A fascinating business conversation.

This week at Web Summit, I had mentor hour.

Mentor hour connects startups with experienced entrepreneurs.

The YC-selected founder who mentored me had grown his company to $100 million in 18 months.

I had 45 minutes to question him.

I've compiled this.

Context

Founder's name is Zack.

After working in private equity, Zack opted to acquire an MBA.

Surrounded by entrepreneurs at a prominent school, he decided to become one himself.

Unsure how to proceed, he bet on two horses.

On one side, he received an offer from folks who needed help running their startup owing to lack of time. On the other hand, he had an idea for a SaaS to start himself.

He just needed to validate it.

Validating

Since Zack's proposal helped companies, he contacted university entrepreneurs for comments.

He contacted university founders.

Once he knew he'd correctly identified the problem and that people were willing to pay to address it, he started developing.

He earned $100k in a university entrepreneurship competition.

His plan was evident by then.

The other startup's founders saw his potential and granted him $400k to launch his own SaaS.

Hiring

He started looking for a tech co-founder because he lacked IT skills.

He interviewed dozens and picked the finest.

As he didn't want to wait for his program to be ready, he contacted hundreds of potential clients and got 15 letters of intent promising they'd join up when it was available.

YC accepted him by then.

He had enough positive signals to raise.

Raising

He didn't say how many VCs he called, but he indicated 50 were interested.

He jammed meetings into two weeks to generate pressure and encourage them to invest.

Seed raise: $11 million.

Selling

His objective was to contact as many entrepreneurs as possible to promote his product.

He first contacted startups by scraping CrunchBase data.

Once he had more money, he started targeting companies with ZoomInfo.

His VC urged him not to hire salespeople until he closed 50 clients himself.

He closed 100 and hired a CRO through a headhunter.

Scaling

Three persons started the business.

1. He primarily works in sales.

2. Coding the product was done by his co-founder.

3. Another person performing operational duties.

He regretted recruiting the third co-founder, who was ineffective (could have hired an employee instead).

He wanted his company to be big, so he hired two young marketing people from a competing company.

After validating several marketing channels, he chose PR.

$100 Million and under

He developed a sales team and now employs 30 individuals.

He raised a $100 million Series A.

Additionally, he stated

• He’s been rejected a lot. Like, a lot.

• Two great books to read: Steve Jobs by Isaacson, and Why Startups Fail by Tom Eisenmann.

• The best skill to learn for non-tech founders is “telling stories”, which means sales. A founder’s main job is to convince: co-founders, employees, investors, and customers. Learn code, or learn sales.

Conclusion

I often read about these stories but hardly take them seriously.

Zack was amazing.

Three things about him stand out:

1. His vision. He possessed a certain amount of fire.

2. His vitality. The man had a lot of enthusiasm and spoke quickly and decisively. He takes no chances and pushes the envelope in all he does.

3. His Rolex.

He didn't do all this in 18 months.

Not really.

He couldn't launch his company without private equity experience.

These accounts disregard entrepreneurs' original knowledge.

Hormozi will tell you how he founded Gym Launch, but he won't tell you how he had a gym first, how he worked at uni to pay for his gym, or how he went to the gym and learnt about fitness, which gave him the idea to open his own.

Nobody knows nothing. If you scale quickly, it's probable because you gained information early.

Lincoln said, "Give me six hours to chop down a tree, and I'll spend four sharpening the axe."

Sharper axes cut trees faster.

Christopher Janz of Point Nine Capital created the SaaS napkin in 2016. This post shows how founders have raised cash in the last 6 years. View raw data.

Round size

Unsurprisingly, round sizes have expanded and will taper down in 2022. In 2016, pre-seed rounds were $200k to $500k; currently, they're $1-$2m. Despite the macroeconomic scenario, Series A have expanded from $3m to $12m in 2016 to $6m and $18m in 2022.

Valuation

There are hints that valuations are rebounding this year. Pre-seed valuations in 2022 are $12m from $3m in 2016, and Series B prices are $270m from $100m in 2016.

Compared to public SaaS multiples, Series B valuations more closely reflect the market, but Seed and Series A prices seem to be inflated regardless of the market.

