Author: luke-kanies

Great Design Is Ruining Software

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The arrival of the smartphone has convinced the world of the value of great software design, but it’s not all good news

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Originally published on my personal site.

The smartphone has reached more people and delivered more value faster than any technology ever seen. Much of the world has had to adapt to this arrival, but software design suffered the greatest reckoning. As the smartphone ascended, developers finally adopted reasonable design principles, realizing that they could not pack every feature ever seen into the smartphone experience. This recognition of the value of design — and especially, minimal design — is a good thing.

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Strategy Is Culture

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How you work determines your destiny

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Peter Drucker famously said, “Culture eats strategy for breakfast.” This is often interpreted as culture being more important than strategy. These might not even be his words, which makes it hard to know his thoughts, but having built a company to almost 500 people, it’s obvious to me that culture isn’t more important than strategy, it is strategy.

I am confident he knew this. He worked with the Japanese manufacturing companies in developing their culture of kaizen, which helped them to dominate the automobile manufacturing world, and their practices have gone on to fundamentally change manufacturing as an industry.

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Moving Beyond Silicon Valley Software Companies

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We need a new financing model to build new, better companies

Two decades into a software career, I’m still moved by its potential to improve people’s lives through connection, automation, and access to information, yet I’m less convinced than ever that our financial systems are built to get the most out of it.

This is the first post in a series I’ll be writing on the structural problems in venture capital. These problems aren’t a condemnation of the industry, they’re an attempt to outline where the industry fails the market. This failure helps to explain people’s experiences, but I think also helps to outline the opportunity and need for other ways of funding companies. These ways will also have flaws — they’ll likely not be great at building unicorns — but they’ll be finding people and markets ignored by the current environment.

Like the general financial industry, the world of venture capital has become adept at using money to create more money, but it does not consider of the wisdom of its actions. It chooses easy answers, thus leaving harder but better questions unexplored, and accepts high collateral damage to the employees, customers, and industry that at best is painful and at worst is pure exploitation.

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Framing the Risk in Your Business

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Growth requires risk. But don’t overdo it.


I was asked by a CEO recently, “How do I know if my product is ready to scale?” He thought he was ready to raise money and start growing the company, but he didn’t really know how to be sure.

Venture capital exists to invest in enterprises that have a huge opportunity but are also a big risk. Yet VC firms tend to actually be pretty conservative, relying on pattern recognition and social networks to make their decisions. This turns investor pitches into bizarre encounters where you have to help them see the huge risks in your business and how this risks can generate massive returns, but you also must convince them that you have all of that risk managed, so there’s no reason to be afraid. I’ve been turned down so many times by investors “until we’d taken the risk out of the business,” and every time, I’d sit in the car outside their office park thinking, “But don’t you exist specifically to make big bets?”

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Productivity Is Not About People

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How best to combine “software” with “management”?


You’re doing productivity wrong. Actually, it’s worse than that. You have no idea what it is. And no, this isn’t some sort of technical, jargon-y sense where I’m arguing over whether to measure it in terms of lines of code, hours spent typing code, or something else. Your core understanding of productivity is entirely wrong, and it’s making your company worse at everything it does.

Productivity in the software world is discussed in terms of the individual, and usually phrased as getting more of a person’s time on the thing they were hired for. “Hey, I didn’t hire you to talk to users or attend training! I hired you to write code!” Even the developers join in: “Every minute I spend in meetings instead of writing code is wasting company money.”

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Leadership Is Direction Plus Constraints

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How I went from a capricious boss to a powerful partner.


Early in my tenure at Puppet, I had one of my employees, José, make laptop stickers. He said we already had some, and I said, yeah, but they suck. So he designed something different. I said nope, still not right. Finally, in frustration, he said, “You clearly know what you want, can you just tell me what it is?”

I expect many of you will recognize this problem. It is sometimes called “Bring Me a Rock”, which pretty well captures its absurdity. Becoming a better leader required I find a way past it.

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When It Comes to Culture, You Can Be Right, or You Can Be Successful

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Apply the lessons of product design to your company culture


Every founder understands the importance of culture in the long-term success of their company. Yet rather than valuing and supporting all employees, organizations like Uber still manage to build a toxic, poisonous one. How does this happen, and what can you as a founder do to prevent it?

We’re still in the early days of understanding how to build great culture. However, the barriers to doing so are surprisingly similar to another area where we’ve come leaps and bounds in the last decade: Creating great products. The similarities in their problems mean the tactics for solving them should be portable, too. In both cases, the barrier is essentially:

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The High Cost of Fitting In

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They say authenticity is the key to success, and once you can fake that, you’ve got it made. My experience says it’s not quite so simple.


When I was 23, I was hired as a system administrator for the first time. I joined BlueStar Communications, which was a young but well-funded company stupid enough to take on the incumbent telecom carriers. Their CEO was a maverick, especially in staid telecom in Nashville, Tennessee. He was bringing always-on internet to small businesses in the southeast (yes, there was a time when this innovative), and blended in about as well as a hockey player in a three piece suit. I was excited to work with someone who I could identify with, and learn from.

He was fired the week I started.

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Start with the Dangerous Questions

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If something makes you uncomfortable, lean into it.


Throughout my 12 years as CEO of Puppet, I made critical decisions that affected nearly everyone involved in the company: What investors should we work with? Who should we hire? What products should we build? Should we take that deal with a customer?

These decisions are scary. Getting them right can be a huge lift for a company, but getting them wrong can destroy one. I worked at a company that lost more than a year of growth and roadmap development because they signed their largest customer ever. One of my advisors told me a payment of more than one hundred million dollars from a partner destroyed his company. I’ve also taken big risks on key employees, and had some of them work out fantastically, and others flame out spectacularly.

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