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.

Great technology opens up an universe of possibilities.

Need a friend? WhatsApp, Telegram, Slack, etc.

Traveling? AirBnB, Expedia, Google Flights, etc.

Money transfer? Use digital banking, e-wallet, or crypto applications

Products inspire us. How do we become great?

I asked product managers in my network:

What does it take to be a great product manager?

52 product managers from 40+ prominent IT businesses in Southeast Asia responded passionately. Many of the PMs I've worked with have built fantastic products, from unicorns (Lazada, Tokopedia, Ovo) to incumbents (Google, PayPal, Experian, WarnerMedia) to growing (etaily, Nium, Shipper).

TL;DR:

• Soft talents are more important than hard skills. Technical expertise was hardly ever stressed by product managers, and empathy was mentioned more than ten times. Janani from Xendit expertly recorded the moment. A superb PM must comprehend that their empathy for the feelings of their users must surpass all logic and data.

• Constant attention to the needs of the user. Many people concur that the closer a PM gets to their customer/user, the more likely it is that the conclusion will be better. There were almost 30 references to customers and users. Focusing on customers has the advantage because it is hard to overshoot, as Rajesh from Lazada puts it best.

• Setting priorities is invaluable. Prioritization is essential because there are so many problems that a PM must deal with every day. My favorite quotation on this is from Rakuten user Yee Jie. Viki, A competent product manager extinguishes fires. A good product manager lets things burn and then prioritizes.

This summary isn't enough to capture what excellent PMs claim it requires. Read below!

What qualities make a successful product manager?

Themed quotes are alphabetized by author.

Embrace your user/customer

Aeriel Dela Paz, Rainmaking Venture Architect, ex-GCash Product Head

Great PMs know what customers need even when they don’t say it directly. It’s about reading between the lines and going through the numbers to address that need.

Anders Nordahl, OrkestraSCS's Product Manager

Understanding the vision of your customer is as important as to get the customer to buy your vision

Angel Mendoza, MetaverseGo's Product Head

Most people think that to be a great product manager, you must have technical know-how. It’s textbook and I do think it is helpful to some extent, but for me the secret sauce is EMPATHY — the ability to see and feel things from someone else’s perspective. You can’t create a solution without deeply understanding the problem.

Senior Product Manager, Tokopedia

Focus on delivering value and helping people (consumer as well as colleague) and everything else will follow

Darren Lau, Deloitte Digital's Head of Customer Experience

Start with the users, and work backwards. Don’t have a solution looking for a problem

Darryl Tan, Grab Product Manager

I would say that a great product manager is able to identify the crucial problems to solve through strong user empathy and synthesis of insights

Diego Perdana, Kitalulus Senior Product Manager

I think to be a great product manager you need to be obsessed with customer problems and most important is solve the right problem with the right solution

Senior Product Manager, AirAsia

Lot of common sense + Customer Obsession. The most important role of a Product manager is to bring clarity of a solution. Your product is good if it solves customer problems. Your product is great if it solves an eco-system problem and disrupts the business in a positive way.

Edward Xie, Mastercard Managing Consultant, ex-Shopee Product Manager

Perfect your product, but be prepared to compromise for right users

AVP Product, Shipper

For me, a great product manager need to be rational enough to find the business opportunities while obsessing the customers.

Janani Gopalakrishnan is a senior product manager of a stealth firm.

While as a good PM it’s important to be data-driven, to be a great PM one needs to understand that their empathy for their users’ emotions must exceed all logic and data. Great PMs also make these product discussions thrive within the team by intently listening to all the members thoughts and influence the team’s skin in the game positively.

Director, Product Management, Indeed

Great product managers put their users first. They discover problems that matter most to their users and inspire their team to find creative solutions.

Grab's Senior Product Manager Lakshay Kalra

Product management is all about finding and solving most important user problems

Quipper's Mega Puji Saraswati

First of all, always remember the value of “user first” to solve what user really needs (the main problem) for guidance to arrange the task priority and develop new ideas. Second, ownership. Treat the product as your “2nd baby”, and the team as your “2nd family”. Third, maintain a good communication, both horizontally and vertically. But on top of those, always remember to have a work — life balance, and know exactly the priority in life :)

Senior Product Manager, Prosa.AI Miswanto Miswanto

A great Product Manager is someone who can be the link between customer needs with the readiness and flexibility of the team. So that it can provide, build, and produce a product that is useful and helps the community to carry out their daily activities. And He/She can improve product quality ongoing basis or continuous to help provide solutions for users or our customer.