I'd like to know how each annual cohort performed for investors, based on the year they invested and the valuations. I can't access this information.

ARR

Seed firms' ARR forecasts have risen from $0 to $0.6m to $0 to $1m. 2016 expected $1.2m to $3m, 2021 $0.5m to $4m, and this year $0.5m to $2.5m, suggesting that Series A firms may raise with less ARR today. Series B minutes fell from $4.2m to $3m.

Capitalization Rate

2022 is the year that VCs start discussing capital efficiency in portfolio meetings. Given the economic shift in the markets and the stealthy VC meltdown, it's not surprising. Christopher Janz added capital efficiency to the SaaS Napkin as a new statistic for Series A (3.5x) and Series B. (2.5x). Your investors must live under a rock if they haven't asked about capital efficiency. If you're unsure:

The Capital Efficiency Ratio is the ratio of how much a company has spent growing revenue and how much they’re receiving in return. It is the broadest measure of company effectiveness in generating ARR

What next?

No one knows what's next, including me. All startup and growing enterprises around me are tightening their belts and extending their runways in anticipation of a difficult fundraising ride. If you're wanting to raise money but can wait, wait till the market is more stable and access to money is easier.

If asked, run.

An entrepreneur asked me about her pitch deck. A Platform as a Service (PaaS).

She told me she hadn't done her 5-year forecasts but would soon.

I said, Don't bother. I added "time-wasting."

“I've been asked”, she said.

“Who asked?”

“a VC”

“5-year forecast?”

“Yes”

“Get another VC. If he asks, it's because he doesn't understand your solution or to waste your time.”

Some VCs are lagging. They're still using steam engines.

10-years ago, 5-year forecasts were requested.

Since then, we've adopted a 3-year plan.

But It's outdated.

Max one year.

What has happened?

Revolutionary technology. NO-CODE.

Revolution's consequences?

Product viability tests are shorter. Hugely. SaaS and PaaS.

Let me explain:

• Building a minimum viable product (MVP) that works only takes a few months.

• 1 to 2 months for practical testing.

• Your company plan can be validated or rejected in 4 months as a consequence.

After validation, you can ask for VC money. Even while a prototype can generate revenue, you may not require any.

Good VCs won't ask for a 3-year business plan in that instance.

One-year, though.

If you want, establish a three-year plan, but realize that the second year will be different.

You may have changed your business model by then.

A VC isn't interested in a three-year business plan because your solution may change.

Your ability to create revenue will be key.

• But also, to pivot.

• They will be interested in your value proposition.

• They will want to know what differentiates you from other competitors and why people will buy your product over another.

• What will interest them is your resilience, your ability to bounce back.

• Not to mention your mindset. The fact that you won’t get discouraged at the slightest setback.

• The grit you have when facing adversity, as challenges will surely mark your journey.

• The authenticity of your approach. They’ll want to know that you’re not just in it for the money, let alone to show off.

• The fact that you put your guts into it and that you are passionate about it. Because entrepreneurship is a leap of faith, a leap into the void.

• They’ll want to make sure you are prepared for it because it’s not going to be a walk in the park.

• They’ll want to know your background and why you got into it.

• They’ll also want to know your family history.

• And what you’re like in real life.

So a 5-year plan…. You can bet they won’t give a damn. Like their first pair of shoes.

It's free now.

Most content writers—including me—write about side hustles because they do well.

I wrote several articles on a profitable programming side hustle.

Later, I learnt about AI content-generating platforms like Jasper.ai and Copy.ai, which I thought were terrible because they required subscriptions and had bad content. Even I dislike automatic online posting.

Since ChatGPT is becoming more popular, I tried it. It's free now.

Note: I wasn’t compensated to write this piece by this tool. In other words, I don’t receive any payment from their founders. There is no affiliate link, and right now it is free to use. Also, ChatGPT can do a lot more than what I ever did.

Begin.

OpenAI account registration requires visiting the website (if you don’t have one). Just write anything into the chatbot and get a response.

First, I wrote about the top 10 2023 side businesses.

This came in seconds.

2023 is shaping up to be a year of growth and opportunity for entrepreneurs and side hustlers. With the rise of remote work and the growing gig economy, there are many income streams to consider launching in the coming year. Here are the top 10 income streams to launch in 2023:

1. Virtual Assistant — The demand for virtual assistants is on the rise as more businesses move online. As a virtual assistant, you can offer administrative, technical, or creative services to clients remotely.

2. Online Tutoring — If you have expertise in a particular subject, consider becoming an online tutor. There are many platforms that connect tutors with students looking for help with their studies.

3. Freelance Writing — If you have a knack for writing, consider becoming a freelance writer. You can offer your services to businesses, bloggers, and individuals looking for content for their websites or social media platforms.

4. Graphic Design — If you have a talent for design, consider starting a graphic design side hustle. You can create logos, banners, and other visual content for businesses and individuals.

5. Social Media Management — Many businesses are looking for help with managing their social media accounts. As a social media manager, you can help businesses create and execute social media strategies to reach their target audience.

6. Dropshipping — Dropshipping is a business model where you sell products without actually holding any inventory. You can partner with suppliers and ship the products directly to the customer on behalf of the business.

7. Pet Sitting — If you love animals, consider starting a pet-sitting side hustle. You can offer your services to pet owners who need someone to take care of their pets while they are away.

8. Home Cleaning — With busy schedules, many people are looking for help with cleaning their homes. As a home cleaning service provider, you can offer your services to help keep homes tidy and organized.

9. Event Planning — If you have a talent for organization and planning, consider starting an event planning side hustle. You can offer your services to help plan and execute events for businesses and individuals.

10. Online Teaching — With the rise of online education, there is a growing demand for online teachers. If you have expertise in a particular subject, consider becoming an online teacher and offer your services to students looking for personalized instruction.

In conclusion, 2023 is shaping up to be a great year for launching new income streams. Whether you are looking to start a virtual assistant business, become an online tutor, or offer home cleaning services, there are many opportunities to turn your skills and expertise into a profitable side hustle.

Better than most online side hustle posts, right?

Write about the top 10 programming side hustles to start in 2023.

I got this.

If you are a programmer looking to start a side hustle, 2023 is the perfect time to launch your own business. With the growing demand for software and app development, there are many opportunities for programmers to turn their skills into a profitable side hustle. Here are the top 10 programming side hustles to start in 2023:

1. App Development — With the rise of smartphones and tablets, there is a growing demand for app development. You can offer your services to businesses and individuals looking to create custom apps for their needs.

2. Website Development — Many businesses and individuals are looking for help with creating and maintaining their websites. As a website developer, you can offer your services to help design, build, and manage websites for your clients.

3. Software Development — If you have expertise in a particular programming language, consider starting a software development side hustle. You can offer your services to businesses and individuals looking to create custom software solutions for their needs.

4. Game Development — The gaming industry is thriving, and there is a growing demand for game development. If you have experience in game development, you can offer your services to businesses and individuals looking to create custom games.

5. Data Analysis — With the rise of big data, there is a growing demand for data analysts. As a data analyst, you can offer your services to businesses and individuals looking to make sense of their data and gain insights from it.

6. Machine Learning — Machine learning is a rapidly growing field, and there is a growing demand for machine learning experts. If you have experience in machine learning, you can offer your services to businesses and individuals looking to develop custom machine learning solutions.

7. Cloud Computing — With the rise of cloud computing, there is a growing demand for cloud experts. If you have experience in cloud computing, you can offer your services to businesses and individuals looking to migrate their applications and data to the cloud.

8. Blockchain Development — Blockchain technology is gaining popularity, and there is a growing demand for blockchain developers. If you have experience in blockchain development, you can offer your services to businesses and individuals looking to develop custom blockchain solutions.

9. Artificial Intelligence — Artificial intelligence is a rapidly growing field, and there is a growing demand for AI experts. If you have experience in artificial intelligence, you can offer your services to businesses and individuals looking to develop custom AI solutions.

10. Virtual Reality — Virtual reality is an exciting and emerging technology, and there is a growing demand for VR developers. If you have experience in VR development, you can offer your services to businesses and individuals looking to create custom VR experiences.

