Who is Robert Schlaff?

I’m a devoted husband and father to an awesome family. For work, I’m a Product Manager who looks at the goals of the business and uses technology to deliver those business and customer goals. I’ve driven transformational change at Citi, AIG, and Amazon Web Services. For more information about what I do at work, please visit my LinkedIn profile.

About This Site

I collect stories. There are so many amazing things happening every day. I need to spend some time writing them down before they slip away. Madeleine L’Engle said that every writer needs to keep an honest, unpublishable journal that nobody reads, nobody but you. But some of this stuff is too good to keep to myself. So I’m sharing it with you.

When I’m writing, I picture having a conversation with some of the world’s smartest and most interesting people — you, my readers. I picture us all sitting around a table telling stories and having fun. I’d like to think we’re a digital version of the Algonquin Round Table. Throughout the 1920s, some friends would meet daily for lunch at the Algonquin Hotel in New York. They included the founding editor of the New Yorker Harold Ross, the playwright George S. Kaufmann and the writer Dorothy Parker. This group, called The Algonquin Round Table,  would meet to tell stories and share quips in a bustling city that was finding its place on the world stage. They were the original raconteurs of New York, getting together to share stories that would enlighten and entertain. In an age when we no longer have two-martini lunches, I wanted to humbly bring that sensibility online.


Life Lessons

Product and Design

Art and Writing


Human Behavior

Math and Logic

On Amazon – A Peculiar Company

Disclaimer: I work at Amazon but this writing does not represent Amazon in any way. Opinions written here are strictly my own.

Amazon has a very strong culture. At other places I’ve worked, culture is an aspiration at the senior level but took a back seat to more pressing concerns like making as much money as possible. Amazon’s culture is embedded in its 14 Leadership Principles that are a common language and framework that form the basis of everything the company does, from interviews to everyday decisions. You can get a good feeling of the Amazon culture by watching videos of Founder and CEO Jeff Bezos. A few good ones are from the Economic Club of Washingtonan interview by his brother Mark,  the Axel Springer Award, and a 60 Minutes Story about Amazon from 1999.

Continue reading “On Amazon – A Peculiar Company”

In Praise of Humility — The Forgotten Story of Edward S. Harkness

The Residential Colleges were created 85 years ago. Though they have the names of many famous Yalies, the donor of these colleges is nowhere to be seen. Why?

What is a Yalie? When I think of the archetypical Yalie, I think of two things. First, a Yalie is someone who will do great things and change the world. Second, a Yalie has great human qualities of humility, philanthropy and caring for others.  While Yalies are always reminded of our great alumni and donors plastered across campus we rarely see the humbler and more human side. That’s why it’s important to remember Edward S. Harkness. Continue reading “In Praise of Humility — The Forgotten Story of Edward S. Harkness”

How to be Happy — Yale’s Most Popular Class

This year Professor Laurie Santos created Yale’s most popular class of all time. The class is titled Psychology and the Good Life but it’s really a course on how to be happy both in the short and long term. I was excited to hear that Yale was offering the course but even more excited to see that the class is available online. While there’s little I hadn’t heard before, it did a great job of focusing me on what’s important and helped me get into the practice of being happier.

Continue reading “How to be Happy — Yale’s Most Popular Class”

The Mother-in-Law’s Guide to Software Testing

This is part of my Mother-in-Law’s Guide to Technology. My Mother-in-Law is a very smart woman even if she isn’t a “computer person.” The goal of this series is to take some big and treacherous sounding ideas and bring them down to earth.

Dearest Mother-in-Law,

Remember when you had kids and you told them to do stuff. And remember how they used to do what you told them but that wasn’t always what you intended them to do? Well, that’s the way computer programs work.

Just like kids, computer programs will do what you tell them, but beyond that, all bets are off. They don’t do anything that directly contradicts what you said but that doesn’t mean they’ll do what you want them to do. Continue reading “The Mother-in-Law’s Guide to Software Testing”

The Mother-in-Law’s Guide to Cloud Computing

This is part of my “Mother-in-Law’s Guide to Technology.” My Mother-in-Law is a very smart woman even if she isn’t a “computer person.” The goal of this post is to take a very big and treacherous sounding idea and bring it down to earth. I tried this before in a post which I’ve now renamed The Mother-In-Law’s Guide to Chaos Engineering.

Dearest Mother-in-Law,

You know when we visit a Target or a Wal-Mart in the suburbs and they have 30 checkout lanes and only 3 are open at any time? I always wondered why that happens. It even sparked someone to write a funny blog post about the phenomenon: Target Store Opens More than Three Checkout Lanes; Shoppers Confused. Continue reading “The Mother-in-Law’s Guide to Cloud Computing”

When a Book Gets Caught Up in the Story. The Art of the Book in the Digital Age

When I was in college, David Foster Wallace (DFW as he was affectionately referred to) was a literary powerhouse. He was the author that all of the literature fanatics loved to read (or at least said that they loved to read). He wrote books like the thousand-page tour-de-force Infinite Jest that were too long and complicated for science geeks like me. DFW gave exactly one talk about his philosophy on life, addressing the graduating class of Kenyan College in 2005. The talk was titled This is Water.

After he died, that speech became a holy relic to the worshippers of DFW. But how do you take that speech and make it into something more, both as a homage to DFW and a way of preserving and extending the insights of the author? You create a book.

I loved the speech and was curious about how it could be transformed into a book. The speech is only 25 minutes long, so it needed to be something special. When I was in college, there was a room in the library for special books called The Art of the Book. It displayed books for their craft and construction, not just their content. The book This Is Water: Some Thoughts, Delivered on a Significant Occasion, about Living a Compassionate Life reminds me of the books in that room. It is a beautiful little volume with DFW’s speech split up over pages, complementing the cadence to the author’s writing. Continue reading “When a Book Gets Caught Up in the Story. The Art of the Book in the Digital Age”

Capture Better Memories Without a Camera

I’m always looking to better capture the special moments of my kids growing up. While having an iPhone in my pocket at all times lets me document these experiences, I feel like I’m not capturing the essence of those moments. I started thinking that technology was part of the problem, and if technology was causing the problem, more technology won’t fix it. Continue reading “Capture Better Memories Without a Camera”

When Millions of Eyes at Amazon Were Wrong

Disclaimer: I worked at Amazon Web Services as the Head of Banking Business Development. This writing does not represent the views of Amazon and opinions written here are strictly my own. Also, I’ll admit that this post wouldn’t be very interesting if it wasn’t about Amazon; however, it does highlight some key things about the company: 1) Amazon, like every other company, makes mistakes 2) Unlike many other companies, Amazon doesn’t view itself as infallible 3) When mistakes are discovered, the company quickly fixes them.

Amazon has a very strong culture. At other places I’ve worked, culture is an aspiration at the senior level but took a back seat to more pressing concerns like making as much money as possible. Amazon embeds its culture in its 14 Leadership Principles. This is a common language and framework that forms the basis of everything the company does, from interviews to everyday decisions. Continue reading “When Millions of Eyes at Amazon Were Wrong”

What a Wonderful Word

From the book Lost in Translation by Ella Frances Sanders

I remember the first time it happened to me. It was the first year of business school and we were working on an economics problem set. My friend Yugin had just arrived from Korea and she was correcting an answer for her economics homework.

She asked me “What’s the English word for after you erase something?”

I thought this was a philosophical question like, “What’s left of an image after you remove it?” Something like the way Robert Rauschenberg erased a drawing by William de Kooning to push the boundaries of art.

So I answered, “When you erase something there’s nothing left. You’ve erased it.”

“No, that’s not what I’m asking. Those little pink things that come off the eraser. What do you call that?”

“Hmmm … eraser shavings maybe. We don’t have a word for that in English.”

“Huh,” she said, “that’s odd. We have a word for that in Korean.”

It kind of blew my mind. I’d known this before but for some reason, it never sunk in. When things have a name it makes them more real. It gives them an identity. Dale Carnegie said that “A person’s name is the sweetest sound.” Mastercard shows the excitement and validation that trans people have when they have their real names (vs. their birth names) on their credit cards.

That’s why I love the young people’s book What a Wonderful Word. This short collection of 24 untranslatable words from around the world is beautifully illustrated and highlights the wonderful and surprising differences in cultures around the world.

Continue reading “What a Wonderful Word”

How Much is That Really Worth? The Mother-in-Law’s Guide to Valuation

Dearest Mother-in-Law,
Last year, when you and I went to the One World Observatory, we saw that famous tourist location—the penny crushing machine. We watched a tourist put her penny in the machine and then added in a dollar. The machine then crushed the penny into a medallion that she could take home as a souvenir. Your quite reasonable reaction was, “Why would you pay a dollar to have your own Penny crushed?”
The Penny I Crushed at 1 World Trade
The way you were looking at it was:
  1. Initial valuation: $1.01.
  2. You start with a penny and a dollar.
  3. Then you put a dollar in a machine that crushes the penny.
  4. You get back the crushed penny.
  5. Final valuation: $0.01.
  6. Result: You feel like you’ve wasted a dollar.

But I think the crushed penny is a pretty good value. To understand why, let’s understand the job that the crushed penny is doing. When most people think about products, they think about the product itself, i.e., I’ve taken a penny and gotten a crushed penny. But people don’t buy most products just to own them, they hire products to perform a job. The famous Harvard marketing professor Theodore Levitt used to tell his students, “People don’t want to buy a quarter-inch drill. They want a quarter-inch hole!”

Clayton Christensen, of Harvard Business School, and Scott Cook, CEO of Intuit, introduce the concept in their article Marketing Malpractice: The Cause and the Cure. I’ve paraphrased some key parts below.

A hypothetical fast-food restaurant is looking to improve sales of its milkshakes. Researchers observed that in the afternoon parents often bought milkshakes, in addition to complete meals, for their children. What job were the parents trying to do? They were exhausted from repeatedly having to say “no” to their kids. They hired milkshakes as an innocuous way to placate their children and feel like loving parents. This was expected and a well known job that milkshakes perform.

However, one researcher was surprised to find that 40% of all milkshakes were purchased in the early morning by customers driving alone in their cars. He found that most bought it to do the job of making their drive to work more interesting and keep them satiated until noon. 

So the milkshake is doing two completely different jobs. With children, the milkshake is a competitor to a toy or candy. However, as an early morning snack, customers may buy a bagel, banana, or donut instead. The key point here is that the milkshake can be hired to do completely different jobs, meaning that it has a very different value depending on the context.

Getting back to my crushed penny. I want it to do the job of a souvenir, providing a physical memento of the trip that the kids can buy and keep. The alternatives are a t-shirt, a stuffed animal, or a postcard. It would be hard to find a souvenir for my boys for cheaper than that.

So I’ve talked to my kids and we agree that the crushed penny is a good souvenir. But how can we make it more valuable than another typical item they might get at the souvenir shop. That’s where the elongated coin album comes in.

The Penny Crusher Album
At the One World Observatory, you asked me why anyone would buy a case for these crushed pennies. “It’s even more useless than the crushed penny!” you insisted. But the album has a wonderful purpose. It lets my boys keep their crushed pennies in a safe place and makes sure they don’t lose them. It turns a crushed penny into a treasured collectible and makes the kids into official crushed penny collectors. Then, when they are deciding between whether they want the crushed penny or an expensive souvenir, we can have a discussion on what we’re likely to keep around longer and value more. The crushed penny and album should do well in that fight.
The Boys Penny Collection (So Far)
I agree with you that crushing a penny for $1 is not a worthwhile exercise. But creating a token souvenir at every tourist attraction we attend for $1 in lieu of something we’d just lose is a great deal! Buying an album is a drop in the bucket and makes each penny that much more valuable to the kids.

