Managers spend much time in 1:1s. Most team members meet with supervisors regularly. 1:1s can help create relationships and tackle tough topics. Few appreciate the 1:1 format's potential. Most of the time, that potential is spent on small talk, surface-level updates, and ranting (Ugh, the marketing team isn’t stepping up the way I want them to).

What if you used that time to have deeper conversations and important insights? What if change was easy?

This post introduces a new 1:1 format to help you dive deeper, faster, and develop genuine relationships without losing impact.

A 1:1 is a chat, you would assume. Why use structure to talk to a coworker? Go! I know how to talk to people. I can write. I've always written. Also, This article was edited by Zoe.

Before you discard something, ask yourself if there's a good reason not to try anything new. Is the 1:1 only a talk, or do you want extra benefits? Try the steps below to discover more.

I. Reflection (5 minutes)

Context-free, broad comments waste time and are useless. Instead, give team members 5 minutes to write these 3 prompts.

1. What's effective?

2. What is decent but could be improved?

3. What is broken or missing?

Why these? They encourage people to be honest about all their experiences. Answering these questions helps people realize something isn't working. These prompts let people consider what's working.

Why take notes? Because you get more in less time. Will you feel awkward sitting quietly while your coworker writes? Probably. Persevere. Multi-task. Take a break from your afternoon meeting marathon. Any awkwardness will pay off.

What happens? After a few minutes of light conversation, create a template like the one given here and have team members fill in their replies. You can pre-share the template (with the caveat that this isn’t meant to take much prep time). Do this with your coworker: Answer the prompts. Everyone can benefit from pondering and obtaining guidance.

This step's output.

Part II: Talk (10-20 minutes)

Most individuals can explain what they see but not what's behind an answer. You don't like a meeting. Why not? Marketing partnership is difficult. What makes working with them difficult? I don't recommend slandering coworkers. Consider how your meetings, decisions, and priorities make work harder. The excellent stuff too. You want to know what's humming so you can reproduce the magic.

First, recognize some facts.

• Real power dynamics exist. To encourage individuals to be honest, you must provide a safe environment and extend clear invites. Even then, it may take a few 1:1s for someone to feel secure enough to go there in person. It is part of your responsibility to admit that it is normal.

• Curiosity and self-disclosure are crucial. Most leaders have received training to present themselves as the authorities. However, you will both benefit more from the dialogue if you can be open and honest about your personal experience, ask questions out of real curiosity, and acknowledge the pertinent sacrifices you're making as a leader.

• Honesty without bias is difficult and important. Due to concern for the feelings of others, people frequently hold back. Or if they do point anything out, they do so in a critical manner. The key is to be open and unapologetic about what you observe while not presuming that your viewpoint is correct and that of the other person is incorrect.

Let's go into some prompts (based on genuine conversations):

• “What do you notice across your answers?”

• “What about the way you/we/they do X, Y, or Z is working well?”

• “ Will you say more about item X in ‘What’s not working?’”

• “I’m surprised there isn’t anything about Z. Why is that?”

• “All of us tend to play some role in maintaining certain patterns. How might you/we be playing a role in this pattern persisting?”

• “How might the way we meet, make decisions, or collaborate play a role in what’s currently happening?”

Consider the preceding example. What about the Monday meeting isn't working? Why? or What about the way we work with marketing makes collaboration harder? Remember to share your honest observations!

Third section: observe patterns (10-15 minutes)

Leaders desire to empower their people but don't know how. We also have many preconceptions about what empowerment means to us and how it works. The next phase in this 1:1 format will assist you and your team member comprehend team power and empowerment. This understanding can help you support and shift your team member's behavior, especially where you disagree.

How to? After discussing the stated responses, ask each team member what they can control, influence, and not control. Mark their replies. You can do the same, adding colors where you disagree.

This step's output.

Next, consider the color constellation. Discuss these questions:

• Is one color much more prevalent than the other? Why, if so?

• Are the colors for the "what's working," "what's fine," and "what's not working" categories clearly distinct? Why, if so?

• Do you have any disagreements? If yes, specifically where does your viewpoint differ? What activities do you object to? (Remember, there is no right or wrong in this. Give explicit details and ask questions with curiosity.)

Example: Based on the colors, you can ask, Is the marketing meeting's quality beyond your control? Were our marketing partners consulted? Are there any parts of team decisions we can control? We can't control people, but have we explored another decision-making method? How can we collaborate and generate governance-related information to reduce work, even if the requirement for prep can't be eliminated?

Consider the top one or two topics for this conversation. No 1:1 can cover everything, and that's OK. Focus on the present.

Part IV: Determine the next step (5 minutes)

Last, examine what this conversation means for you and your team member. It's easy to think we know the next moves when we don't.

Like what? You and your teammate answer these questions.

1. What does this signify moving ahead for me? What can I do to change this? Make requests, for instance, and see how people respond before thinking they won't be responsive.

2. What demands do I have on other people or my partners? What should I do first? E.g. Make a suggestion to marketing that we hold a monthly retrospective so we can address problems and exchange input more frequently. Include it on the meeting's agenda for next Monday.

