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Posts posted in 2025

The art of communication part 2: Know your audience

My sons,

I have had the unnatural privilege of working closely with several great orators of my time. Powerhouse communicators who could not only take complex concepts and ideas and distill them down to their essence but inspire you to run hard after them. Leaders who could not only move organizations but could shape the industry simply by speaking. Being in the presence of leaders like Anders Hjelsberg, Elissa Murphy, and Blake Irving has given me the distinct experience not only of being inspired by the best, but of being able to witness the life changing power of great communication.

We’ve discussed the need to understand yourself first and foremost as a primary participant in communication. We’ll now move on to the second party in any communication: your audience.

Early on in my career I was lucky enough to be on a team that allowed me the opportunity to speak and present to our customers. As a part of the deal, I got to spend a bit of time with a speaking coach that helped me refine my presentation skills, and something she said to me very early on has stuck with me. She informed me that whenever you are communicating anything,

your audience will have a predetermined set of thoughts, questions, concerns, and worries that will prevent them from truly hearing you until addressed.

Whether we’re talking about a presentation to my execs, trying to convince my partner of a particular vacation spot, or advocating for my children to try something new, each of them will have a set of concerns that need to be addressed before they can hear me. So how do I figure out what those are, and by doing so address them and give myself the best chance of being truly heard?

The art of seeing people

I’ve been on a journey to build better relationships. With my children, with my partner, with my aging parents, with my brother and his wonderful family, with close friends, and with my team, I’ve been on a mission to figure out how to build deeper and stronger connections across the gamut of these relationships. I read a wonderful book last fall by David Brooks called How to know a person that discussed in depth not only how to know people well, but various character traits that prevent us from knowing others and from achieving that level of vulnerability and trust that breathe life into relationships.

So before we get into how to see people and understand them, I thought it would be fun to take a quick antagonist view at how not to see people well, and for us to honestly evaluate how many of these traps we fall into. So without further ado, the list!

1. Egotism. This is the trait that makes us simply not interested in other people. We are self-absorbed, self-interested, dare I say self-obsessed. Instagram culture (or TikTok or whatever the latest craze of the day happens to be) further exacerbates this problem, but make no mistake: this is a huge problem with our world!
2. Anxiety. Have you ever taken time to listen to what’s going on inside your head? There are many studies that show that there is so much noise going on in our own heads that we are unable to even think about other people with all that racket going on! There’s a really great book I read recently called The Anxious Generation that talks about the increase in anxiety if you’re curious to learn more.
3. Naive realism. This is the quality that believes that our own point of view is the objective truth. Youthful zeal often falls into this trap, but the reality is that we all interpret the world with our filters; we do not see the world as it is.
4. Lesser minds problem. This is a funny one. This is simply the act of thinking everyone else is dumber than we are. Sadly, this happens much more often than we’d like to admit.
5. Objectivism. Instead of seeing others as people, we see them in the groups that they belong to and detach emotion from the situation altogether. We do this at work a lot - instead of saying “so and so’s team is failing”, we say “team x is failing”, removing the human element from the interaction.
6. Essentialism. This is effectively stereotyping, boiling people down to their essential common traits instead of seeing them as complex beings with much depth and unique experience.
7. Static mindset. Also known as a fixed mindset, this is the belief that people don’t change. Once we’ve made up our minds about someone, we hold onto that frame and do not give any consideration to the changes that they undergo.

Ever fall into any of those traps? I certainly have, and it has undoubtedly prevented me from understanding others, from developing better bonds, and from being more effective in my communication with them.

The good news is that these are not insurmountable. With a little bit of awareness and a lot of hard work, we can indeed change these traits and begin to see people as they are, not as we imagine them to be, and in doing so understand how to better communicate with them.

So how do we learn to see people, to understand what makes them tick, and to figure out how to be most effective in our relationships and communications with them?

1. Be aware of your attention

We live in an attention economy. Companies and products no longer vie for our money as a primary; no, they vie for our attention. Attention is money. Monthly active users. Daily active users. Hours spent per session. All of these are metrics that any company worth their salt tracks and tries to maximize.

It is that technological and social environment that we find ourselves in, and it therefore behooves us to understand why our attention matters, and what forces we fight against when we try to control that attention.

First of all, know that there are two types of attention: spotlight and starlight. Spotlight attention is our ability to focus actively on a single task or conversation intently and intentionally, whereas starlight attention is our ability to have a longer term sustained focus on goals and objectives.

