Answering questions

I was in a meeting recently where I was asked a flurry of questions. I responded by answering them.

That’s the natural thing to do, right? That’s what we were taught in school. Answering questions well is a good thing.

On reflection, however, I realized I spent more time answering question versus understanding the question behind the question. It isn’t the first time I’m realizing it – but, it is one of those moments when this insight crystallized.

I think I’ve taken two things from that experience. First, beware rapid fire answering of questions. If there are a flurry of questions, it is worth pausing and understanding the question behind the question.

Second, if you’re unable to understand the question behind the question, ask.

Finding opportunities to teach to learn

If you want to learn something, put in effort to teach it well. Good teaching deals with taking facts, knowledge and procedures and condensing them into mental models.

And, that process of synthesizing knowledge into mental models that drive action is exactly how learning is done.

But, where can you find a willing student? It turns out that you don’t need a willing student at a desk to learn how to teach. Here are a few ideas –

  • Write a great training manual for your next hire and share it for feedback
  • Put your thoughts down on a blog
  • Create a training program or improve an existing one
  • Explain it to your dog or a wall

At some point, all this practice will actually make you a good teacher. When that happens, willing students will find you.

But, as you probably have guessed, that is the just the by product of a good process.

Perspective and Politics

I define perspective as the trait which enables us to understand ourselves and our place in the universe. Politics, on the other hand, is the furthering of one’s idea on a basis other than merit.

Most of us experience some form of politics in our workplaces. Some of us experience it in our homes. And, for those who work on large non profits or community service initiatives, we definitely experience it in those. I’ve heard it said that politics simply requires two people in a room. Sadly, that is often true.

There’s a strong correlation between a lack of perspective and an individual’s propensity to engage in politics. As a friend beautifully expressed it – “It strikes me that the narrower one’s world-view is, the less perspective one has and the higher one’s propensity for politics in that narrow arena. E.g., the power-hungry mother-in-law whose entire world revolves around a household will be Machiavellian in creating wedges in the family.” 

I’ve also observed a strong correlation between a lack of perspective and unhappiness. The causation there is straightforward – narrow views and constant politics do not a happy life make.

If that is the case, where does perspective come from? And, how can we get more of it?

When I think of perspective these days, I think of this Joseph Addison quote.

“When I look upon the tombs of the great, every emotion of envy dies in me; when I read the epitaphs of the beautiful, every inordinate desire goes out; when I meet with the grief of parents upon a tombstone, my heart melts with compassion; when I see the tombs of the parents themselves, I consider the vanity of grieving for those whom we must quickly follow; when I see kings lying by those who deposed them, when I consider rival wits placed side by side, or the men that divided the world with their contests and disputes, I reflect with sorrow and astonishment on the little competitions, factions, and debates of mankind. When I read the several dates of the tombs, of some that died yesterday, and some six hundred years ago, I consider that great Day when we shall all of us be contemporaries, and make our appearance together”

If this doesn’t give us perspective, I don’t know what will.

It follows that I think perspective comes from being acutely aware of our own mortality. That, in turn, brings a strong sense of what actually matters in the really long run.

Dag Hammarskold once said – “In the last analysis it is our conception of death which decides our answers to all the questions life puts to us.” This quote sums it up beautifully. If we knew we have five days to live, we’d likely go about our work and life very differently. We’d pay less attention to petty arguments and turf wars and, instead, lavish attention and care to the things we care about.

That’s the approach to life that comes with perspective.

And, it is an approach I’ve learned to value above all others.

It could always be better and worse

Sometimes, I think life, happiness and all the other good stuff is just about learning to balance two ideas. The first is that it could always be better. And, the second is that it could always be worse.

They seem in conflict. But, they aren’t.

It could always be better is what inspires us to wake up in the morning and get things done. We’re taking up space in this world and we might as well make it count. This pursuit to make things better makes us better. And, in time, as we get better, we can choose (for it is a choice) to help make our families and communities better.

But, a blind pursuit of better rarely brings happiness. Gratitude, on the other hand, does. And, gratitude comes with realizing that it could always be worse. There is so much we take for granted every single day.

