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.

10-sketch explanation

Choosing Tasks

Bringing News

carrying out 1:1s

providing critique

Managing Turbulence

Let's see this once-dominant IT corporation crumble.

What's the capital of Kazakhstan? If you don't know the answer, you can probably find it by Googling. Google Search returned results for Nur-Sultan in 0.66 seconds.

Google is the best search engine I've ever used. Did you know another search engine ruled the Internet? I'm sure you guessed Yahoo!

Google's friendly UI and wide selection of services make it my top choice. Let's explore Yahoo's decline.

Yahoo!

YAHOO stands for Yet Another Hierarchically Organized Oracle. Jerry Yang and David Filo established Yahoo.

Yahoo is primarily a search engine and email provider. It offers News and an advertising platform. It was a popular website in 1995 that let people search the Internet directly. Yahoo began offering free email in 1997 by acquiring RocketMail.

According to a study, Yahoo used Google Search Engine technology until 2000 and then developed its own in 2004.

Yahoo! rejected buying Google for $1 billion

Larry Page and Sergey Brin, Google's founders, approached Yahoo in 1998 to sell Google for $1 billion so they could focus on their studies. Yahoo denied the offer, thinking it was overvalued at the time.

Yahoo realized its error and offered Google $3 billion in 2002, but Google demanded $5 billion since it was more valuable. Yahoo thought $5 billion was overpriced for the existing market.

In 2022, Google is worth $1.56 Trillion.

What happened to Yahoo!

Yahoo refused to buy Google, and Google's valuation rose, making a purchase unfeasible.

Yahoo started losing users when Google launched Gmail. Google's UI was far cleaner than Yahoo's.

Yahoo offered $1 billion to buy Facebook in July 2006, but Zuckerberg and the board sought $1.1 billion. Yahoo rejected, and Facebook's valuation rose, making it difficult to buy.

Yahoo was losing users daily while Google and Facebook gained many. Google and Facebook's popularity soared. Yahoo lost value daily.

Microsoft offered $45 billion to buy Yahoo in February 2008, but Yahoo declined. Microsoft increased its bid to $47 billion after Yahoo said it was too low, but Yahoo rejected it. Then Microsoft rejected Yahoo’s 10% bid increase in May 2008.

In 2015, Verizon bought Yahoo for $4.5 billion, and Apollo Global Management bought 90% of Yahoo's shares for $5 billion in May 2021. Verizon kept 10%.

Yahoo's opportunity to acquire Google and Facebook could have been a turning moment. It declined Microsoft's $45 billion deal in 2008 and was sold to Verizon for $4.5 billion in 2015. Poor decisions and lack of vision caused its downfall. Yahoo's aim wasn't obvious and it didn't stick to a single domain.

Hence, a corporation needs a clear vision and a leader who can see its future.

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> Say Hello To The Lean-Hedge Model

People think starting a business requires significant debt and investment. Like Shark Tank, you need a world-changing idea. I'm not saying to avoid investors or brilliant ideas.

Investing is essential to build a genuinely profitable company. Think Apple or Starbucks.

Entrepreneurship is risky because many people go bankrupt from debt. As starters, we shouldn't do it. Instead, use lean-hedge.

Simply defined, you construct a cash-flow business to hedge against long-term investment-heavy business expenses.

What the “fx!$rench-toast” is the lean-hedge model?

When you start a business, your money should move down, down, down, then up when it becomes profitable.

Many people don't survive the business's initial losses and debt. What if, we created a cash-flow business BEFORE we started our Starbucks to hedge against its initial expenses?

Lean-hedge has two sections. Start a cash-flow business. A cash-flow business takes minimal investment and usually involves sweat and time.

Let’s take a look at some examples:

A Translation company

Personal portfolio website (you make a site then you do cold e-mail marketing)

FREELANCE (UpWork, Fiverr).

Educational business.

Infomarketing. (You design a knowledge-based product. You sell the info).

Online fitness/diet/health coaching ($50-$300/month, calls, training plan)

Amazon e-book publishing. (Medium writers do this)

YouTube, cash-flow channel

A web development agency (I'm a dev, but if you're not, a graphic design agency, etc.) (Sell your time.)

Digital Marketing

Online paralegal (A million lawyers work in the U.S).

Some dropshipping (Organic Tik Tok dropshipping, where you create content to drive traffic to your shopify store instead of spend money on ads).

(Disclaimer: My first two cash-flow enterprises, which were language teaching, failed terribly. My translation firm is now booming because B2B e-mail marketing is easy.)

