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In my previous article, Who Gains? A Guide to Better Understanding Motivations, I discussed the following:

As a leader, there will be times when you have to make difficult requests of your employees. Have empathy for those you’re about to put a burden onto: they are the ones who have to put in the work to make things happen, yet you are the one who typically stands to gain the most.

While researching how morale impacts organizational outcomes, I came across possibly one of the greatest leaders in history, Genghis Khan, who founded the Mongol Empire and established the foundation for what would become the largest contiguous empire in history. …

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One of the first lessons taught in negotiation is to build alignment, which is achieved by convincing the other person that you are both on the same side. However, sometimes savvy negotiators use this technique to their advantage and run circles around you, leaving you in the dust once you’ve realized what’s actually happened. Other times, alignment is based on a misunderstanding: for example, have you ever walked out of a meeting where everyone seemingly came to an agreement only to realize later on that everyone had a different interpretation of said agreement?

Here are two techniques I’ve found useful in preventing these types of false…

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Let’s try a thought experiment. If I gave you the opportunity to cure cancer, but it would cause you to be broke for the rest of your life, would you take the offer? Depending on the person, I’m sure many would and many wouldn’t.

Now let’s take this scenario one step further: if you found out that by curing cancer, you would make me a billionaire. Would you still take the offer? Even if you still would, you would likely at least question my motivations for pushing you to take the offer.

I’d like to offer a framework for how to evaluate such a request if you were on the receiving end, inspired by the crime detective show, Numb3rs. As with most crime detective shows, the detectives look for both evidence and motive. In particular, one scene stayed in my memory over the…

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One of the prevalent beliefs in Silicon Valley is to optimize for speed. Be it The Lean Startup or Blitzscaling, much of popular advice about building products puts an emphasis on speed. The idea is that getting a product out there sooner is better than waiting for the perfect product — sometimes you don’t know what the perfect product is without testing the waters and then iterating on it. While that mindset is highly valuable in many situations, I’d like to talk about an alternative approach: timing and precision.


When I first set foot in a Martial Arts fighting gym, I was terrified. Everyone looked tough, and I wasn’t sure if I could fit in. While I knew I was strong and could develop my fight cardio over time, I wasn’t as explosive as some other fighters, whose impressive speed is determined primarily by genetics. …

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After I published the first article of this series, Why Transparency Is Especially Critical in Times of Crisis, a friend of mine provided some feedback:

“Sometimes the lack of transparency is due to leaders’ unwillingness to communicate uncertainty. It may make them look weak, or require them to be vulnerable. As a result, they prefer to wait till everything is set in stone before announcing further information.”

This is a valid point. When Airbnb CEO Brian Chesky announced the layoffs to employees in May, he listed the following as one of the principles:

“Wait to communicate any decisions until all details are landed — transparency of only partial information can make matters worse.” …

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As the economy declines, an increasing number of companies are pivoting from peacetime management to wartime management. Renowned entrepreneur and venture capitalist Ben Horowitz wrote a blog post “Peacetime CEO / Wartime CEO” in which he lists the many differences between the two types of company management. In particular, the following caught my eye:

Peacetime CEO focuses on the big picture and empowers her people to make detailed decisions. Wartime CEO cares about a speck of dust on a gnat’s ass if it interferes with the prime directive.

Peacetime CEO strives for broad based buy in. Wartime CEO neither indulges consensus-building nor tolerates disagreements. …

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As we witness much of the world’s economy crumbling and unemployment surging due to the lasting effects of COVID-19, most companies are losing a significant portion of their revenue. Many are scrambling to cut costs to survive, and the tech industry is no exception. In April, Yelp laid off 17% of its staff and furloughed another 17%, and many others have followed suit, including Lyft, Opendoor, and Uber to name a few. The layoffs have shown that one thing is true: transparent communication from leaders is key to gaining employees’ trust and building your company’s brand.

Bird laid off approximately one-third of its staff via a two-minute Zoom call and locked employees out of their accounts, a move that has been referred to as “the sh*ttiest layoff in corporate history.” Employees and critics alike felt the dismissal lacked transparency — some even openly questioned whether the two-minute message was pre-recorded — leaving employees dumbfounded. …

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“Rules…without them we live with the animals.”

— John Wick

Back in the 18th century, the most popular combat sport in the U.K. was bare-knuckle boxing. Two fighters would get together and fight without any modern rules or equipment, such as padding or gloves. The sport looked nothing like modern boxing, as boxers kept their hands low (at chest level), mostly punched to the body, and wrestled a lot.

The reason old-school bare-knuckle boxing looks so different from modern boxing is because of rule changes. When a ruleset changes, the players involved typically have a set of immediate reactions to said rules. Over time, as the rules sink in, patterns tend to emerge that may not be obviously related to the explicit rules, which I will call “derived behaviors.” Finally, there are also implicit rules: rules that are not explicitly stated but picked up by players from observing which behaviors get rewarded or punished. …

3 Steps to Assess Your Prospective Employer’s Culture

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Image by Christina via Unsplash

Over the past month, I’ve been approached by a handful of friends who all asked me the same question: “How do I assess a company’s culture?” I typically point them to the previous article in this series, where I discussed how to interview candidates for soft skills, and then explained that the techniques are applicable for when candidates ask employers questions, too. However, I realized that there are enough nuances to warrant its own article.

For companies interviewing candidates, I suggested three types of interview questions to assess soft skills:

  1. Ask open-ended questions
  2. Look for specific examples (or ask them…

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In my last article, I discussed the importance of framing: saying the same concept in different ways to capture different audiences. That said, one can also take framing too far. A former coworker once exclaimed, “I feel like when business development folks talk about ‘framing’, really they’re just lying.” While that is a gross generalization, there is a fine line between framing and lying!

Years ago, someone once submitted a question for a company-all hand about the 12% churn in the engineering department the previous quarter. The executive reworded the question — the contents of the submission was private — to instead ask about the 8% company-wide churn. He then explained that the company goal is to be within 5% annual churn so that 8% is only 3% higher than the target. However, if you have been following, you may have noticed that this is comparing apples to oranges: even after the “reframing” from engineering churn to company churn, the 8% in the revised question referred to quarterly churn, whereas the 5% target in the explanation was annual churn. …


Ken Kao

Product-minded Engineering Leader. Organization & Cultural Builder. Traveler. Martial Artist (Muay Thai & Pekiti Tirsia Kali).

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