The Looking Glass: You Cannot Teach Wisdom

7 key questions for interviewing a prospective user, the true bar, why go to a top company + being afraid

Hello readers!

This week’s tidbits:

1. 7 key questions for interviewing a prospective user of your product

2. You cannot teach wisdom

3. The true bar

4. From the archives: Pitching a product idea

For paid subscribers:

1. Subscriber mailbag: What values should designers live and uphold that cut across industries?

2. Why go to a top company or school

3. Afraid

4. I was a bad manager

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As a reminder, paying for a subscription (about the price of buying me a fancy coffee every month) encourages me to publish more and helps me hire someone to reduce the glaring grammatical errors of this publication. You’ll also get subscriber-only essays, Q&A, and rawer journal entries I’m afraid to share more broadly.

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7 Key Questions for Interviewing a Prospective User of your Product

1. Capture eyewitness account: Describe the last time you <had X problem>. What happened? What did you do? Why did you do that?

2. Check table stakes: What works for you about <existing solution Y>?

3. Probe for pain: What’s the worst part about trying to <solve problem X?>? How much does this suck?

4. Research cost: How much <money, time, effort> did you spend to <solve problem X with existing solution Y>?

5. Determine the bar: What’s the best experience you’ve ever had in <solving problem X>?

6. Gather potential visions: If you had a magic wand for <problem X>, what would you use it on?

7. Test your thesis: If I gave you a <proposed solution>, what parts about <problem X> would it help with or not help with?

You cannot teach wisdom

A friend celebrated his 40th birthday the other day. He said, you know, the older I get, the more the cliches seem deeply true.

Cliches like, The days are long but the years are short. Or Having less is having more.

In my teens and 20s I rolled my eyes at statements like these.

They seemed like a soda can’s empty calories. Everywhere and cheap. No nuance, no inventiveness. The easiest thing to serve up when you don’t want to put in effort.

But now, when we utter them to each other — swallowing back the lump in the throat at a child’s birthday party, fingering an exquisite dress before walking away, offering gentle words to a partner after a hell of a week, or mari-kondo-ing the shit out of January — we glimpse the profundity of these so-called words of wisdom, as clear and essential as water.

What I failed to realize back then is that the words are merely containers.

In my teens, the containers were shallow, filled with black-and-white plotlines and youth’s arrogance.

But year over year, these containers gathered more memories. Hues of heartbreak. Textures of love. Mistakes and their sharp aftermaths, slowly eroding the edges of hubris.

The containers became fuller. And speaking their words felt like uttering prayers, like drinking in the past itself. Exquisite and complex. A prized wine growing ever finer.

That elixir is wisdom. How I wish we could drink of each others’ collections!

Oh, but we try. To weave that wisdom into our stories. To convey it in our art. To capture it in our words. Humanity’s best attempts become today’s cliches.

But all of these attempts are still containers, containers of all shapes and sizes, bouncing in our minds.

They have their value; after all, our minds are like houses — more likely to be tidy with a larger collection of containers.

But do not mix up the containers themselves with the wisdom inside them.

To my young-hearted friends: read and learn. Reflect and absorb.

But never forget: Wisdom is life itself.

Sometimes, there is no more advice left to give.

Sometimes, you must simply live.

The true bar

My friend said, with wildfire in his eyes: “I don’t care if I’m great.” He paused, “I mean I want to be great…” he trailed off.

I knew exactly what he meant.

He desired not to earn the label of great.

He simply wanted to create things that satisfied his own bar of great.

From the Archives: Pitching a product idea

Q: Our team is planning for next year. What tips do you have for how I can present my product ideas effectively to the team’s leaders so they’ll get support?

While nobody likes to admit to judging a book by its cover, there is no denying that the same product idea can be presented in a compelling way that gets a room yelling “where can I sign up to build this?” or be described in bland, uninspiring terms that leave folks wondering “What’s the point?”

Communication matters. Here are a few ideas to help communicate product ideas effectively:

Describe the problem you’re solving.