PS: This is a classic illustration of the importance of opposing forces in our lives. Such forces bring the necessary tension for learning and growth. Extremes are rarely useful because we lose the opportunity to learn from each other. That’s a useful lesson as we discuss and embrace faith, ideology and even political views.


The word “essay” comes from the French word Essayer which means “to try.” An essay is something you try to figure something out. Paul Graham, who shared this thought on his blog continues —

Figure out what? You don’t know yet. And so you can’t begin with a thesis, because you don’t have one, and may never have one. An essay doesn’t begin with a statement, but with a question. In a real essay, you don’t take a position and defend it. You notice a door that’s ajar, and you open it and walk in to see what’s inside.

If all you want to do is figure things out, why do you need to write anything, though? Why not just sit and think? Well, there precisely is Montaigne’s great discovery. Expressing ideas helps to form them. Indeed, helps is far too weak a word. Most of what ends up in my essays I only thought of when I sat down to write them. That’s why I write them.

In the things you write in school you are, in theory, merely explaining yourself to the reader. In a real essay you’re writing for yourself. You’re thinking out loud.

I shared this today as part of my last technology note this year as part of the Notes by Ada project. I generally share the longer version of these notes on Medium and LinkedIn (experimented with both over the course of the year) and a synopsis of sorts here. I thought the above paragraphs beautifully summarized why I set out to do this. I had many questions about technology and figured I’d write my way to clarity.

This is also why writing here every day is such a fascinating experience. Writing clarifies thinking and I’m grateful for the opportunity to think out loud, share my notes with you and, every once a while, hear back from you when things resonate.

Here’s to more essayer. :)

What happened

We have a natural propensity to spend a lot of time in our lives sharing what happened.

As a result, we’re stuck with status update meetings, chronological/career focused introductions and dinner table conversations about events around us.

What happened, it turns out, isn’t a good question. There are numerous other questions that are more powerful. For example –

  • What did you learn from what happened?
  • How has what happened change your perspective?
  • What are you going to do about it?

If a poker game was decided simply by the cards that were dealt, it would be a really boring game indeed.

So, the next time you’re tempted to talk about or agonize about what happened, consider re-framing the question. In conversations, meetings, careers, and life, what happened matters far less than what you decide to do about it.

Adam Robinson on Understanding

WordPress Founder Matt Mullenweg shared an excerpt from from Adam Robinson. It is from Tribe of Mentors by Tim Ferriss. Matt’s note – “Worth considering, especially if you strive to work in a data-informed product organization.”

Virtually all investors have been told when they were younger — or implicitly believe, or have been tacitly encouraged to do so by the cookie-cutter curriculums of the business schools they all attend — that the more they understand the world, the better their investment results. It makes sense, doesn’t it? The more information we acquire and evaluate, the “better informed” we become, the better our decisions. Accumulating information, becoming “better informed,” is certainly an advantage in numerous, if not most, fields.

But not in the counter-intuitive world of investing, where accumulating information can hurt your investment results.

In 1974, Paul Slovic — a world-class psychologist, and a peer of Nobel laureate Daniel Kahneman — decided to evaluate the effect of information on decision-making. This study should be taught at every business school in the country. Slovic gathered eight professional horse handicappers and announced, “I want to see how well you predict the winners of horse races.” Now, these handicappers were all seasoned professionals who made their livings solely on their gambling skills.

Slovic told them the test would consist of predicting 40 horse races in four consecutive rounds. In the first round, each gambler would be given the five pieces of information he wanted on each horse, which would vary from handicapper to handicapper. One handicapper might want the years of experience the jockey had as one of his top five variables, while another might not care about that at all but want the fastest speed any given horse had achieved in the past year, or whatever.

Finally, in addition to asking the handicappers to predict the winner of each race, he asked each one also to state how confident he was in his prediction. Now, as it turns out, there were an average of ten horses in each race, so we would expect by blind chance — random guessing — each handicapper would be right 10 percent of the time, and that their confidence with a blind guess to be 10 percent.

So in round one, with just five pieces of information, the handicappers were 17 percent accurate, which is pretty good, 70 percent better than the 10 percent chance they started with when given zero pieces of information. And interestingly, their confidence was 19 percent — almost exactly as confident as they should have been. They were 17 percent accurate and 19 percent confident in their predictions.

In round two, they were given ten pieces of information. In round three, 20 pieces of information. And in the fourth and final round, 40 pieces of information. That’s a whole lot more than the five pieces of information they started with. Surprisingly, their accuracy had flatlined at 17 percent; they were no more accurate with the additional 35 pieces of information. Unfortunately, their confidence nearly doubled — to 34 percent! So the additional information made them no more accurate but a whole lot more confident. Which would have led them to increase the size of their bets and lose money as a result.

Beyond a certain minimum amount, additional information only feeds — leaving aside the considerable cost of and delay occasioned in acquiring it — what psychologists call “confirmation bias.” The information we gain that conflicts with our original assessment or conclusion, we conveniently ignore or dismiss, while the information that confirms our original decision makes us increasingly certain that our conclusion was correct.

So, to return to investing, the second problem with trying to understand the world is that it is simply far too complex to grasp, and the more dogged our at- tempts to understand the world, the more we earnestly want to “explain” events and trends in it, the more we become attached to our resulting beliefs — which are always more or less mistaken — blinding us to the financial trends that are actually unfolding. Worse, we think we understand the world, giving investors a false sense of confidence, when in fact we always more or less misunderstand it.

You hear it all the time from even the most seasoned investors and financial “experts” that this trend or that “doesn’t make sense.” “It doesn’t make sense that the dollar keeps going lower” or “it makes no sense that stocks keep going higher.” But what’s really going on when investors say that something makes no sense is that they have a dozen or whatever reasons why the trend should be moving in the opposite direction.. yet it keeps moving in the current direction. So they believe the trend makes no sense. But what makes no sense is their model of the world. That’s what doesn’t make sense. The world always makes sense.

In fact, because financial trends involve human behavior and human beliefs on a global scale, the most powerful trends won’t make sense until it becomes too late to profit from them. By the time investors formulate an understanding that gives them the confidence to invest, the investment opportunity has already passed.

So when I hear sophisticated investors or financial commentators say, for example, that it makes no sense how energy stocks keep going lower, I know that energy stocks have a lot lower to go. Because all those investors are on the wrong side of the trade, in denial, probably doubling down on their original decision to buy energy stocks. Eventually they will throw in the towel and have to sell those energy stocks, driving prices lower still.

The whole world

I am reminded of the “I love the whole world” song from the Discovery Channel this morning.

I was fortunate to spend the whole day yesterday in a place with a wonderful view. I spent a lot of time just taking in the fresh air and feeling grateful.

The world is a beautiful place and we are very lucky to have the opportunity to share it with each other. It is hard to keep that luck in perspective on a daily basis while we’re busy fighting our many, often trivial, battles.

But, that’s what traditions like thanksgiving are for. If you are reading this on a laptop or a cell phone somewhere, it is likely that you have plenty of privilege to be grateful for.

Here’s to making that privilege count.

Old self behavior

A friend recently described a moment he had recently. He was in a situation where he realized exactly what his old self would have done. As he chose a new and different response, he realized how much had changed over the past few years.

I go through moments like that every once a while and can speak to how liberating it feels. You know you’d have been tied to a certain script a while ago. But, now, you can choose different.

It feels great.

I’ve met and spoken to people who are steadfast in their belief that people can’t change – that they think a certain way or are only capable of doing a certain kind of thing. There’s a part of me that always finds that sad. It isn’t sad because they think less of people around them. It is also not because they are always wrong.

But, I’ve come to realize that where there is desire and strength of character, change is not just possible. It is probable.

And, I am saddened because looking at everyone around us with a fixed mindset confines us to one too. There is certainly joy in watching others change because of something we did.

But, there are few more powerful moments in our lives when we’re able to look into ourselves in the mirror and say – “I can change.”

The possibilities are endless.

Pick up the phone

If an email exchange exceeds 4 back-and-forth emails with limited progress on what you’re trying to communicate – stop. Pick up the phone.

If you are going back and forth on whatever chat tool you use for longer than a minute – stop. Pick up the phone.

If your text message spree isn’t solving the problem – stop. Pick up the phone.

If you are attempting to text while driving – definitely stop. Pick up the phone.

Or, if these folks live with you or work close to you, go meet them in person.

Asynchronous communication has a time and place. Best to use it when it is effective.