In order to really see a person, we must be able to start by applying our spotlight focus to them in our interactions, which in turn allows us to eventually apply our starlight focus. We’ve got to take a few intentional steps:

1. Be present. This is becoming so hard for people that every training or offsite I’ve attended in the last 5 years has started with a strong reminder to be present.
2. Remove distractions. In other words, don’t take out your phone. Not only does it not allow you to focus your spotlight attention on someone, it also makes them feel less important and not seen.
3. Treat attention as all or nothing. Sit up, lean forward/lean in, ask questions, and show positive signs of understanding. This may mean nodding when appropriate, or adding +1s or whatever is culturally accepted for you to do.

Our attention matters. A lot. It conveys respect, care, and consideration. It tells the other person we want to know them.

2. Be an active listener

Most of us believe that we’re decent listeners - 96% of us according to a recent HBR study, but 34% of adults in America feel misunderstood “often” or “very often”. What gives?

First, we need to understand that there are different levels of listening:

1. Self-focused listening. This is where the listener is really thinking about how they will respond more than they are listening.
2. Person-focused listening. This is where the listener is solely focused on what the speaker is saying.
3. Environment-aware listening. This is where the listener is not only focused on what the speaker is saying but on what the context, environment, other people in the room etc are doing as well.

That same HBR study showed that the vast majority of us are self-focused when we listen. We are thinking about how to respond. We need to graduate beyond that! The more we are able to actively engage in listening, the more we are able to draw the other party/parties of our communication into an active partnership of give and take, of dialogue, and of common understanding.

Knowing your audience

Regardless of whether we’re chatting 1-1 with someone, hanging out in a group of friends, in a meeting at work, or speaking in front of thousands, it is on us as the speaker to understand the receiver so that we frame our words in a way that the other person can hear.

A face to face interaction requires focused attention with good back and forth. The more we actively listen to them, the more they will feel heard and will be willing to connect and further the conversation.

A group conversation requires environment awareness and perceptiveness as to each person’s state. The more we understand each member of the group’s feelings, inclinations, and worries, the more we can ensure they are engaged.

A large presentation requires understanding where your audience is coming from, what their cares and concerns are. The more we do our research and learn about the cares and perspectives of those sitting in the audience, the more relatable we can be to them.

The most effective communicators are able to understand their audience, are in tune with their cares and worries, and are able to adjust not only what they say, but how they say it to give their listeners the greatest chance of hearing deeply what the speaker is trying to communicate.

The art of communication part 1: Know yourself

My sons,

It has been said that the most important thing one can do in one’s life is to communicate. We are a social species, a communal people. We were made for community and for communion. From the moment of birth we reach for connection with those around us. From our first breath we spend an inordinate amount of energy learning to relate, to connect, to be understood, and to understand.

If that’s true, why is it that so many of us communicate poorly? Why do we go through life feeling unheard and misunderstood? And why, oh why, do our best attempts at expressing ourselves often have disastrous results? Whether personal or professional, with friends or with colleagues, communicating about our personal hopes or our career goals, we often fail to convey our thoughts and feelings in a way that produces more understanding and connection.

Why is that?

It turns out that communicating is a skill. Not only that, but it is a difficult skill to master! It, like every other skill, requires practice, instruction, correction, dedication, and effort. And like every other learned skill, it can come with failures that are often painful, personal, and potentially very public.

But it is a skill that, with the right attention and instruction, can be mastered like every other.

I’ve been a snowboarder much of my adult life, but recently I’ve decided to try my hand at skiing. Call it a mid-life crisis desire to connect more with my children (skiing feels more multi-generational), call it a desire to be lazier (skiing also feels less effortful), or even call it vanity (skiing seems to be on the rise again, and snowboarding seems to have petered out after the Shawn White years); whatever the reason, I’ve taken up skiing. And man does it hurt. It feels like three steps forward, one major yard sale backwards.

But I know I’m learning. I know I’m making forward progress. Painful as it is, I can tangibly feel the improvement after each outing. My muscles are a little less sore, my instincts a little less fried, my attention span a little less taxed. These are all signs that my body is building a new skillset and incorporating and assimilating it into its ethos. I am a skier. Or dammit, at least I will be a skier. Someday.

The same is true of communicating. Many of us tell ourselves that we’re not that good at communicating, that we’re private people, that we leave the flu-flu stuff to the artsy types. But deep down, we long to be understood. Deep down, in places where we’re not ready to admit even to ourselves, we yearn for connection, to know, and to be known, to love, and to be loved as we are.

So how do we get better at communicating? How can we develop these skills so that we too can find our identities as communicators?

We’ll talk about this in three parts: 1. knowing yourself, 2. knowing who you’re communicating with, and 3. building and practicing your personal communication style.

Know thyself

First and foremost, we need to know ourselves. We need to know our proclivities, our preferences, and our blind spots. Communication is a two-way street, and if we want to successfully navigate those streets, we’ve got to understand the role that we play in the communication process. This begins with knowing our values, our triggers, and our style.

