve always desired to be hospitable. When I was younger, I lived in a tiny 500 sqft studio apartment, but would regularly host groups of 4-5 of my friends to have a home cooked dinner and to play board games until late into the evening. I didn’t even own a dining table, so we all sat cross legged on the floor around my coffee table, which doubled as our board game surface once dinner was done. Every home I’ve had since then has been purchased with a view of how I can entertain people, and how I can grow the set of things as I learned to be more hospitable.

The more I’ve learned though, the more I’ve discovered that my view of hospitality was limited and very, very incomplete.

For whatever reason, my view of hospitality was that it was simply the willingness/desire for people to host others in their home. This was almost a direct reflection of a few traits:

  • Willingness to clean up after people leave
  • Enjoyment of making food or having food delivered
  • Comfort letting others into your space

As I learned more about what it really means to be hospitable, I realized that hospitality is not just about your willingness to physically serve others. It is a mindset. The hospitality mindset is one of putting people at ease, of being more interested in the lives of others than in telling others about our own lives, and of having the thoughtfulness to think of others even when you’re not physically with them.

How to cultivate a mindset of hospitality

One of the hardest things to do in this life is to adjust one’s mindset. There are a myriad books out there that talk about this - Think Again by Adam Grant and Switch by Dan and Chip Heath are two of my favorites and provide great insight into the psychology of our default behaviors as well as some greatly actionable advice on how to challenge and change our own thinking and behaviors.

Once we’ve identified, acknowledged, and determined the need to change our mindset and have understood the mechanics of changing our behaviors, we need to determine what new habits to instill, and what the goals of those habits are.

1. Build a rich thought life

One of my favorite books of all time is The Count of Monte Cristo by Alexandre Dumas. I first read this book in my teen years, and again many times since, but that very first reading changed my life. In the book, our hero Edmond Dantes is wrongfully imprisoned for several years, and during that time he meets a prisoner that has been there even longer than he, yet who seems to have discovered a way to avoid the madness and depression that isolation typically brings. Instead, he has developed a rich thought life, one that keeps him busy studying, inventing, analyzing, and exploring, all within the recesses of his mind.

I loved that example and aspired to have that same richness in my thought life. As a teen, I realized that there were any number of mundane times where I was left alone without anything to distract. Whether it was sitting on the bus on the way to school, showering every morning, or the minutes dozing before falling asleep at night, there were many daily spaces that could be utilized better, so as often as I could remember, I started making adjustments.

I started small. I simply got myself to think about an idea instead of a situation. Instead of reliving the day on my bus ride home, I’d take an idea and work it out. Instead of imagining waking up early and playing my favorite epic video game (Final Fantasy 2) while falling asleep Friday evening, I’d think about the themes of the game (loyalty, betrayal, love) and ruminate on how I’d seen those themes play out in my life.

Over the years my thought life has developed to the point where I no longer experience boredom acutely, and where I welcome times of inactivity throughout my day so that I can spend time expanding on these ideas, themes, and debates in my mind. This is constantly challenged by the temptation of picking up that little rectangular device and being entertained by it, but the combination of identity (I believe that I am not a person that wastes time on my phone) and habit (I have a daily ritual of reclining in my Eames chair with a glass of wine to read) has helped me fend that off pretty effectively.

2. Put yourself in a position to experience hospitality from others

There are many great things about our hyper connected world and the technologies that enable it. One down side however, is that it enables - nay, causes - our world to become smaller. Why go through the discomfort of striking up a conversation with a stranger at a coffee shop when your little rectangular device enables you to interact with people you already know? Why put yourself through the stress of not understanding everything on the menu at a new restaurant when you can eat at your favorite haunt again, or can eat at home on your own?

By shrinking our world, we experience the hospitality of others less. By staying in the same small social circles, we limit our understanding and experience of hospitality to those we already know.

In contrast, expanding our world allows us to experience new ways of being hospitable. By trying new restaurants, by meeting new people and being invited to share in their hospitality, and by going to different countries to see how other cultures behave, we grow our awareness and understanding of hospitality and further our own style in how we demonstrate it to others.

3. Talk about it with others

In many ways, hospitality has fallen out of fashion in our modern world. Just the other day, we went to a digital food court. The whole idea is that you order your food via touch screen and the machine assigns you a locker number. Once you’ve ordered, someone somewhere prepares your food and deposits the food into the locker through the back and triggers the notification so that your locker lights up and you can open the front door to retrieve your food. Completely contact-less.