Lead Product Manager, Tokopedia, Oriza Wahyu Utami

Be a great listener, be curious and be determined. every great product manager have the ability to listen the pain points and understand the problems, they are always curious on the users feedback, and they also very determined to look for the solutions that benefited users and the business.

99 Group CPO Rajesh Sangati

The advantage of focusing on customers: it’s impossible to overshoot

Ray Jang, founder of Scenius, formerly of ByteDance

The difference between good and great product managers is that great product managers are willing to go the unsexy and unglamorous extra mile by rolling up their sleeves and ironing out all minutiae details of the product such that when the user uses the product, they can’t help but say “This was made for me.”

BCG Digital Ventures' Sid Narayanan

Great product managers ensure that what gets built and shipped is at the intersection of what creates value for the customer and for the business that’s building the product…often times, especially in today’s highly liquid funding environment, the unit economics, aka ensuring that what gets shipped creates value for the business and is sustainable, gets overlooked

Stephanie Brownlee, BCG Digital Ventures Product Manager

There is software in the world that does more harm than good to people and society. Great Product Managers build products that solve problems not create problems

Experiment constantly

Delivery Hero's Abhishek Muralidharan

Embracing your failure is the key to become a great Product Manager

DeliveryHero's Anuraag Burman

Product Managers should be thick skinned to deal with criticism and the stomach to take risk and face failures.

DataSpark Product Head Apurva Lawale

Great product managers enjoy the creative process with their team to deliver intuitive user experiences to benefit users.

Dexter Zhuang, Xendit Product Manager

The key to creating winning products is building what customers want as quickly as you can — testing and learning along the way.

PayPal's Jay Ko

To me, great product managers always remain relentlessly curious. They are empathetic leaders and problem solvers that glean customer insights into building impactful products

Home Credit Philippines' Jedd Flores

Great Product Managers are the best dreamers; they think of what can be possible for the customers, for the company and the positive impact that it will have in the industry that they’re part of

Set priorities first, foremost, foremost.

HBO Go Product Manager Akshay Ishwar

Good product managers strive to balance the signal to noise ratio, Great product managers know when to turn the dials for each up exactly

Zuellig Pharma's Guojie Su

Have the courage to say no. Managing egos and request is never easy and rejecting them makes it harder but necessary to deliver the best value for the customers.

Ninja Van's John Prawira

(1) PMs should be able to ruthlessly prioritize. In order to be effective, PMs should anchor their product development process with their north stars (success metrics) and always communicate with a purpose. (2) User-first when validating assumptions. PMs should validate assumptions early and often to manage risk when leading initiatives with a focus on generating the highest impact to solving a particular user pain-point. We can’t expect a product/feature launch to be perfect (there might be bugs or we might not achieve our success metric — which is where iteration comes in), but we should try our best to optimize on user-experience earlier on.

Nium Product Manager Keika Sugiyama

I’d say a great PM holds the ability to balance ruthlessness and empathy at the same time. It’s easier said than done for sure!

ShopBack product manager Li Cai

Great product managers are like great Directors of movies. They do not create great products/movies by themselves. They deliver it by Defining, Prioritising, Energising the team to deliver what customers love.

Quincus' Michael Lim

A great product manager, keeps a pulse on the company’s big picture, identifies key problems, and discerns its rightful prioritization, is able to switch between the macro perspective to micro specifics, and communicates concisely with humility that influences naturally for execution

Mathieu François-Barseghian, SVP, Citi Ventures

“You ship your org chart”. This is Conway’s Law short version (1967!): the fundamental socio-technical driver behind innovation successes (Netflix) and failures (your typical bank). The hype behind micro-services is just another reflection of Conway’s Law

Mastercard's Regional Product Manager Nikhil Moorthy

A great PM should always look to build products which are scalable & viable , always keep the end consumer journey in mind. Keeping things simple & having a MVP based approach helps roll out products faster. One has to test & learn & then accordingly enhance / adapt, these are key to success

Rendy Andi, Tokopedia Product Manager

Articulate a clear vision and the path to get there, Create a process that delivers the best results and Be serious about customers.