Thank You for Being a Friend

If you threw a party and invited everyone you knew, you would see the biggest gift would be from me and the card attached would say, “Thank you for being a friend.”
Theme Song from The Golden Girls

In Judaism, the word minyan refers to a group of 10 adults that come together to pray.  For certain prayers, most importantly prayers of mourning, a minyan must be present. It’s a struggle to find 10 Jewish men and women on a Sunday morning at our shul. On one cold day, I volunteered and was the 8th adult there. Not convinced we’d get to 10, we started the service. I was wondering why we had this arbitrary number of 10. Why are we dragging some people out of bed who don’t want to be there? Just then, surprisingly, the 10th person showed up and in a palpable way, and we were transformed. We went from praying as individuals to praying as a community. I felt like we were the lions forming Voltron.

It made me think about friendship. Friendship is about being there for one another. Anyone can celebrate with you when it’s convenient. A true friend is always standing by you even when especially when things are tough. Continue reading “Thank You for Being a Friend”

Mother-in-Law’s Guide to Open Banking

Dearest Mother-in-Law,

First of all, Open Banking is not about keeping banks open later in the day or having more banks open on Sundays. Open Banking is about 2 things:

  1. Open Banking Regulation: Many countries are regulating how banking data can be used. Open Banking refers to customer ownership of their own banking data. This article will focus on Open Banking regulation.
  2. Open Banking Collaboration: Even when this regulation doesn’t exist, banks see the benefit of collaboration and the usage of APIs (which is just a technical word for being able to use stuff from other banks). This version of Open Banking is broader and I’ll try to cover it in another post at some point.

Continue reading “Mother-in-Law’s Guide to Open Banking”

Creating Great Social Experiences

Creating products is about building great experiences for customers. In the past, companies would create products to tell a story to customers. But my old boss, Raja Rajamannar, CMO of Mastercard, says, Storytelling is Dead. Jeff Bezos says that at Amazon, “We see our customers as invited guests to a party, and we are the hosts. It’s our job every day to make every important aspect of the customer experience a little bit better.” However you cut it, customers are now engaged participants rather than passive recipients. It’s the job of companies to engage with customers rather than just treat them as an audience. Continue reading “Creating Great Social Experiences”

Carpe Diem! How to Live Like an Emperor

At the end of last year, Bubbie, my last living grandparent, was fading away. She couldn’t see, could barely walk, and her kidneys were failing. It was becoming clear that we needed to savor each moment with her. So we created some great memories — like the last time we had a steak dinner with her and needed to push her on her walker around the corner to the restaurant. Or the last time she came to our house and Ari asked if he could snuggle her because he really likes snuggling people. We spent those last months finding special moments with Bubbie. And it was exciting because Bubbie was always up for some good fun.

I needed to focus on the quality of the time with Bubbie, not the quantity. You’d think that you could amass enough of something to make you happy, but it rarely does. Take ice cream for example. Bubbie loved ice cream. When I go to a great ice cream shop like the Sugar Factory I want to get the biggest and best thing they have. At Sugar Factory this would be an Insane Milkshake. On the menu, these milkshakes look awesome! They are the biggest most wonderful things on the planet. And I think that if I drink the whole thing, I will be happy forever. And then it comes. And the first sip is incredible. There’s even candy on top and chocolate covering on the outside of the mug. But as I eat it, it tastes less good and by the end, it becomes an unhappy challenge to even finish it. Eventually, through multiple visits, I learned that savoring a little bit of ice cream is far better than trying to eat all the ice cream in the world.

When I look at experiences I feel the same way. I think about all the places I haven’t been and adventures I haven’t tried. I want to pack them all into my bag of experiences and it just becomes overwhelming. But then I get excited at the wealth of possible adventures that I can explore every day. I just need to pay more attention. In my office building, there’s a skylight looking up at the Empire State Building that I didn’t even notice until my son pointed it out. I was always rushing by it to get lunch. There’s a great book on how dense the world is and how much we don’t see called On Looking: A Walker’s Guide to the Art of Observation by Alexandra Horowitz. In the book, Dr. Horowitz takes us down the same street with 11 different experts and shows us how much we’re missing as we walk down the street.