Why this is a feature and a desired experience I don’t know, but it was a reminder of just how much technology has enabled our world to become less hospitable.

As such, it becomes incredibly important for us to discuss, to share our experiences, and to talk about our ideas of hospitality with others! We are a social species. We learn from others. We think through talking. If we want to grow our mindset of hospitality, we need to be discussing it with others.

Making magic

Hospitality is about making magic for others. It is about caring for another’s experience. It is about thoughtfully surprising others with how valued, cared for, and known they are. And it is contagious!

Every child has wanted to be a magician at one point in their lives. Some entertain the thought for a mere minute while others spend summers at magic camp. But regardless of how intense the interaction, when one experiences the pure delight and joy that magic brings, one immediately desires to replicate and to be able to perform such feats themselves.

So too is the magic brought from hospitality. When we experience a truly magical moment of hospitality we are compelled to share it. Let us then discuss these moments with others, and let us arm ourselves with the skills to recreate these moments so that we can bring more magic to our world.


My sons,

Anything in our world that is worth doing requires teams. We are past the age where any one person can do something truly impactful on their own. Yes, we can tinker, we can prototype, we can come up with ideas on our own (that too is arguable - whether any thought is truly done in isolation is debatable, but that’s another topic for another day), but we cannot build anything worth mentioning on our own.

We need teams.

I’ve been in the business of building, managing, cultivating, and leading teams for almost two decades now, and have been in the study of excellence on the subject for at least as long. I’ve read books and articles dedicated to the subject, listened to the leading experts in the fields of leadership, human psychology, and business, and have experimented with many approaches within my teams. The undeniable truth about all the best teams is this: they have a high amount of psychological safety.

The best of the best actively and intentionally cultivate, nurture, and grow that safety, and are proactive in weeding out individuals, practices, and experiences that take away from it. At the root of that safety is a strong web of relationships built on trust, humility, and shared experiences.

Learning from the best

I once sat in a large exec review with our Senior Vice President with about 20 other people reviewing our organization’s roadmap doc, a small section of which I was responsible for. As we reviewed, our SVP had a question about something in my section. After I answered, he looked over at me and said, “hey, sorry, I know we’ve met before cause I’ve seen you in these meetings a bunch, but we haven’t actually been introduced. What’s your name? … Great to meet you, Sam. Okay, so, I know you know your stuff, and everyone else seems to be nodding at your answer, but I don’t get it yet. Do me a favor will you? In the next month or so, write me a quick doc explaining this to me.”

I would follow that guy anywhere.

In a room of 20 people, probably 6-7 of which were VPs themselves, he took the time to make me feel seen and heard. It took him all of 2 minutes, and I’m sure he’s done that a thousand times and doesn’t remember the incident, but for me, that was magic. That is a moment that I will likely remember for the rest of my career.

Undoubtedly one of the reasons he’s so beloved and successful is that he has intentionally cultivated a practice of hospitality. I’m sure that not only has he reaped the rewards of that, but he has brought that same type of magical experience into the lives of many others.

Hospitality pays

We live in a world where a large majority of our GDP is coming from the service industry and that the most important capital in our world is human capital. It is widely recognized that companies and industries rise and fall because of the teams of people that they are able to hire, attract, and retain. In that world, people matter. Teams matter.

And yet these skills are as undervalued as they are important!

Why do so many companies and teams undervalue these traits? The simple answer is because they are hard to measure, especially in the short term. It’s hard to quantify the gain that we get by investing the time and resources necessary to create a hospitable culture because culture is not a yes or no thing. There’s no measuring before and after because that distinction is binary, and cultural change is a gradient.

There are many examples of companies and industries that are moving towards building sustainable, helpful, fulfilling businesses in a way that values culture and integrity as much as they value profits. In his book Screw Business as usual, Sir Richard Branson talks about the work that he and many others like him have been doing to rethink the way we build teams, companies, and industries, and the impact that those endeavors have on local and global communities. While most of us will likely never be able to build multiple companies and industries in our lifetime, there are many lessons that we can learn from those that do.

1. Make sure everyone knows the goal.

The first and foremost important thing is to ensure that everyone on your team knows what the goal is. The goal is not to build a great product. It is to build a great product that customers will love, so that they will love your brand and the impact it has on their lives and will purchase, so that your company can make money. The goal is not to create a great recipe that is delicious. It is to create a great recipe that is delicious, so that the front of house can offer it to guests at a rate which guests will love, so that guests have a great overall dining experience, so that they will recommend the restaurant to their friends, so that their friends will come and pack the house, so that the restaurant will make money.