Senior Product Manager, DANA Indonesia

Own the problem, not the solution — Great PMs are outstanding problem preventers. Great PMs are discerning about which problems to prevent, which problems to solve, and which problems not to solve

Tat Leong Seah, LionsBot International Senior UX Engineer, ex-ViSenze Product Manager

Prioritize outcomes for your users, not outputs of your system” or more succinctly “be agile in delivering value; not features”

Senior Product Manager, Rakuten Viki

A good product manager puts out fires. A great product manager lets fires burn and prioritize from there

acquire fundamental soft skills

Oracle NetSuite's Astrid April Dominguez

Personally, i believe that it takes grit, empathy, and optimistic mindset to become a great PM

Ovo Lead Product Manager Boy Al Idrus

Contrary to popular beliefs, being a great product manager doesn’t have anything to do with technicals, it sure plays a part but most important weapons are: understanding pain points of users, project management, sympathy in leadership and business critical skills; these 4 aspects would definitely help you to become a great product manager.

PwC Product Manager Eric Koh

Product managers need to be courageous to be successful. Courage is required to dive deep, solving big problems at its root and also to think far and dream big to achieve bold visions for your product

Ninja Van's Product Director

In my opinion the two most important ingredients to become a successful product manager is: 1. Strong critical thinking 2. Strong passion for the work. As product managers, we typically need to solve very complex problems where the answers are often very ambiguous. The work is tough and at times can be really frustrating. The 2 ingredients I mentioned earlier will be critical towards helping you to slowly discover the solution that may become a game changer.

PayPal's Lead Product Manager

A great PM has an eye of a designer, the brain of an engineer and the tongue of a diplomat

Product Manager Irene Chan

A great Product Manager is able to think like a CEO of the company. Visionary with Agile Execution in mind

Isabella Yamin, Rakuten Viki Product Manager

There is no one model of being a great product person but what I’ve observed from people I’ve had the privilege working with is an overflowing passion for the user problem, sprinkled with a knack for data and negotiation

Google product manager Jachin Cheng

Great product managers start with abundant intellectual curiosity and grow into a classic T-shape. Horizontally: generalists who range widely, communicate fluidly and collaborate easily cross-functionally, connect unexpected dots, and have the pulse both internally and externally across users, stakeholders, and ecosystem players. Vertically: deep product craftsmanship comes from connecting relentless user obsession with storytelling, business strategy with detailed features and execution, inspiring leadership with risk mitigation, and applying the most relevant tools to solving the right problems.

Jene Lim, Experian's Product Manager

3 Cs and 3 Rs. Critical thinking , Customer empathy, Creativity. Resourcefulness, Resilience, Results orientation.

Nirenj George, Envision Digital's Security Product Manager

A great product manager is someone who can lead, collaborate and influence different stakeholders around the product vision, and should be able to execute the product strategy based on customer insights, as well as take ownership of the product roadmap to create a greater impact on customers.

Grab's Lead Product Manager

Product Management is a multi-dimensional role that looks very different across each product team so each product manager has different challenges to deal with but what I have found common among great product managers is ability to create leverage through their efforts to drive outsized impacts for their products. This leverage is built using data with intuition, building consensus with stakeholders, empowering their teams and focussed efforts on needle moving work.

NCS Product Manager Umar Masagos

To be a great product manager, one must master both the science and art of Product Management. On one hand, you need have a strong understanding of the tools, metrics and data you need to drive your product. On the other hand, you need an in-depth understanding of your organization, your target market and target users, which is often the more challenging aspect to master.

M1 product manager Wei Jiao Keong

A great product manager is multi-faceted. First, you need to have the ability to see the bigger picture, yet have a keen eye for detail. Secondly, you are empathetic and is able to deliver products with exceptional user experience while being analytical enough to achieve business outcomes. Lastly, you are highly resourceful and independent yet comfortable working cross-functionally.

Yudha Utomo, ex-Senior Product Manager, Tokopedia

A great Product Manager is essentially an effective note-taker. In order to achieve the product goals, It is PM’s job to ensure objective has been clearly conveyed, efforts are assessed, and tasks are properly tracked and managed. PM can do this by having top-notch documentation skills.