I even ignore the truly glorious things that are right in front of me. I remember when Ari was in preschool next to Central Park. How lucky was I! I got to walk to work by Central Park after dropping him off! One day I realized that I’d walked by Central Park thinking about work and what I had to do. All of a sudden I’d be at the subway, having completely checked out from the experience.  It struck me that this wasn’t going to last forever, Ari was going to graduate, and I wouldn’t be able to do this anymore. I thought about how I could make the most of the time I had left. Each day, I would take a full minute when I got to the park (I timed it) to just appreciate how lucky I was. A few times, I even took pictures of how pretty the landscape was because I knew that every day it would look slightly different. Finally, I played a game called, “Last Day” where I walked through the park like it was the last day of school. It’s an oddly fun game and it’s amazing how you can have that “Last Day” experience many times.

Central Park in the Spring
Central Park in the Winter

I’d forgotten about this Central Park experience for quite a while. Then I found myself in Japan at a work conference. I had some time to explore Tokyo one afternoon and ended up at the Imperial Palace. I ran around the place for a while seeing some amazing things like the burned down area where the concubines used to live. And the giant Tenshu tower that burned down in 1657 and was not rebuilt because one of the elders felt that the Shogunate had done such a good job protecting the peace that a proper tower was not necessary so it was never rebuilt.

As I walked through the East Gardens of the Imperial Palace, things seemed beautiful yet familiar. I was kind of annoyed at first thinking “WTF. I’ve come halfway around the world to see this Imperial Garden and it’s not any better than the park down the street.” Then I realized that I can’t compare them. Even though the Imperial Garden isn’t that different from Central Park, it doesn’t make it any less wonderful. I need to really step in and appreciate it slowly and take a minute and really absorb the place rather than compare it to someplace else.

The way to really appreciate the Imperial garden is the same way to appreciate Central Park. I need to soak in the little things as much as the big ones — reveling in and appreciating the moment.

It’s a pretty amazing experience. The Emperor of Japan opened his private garden to the public so that laypeople like you and me can see what it’s like to be an emperor. And it hit me: WE ARE LITERALLY LIVING LIKE EMPERORS.

Approaching the Emperor’s Iris Garden
In the Emperor’s Iris Garden

This was a profound experience. I was literally an Emperor for an hour and it didn’t make me happy. But when I took a step back to savor the moment, that filled me with joy. My friend, the Reverend Steve Singleton, likes to call out the difference between happiness and joy. Happiness (from the root “hap” meaning lucky) is what happens to you vs. joy is something that comes from you.

I started this piece by contemplating how important it is to savor every moment when someone is dying. But I know that every moment dies once it’s over. I remember when Blake was at his second birthday party. He turned to me and said, “Are all of these presents for me?” I thought this was wonderful, I’d raised the perfect humble selfless child who would always be like that. But of course I hadn’t. He changed into a normal kid on his next birthday screaming, “I want more presents!” I learned that when the kids do something cute and I say, “I’ll take a picture of it next week,” they’ve already grown out of it by the time I get around to snapping a photo.

The key to living like a king is to savor life, sucking all of the marrow you can out of each experience. Anna Quindlen, in her book A Short Guide to a Happy Life, has a great quote from Gwendolyn Brooks that sums it up well:




Focusing on the Most Important Thing

Focusing on the right thing is key to being successful in work and life.  If you focus on one thing, you can accomplish anything. But, as a mentor once told me, “If you have 12 apples, don’t take one bite of each.”

But figuring out what to prioritize can be tricky. At my college reunion, my friend Lutz and I were spending the day with our families. We’d jam-packed the day with great activities. As we were walking down the street, I saw a sign for Ashley’s Homemade Ice Cream.

I said, “Lutz, I’d really like to buy my family some ice cream.”

Being the logical German, he said, “Yes. That would be nice but there’s no time left in the day. We need to go hear the President of the University speak.”

“Lutz,” I said, “you have to prioritize. You can always watch the video of the President’s speech or read a transcript. But how often are you able to spend time with your family on a beautiful spring day, sitting on the college lawn eating ice cream?”

He said, “You’re right. Let’s get the ice cream.”

And it was the best decision we’d made that weekend.