Even if you are working at a non-profit, there is the uber goal of the organization that everyone needs to be keenly aware of so that they can take ownership of their space. It is only by knowing the true goal that individuals on our teams can see how their hospitable practices move the needle and impact the thing that really matters.

2. Give lots of credit where it’s due.

Give credit where it’s due. No matter how much value you bring to a team yourself, it is to the team. When there are individuals that do great work, go out of your way to recognize that. As a leader on the team, you naturally get enough spotlight and attention - take every opportunity to shine the spotlight for greatness in other people’s direction.

As leaders, we need to take pride in creating an environment where greatness can happen and can flourish - that is the mark and reward of a great leader, and is the mark of a team that people love, take ownership of, and do their best work for.

3. Deeply understand what it means to be right a lot.

This one tends to trip people up a lot. Especially if you’re a tech person, you’ll have been bombarded with messages telling you that being right is critically important. At Amazon, it’s even one of the leadership principles.

I’m not saying there’s anything wrong with being right about the topic at hand. It’s a good thing to have good instincts and intuition, and to be objectively right. But there’s much more to being situationally right than just the objective debate at hand.

Being right is irrelevant when you break the relationship. This is true in our personal relationships as well as our professional ones. When you are hospitable and charitable to people, you often will be the one that needs to suck it up and adjust, even when you’re objectively right. This is always going to be best in the long run.

This is especially hard in the business context, because we often believe that when we’re seen as being in the wrong, it will reflect poorly on our performance. This is multiplied if your manager is the one that is seeing you as being in the wrong. This is amplified further if you’re seen as wrong in a large meeting with multiple stakeholders/leaders.

I am fundamentally a long game player, and the long game is all about relationships. Being right is irrelevant when you break the relationship. When you are hospitable and charitable to people, you often will be the one that needs to suck it up and adjust, even when you’re clearly right.

I’ll go even further.

If you’ve corrected someone because you don’t want them to think you’ve made a mistake, you’ve made a much bigger mistake.

The common response to this is that “sucking it up when I know I’m right feels demeaning” - yes, true, but the benefit you get to the relationship far outweighs any you lose from making a so-called mistake, especially if/when the other party realizes or discovers that they were actually wrong in the matter. The feeling you leave them with is a far greater testament to your impact than you proving that you are right.

I’m not saying that we should not go back and correct the error - do that, but do it in private. And do it in a way that preserves, and even strengthens the relationship.

Being right a lot isn’t about being objectively right. It’s not about being seen as right. It is about being relationally, long term right. It is about having the tact to know when to correct, and how to continually strengthen the relationship. And that is the definition of hospitality at work.


My sons,

We are a relational species. Whether we like it or not, we are wired for connection, for relationship, for feeling. In my younger years I tried to shed that; I tried to argue that intellect and reason were far superior to feeling. I took pride in this.

As I’ve grown over the years, my personality trait scores have drifted. In my youth and well into my early career, I scored very clearly in the INTJ bucket (for those unfamiliar with the Meyers-Briggs personality tests, INTJ is Introvert, iNtuitive, Thinking, Judgment and is pretty much the quintessential engineer). Over time, I drifted from an “I” to an “E” (ie Extrovert), but that was still fine.

But then came trouble.

One fine day, I tested as an ENFJ! Horror of all horrors, I was a feeler! That test had to be wrong. So I took the test again. And again. And a fourth time. And still, ENFJ. I went home from work early that day. I cried inside.

But as the stages of grief kicked through to acceptance, I realized this was actually a natural evolution for me, and a beneficial one at that. That famous quote from Maya Angelou resurfaced in a strong way:

”People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

I realized how true that statement was in my own life, and realized that without knowing it, I had grown into a person that desired to impact people more than I cared to say, do, or build great things. And the best way to do that was to make sure I was thoughtful about how I made others feel.

Thus began my journey to better understand this concept of hospitality.

Understanding hospitality

When I first encountered the term, I thought it applied to the service industry only. As I dove into the concept and read about the giants in the space, my understanding evolved. Reflecting on my experiences, I realized that among my friends there were certain homes that I liked visiting more, and there were certain people that I enjoyed lingering with, laughing with, and simply being around more. It never occurred to me that this was hospitality applied to my social circle.