Sketch or Figma?

Designers are pissed.

The beast ate the beauty.

Figma deserves $20B.

Do designers deserve Adobe?

Adobe devours new creative tools and spits them out with a slimy Adobe aftertaste.

• Frame.io — $1.3B

• Magento — $1.7B

• Macromedia — $3.6B

Nothing compares to the risky $20B acquisition.

If they can't be beaten, buy them.

And then make them boring.

Adobe's everywhere.

Like that friend who dabbles in everything creatively, there's not enough time to master one thing.

Figma was Adobe's thigh-mounted battle axe.

• a UX design instrument with a sizable free tier.

• a UX design tool with a simple and quick user interface.

• a tool for fluid collaboration in user experience design.

• a web-based UX design tool that functions well.

• a UX design tool with a singular goal of perfection.

UX design software that replaced Adobe XD.

Adobe XD could do many of Figma's things, but it didn't focus on the details. This is a major issue when working with detail-oriented professionals.

UX designers.

Design enthusiasts first used Figma. More professionals used it. Institutions taught it. Finally, major brands adopted Figma.

Adobe hated that.

Adobe dispatched a team of lawyers to resolve the Figma issue, as big companies do. Figma didn’t bite for months.

Oh no.

Figma resisted.

Figma helped designers leave Adobe. Figma couldn't replace Photoshop, but most designers used it to remove backgrounds.

Online background removal tools improved.

The Figma problem grew into a thorn, a knife, and a battle ax in Adobe's soft inner thigh.

Figma appeared to be going public. Adobe couldn’t allow that. It bought Figma for $20B during the IPO drought.

Adobe has a new issue—investors are upset.

The actual cause of investors' ire toward Adobe

Spoiler: The math just doesn’t add up.

According to Adobe's press release, Figma's annual recurring revenue (ARR) is $400M and growing rapidly.

The $20B valuation requires a 50X revenue multiple, which is unheard of.

Venture capitalists typically use:

• 10% to 29% growth per year: ARR multiplied by 1 to 5

• 30% to 99% growth per year: ARR multiplied by 6 to 10

• 100% to 400% growth per year: ARR multiplied by 10 to 20

Showing an investor a 50x multiple is like telling friends you saw a UFO. They'll think you're crazy.

Adobe's stock fell immediately after the acquisition because it didn't make sense to a number-cruncher.

Designers started a Tweet storm in the digital town hall where VCs and designers often meet.

Adobe acquired Workfront for $1.5 billion at the end of 2020. This purchase made sense for investors.

Many investors missed the fact that Adobe is acquiring Figma not only for its ARR but also for its brilliant collaboration tech.

Adobe could use Figmas web app technology to make more products web-based to compete with Canva.

Figma's high-profile clients could switch to Adobe's enterprise software.

However, questions arise:

• Will Adobe make Figma boring?

• Will Adobe tone down Figma to boost XD?

• Would you ditch Adobe and Figma for Sketch?

What does Ukraine's murderous craziness mean?

Vladimir Putin expressed his patience to Israeli Prime Minister Naftali Bennet. Thousands, even hundreds of thousands of young and middle-aged males in his country have no meaning to him.

During a meeting in March with Prime Minister Naftali Bennett of Israel, Mr. Putin admitted that the Ukrainians were tougher “than I was told,” according to two people familiar with the exchange. “This will probably be much more difficult than we thought. But the war is on their territory, not ours. We are a big country and we have patience (The Inside Story of a Catastrophe).”

Putin should explain to Russian mothers how patient he is with his invasion of Ukraine.

Putin is rich. Even while sanctions have certainly limited Putin's access to his fortune, he has access to everything in Russia. Unlimited wealth.

The Russian leader's infrastructure was designed with his whims in mind. Vladimir Putin is one of the wealthiest and most catered-to people alive. He's also all-powerful, as his lack of opposition shows. His incredible wealth and power have isolated him from average people so much that he doesn't mind turning lives upside down to prove a point.

For many, losing a Russian spouse or son is painful. Whether the soldier was a big breadwinner or unemployed, the loss of a male figure leaves many families bewildered and anxious. Putin, Russia's revered president, seems unfazed.

