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.

Wishing for Lasting Companies, Not Penny Stocks or Goodwill Write-Downs

Get me a NASCAR-style company-logoed cremation urn (notice to the executor of my will, theres gonna be a lot of weird requests). I believe in working on projects that would be on your tombstone. As the Homebrew logo is tattooed on my shoulder, expanding the portfolio to my posthumous commemoration is easy. But this isn't an IRR victory lap; it's a hope that the firms we worked for would last beyond my lifetime.

Venture investors too often take credit or distance themselves from startups based on circumstances. Successful companies tell stories of crucial introductions, strategy conversations, and other value. Defeats Even whether our term involves Board service or systematic ethical violations, I'm just a little investment, so there's not much I can do. Since I'm guilty, I'm tossing stones from within the glass home (although we try to own our decisions through the lifecycle).

Post-exit company trajectories are usually unconfounded. Off the cap table, no longer a shareholder (or a diminishing one as you sell off/distribute), eventually leaving the Board. You can cheer for the squad or forget about it, but you've freed the corporation and it's back to portfolio work.

As I look at the downward track of most SPACs and other tarnished IPOs from the last few years, I wonder how I would feel if those were my legacy. Is my job done? Yes. When investing in a business, the odds are against it surviving, let alone thriving and being able to find sunlight. SPAC sponsors, institutional buyers, retail investments. Free trade in an open market is their right. Risking and losing capital is the system working! But

We were lead or co-lead investors in our first three funds, but as additional VCs joined the company, we were pushed down the cap table. Voting your shares rarely matters; supporting the firm when they need it does. Being valuable, consistent, and helping the company improve builds trust with the founders.

I hope every startup we sponsor becomes a successful public company before, during, and after we benefit. My perspective of American capitalism. Well, a stock ticker has a lot of garbage, and I support all types of regulation simplification (in addition to being a person investor in the Long-Term Stock Exchange). Yet being owned by a large group of investors and making actual gains for them is great. Likewise does seeing someone you met when they were just starting out become a public company CEO without losing their voice, leadership, or beliefs.

I'm just thinking about what we can do from the start to realize value from our investments and build companies with bright futures. Maybe seed venture financing shouldn't impact those outcomes, but I'm not comfortable giving up that obligation.

Offices without books are like bodies without souls.

After 10 years, my CEO sold his company for $30 million. I've shared many of his lessons on medium. You could ask him anything at his always-open office. He also said we could use his office for meetings while he was away. When I used his office for work, I was always struck by how many books he had.

Books are useful in almost every aspect of learning. Building a business, improving family relationships, learning a new language, a new skill... Books teach, guide, and structure. Whether fiction or nonfiction, books inspire, give ideas, and develop critical thinking skills.

My CEO prefers non-fiction and attends a Friday book club. This article discusses 5 books I found in his office that impacted my life/business. My CEO sold his company for $30 million, but I've built a steady business through blogging and video making.

I recall events and lessons I learned from my CEO and how they relate to each book, and I explain how I applied the book's lessons to my business and life.

Note: This post has no affiliate links.

1. The One Thing — Gary Keller

Gary Keller, a real estate agent, wanted more customers. So he and his team brainstormed ways to get more customers. They decided to write a bestseller about work and productivity. The more people who saw the book, the more customers they'd get.

Gary Keller focused on writing the best book on productivity, work, and efficiency for months. His business experience. Keller's business grew after the book's release.

The author summarizes the book in one question.

"What's the one thing that will make everything else easier or unnecessary?"

When I started my blog and business alongside my 9–5, I quickly identified my one thing: writing. My business relied on it, so it had to be great. Without writing, there was no content, traffic, or business.

My CEO focused on funding when he started his business. Even in his final years, he spent a lot of time on the phone with investors, either to get more money or to explain what he was doing with it. My CEO's top concern was money, and the other super important factors were handled by separate teams.

• Product tech and design

• Incredible customer support team

• Excellent promotion team

• Profitable sales team

My CEO didn't always focus on one thing and ignore the rest. He was on all of those teams when I started my job. He'd start his day in tech, have lunch with marketing, and then work in sales. He was in his office on the phone at night.

He eventually realized his errors. Investors told him he couldn't do everything for the company. If needed, he had to change internally. He learned to let go, mind his own business, and focus for the next four years. Then he sold for $30 million.

The bigger your project/company/idea, the more you'll need to delegate to stay laser-focused. I started something new every few months for 10 years before realizing this. So much to do makes it easy to avoid progress. Once you identify the most important aspect of your project and enlist others' help, you'll be successful.

2. Eat That Frog — Brian Tracy

The author quote sums up book's essence:

Mark Twain said that if you eat a live frog in the morning, it's probably the worst thing that will happen to you all day. Your "frog" is the biggest, most important task you're most likely to procrastinate on.

