At some point or another, I’d imagine virtually all of us have answered some form of the “money is no object” question. Essentially this: If you didn’t have to worry about money at all, what would you do?
My standard reply is to open some form of bookstore and coffee shop.
There would be no WiFi, and we’d stack the whole place with good old-fashioned physical books. If we want to get really specific, I’d name it “Penny University,” a callback to English coffeehouses in the 17th and 18th century. Oh, and we’d have monthly discussions where we call in experts to debate both sides of a “hot topic” (education, politics, poverty, future of work, etc).
I’ve thought about this a lot!
As much as I love this idea though, I’m probably not going to open a bookstore. The whole thing just feels so risky, especially as we talk about a worldwide pandemic (setting aside the ebook vs. physical book discussion).
Imagine my shock and delight when I read about Ryan Holiday’s new bookstore outside of Austin, Texas—The Painted Porch. He wrote a piece for the Texas Monthly aptly titled “Opening a Small-Town Bookstore During the Pandemic Was the Craziest Thing We Ever Did.“
The whole experience was fascinating, but one piece stuck out, what I would equate to a version of red teaming:
Whenever I’m considering an idea I’m excited about, I like to ask friends to talk me out of it.
I’m constantly drawn to leaders in military settings. I suspect it’s because of the immense gravity surrounding their specific situation.
It’s hard to fathom what it’s like to lead a country being bombed on a nightly basis like Churchill or finding a way to stay positive when you’re facing a seemingly dominant adversary with a dwindling force and no money to pay new recruits like Washington.
These situations only magnify the importance of great leadership, which makes them all the more useful for us to learn from.
Recently, I finished reading Call Sign Chaos by four-star General James Mattis and Bing West. The book traces Mattis’ 44-year career through the Marine Corps and the various leadership lessons he learned along the way. Outside of the direct experience he gained leading millions of troops in battle, Mattis is a voracious student of military history.
When someone with this much experience offers to share their knowledge, it’s not a bad idea to listen!
Mattis continually referred to the “Listen, learn, and help. Then, lead” leadership style attributed to George Washington. This approach provides a helpful contrast against the typical power-hungry
It seems like more people are reading actual books these days. Admittedly, I have no data to back this up outside of my observations of friends in-person and on social media. However, more people I know are posting reading lists, book reviews, and photos of their physical library.
I love this trend! I’m a big believer in the power of continued learning. Books are one way (and my preferred method) of learning. There is a trap lurking though.
It’s easy to quantify the number of books we read in a year. As with anything else quantifiable, the total number emerges as some sort of status symbol.
Today’s post deviates a bit from the norm. I’ve been reading quite a bit about history and Stoicism in particular. A few concepts are sticking out like this idea of a moral ledger. So, let’s explore and start with a story!
In September of 1855, John D. Rockefeller landed his first job after spending weeks searching high and low for work. Shortly therafter, he purchased a small red-covered notebook referred to forever after as “Ledger A.”
The eventual business titan kept scrupulous notes for every transaction and tracked everything down to the cent. Many years later, he acknowledged the importance the book held:
I haven’t seen this book for twenty-five years. You couldn’t get it from me for all the modern ledgers in New York and what they all would bring in.John D. Rockefeller, Sr.
One can posit many reasons why Ledger A held such importance. Rockefeller was fascinated by money since a young age. The book also marked the start of his professional career and his self-sufficiency in life.
More than that though, ledgers represented a hedge against fallible emotion and a tool to aid in decision-making. They grounded the idea of business in a firm reality of additions and subtractions.
We can appreciate Rockefeller’s attention to detail when it came to bookkeeping, but this attention to detail expanded beyond accounting into the moral realm. I found the moral aspects far more interesting and applicable to the present day.
For the past few weeks, I’ve been going through an internal workshop at Zapier called “Coaching For Performance.” I have many takeaways that I’m trying to implement in my own work. By far the most difficult strategy though involves “taming the advice monster.”
I imagine you’re familiar with this concept already. The advice monster frequently rears its head when someone approaches you with a problem. You listen patiently for a minute or two and then immediately begin offering up your advice.