Close the 1:1 by sharing what you noticed about the chat. Observations? Learn anything?

Yourself, you, and the 1:1

As a leader, you either reinforce or disrupt habits. Try this template if you desire greater ownership, empowerment, or creativity. Consider how you affect surrounding dynamics. How can you expect others to try something new in high-stakes scenarios, like meetings with cross-functional partners or senior stakeholders, if you won't? How can you expect deep thought and relationship if you don't encourage it in 1:1s? What pattern could this new format disrupt or reinforce?

Fight reluctance. First attempts won't be ideal, and that's OK. You'll only learn by trying.

There’s a funny part of ‘Steve Jobs’ by Walter Isaacson where Jobs says that Bill Gates was more a copier than an innovator:

“Bill is basically unimaginative and has never invented anything, which is why I think he’s more comfortable now in philanthropy than technology. He just shamelessly ripped off other people’s ideas….He’d be a broader guy if he had dropped acid once or gone off to an ashram when he was younger.”

Gates lacked flavor. Nobody ever got excited about a Microsoft launch, despite their good products. Jobs had the world's best product taste. Apple vs. Microsoft.

A CEO's core job functions are all driven by taste: recruiting, vision, and company culture all require good taste. Depending on the type of company you want to build, know where you stand between Microsoft and Apple.

How can you improve your product judgment? How to acquire taste?

Test and refine

Product development follows two parallel paths: the ‘customer obsession’ path and the ‘taste and iterate’ path.

The customer obsession path involves solving customer problems. Lean Startup frameworks show you what to build at each step.

Taste-and-iterate doesn't involve the customer. You iterate internally and rely on product leaders' taste and judgment.

Creative Selection by Ken Kocienda explains this method. In Creative Selection, demos are iterated and presented to product leaders. Your boss presents to their boss, and so on up to Steve Jobs. If you have good product taste, you can be a panelist.

The iPhone follows this path. Before seeing an iPhone, consumers couldn't want one. Customer obsession wouldn't have gotten you far because iPhone buyers didn't know they wanted one.

In The Hard Thing About Hard Things, Ben Horowitz writes:

“It turns out that is exactly what product strategy is all about — figuring out the right product is the innovator’s job, not the customer’s job. The customer only knows what she thinks she wants based on her experience with the current product. The innovator can take into account everything that’s possible, but often must go against what she knows to be true. As a result, innovation requires a combination of knowledge, skill, and courage.“

One path solves a problem the customer knows they have, and the other doesn't. Instead of asking a person what they want, observe them and give them something they didn't know they needed.

It's much harder. Apple is the world's most valuable company because it's more valuable. It changes industries permanently.

If you want to build superior products, use the iPhone of your industry.

How to Improve Your Taste

I. Work for a company that has taste.

People with the best taste in products, markets, and people are rewarded for building great companies. Tasteful people know quality even when they can't describe it. Taste isn't writable. It's feel-based.

Moving into a community that's already doing what you want to do may be the best way to develop entrepreneurial taste. Most company-building knowledge is tacit.

Joining a company you want to emulate allows you to learn its inner workings. It reveals internal patterns intuitively. Many successful founders come from successful companies.

Consumption determines taste. Excellence will refine you. This is why restauranteurs visit the world's best restaurants and serious painters visit Paris or New York. Joining a company with good taste is beneficial.

2. Possess a wide range of interests

“Edwin Land of Polaroid talked about the intersection of the humanities and science. I like that intersection. There’s something magical about that place… The reason Apple resonates with people is that there’s a deep current of humanity in our innovation. I think great artists and great engineers are similar, in that they both have a desire to express themselves.” — Steve Jobs

I recently discovered Edwin Land. Jobs modeled much of his career after Land's. It makes sense that Apple was inspired by Land.

A Triumph of Genius: Edwin Land, Polaroid, and the Kodak Patent War notes:

“Land was introverted in person, but supremely confident when he came to his ideas… Alongside his scientific passions, lay knowledge of art, music, and literature. He was a cultured person growing even more so as he got older, and his interests filtered into the ethos of Polaroid.”

Founders' philosophies shape companies. Jobs and Land were invested. It showed in the products their companies made. Different. His obsession was spreading Microsoft software worldwide. Microsoft's success is why their products are bland and boring.

Experience is important. It's probably why startups are built by generalists and scaled by specialists.

Jobs combined design, typography, storytelling, and product taste at Apple. Some of the best original Mac developers were poets and musicians. Edwin Land liked broad-minded people, according to his biography. Physicist-musicians or physicist-photographers.

Da Vinci was a master of art, engineering, architecture, anatomy, and more. He wrote and drew at the same desk. His genius is remembered centuries after his death. Da Vinci's statue would stand at the intersection of humanities and science.

We find incredibly creative people here. Superhumans. Designers, creators, and world-improvers. These are the people we need to navigate technology and lead world-changing companies. Generalists lead.

And retire sooner.

Books can make you filthy rich.

If you apply what you learn. In 2011, I was broke and had broken dreams.