"Frog" and "One Thing" are both about focusing on what's most important. Eat That Frog recommends doing the most important task first thing in the morning.

I shared my CEO's calendar in an article 10 months ago. Like this:

CEO's average week (some information crossed out for confidentiality)

Notice anything about 8am-8:45am? Almost every day is the same (except Friday). My CEO started his day with a management check-in for 2 reasons:

• Checking in with all managers is cognitively demanding, and my CEO is a morning person.

• In a young startup where everyone is busy, the morning management check-in was crucial. After 10 am, you couldn't gather all managers.

When I started my blog, writing was my passion. I'm a morning person, so I woke up at 6 am and started writing by 6:30 am every day for a year. This allowed me to publish 3 articles a week for 52 weeks to build my blog and audience. After 2 years, I'm not stopping.

3. Deep Work — Cal Newport

Deep work is focusing on a cognitively demanding task without distractions (like a morning management meeting). It helps you master complex information quickly and produce better results faster. In a competitive world 10 or 20 years ago, focus wasn't a huge advantage. Smartphones, emails, and social media made focus a rare, valuable skill.

Most people can't focus anymore. Screens light up, notifications buzz, emails arrive, Instagram feeds... Many people don't realize they're interrupted because it's become part of their normal workflow.

Cal Newport mentions Bill Gates' "Think Weeks" in Deep Work.

Microsoft CEO Bill Gates would isolate himself (often in a lakeside cottage) twice a year to read and think big thoughts.

Inside Bill's Brain on Netflix shows Newport's lakeside cottage. I've always wanted a lakeside cabin to work in. My CEO bought a lakehouse after selling his company, but now he's retired.

As a company grows, you can focus less on it. In a previous section, I said investors told my CEO to get back to basics and stop micromanaging. My CEO's commitment and ability to get work done helped save the company. His deep work and new frameworks helped us survive the corona crisis (more on this later).

The ability to deep work will be a huge competitive advantage in the next century. Those who learn to work deeply will likely be successful while everyone else is glued to their screens, Bluetooth-synced to their watches, and playing Candy Crush on their tablets.

4. The 7 Habits of Highly Effective People — Stephen R. Covey

It took me a while to start reading this book because it seemed like another shallow self-help bible. I kept finding this book when researching self-improvement. I tried it because it was everywhere.

Stephen Covey taught me 2 years ago to have a personal mission statement.

A 7 Habits mission statement describes the life you want to lead, the character traits you want to embody, and the impact you want to have on others. shortform.com

I've had many lunches with my CEO and talked about Vipassana meditation and Sunday forest runs, but I've never seen his mission statement. I'm sure his family is important, though. In the above calendar screenshot, you can see he always included family events (in green) so we could all see those time slots. We couldn't book him then. Although he never spent as much time with his family as he wanted, he always made sure to be on time for his kid's birthday rather than a conference call.

My CEO emphasized his company's mission. Your mission statement should answer 3 questions.

• What does your company do?

• How does it do it?

• Why does your company do it?

As a graphic designer, I had to create mission-statement posters. My CEO hung posters in each office.

5. Measure What Matters — John Doerr

This book is about Andrew Grove's OKR strategy, developed in 1968. When he joined Google's early investors board, he introduced it to Larry Page and Sergey Brin. Google still uses OKR.

Objective Key Results

• Objective: It explains your goals and desired outcome. When one goal is reached, another replaces it. OKR objectives aren't technical, measured, or numerical. They must be clear.

• Key Result should be precise, technical, and measurable, unlike the Objective. It shows if the Goal is being worked on. Time-bound results are quarterly or yearly.

Our company almost sank several times. Sales goals were missed, management failed, and bad decisions were made. On a Monday, our CEO announced we'd implement OKR to revamp our processes.

This was a year before the pandemic, and I'm certain we wouldn't have sold millions or survived without this change. This book impacted the company the most, not just management but all levels. Organization and transparency improved. We reached realistic goals. Happy investors. We used the online tool Gtmhub to implement OKR across the organization.

My CEO's company went from near bankruptcy to being acquired for $30 million in 2 years after implementing OKR.

I hope you enjoyed this booklist. Here's a recap of the 5 books and the lessons I learned from each.

1. The 7 Habits of Highly Effective People — Stephen R. Covey

Have a mission statement that outlines your goals, character traits, and impact on others.

1. Deep Work — Cal Newport

Focus is a rare skill; master it. Deep workers will succeed in our hyper-connected, distracted world.

1. The One Thing — Gary Keller

What can you do that will make everything else easier or unnecessary? Once you've identified it, focus on it.

1. Eat That Frog — Brian Tracy

Identify your most important task the night before and do it first thing in the morning. You'll have a lighter day.

1. Measure What Matters — John Doerr

On a timeline, divide each long-term goal into chunks. Divide those slices into daily tasks (your goals). Time-bound results are quarterly or yearly. Objectives aren't measured or numbered.