In his book Unreasonable Hospitality, Will Guidara, former owner of Eleven Madison Park, describes his journey of understanding hospitality. He began by asking many in the service industry a simple question: “What’s the difference between service and hospitality?” He shares one of the best answers that he heard:

“Service is black and white - hospitality is color”.

Love that. Service is about ensuring the napkins are folded properly, that all the children’s toys have been put away, and that all the food is perfectly made, timed, and served. Hospitality is about ensuring that those coming over for dinner know that they belong, are seen, and feel heard. Service is about efficiency, correctness, and promptness, while hospitality is about effectiveness, experience, and connection.

Put in those terms, everyone can be hospitable.

We all live in the mundane, the day to day, in the valleys of life. Hospitality is an opportunity to transport someone to the mountaintop, to elevate their experience, and to make a wonderful memory that lasts. It is an opportunity to bring magic into their lives. It is an opportunity to create a moment that will last in their minds - a moment of pure joy, of perfect alignment, where they’re able to suspend reality, if only for a moment.

Hospitality requires intention

Turns out being hospitable isn’t easy, nor is it natural for most of us. While skill, practice, and environment are all helpful elements, the most important ingredient of hospitality is intention. Intention means that every decision, from the most obviously significant to the seemingly mundane, matters. It is a mindset that begins with a posture that no detail is too small to be ignored, and no task is beneath us.

Being intentional requires focus and effort. It is not easy, nor is it common. It is not obvious, nor is it natural. It requires skill, and it requires practice. It does not have a high barrier to entry. It simply requires a mindset of growth and learning combined with a desire to be the best versions of ourselves that we can be.

For as long as I can remember, I’ve always wanted to help people. When I was in College, I spent a bunch of my time helping younger students; whether it was being a TA, running study sessions, or just hanging out and showing others the ropes, I spent my time trying to guide and shape others just as some that went before me poured into my life.

One of my advisors gave me some sage advice that has stuck with me to this day. “Sam”, he said, “if you really want to impact others, you’ve got to plan for it. You’ve got to walk to class early, you’ve got to keep a fairly clear schedule, and you’ve got to recognize that none of it will happen on your schedule. You can’t plan when others are going to go through a tough time and need to talk. You can’t predict when a seemingly mundane conversation sparks into an hours-long one where someone bares a part of their soul to you. If you don’t plan for space to be available to others, you will not reach them.”

Every memorable connection that was built during my time in College happened in those spaces. From walking a friend home just to end up chatting until the wee hours of morning about life things to overnight study sessions ending in running outside to catch the sunrise, from standing outside GameStop at 2am waiting for the release of Halo 2 to commiserating with a friend on a deep heartbreak over coffee, each of the magical moments in those years happened because I had the time and space for those moments to happen.

Over the years, I learned that hospitality is about more than just creating space and margin for others; it’s about intentionally thinking about what they need, about how you can show up for them, and how you can bless them. That that requires thoughtfulness and intention.

Hospitality is a virtuous cycle

In our world, there are many vicious cycles out there. Shame, hate, anger, violence, suspicion, just to name a few. In contrast, there are fewer natural virtuous cycles, and far fewer examples of them going around.

Hospitality is an opportunity for us to change that.

Perhaps I’m an optimist, perhaps I’m naive, or perhaps I simply want it to be true, but every time I see a charitable act, a display of hospitality, or a picture of generosity, my soul lifts a little and I’m inspired to do the same, if only a little. But that’s it, isn’t it? By being intentionally hospitable to others, we lift them and everyone around them up just a little. Over time, as these little increases build up, it inspires them to turn around and do the same, if only for one person.

That’s the definition of a virtuous cycle and is exactly the type of thing our world needs.

The more we experience hospitality, the more we are motivated to be hospitable ourselves. The influential thinkers of our age have known this all along. From Aristotle to Confucius, from Ralph Waldo Emerson to David Brooks, all the greats speak about this. In Atomic Habits, James Clear lays this out explicitly:

“You don’t rise to the level of your goals. You fall to the level of your systems. And your systems are largely shaped by the people and environments you surround yourself with.”

By surrounding ourselves with hospitable people, we shape our systems, our mindset, and our actions to be more hospitable ourselves. By being hospitable, we shape the systems, mindset, and actions of those around us to be more hospitable as well. And maybe just maybe, we can bring a little more magic to our world.


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