In conclusion, 2023 is a great time to start a programming side hustle. Whether you are interested in app development, website development, or machine learning, there are many opportunities for programmers to turn their skills into a profitable business.

These two blogs show that AI can simplify blog authoring.

I asked some tough programming questions, and most were suitable.

The content may occasionally not be what we want, but it will almost always be very helpful to you.

Enjoy.

Elon Musk, Matt Taibbi, the 'Twitter Files,' and Hunter Biden's laptop: what gives?

Explaining Twitter Files

Matt Taibbi released "The Twitter Files," a batch of emails sent by Twitter executives discussing the company's decision to stop an October 2020 New York Post story online.

What's on Twitter? New York Post and Fox News call them "bombshell" documents. Or, as a Post columnist admitted, are they "not the smoking gun"? Onward!

What started this?

The New York Post published an exclusive, potentially explosive story in October 2020: Biden's Secret Emails: Ukrainian executive thanks Hunter Biden for'meeting' veep dad. The story purported to report the contents of a laptop brought to the tabloid by a Delaware computer repair shop owner who said it belonged to President Biden's second son, Hunter Biden. Emails and files on the laptop allegedly showed how Hunter peddled influence with Ukranian businessmen and included a "raunchy 12-minute video" of Hunter smoking crack and having sex.

Twitter banned links to the Post story after it was published, calling it "hacked material." The Post's Twitter account was suspended for multiple days.

Why? Yoel Roth, Twitter's former head of trust and safety, said the company couldn't verify the story, implying they didn't trust the Post.

Twitter's stated purpose rarely includes verifying news stories. This seemed like intentional political interference. This story was hard to verify because the people who claimed to have found the laptop wouldn't give it to other newspapers. (Much of the story, including Hunter's business dealings in Ukraine and China, was later confirmed.)

Roth: "It looked like a hack and leak."

So what are the “Twitter Files?”

Twitter's decision to bury the story became a political scandal, and new CEO Elon Musk promised an explanation. The Twitter Files, named after Facebook leaks.

Musk promised exclusive details of "what really happened" with Hunter Biden late Friday afternoon. The tweet was punctuated with a popcorn emoji.

Explaining Twitter Files

Three hours later, journalist Matt Taibbi tweeted more than three dozen tweets based on internal Twitter documents that revealed "a Frankensteinian tale of a human-built mechanism grown out of its designer's control."

Musk sees this release as a way to shape Twitter's public perception and internal culture in his image. We don't know if the CEO gave Taibbi the documents. Musk hyped the document dump before and during publication, but Taibbi cited "internal sources."

Taibbi shares email screenshots showing Twitter execs discussing the Post story and blocking its distribution. Taibbi says the emails show Twitter's "extraordinary steps" to bury the story.

Twitter communications chief Brandon Borrman has the most damning quote in the Files. Can we say this is policy? The story seemed unbelievable. It seemed like a hack... or not? Could Twitter, which ex-CEO Dick Costolo called "the free speech wing of the free speech party," censor a news story?

Many on the right say the Twitter Files prove the company acted at the behest of Democrats. Both parties had these tools, writes Taibbi. In 2020, both the Trump White House and Biden campaign made requests. He says the system for reporting tweets for deletion is unbalanced because Twitter employees' political donations favor Democrats. Perhaps. These donations may have helped Democrats connect with Twitter staff, but it's also possible they didn't. No emails in Taibbi's cache show these alleged illicit relations or any actions Twitter employees took as a result.

Even Musk's supporters were surprised by the drop. Miranda Devine of the New York Post told Tucker Carlson the documents weren't "the smoking gun we'd hoped for." Sebastian Gorka said on Truth Social, "So far, I'm deeply underwhelmed." DC Democrats collude with Palo Alto Democrats. Whoop!” The Washington Free Beacon's Joe Simonson said the Twitter files are "underwhelming." Twitter was staffed by Democrats who did their bidding. (Why?)

If "The Twitter Files" matter, why?

These emails led Twitter to suppress the Hunter Biden laptop story has real news value. It's rare for a large and valuable company like Twitter to address wrongdoing so thoroughly. Emails resemble FOIA documents. They describe internal drama at a company with government-level power. Katie Notopoulos tweeted, "Any news outlet would've loved this scoop!" It's not a'scandal' as teased."