There’s a lovely quote I read once that speaks volumes here:

”We do not see things as they are; we see things as we are” - Anais Nin

In order to understand ourselves, our biases, and our points of view as we communicate, we need to be aware of the fact that the world is not as we see it! We see things through our own perspectives, through our experiences, through how we respond to those experiences. It therefore behooves us to understand how these perspectives are formed!

Some of this is work for the therapist’s office, and I won’t pretend to know enough to walk through that. But let me share a few things that have helped me along the way.

1. Understand how our experiences shape us

We all see the world with our own unique perspectives. These perspectives are influenced by two major factors: our mood, and our experiences.

The preeminent filter is our mood - when we are not in a calm and collected mood, every input that we receive gets strongly tainted with it. When we are sad, every input is dampened. When we are excited, every input is amplified.

Recently, my little guy has been using the phrase “me no happy” a bunch - partly as a cutesy way to express himself, but also partly as a way to communicate something that he’s unhappy about. Our bedtime routine has us each sharing three things that we’re thankful for that day, but his unhappy mood made each thing he said tainted with sadness. He had nothing to be thankful for that day, and declared that he didn’t enjoy any of it. After a good night’s sleep (of ~10 hours), he completely changed his tune and happily proclaimed that yesterday was an awesome day because of the 15 things that we had done together as a family.

This is the impact of our mood - it is the lens by which we interpret our inputs from the world. While not entirely controllable, our mood is certainly steerable. The factors immediately in our control are things such as the length and quality of our sleep, our diet and nutrition, and the amount and regularity of our physical exercise. Do we get the requisite 8 hours a night of sleep? Are we eating healthy and with moderation? Are we regularly engaging in physical activity that raises our heart rate and releases endorphins?

Then there are the factors that, while still in our control, aren’t as immediate. Things like the amount of stress we have in our lives, the environments that we place ourselves in, and the quality and security of our social connections are all factors that strongly influence our mood.

Next, our experiences. In his essay “Texts and Pretexts”, Aldous Huxley wrote that

“Experience is not what happens to you, but rather what you do with what happens to you”.

Each event that happens to us is a neutral event in and of itself, but take that event, filter it through our mood, and add a response to it and you’ve got an experience. This is why two people can be present for the same event and experience it so differently! One person may be in a pensive mood and, combined with their predisposition may choose to respond positively to an event while another may have a very different response. These responses create an experience that our minds store up and accumulate. Over time, these experiences shape our perspective and become a critical part of our decision making process, and by extension our communication process.

2. Know what we gravitate towards

We all have biases. Some of these are natural, evolutionary biases engrained in our species over centuries. Some of these are cultural biases reinforced by our experiences and our environment. Some of these are personal biases shaped by the inputs and our responses to those inputs over the years that have elevated to the realm of character.

All of these strongly influence the things that we gravitate towards; the subjects we find interesting, the ideals we are inspired by, the values we desire to emanate, and the style of communication that we prefer.

It is a fool’s errand to attempt to eliminate our biases. Rather, we should accept them, analyze them, and be acutely aware of how they influence us so that when we communicate with others we can be sensitive to their impact. A helpful exercise here is to regularly reflect on our experiences and to note (or take note of) biases and trends in our responses so that we can form a holistic picture of our biases.

3. Learn how to detect our blind spots

Lastly, we all have blind spots. Whether these are technical (ie things we don’t have the knowledge about), emotional (ie feelings we haven’t fully developed yet), mental (ie ideas we haven’t fully fleshed out, learned about, and considered), or spiritual (ie pertaining to the metaphysical, spiritual, and mystical realms), we all have many blind spots and gaps.

These blind spots end up impacting our communication in a generally negative fashion. At best they can create an awkward moment; at worst they can greatly impact our credibility and hence our ability to communicate effectively in the future.

A couple quick notes on how to detect these:

1. Be careful about strong opinions. When you find yourself expressing a strong opinion, check yourself. Strong opinions tend to be emotionally based, instead of being rational and knowledge based, and as such are generally indicators of a gap.
2. Check your defenses. Being defensive is another sign that there might be a gap. Especially when we’re not being attacked, things that trigger defensive responses are usually signs that we haven’t vulnerably fleshed out the topic and therefore have a gap there.
3. Listen to your believable people. Believable people are people who have proven track record of being right about a specific area. When they point out things in your life, listen to them!

Good communication requires deep understanding of the topic, the context, and the parties involved. The more work we do to understand ourselves and how we show up the more impact we’ll end up being able to have on the outcome of our communicative interactions!

Moments of clarity

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.