Thanks for reading. Enjoy the ride!

4 Pricey Tools That Are Valuable

I pay based on ROI (return on investment).

If a $20/month tool or $500 online course doubles my return, I'm in.

Investing helps me build wealth.

Canva Pro

I initially refused to pay.

My course content needed updating a few months ago. My Google Docs text looked cleaner and more professional in Canva.

I've used it to:

• product cover pages

• eBook covers

• Product page infographics

See my Google Sheets vs. Canva product page graph.

Google Sheets vs Canva

Yesterday, I used it to make a LinkedIn video thumbnail. It took less than 5 minutes and improved my video.

In 30 hours, the video had 39,000 views.

Here's more.

HypeFury

Hypefury rocks!

It builds my brand as I sleep. What else?

Because I'm traveling this weekend, I planned tweets for 10 days. It took me 80 minutes.

So while I travel or am absent, my content mill keeps producing.

Also I like:

• I can reach hundreds of people thanks to auto-DMs. I utilize it to advertise freebies; for instance, leave an emoji remark to receive my checklist. And they automatically receive a message in their DM.

• Scheduled Retweets: By appearing in a different time zone, they give my tweet a second chance.

It helps me save time and expand my following, so that's my favorite part.

It’s also super neat:

Zoom Pro

My course involves weekly and monthly calls for alumni.

Google Meet isn't great for group calls. The interface isn't great.

Zoom Pro is expensive, and the monthly payments suck, but it's necessary.

It gives my students a smooth experience.

Previously, we'd do 40-minute meetings and then reconvene.

Zoom's free edition limits group calls to 40 minutes.

This wouldn't be a good online course if I paid hundreds of dollars.

So I felt obligated to help.

YouTube Premium

My laptop has an ad blocker.

I bought an iPad recently.

When you're self-employed and work from home, the line between the two blurs. My bed is only 5 steps away!

When I read or watched videos on my laptop, I'd slide into work mode. Only option was to view on phone, which is awkward.

YouTube premium handles it. No more advertisements and I can listen on the move.

3 Expensive Tools That Aren't Valuable

Marketing strategies are sometimes aimed to make you feel you need 38474 cool features when you don’t.

Certain tools are useless.

I found it useless.

Depending on your needs. As a writer and creator, I get no return.

They could for other jobs.

Shield Analytics

It tracks LinkedIn stats, like:

• follower growth

• trend chart for impressions

• Engagement, views, and comment stats for posts

• and much more.

Middle-tier creator costs $12/month.

I got a 25% off coupon but canceled my free trial before writing this. It's not worth the discount.

Why?

LinkedIn provides free analytics. See:

Not thorough and won't show top posts.

I don't need to see my top posts because I love experimenting with writing.

Slack Premium

Slack was my classroom. Slack provided me a premium trial during the prior cohort.

I skipped it.

Sure, voice notes are better than a big paragraph. I didn't require pro features.

Marketing methods sometimes make you think you need 38474 amazing features. Don’t fall for it.

Calendly Pro

This may be worth it if you get many calls.

I avoid calls. During my 9-5, I had too many pointless calls.

I don't need:

• ability to schedule calls for 15, 30, or 60 minutes: I just distribute each link separately.

• I have a Gumroad consultation page with a payment option.

• follow-up emails: I hardly ever make calls, so

• I just use one calendar, therefore I link to various calendars.

I'll admit, the integrations are cool. Not for me.

If you're a coach or consultant, the features may be helpful. Or book meetings.

Conclusion

Investing is spending to make money.

Use my technique — put money in tools that help you make money. This separates it from being an investment instead of an expense.

Try free versions of these tools before buying them since everyone else is.

When you stop blogging for a few weeks, your views and profits plummet.

Because you're writing fascinating posts for others. Everyone's done ithat…

If I keep writing, the graph should maintain velocity, you could say. If I wrote more, it could rise.

However, entertaining pieces still tend to roller coaster and jump.

this type of writing is like a candle. They burn out and must be replaced. You must continuously light new ones to maintain the illumination.

When you quit writing, your income stops.

A substitute

Instead of producing amusing articles, try solving people's issues. You should answer their search questions.

Here's what happens when you answer their searches.

My website's Google analytics. As a dentist, I answer oral health questions.

This chart vs. Medium is pretty glaring, right?

As of yesterday, it was averaging 15k page views each day.

How much would you make on Medium with 15k daily views?

Evergreen materials

In SEO, this is called evergreen content.

Your content is like a lush, evergreen forest, and by green I mean Benjamins.

Do you have knowledge that you can leverage? Why not help your neighbors and the world?

Answer search inquiries and help others. You'll be well rewarded.

This is better than crafting candle-like content that fizzles out quickly.

Is beauty really ephemeral like how flowers bloom? Nah, I prefer watching forests grow instead (: