Josh Evnin

Everybody is talking about AI these days. Many are excited, some are reticent, and most people in the real world simply don’t know where to start. Let’s talk about it.

But wait, why?

There are so many good reasons to start using AI tools, but mostly so that you know how they can help you. There is so much chatter out there right now regarding AI. Ignore that, and start selfishly. Ask yourself: how can these tools make my day easier, starting right now?

Even more importantly, recent AI tools can be an incredibly powerful tool to sharpen your thinking. How can that not be a good thing? Later in this article I’ll give more detail about the most important thing these tools do to advance your cognition.

Open a Tab

First of all, you can start for free, though there will eventually be some limitations or the tools will start to slow down. When that happens, you can jump to another tool for a bit and give the next one a try! Tabs you should open:

• ChatGPT
• Claude
• Gemini

The first thing you’ll want to do is simply keep an AI tool open in one of your browser tabs. Doing that will trigger you to use these tools when you need them. Otherwise, you are likely to fall back into your habits.

Just Get Started

Don’t be intimidated by the text box. One of the most revolutionary things about AI tools and LLMs specifically is that they support your natural way of speaking and working.

You don’t remember it, but at some point you had to learn the “right ways” to search Google. You don’t have to do that anymore. Sure, there are ways to optimize your prompts (which we can get into later), but at first it isn’t necessary.

Start Talking

Let’s say you are excited about making pancakes, but you have all of the ingredients except milk. Oy. ChatGPT (or Claude, or Gemini, or whatever) to the rescue:

Easy peasy. You can even ask a followup, as I did, to see if Half & Half was a suitable option. It’s that easy, you just chat.

The Most Powerful Part

Now, that example was pretty trivial, but hopefully it helps you dive in (and make some yummy pancakes). Beyond just getting started, when it comes to life and work, AI Chat tools can help you:

• think more deeply, clearly, and comprehensively than you have before
• get started on things that you put off because you know they will take a lot of thought
• think of things you never would have considered

These tools have the ability to draw out even more about what makes you, you. Amazing!

The more you use these tools, the more comfortable you will become with simply having a chat that holds a mirror up for your own thoughts.

For me, that’s the most powerful thing. I can dump my half-formed thoughts in, and 5 to 30 minutes later my thoughts are formed. That is a huge advancement. And the AI tool isn’t replacing me – it’s making me even better at being me.

Sure there are drawbacks to these tools, but for me, these advancements are worth it so far!

I figured out a magic question that I use at the beginning of every single 1:1 meeting, or any meeting I have with another individual, be it a direct report, skip level, investor, boss, whatever. Ready?

Magic Questions

First, I have to say, I spend every day seeking Magic Questions. If you know me, you know that I am always searching for hacks that make my efforts more effective.

A healthy part of my time as a UX leader was devoted to thinking about the perfect things to ask at a given moment. When you nail the perfect question, you unlock the most insightful answers, which is the most effective way to get to the right solutions.

The Magic Question for 1:1s

This question assumes you are meeting on a regular cadence with the other person, and the question is really easy:

So, how is it going?

Now there are a few tricks to asking this question:

1. It should be the first thing that you say to the other person. I mean, maaaaybe you can have a little small talk first, but use this question when you round the corner to the meat of the meeting.
2. You should ask it in the same way, with the same tone, every single time.
3. And the tone you use has to be normal, boring even.

Finally, the most important part: You have to listen and observe the speaker as they respond. Nine times out of ten, the response will not be anything interesting. They will simply say, “fine” or “oh you know, work is busy but good” or “great!”. You won’t think twice about it.

But then, every once in a while, you’ll notice something different. A slight twinge in the person’s voice, or a hesitation before they respond. That is the moment where there is likely something you can help with.

When you notice that difference in tone, dive in. Ask, “are you sure?” You can also point out whatever you noticed. Most of the time, this will help open up the conversation so you can move forward and improve things.

That’s it! It’s easy, as long as you are diligent and attentive. I hope this helps!

Often in business, we get caught working without an intentional strategy. 

Though there are many causes, it is important to understand that you are always operating with a strategy, it’s just that without intention, that path will yield uncontrollable results.