Every product should have a reason for existence and a story for why people’s lives will be better after this product comes to the rescue. But before you can talk about the superior future you want to create, you should set the stage by describing the dismal present we currently living in.

Envision the start of an infomercial, where people are stumbling around in black and white, wallowing in tears while cutting onions… because they don’t yet have the Slap Chop!

Or imagine the problem statement for ride-sharing apps: “Getting a taxi is sooo hard. How many times have you stood by the side of the road (sometimes when it’s rainy or cold outside!) holding out your arm, only to see taxi after taxi driving by already occupied? You feel annoyed, maybe anxious. You have an appointment in 20 minutes, and who knows how long this is going to take? Maybe you should drive? Ugh but parking takes forever as well, not to mention it’s expensive!”

Stories like this paint an instant picture of what people are doing today, and why today’s world isn’t ideal.

Even if you’re building products for people who aren’t like yourself, it’s important to set the stage, ideally through research. Research helps us build empathy with customers. Perhaps your products are for business users (not consumers) or people living in different countries. Gather and share stories of real people, what their lives are like, and what problem they’re having that there isn’t a great solution for. This is most powerful when you include quotes, pictures, and a clear depiction of what people are trying to do, and why it isn’t working for them.

Describe how many people have this problem.

Now that you’ve broken it down to human terms, the next step is to expand this with market research to show just how large this problem is.

Imagine a fitness monitoring app that encourages people to keep their exercise goals: “Meet Larry. Every year, he starts with a new year’s resolution to live a healthier life. And every year, by April, he gives up and falls back into old bad habits. Larry is not alone. Last year, 30% of Americans made a resolution to lose weight, and less than half of them kept their goal after three months.”

Whether you’re describing a new product, or new features within an existing product, talking about the potential impact these changes will have is a worthwhile exercise not just for knowing the size of the opportunity you’re going after, but for ensuring you’re working on an important problem.

Talk about the solution in terms of the experience, not the product.

I used to think pitching a product idea was all about coming in with a shiny prototype. You do the big Mad-Men style reveal, you go through all of the features, one-by-one, you show a bunch of beautiful, slick visuals.

Through the years of discussing new product ideas, I’ve realized that’s the wrong approach completely, and can lure teams down a path towards building a products that look great but that no one will ever use.

Instead, you should focus on the experience. Bring this back to the people discussed in your intro. Let’s assume you product got released in the market and now people are using it, people who had that big, annoying problem earlier. What’s different about their lives now? What are they doing differently, or how are they thinking differently now that your product exists? How do you imagine they will use it? When they’re waiting in line? After they sit down on their couch at the end of a long hard day?

Having something visual to look at is valuable, to be sure, and will help ground the discussion and remove potential confusion. But you should show only as much as is needed to get your idea across and help ensure folks are on the same page about what you’d build. That’s it. This might be storyboards, wireframes, or maybe go with high-fidelity videos. But keep in mind: it’s about the change in people’s experiences, not about the change in the pixels.

Let go of “mine” or “yours”, embrace “ours”

Something to be mindful of: In your question, you asked “how can I present my product ideas”, and it occurred to me the use of the word “my” here may cause problems down the road. While you should certainly be generating ideas and advocating for what you believe are the strongest plans, what matters most is that the team is doing work that gets the best outcomes. It’s not about whether the team is working on “my idea” or “your idea.” When teams are operating at their best, there is a shared sense of ownership, ideas come from many different sources, and the end result reflects the strength of the team, which should be better than any one or two individuals could have done on their own.

So when preparing, explore the ideas as they are forming with people across your team. Be happy to be wrong in these discussions, and be open to listening and incorporating good suggestions and feedback from others. At the point in which you’re presenting the proposal, lead forward with work that has many fingerprints on it.

Ultimately, in presenting product ideas, your aim is to ensure not just that the audience understands what the product is, but also why the company should dedicate the time and energy to bring this idea to life. This means not only do you need to communicate clearly what you’re hoping to build, but also why this should be built.

How will this make things better for your customers and for the company? And how might you get this done?