Crossover occurs. Your long-term business starts earning more money than your cash flow business.

My cash-flow business (freelancing, translation) makes $7k+/month.

I’ve decided to start a slightly more investment-heavy digital marketing agency

Here are the anticipated business's time- and money-intensive investments:

1. ($$$) Top Front-End designer's Figma/UI-UX design (in negotiation)

2. (Time): A little copywriting (I will do this myself)

3. ($$) Creating an animated webpage with HTML (in negotiation)

4. Backend Development (Duration) (I'll carry out this myself using Laravel.)

5. Logo Design ($$)

6. Logo Intro Video for $

7. Video Intro (I’ll edit this myself with Premiere Pro)

etc.

Then evaluate product, place, price, and promotion. Consider promotion and pricing.

The lean-hedge model's point is:

Don't gamble. Avoid debt. First create a cash-flow project, then grow it steadily.

Check read my previous posts on “Nightmare Mode” (which teaches you how to make work as interesting as video games) and Why most people can't escape a 9-5 to learn how to develop a cash-flow business.

WTF is wrong with you people?

When I was laid off as editor of my town's daily newspaper, I went silent on social media. I knew it was coming and had been quietly removing personal items each day, but the pain was intense.

I posted a day later. I didn't bad-mouth GateHouse Media but expressed my sadness at leaving the newspaper industry, pride in my accomplishments, and hope for success in another industry.

Normal job-loss response.

What do you recognize as abnormal?

The bullshit I’ve been reading from laid-off folks on LinkedIn.

If you're there, you know. Many Twitter or Facebook/Meta employees recently lost their jobs.

Well, many of them did not “lose their job,” actually. They were “impacted by the layoffs” at their former employer. I keep seeing that phrase.

Why don’t they want to actually say it? Why the euphemism?

Many are excited about the opportunities ahead. The jobless deny being sad.

They're ecstatic! They have big plans.

Hope so. Sincerely! Being laid off stinks, especially if, like me, your skills are obsolete. It's worse if, like me, you're too old to start a new career. Ageism exists despite denials.

Nowadays, professionalism seems to demand psychotic levels of fake optimism.

Why? Life is unpredictable. That's indisputable. You shouldn't constantly complain or cry in public, but you also shouldn't pretend everything's great.

It makes you look psychotic, not positive. It's like saying at work:

“I was impacted by the death of my spouse of 20 years this week, and many of you have reached out to me, expressing your sympathy. However, I’m choosing to remember the amazing things we shared. I feel confident that there is another marriage out there for me, and after taking a quiet weekend trip to reset myself, I’ll be out there looking for the next great marital adventure! #staypositive #available #opentolove

Also:

“Now looking for our next #dreamhome after our entire neighborhood was demolished by a wildfire last night. We feel so lucky to have lived near so many amazing and inspirational neighbors, all of whom we will miss as we go on our next housing adventure. The best house for us is yet to come! If you have a great neighborhood you’d recommend, please feel free to reach out and touch base with us! #newhouse #newneighborhood #newlife

Admit it. That’s creepy.

The constant optimism makes me feel sick to my stomach.

Viscerally.

I hate fakes.

Imagine a fake wood grain desk. Wouldn't it be better if the designer accepted that it's plastic and went with that?

Real is better but not always nice. When something isn't nice, you don't have to go into detail, but you also shouldn't pretend it's great.

How to announce your job loss to the world.

Do not pretend to be happy, but don't cry and drink vodka all afternoon.

Say you loved your job, and that you're looking for new opportunities.

Yes, if you'll miss your coworkers. Otherwise, don't badmouth. No bridge-burning!

Please specify the job you want. You may want to pivot.

Alternatively, try this.

You could always flame out.

If you've pushed yourself too far into toxic positivity, you may be ready to burn it all down. If so, make it worthwhile by writing something like this:

Well, I was shitcanned by the losers at #Acme today. That bitch Linda in HR threw me under the bus just because she saw that one of my “friends” tagged me in some beach pics on social media after I called in sick with Covid. The good thing is I will no longer have to watch my ass around that #asspincher Ron in accounting, but I’m sad that I will no longer have a cushy job with high pay or access to the primo office supplies I’ve been sneaking home for the last five years. (Those gel pens were the best!) I am going to be taking some time off to enjoy my unemployment and hammer down shots of Jägermeister but in about five months I’ll be looking for anything easy with high pay and great benefits. Reach out if you can help! #officesupplies #unemploymentrocks #drinkinglikeagirlboss #acmesucks

It beats the fake positivity.

Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!