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.

Elon's rides start rough, but then...

Elon Musk has never been so hated.

They don’t get Elon.

• He began using PayPal in this manner.

• He began with SpaceX in a similar manner.

• He began with Tesla in this manner.

Disruptive.

Elon had rocky starts. His creativity requires it. Just like writing a first draft.

His fastest way to find the way is to avoid it.

PayPal's pricey launch

PayPal was a 1999 business flop.

They were considered insane.

Elon and his co-founders had big plans for PayPal. They adopted the popular philosophy of the time, exchanging short-term profit for growth, and pulled off a miracle just before the bubble burst.

PayPal was created as a dollar alternative. Original PayPal software allowed PalmPilot money transfers. Unfortunately, there weren't enough PalmPilot users.

Since everyone had email, the company emailed payments. Costs rose faster than sales.

The startup wanted to get a million subscribers by paying $10 to sign up and $10 for each referral. Elon thought the price was fair because PayPal made money by charging transaction fees. They needed to make money quickly.

A Wall Street Journal article valuing PayPal at $500 million attracted investors. The dot-com bubble burst soon after they rushed to get financing.

Musk and his partners sold PayPal to eBay for $1.5 billion in 2002. Musk's most successful company was PayPal.

SpaceX's start-up error

Elon and his friends bought a reconditioned ICBM in Russia in 2002.

He planned to invest much of his wealth in a stunt to promote NASA and space travel.

Many called Elon crazy.

The goal was to buy a cheap Russian rocket to launch mice or plants to Mars and return them. He thought SpaceX would revive global space interest. After a bad meeting in Moscow, Elon decided to build his own rockets to undercut launch contracts.

Then SpaceX was founded.

Elon’s plan was harder than expected.

Explosions followed explosions.

• Millions lost on cargo.

• Millions lost on the rockets.

Investors thought Elon was crazy, but he wasn't.

NASA's biggest competitor became SpaceX. NASA hired SpaceX to handle many of its missions.

Tesla's shaky beginning

Tesla began shakily.

• Clients detested their roadster.

• They continued to miss deadlines.

Lotus would handle the car while Tesla focused on the EV component, easing Tesla's entry. The business experienced elegance creep. Modifying specific parts kept the car from getting worse.

Cost overruns, delays, and other factors changed the Elise-like car's appearance. Only 7% of the Tesla Roadster's parts matched its Lotus twin.

Tesla was about to die.

Elon saved the mess as CEO.

He fired 25% of the workforce to reduce costs.

Elon Musk transformed Tesla into the world's most valuable automaker by running it like a startup.

Tesla hasn't spent a dime on advertising. They let the media do the talking by investing in innovation.

Elon sheds. Elon tries. Elon learns. Elon refines.

Twitter doesn't worry me.

The media is shocked. I’m not.

This is just Elon being Elon.

• Elon makes lean.

• Elon tries new things.

• Elon listens to feedback.

• Elon refines.

Besides Twitter will always be Twitter.

How much do startup founders make after an IPO? We looked at 2018's major tech IPOs. Paydays aren't what founders took home at the IPO (shares are normally locked up for 6 months), but what they were worth at the IPO price on the day the firm went public. It's not cash, but it's nice. Here's the data.

Several points are noteworthy.

Huge payoffs. Median and average pay were $399m and $918m. Average and median homeownership were 9% and 12%.

Coinbase, Uber, UI Path. Uber, Zoom, Spotify, UI Path, and Coinbase founders raised billions. Zoom's founder owned 19% and Spotify's 28% and 13%. Brian Armstrong controlled 20% of Coinbase at IPO and was worth $15bn. Preserving as much equity as possible by staying cash-efficient or raising at high valuations also helps.

The smallest was Ping. Ping's compensation was the smallest. Andre Duand owned 2% but was worth $20m at IPO. That's less than some billion-dollar paydays, but still good.

IPOs can be lucrative, as you can see. Preserving equity could be the difference between a $20mm and $15bln payday (Coinbase).

How did his money blind me?

Like most fledgling entrepreneurs, I wanted a mentor. I met as many nearby folks with "entrepreneur" in their LinkedIn biographies for coffee.

These meetings taught me a lot, and I'd suggest them to any new creator. Attention! Meeting with many experienced entrepreneurs means getting contradictory advice. One entrepreneur will tell you to do X, then the next one you talk to may tell you to do Y, which are sometimes opposites. You'll have to chose which suggestion to take after the chats.

I experienced this. Same afternoon, I had two coffee meetings with experienced entrepreneurs. The first meeting was with a billionaire entrepreneur who took his company public.

I met him in a swanky hotel lobby and ordered a drink I didn't pay for. As a fledgling entrepreneur, money was scarce.

During the meeting, I demoed the software I'd built, he liked it, and we spent the hour discussing what features would make it a success. By the end of the meeting, he requested I include a killer feature we both agreed would attract buyers. The feature was complex and would require some time. The billionaire I was sipping coffee with in a beautiful hotel lobby insisted people would love it, and that got me enthusiastic.

The second meeting was with a young entrepreneur who had recently raised a small amount of investment and looked as eager to pitch me as I was to pitch him. I forgot his name. I mostly recall meeting him in a filthy coffee shop in a bad section of town and buying his pricey cappuccino. Water for me.

After his pitch, I demoed my app. When I was done, he barely noticed. He questioned my customer acquisition plan. Who was my client? What did they offer? What was my plan? Etc. No decent answers.

After our meeting, he insisted I spend more time learning my market and selling. He ignored my questions about features. Don't worry about features, he said. Customers will request features. First, find them.

Putting your faith in results over relevance

Problems plagued my afternoon. I met with two entrepreneurs who gave me differing advice about how to proceed, and I had to decide which to pursue. I couldn't decide.

Ultimately, I followed the advice of the billionaire.

Obviously.

Who wouldn’t? That was the guy who clearly knew more.

A few months later, I constructed the feature the billionaire said people would line up for.

The new feature was unpopular. I couldn't even get the billionaire to answer an email showing him what I'd done. He disappeared.

Within a few months, I shut down the company, wasting all the time and effort I'd invested into constructing the killer feature the billionaire said I required.

Would follow the struggling entrepreneur's advice have saved my company? It would have saved me time in retrospect. Potential consumers would have told me they didn't want what I was producing, and I could have shut down the company sooner or built something they did want. Both outcomes would have been better.

Now I know, but not then. I favored achievement above relevance.

Success vs. relevance

The millionaire gave me advice on building a large, successful public firm. A successful public firm is different from a startup. Priorities change in the last phase of business building, which few entrepreneurs reach. He gave wonderful advice to founders trying to double their stock values in two years, but it wasn't beneficial for me.

The other failing entrepreneur had relevant, recent experience. He'd recently been in my shoes. We still had lots of problems. He may not have achieved huge success, but he had valuable advice on how to pass the closest hurdle.

The money blinded me at the moment. Not alone So much of company success is defined by money valuations, fundraising, exits, etc., so entrepreneurs easily fall into this trap. Money chatter obscures the value of knowledge.

Don't base startup advice on a person's income. Focus on what and when the person has learned. Relevance to you and your goals is more important than a person's accomplishments when considering advice.