Asking Why

Young children as so great at asking “Why?”, but somewhere on the road to becoming adults, we stop¹ . Being curious is one of the most powerful tools we have.

“Why” comes in so many different forms, all of which are valuable:

• Values & strategy: Why did we decide to do A over B? Why is this important?

• Personal motivation: Why was she your favorite manager? Why did you hate that job?

• Interpersonal dynamics & politics: Why is [stakeholder] not aligned? Why does the founder not trust them?

• Process & operations: Why do we do Agile in this way² ? Why are these steps required?

Take the opportunity to be curious in three different ways:

1. To the people you work with or work for you: What makes them tick? What about their work do they love or hate? What’s their preferred communication style?

2. When something goes wrong: What are the underlying reasons that led to our situation? Why do those underlying reasons exist? Are we OK with those tradeoffs? Does it reflect our values?

3. When decisions get made: How does this illuminate and address the most important problems we need to solve? What factors and dynamics led to this decision? Could we have done better?

If you are in a position of seniority, your curiosity comes with some ability to influence. Use it. But even if not, curiosity is a powerful vehicle for learning, which you can take with you to the next project, the next crisis, and the next job.

The Workshop

This is a newsletter-only section where I share a half-baked idea in hopes that y’all who are smarter than me can work it out with me.

I think a lot of people are recognizing that GenAI is in a crazy hype cycle right now, with the potential for impact far outpacing the reality. It’s crypto / web3 but way, way bigger, I think in part because us humans are social animals, with written, spoken, and visual language baked into our brains, and LLMs speak directly to that.

To be clear, I’m not bearish on GenAI. It’s clearly already having massive impact and will continue to do so. But its limitations — hallucinations and the fact that it’s more of a language prediction mechanism than true logical reasoning — are hard to dismiss.

I would put it on the scale of the invention of the mouse and the graphical interface. Bigger than most innovations, but smaller than the printing press or the Internet.

One of the best results of this hype cycle will be waking up companies who had previously ignored data science, machine learning, NLP, and other forms of AI that there are huge wins to be gained by applying AI to their operations. So, as a form of awareness marketing, I think it’ll be transformative. But I don’t believe GenAI itself will be the primary value creation driver.

1  I’m not qualified to give a full accounting for why we stop asking why, but I will say that, in American culture, our society teaches kids to stop asking why from an early age. Schools often value discipline (following the rules, doing as you are instructed) over curiosity, as do some religions. Corporations, long ago built upon the structure and culture of military organizations, expect orders to be followed. It’s the efficiency of top down command & control. When the leader (or teacher, or parent) lacks the time, resources, empathy, self-awareness, patience, etc to get everyone bought in properly, the backstop is “Do as I tell you, or be punished”. I am not a fan of anarchy, or libertarianism, or communism, or flat corporations with no management. Hierarchical structure has value. But I think too often we fail to help those we have power over understand and believe — either because we ourselves don’t understand, or we lack the time & patience, we’re tired, we have ego, we like the feeling of power, we’re scared, etc — so instead we dominate and subjugate.

2  Teaching has been one of the best vehicles for forcing me to understand, at a first principles level, why we do the things we do in Product. Why scrum, why PMF, why MVEs, why strategy. I recommend everyone take on some mentorship or teaching opportunities. When you get asked “Why”, do you feel good about your answer?