Twitter's new owner calls it "the de facto public town square," implying public accountability. Like a government agency. Though it's exciting to receive once-hidden documents in response to a FOIA, they may be boring and tell you nothing new. Like Twitter files. We learned how Twitter blocked the Post's story, but not why. Before these documents were released, we knew Twitter had suppressed the story and who was involved.

These people were disciplined and left Twitter. Musk fired Vijaya Gadde, the former CLO who reportedly played a "key role" in the decision. Roth quit over Musk's "dictatorship." Musk arrived after Borrman left. Jack Dorsey, then-CEO, has left. Did those who digitally quarantined the Post's story favor Joe Biden and the Democrats? Republican Party opposition and Trump hatred? New York Post distaste? According to our documents, no. Was there political and press interference? True. We knew.

Taibbi interviewed anonymous ex-Twitter employees about the decision; all expressed shock and outrage. One source said, "Everyone knew this was fucked." Since Taibbi doesn't quote that expletive, we can assume the leaked emails contained few or no sensational quotes. These executives said little to support nefarious claims.

Outlets more invested in the Hunter Biden story than Gizmodo seem vexed by the release and muted headlines. The New York Post, which has never shied away from a blaring headline in its 221-year history, owns the story of Hunter Biden's laptop. Two Friday-night Post alerts about Musk's actions were restrained. Elon Musk will drop Twitter files on NY Post-Hunter Biden laptop censorship today. Elon Musk's Twitter dropped Post censorship details from Biden's laptop. Fox News' Apple News push alert read, "Elon Musk drops Twitter censorship documents."

Bombshell, bombshell, bombshell… what, exactly, is the bombshell? Maybe we've heard this story too much and are missing the big picture. Maybe these documents detail a well-documented decision.

The Post explains why on its website. "Hunter Biden laptop bombshell: Twitter invented reason to censor Post's reporting," its headline says.

Twitter's ad hoc decision to moderate a tabloid's content is not surprising. The social network had done this for years as it battled toxic users—violent white nationalists, virulent transphobes, harassers and bullies of all political stripes, etc. No matter how much Musk crows, the company never had content moderation under control. Buzzfeed's 2016 investigation showed how Twitter has struggled with abusive posters since 2006. Jack Dorsey and his executives improvised, like Musk.

Did the US government interfere with the ex-social VP's media company? That's shocking, a bombshell. Musk said Friday, "Twitter suppressing free speech by itself is not a 1st amendment violation, but acting under government orders with no judicial review is." Indeed! Taibbi believed this. August 2022: "The laptop is secondary." Zeynep Tufecki, a Columbia professor and New York Times columnist, says the FBI is cutting true story distribution. Taibbi retracted the claim Friday night: "I've seen no evidence of government involvement in the laptop story."

What’s the bottom line?

I'm still not sure what's at stake in the Hunter Biden scandal after dozens of New York Post articles, hundreds of hours of Fox News airtime, and thousands of tweets. Briefly: Joe Biden's son left his laptop with a questionable repairman. FBI confiscated it? The repairman made a copy and gave it to Rudy Giuliani's lawyer. The Post got it from Steve Bannon. On that laptop were videos of Hunter Biden smoking crack, cavorting with prostitutes, and emails about introducing his father to a Ukrainian businessman for $50,000 a month. Joe Biden urged Ukraine to fire a prosecutor investigating the company. What? The story seems to be about Biden family business dealings, right?

The discussion has moved past that point anyway. Now, the story is the censorship of it. Adrienne Rich wrote in "Diving Into the Wreck" that she came for "the wreck and not the story of the wreck" No matter how far we go, Hunter Biden's laptop is done. Now, the crash's story matters.

I'm dizzy. Katherine Miller of BuzzFeed wrote, "I know who I believe, and you probably do, too. To believe one is to disbelieve the other, which implicates us in the decision; we're stuck." I'm stuck. Hunter Biden's laptop is a political fabrication. You choose. I've decided.

This could change. Twitter Files drama continues. Taibbi said, "Much more to come." I'm dizzy.

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.