People who know Mr. Putin say he is ready to sacrifice untold lives and treasure for as long as it takes, and in a rare face-to-face meeting with the Americans last month the Russians wanted to deliver a stark message to President Biden: No matter how many Russian soldiers are killed or wounded on the battlefield, Russia will not give up (The Inside Story of a Catastrophe).

Imagine a country's leader publicly admitting a mistake he's made. Imagine getting Putin's undivided attention.

So, I underestimated Ukrainians. I can't allow them make me appear terrible, so I'll utilize as many drunken dopes as possible to cover up my error. They'll die fulfilled and heroic.

Russia's human resources are limited, but its willingness to cause suffering is not. How many Russian families must die before the curse is broken? If mass protests started tomorrow, Russia's authorities couldn't stop them.

When Moscovites faced down tanks in August 1991, the Gorbachev coup ended in three days. Even though few city residents showed up, everything collapsed. This wicked disaster won't require many Russians.

One NATO member is warning allies that Mr. Putin is ready to accept the deaths or injuries of as many as 300,000 Russian troops — roughly three times his estimated losses so far.

If 100,000 Russians have died in Ukraine and Putin doesn't mind another 200,000 dying, why don't these 200,000 ghosts stand up and save themselves? Putin plays the role of concerned and benevolent leader effectively, but things aren't going well for Russia.

What would 300,000 or more missing men signify for Russia's future? How many kids will have broken homes? How many families won't form, and what will the economy do?

Putin reportedly cared about his legacy. His place in Russian history Putin's invasion of Ukraine settled his legacy. He has single-handedly weakened and despaired Russia since the 1980s.

Putin will be viewed by sensible people as one of Russia's worst adversaries, but Russians will think he was fantastic despite Ukraine.

The more setbacks Mr. Putin endures on the battlefield, the more fears grow over how far he is willing to go. He has killed tens of thousands in Ukraine, leveled cities, and targeted civilians for maximum pain — obliterating hospitals, schools, and apartment buildings while cutting off power and water to millions before winter. Each time Ukrainian forces score a major blow against Russia, the bombing of their country intensifies. And Mr. Putin has repeatedly reminded the world that he can use anything at his disposal, including nuclear arms, to pursue his notion of victory.

How much death and damage will there be in Ukraine if Putin sends 200,000 more Russians to the front? It's scary, sad, and sick.

Monster.

Or the “lie to me” method.

I can predict a startup's success in minutes.

Just interview its founder.

Ask "why?"

I question "why" till I sense him.

I need to feel the person I have in front of me. I need to know if he or she can deliver. Startups aren't easy. Without abilities, a brilliant idea will fail.

Good entrepreneurs have these qualities: He's a leader, determined, and resilient.

For me, they can be split in two categories.

The first entrepreneur aspires to live meaningfully. The second wants to get rich. The second is communicative. He wants to wow the crowd. He's motivated by the thought of one day sailing a boat past palm trees and sunny beaches.

What drives the first entrepreneur is evident in his speech, face, and voice. He will not speak about his product. He's (nearly) uninterested. He's not selling anything. He's not a salesman. He wants to succeed. The product is his fuel.

He'll explain his decision. He'll share his motivations. His desire. And he'll use meaningful words.

Paul Ekman has shown that face expressions aren't cultural. His study influenced the American TV series "lie to me" about body language and speech.

Passionate entrepreneurs are obvious. It's palpable. Faking passion is tough. Someone who wants your favor and money will expose his actual motives through his expressions and language.

The good liar will be able to fool you for a while, but not for long if you pay attention to his body language and how he expresses himself.

And also, if you look at his business plan.

His business plan reveals his goals. Read between the lines.

Entrepreneur 1 will focus on his "why", whereas Entrepreneur 2 will focus on the "how".

Entrepreneur 1 will develop a vision-driven culture.

The second, on the other hand, will focus on his EBITDA.

Why is the culture so critical? Because it will allow entrepreneur 1 to develop a solid team that can tackle his problems and trials. His team's "why" will keep them together in tough times.

"Give me a terrific start-up team with a mediocre idea over a weak one any day." Because a great team knows when to pivot and trusts each other. Weak teams fail.” — Bernhard Schroeder

Closings thoughts

Every VC must ask Why. Entrepreneur's motivations. This "why" will create the team's culture. This culture will help the team adjust to any setback.

Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.