Believe me, I have heard the pushback many times over: “But Josh, creating a strategy is hard. It’s such a vague task.”

That’s right, and it’s wrong. People make strategy more complex than it needs to be, but that is not a great excuse for not being intentional. In the end, it’s important to articulate a strategy in order to understand how to operate, and to define what you need in order to succeed. 

In retrospect, the greatest product and business strategies seem brilliant. Let’s lower the bar for ourselves – our goal is not to create the next Moneyball. At first, we just start. (Later, Michael Lewis will figure out how to tell our story.)  

Let’s start with an example

In the early 1900s, Henry Ford decided to double workers’ hourly pay to $5, and simultaneously shorten their workday to 8 hours. These seem like paltry benefits now, but they were groundbreaking at the time. Can you imagine the feedback from Ford’s CFO? Ford was working against the strategic thesis that improving workers’ work conditions would increase productivity and loyalty. 

Ford realized that they would win the market in part by having a happier, longer tenured workforce who could afford the product they were making. It’s a pretty easy bet to have made in retrospect.

What’s not going to change?

When forming a strategy, Jeff Bezos asks the question, “What’s not going to change in the next 10 years?” This is a great place to start. For Amazon’s customers, there is no doubt that even lower prices will be welcome change 10 years from now. Same with faster shipping.

Thinking back on the Ford example above, the question might be “will workers desire higher pay in 10 years?” Obviously, the answer to that is yes. 

For Netflix, a critical bet was made on customers preferring streaming over DVD rentals, and you can imagine that at some point someone said, “we made movie consumption easier by shipping DVDs to customers’ doors. Will consumers prefer even less friction in the future?” Of course they would. 

Ideally, you are starting from a place of ample user research and analytics so that you understand what your users desire, and what behaviors are here to stay.

Roger Martin’s Simple Strategy Framework

I like Roger Martin’s Strategic Framework best. At it’s core, Strategy breaks down to:

• What is our aspiration?
• Where we’ll play
• How we’ll win

Well articulated responses to those questions become the overarching guide for the success of a company and/or product. If you have great answers to those questions, it becomes easier to prioritize what work is important, and where to divest effort. And, perhaps most importantly, it leads to clarity around what capabilities and management systems are needed within the business.

This framework is powerful because it is simple to understand, and yields articulations of a strategy that are similarly simple to understand.

Complexity, bad. Simplicity, good.

Assessing Ford’s $5/hour strategy

Ford’s aspiration

Ford aimed to become a dominant automaker by achieving mass market adoption. To get there, they needed to build profitably build cars that were affordable to middle class families (including his own workers’ families).

Where they played: Mass Production for growing US markets

Mass production was necessary in order to unlock Ford’s ability to scale profitably in the urban and industrial markets in the US with a rising working class population.

How they won: Create a loyal, skilled workforce and earn a demand loop, simultaneously

Ford’s strategy was brilliant in retrospect because he realized that his workers were ultimately a subset of his desired customers. So, he turned up the wages, standardized working hours, and made sure cars were priced within reach of his workforce.

Keep it Simple

In the end, strategy doesn’t have to be over-engineered. Pull together your brain trust. Then, together, define a clear aspiration, think about where you want to play, and decide how you’ll win. Generate lots of ideas along the way.

Keep it simple, grounded, and focused on what won’t change. Whether you’re crafting the next groundbreaking move or simply charting a course forward, remember: the brilliance of strategy often lies in its simplicity.

Prototyping has long been an undervalued task in the world of software. It’s often seen as a necessary evil—useful, but riddled with downsides:

• The output of a prototype is rarely production-ready because less care and attention go into crafting the backend and code.
• Often, what you learn from a prototype reveals that the thing you tested isn’t relevant to the intended audience.
• Coding a prototype is expensive compared to visualizing software with mockups in tools like Figma or even sketches on a whiteboard.

And yet, working prototypes are great for several reasons:

• They are significantly less expensive to build than a production-ready version.
• They help you learn what is most important to users in a context that looks and feels real.
• Because they are disposable, there’s less pressure to get everything perfect.
• High-fidelity prototypes make it easier for stakeholders to visualize the solution and provide meaningful feedback. In my professional life, I’ve often said, “The person who brings the highest fidelity prototype to the meeting wins.” Let’s call this Evnin’s Law.