Someone suggested I read finance books. One Up On Wall Street was his first recommendation.

Finance books were my crack.

I've read every money book since then. Some are good, but most stink.

These books will make you rich.

The Almanack of Naval Ravikant by Eric Jorgenson

This isn't a cliche book.

This book was inspired by a How to Get Rich tweet thread.

It’s one of the best tweets I’ve ever read.

Naval thinks differently. He nukes ordinary ideas. I've never heard better money advice.

Eric Jorgenson wrote a book about this tweet thread with Navals permission. A must-read, easy-to-digest book.

Best quote

Seek wealth, not money or status. Wealth is having assets that earn while you sleep. Money is how we transfer time and wealth. Status is your place in the social hierarchy — Naval

Morgan Housel's The Psychology of Money

Many finance books advise investing like a dunce.

They almost all peddle the buy an index fund BS. Different book.

It's about money-making psychology. Because any fool can get rich and drunk on their ego. Few can consistently make money.

Each chapter is short. A single-page chapter breaks all book publishing rules.

Best quote

Spending money to show people how much money you have is the fastest way to have less money — Morgan Housel

J.L. Collins' The Simple Path to Wealth

Most of the best money books were written by bloggers.

JL Collins blogs. This easy-to-read book was written for his daughter.

This book popularized the phrase F You Money. With enough money in your bank account and investment portfolio, you can say F You more.

A bad boss is an example. You can leave instead of enduring his wrath.

You can then sit at home and look for another job while financially secure. JL says its mind-freedom is powerful.

Best phrasing

You own the things you own and they in turn own you — J.L. Collins

Tony Robbins' Unshakeable

I like Tony. This book makes me sweaty.

Tony interviews the world's top financiers. He interviews people who rarely do so.

This book taught me all-weather portfolio. It's a way to invest in different asset classes in good, bad, recession, or depression times.

Look at it:

Investing isn’t about buying one big winner — that’s gambling. It’s about investing in a diversified portfolio of assets.

Best phrasing

The best opportunities come in times of maximum pessimism — Tony Robbins

Ben Graham's The Intelligent Investor

This book helped me distinguish between a spectator and an investor.

Spectators are those who shout that crypto, NFTs, or XYZ platform will die.

Tourists. They want attention and to say "I told you so." They make short-term and long-term predictions like fortunetellers. LOL. Idiots.

Benjamin Graham teaches smart investing. You'll buy a long-term asset. To be confident in recessions, use dollar-cost averaging.

Best phrasing

Those who do not remember the past are condemned to repeat it. — Benjamin Graham

The Napoleon Hill book Think and Grow Rich

This classic book introduced positive thinking to modern self-help.

Lazy pessimists can't become rich. No way.

Napoleon said, "Thoughts create reality."

No surprise that he discusses obsession and focus in this book. They are the fastest ways to make more money to invest in time and wealth-protecting assets.

Best phrasing

The starting point of all achievement is DESIRE. Keep this constantly in mind. Weak desire brings weak results, just as a small fire makes a small amount of heat — Napoleon Hill

Ramit Sethi's book I Will Teach You To Be Rich

This book is mostly good.  The part about credit cards is trash.

Avoid credit card temptations. I don't care about their airline points.

This book teaches you to master money basics (that many people mess up) then automate it so your monkey brain doesn't ruin your financial future.

The book includes great negotiation tactics to help you make more money in less time.

Best quote

The 85 Percent Solution: Getting started is more important than becoming an expert — Ramit Sethi

David Bach's The Automatic Millionaire

You've probably met a six- or seven-figure earner who's broke. All their money goes to useless things like cars.

Money isn't as essential as what you do with it. David teaches how to automate your earnings for more money.

Compounding works once investing is automated. So you get rich.

His strategy eliminates luck and (almost) guarantees millionaire status.

Best phrasing

Every time you earn one dollar, make sure to pay yourself first — David Bach

Thomas J. Stanley's The Millionaire Next Door

Thomas defies the definition of rich.

He spends much of the book highlighting millionaire traits he's studied.

Rich people are quiet, so you wouldn't know they're wealthy. They don't earn much money or drive a BMW.

Thomas will give you the math to get started.

Best phrasing

I am not impressed with what people own. But I’m impressed with what they achieve. I’m proud to be a physician. Always strive to be the best in your field…. Don’t chase money. If you are the best in your field, money will find you. — Thomas J. Stanley

by Bill Perkins "Die With Zero"

Let’s end with one last book.

Bill's book angered many people. He says we spend too much time saving for retirement and die rich. That bank money is lost time.

Your grandkids could use the money. When children inherit money, they become lazy, entitled a-holes.

Bill wants us to spend our money on life-enhancing experiences. Stop saving money like monopoly monkeys.

Best phrasing

You should be focusing on maximizing your life enjoyment rather than on maximizing your wealth. Those are two very different goals. Money is just a means to an end: Having money helps you to achieve the more important goal of enjoying your life. But trying to maximize money actually gets in the way of achieving the more important goal — Bill Perkins