Because, obviously, you have the solution, and they need to hear how awesome it is!
Maybe a solution is exactly what the person was looking for but probably not. Maybe they just wanted to talk through the issue and be heard. Maybe they wanted your feedback on a specific piece. Maybe they could come up with a solution on their own.
Engaging your advice monster has some obvious negative consequences:
- You’re robbing the other person of a learning opportunity. Giving answers works in the short-term but not in the long-term.
- You’re reducing their sense of autonomy. Instead of empowering them to resolve their own issues, you’re creating a bottleneck where you’re the answer provider.
- You’re sending the subtle message of “You can’t figure this out yourself.”
The list goes on!
These downsides are obvious. You and I both know better than to continually engage our advice monsters. So, why do we do it constantly?
It feels like a gross understatement to say that the pandemic has changed the future of work.
Unemployment, remote work, shifting industries…you get it. I’m not saying anything you haven’t heard about many times over already. I do want to drill down on a particular aspect of leading remote teams though. How do you know when anyone is getting work done?
In an in-person office, we start with the assumption that if you’re at work, you’re getting work done. Rightly or wrongly. Even if you accomplished nothing during the week, you could say, “I was here.” (Bad) Leaders can therefore fall back on “butt-in-seat management” wherein visible attendance equals valuable output.
This obviously gets trickier in a remote environment! There isn’t an “office” to show up to on Monday morning. Sure, most companies have some kind of communication tool like Slack. Unless your leader is really nosy though, they probably have little idea when you’re actually around.
So, what do leaders do? And, how can we, as teammates, help?
Recently, I came across Patrick McKenzie’s blog post about working at Stripe. He breaks down why he feels like Stripe has been able to move faster than most other companies of the same size.
There are obviously many factors at play here including organizational policies, team structure, communication norms, hiring…the list goes on. I really loved this line of questioning though:
I have seen truly silly improvements occasioned by someone just consistently asking in meetings “Could we do that faster? What is the minimum increment required to ship? Could that be done faster?” It’s the Charge More of management strategy; the upside is so dramatic, the cost so low, and the hit rate so high that you should just invoke it ritualistically.
Most organizations operate at nowhere near the frontier of their capabilities. That is a choice, and strikes me as a valid choice, but you can choose to move closer to the frontier, too.What Working At Stripe Has Been Like, Patrick McKenzie,
There truly is very little downside in asking the simple question “Could we do that faster?”
That question has been bouncing around in my head for quite some time specifically as it relates to my role in leading people and teams. How can I create an environment that increases the cadence of our team? What obstacles commonly get in the way? How can we avoid them?
Here’s a non-exhaustive list I’ve compiled on why teams move slower than necessary and how to address each.
I recently finished reading Powerful: Building a Culture of Freedom and Responsibility by Patty McCord, former Chief Talent Officer at Netflix. Hat tip to my former colleague Kelly for the recommendation!
The Netflix culture has drawn quite a bit of attention since their Culture deck was made public. In many ways, the book was an expansion on the key bullet points in the deck, but I found the additional context and detail in the book really interesting.
There’s no question that Netflix has been extraordinarily successful over the past decade. It was interesting to get a peek behind the curtain at the culture of the company and a first-hand account of how it contributed to their success.
Here are some notes and highlights I made as I went through each chapter.
I found this post about awkward 1:1s valuable and hope to begin incorporating some of the suggestions in 1:1s.
Very often, people waste most of the 1:1s potential. You might make a little agenda, and then give some updates, some light feedback, and share some complaints. It’s helpful and valuable and nice. But, ask yourself: is the conversation hard? Are you a little nervous or unsure how to get out what you’re trying to say? Is it awkward?
Because if it’s not a bit awkward, you’re not talking about the real stuff.
This rule especially resonated:
Don’t talk about any topic that you could discuss in the open, among your team desks or in the cafe. If it’s safe enough to be overheard — it’s not the right content for a 1:1. Email it, send it in Slack, discuss among the desks, say it at a meeting, anything but a 1:1.
I enjoyed the follow-on post as well – Awkward 1:1s: How To Get Honest Feedback.