For these reasons, product designers and user experience practitioners have long valued prototyping as a means to validate concepts before releasing them into the world.

The Evolution of Prototyping Tools

In the early days, experienced software designers relied on paper prototypes to mock up digital experiences and physical objects. Over time, digital tools evolved rapidly:

• Microsoft PowerPoint was once my go-to for building complex interactions!
• Adobe Fireworks offered a powerful toolset for static and dynamic prototypes.
• Sketch and InVision made it easier to create clickable prototypes that “worked”—to some degree.
• Figma entered the scene, steadily improving the experience but not quite reaching the finish line for creating fully functional prototypes.

Enter the Golden Age

Some critics complain that LLMs generate low quality code. That may be true if you’re thinking about production applications that serve tens, hundreds, or thousands of users. But no matter how you slice it, today’s LLMs are excellent at assisting with building simple applications – prototypes.

We are living in a golden age of prototyping, where AI and large language models (LLMs) have revolutionized the process. With these tools, you can mock up real software quickly. While the code quality can vary, it has never been easier to create functional prototypes from scratch.

Over the past few months, I’ve built a variety of prototypes with LLMs as my guide. There are so many tools out there available for free or cheap. LLMs like ChatGPT, Claude Sonnet, and Ollama. IDEs like Cursor, Windsurf (My current favorite!), and Zed.

Once you start toying with ideas, it’s hard not to start building.

Prototypes I’ve Built

1. Storybuilder: Creates personalized stories for kids (storybuilder.club). Read more
2. Trustfall: Helps parents quickly get and stay organized (go.trustfall.app).
3. A phone number you can call to practice job interviews and receive feedback.
4. A site that provides compensation information for various job titles.
5. An iPhone app that puts silly images on my kids’ faces in a photo.

Each of these has taken me a few minutes to a few hours to build the basic concept out and get a feel for the interface. It’s such a powerful feeling!

The Call to Action

Prototyping has moved from a behind-the-scenes option to a tool that can be used early and often, empowering builders to move faster, test smarter, dream bigger, and build things that people want! The barrier to entry has never been lower, and the potential to create impactful, real-world solutions has never been greater. Whether you’re experienced or just starting out, there’s no excuse to sit on the sidelines.

The tools are accessible, and the opportunities are endless. If you’re ready to explore, reach out—I’d be delighted to give feedback on your practice.

Sometimes I think back on precisely how blessed I have been in my career. It started in picturesque Malibu, California, on a ropes course that overlooked the Pacific Ocean. Here, I’ll show you a picture:

Beautiful, right? Anyway, I landed this job after a few summers of training under a guy named Michael. He taught me about knots, safety protocols, group facilitation, and life.

My job was important

If I missed a step in setting up a component on the course, someone could be seriously injured. If a member of my team did not set up a child’s harness correctly, they could be seriously injured. And if the kids themselves couldn’t focus their attention on the activity, well, again, someone could be seriously injured.

Because of the inherent dangers present on the course, everyone tended to respect the situation as one with grave consequences.

These days, my work setting is far “safer” than the ropes course. The likelihood of serious injury working in an office or work from home environment is exceedingly low. But in the work setting, the goal is not only safety. We care about impact on customers, employees, and the overarching business, which commands as much respect as the dangers of a ropes course.

The Lesson

I think the lesson that I most took to heart on the ropes course has to do with intentionally setting the right conditions and systems for the outcome that is desired. If one desires safety, you cannot just tell people to be safe. The leader has to remove unsafe conditions from the physical space, and condition the people who are taking part to carry out safe practices without trying too hard.

In the workplace, it’s the same. Conditions and systems (and related emotions) are set by the leaders and teammates, and are practiced with regularity.

I loved that ropes course. It taught me that when the stakes are high, success doesn’t rely on hoping for the best—it comes from designing environments that make the best possible. Whether it’s preventing a fall on the ropes or achieving business impact in a boardroom, the principle remains the same: systems create outcomes.

The ropes course may have burned down, but the lessons live on, reminding me regularly that the most important thing a leader can build isn’t just a system—it’s trust in the system they’ve built. That’s a foundation that doesn’t burn away.