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Month: March 2016

Reader question: “What to do once you’re inside?”

Reader question: “What to do once you’re inside?”


Newsletter reader recently got a new job (congrats SD!) and sent me the following email:

“I’ve joined a startup in NYC as a Product Specialist. First week in so far and I really like it. Question: I feel like there’s a lot of writing out there about getting what you want, but once you get it… Then what? Once you’re in a new organization, what should you look for? What things should you keep in mind? How should you behave?”

I like this question because it illuminates the education we lack about marrying being a good employee with growing as an ambitious and independent professional. The reader understands that if he neglects these questions, he will fail to leverage his new partnership. He wants to exceed expectations of himself and his employers so he can be rewarded with more skills, money, respect, autonomy, and optionality, both in his new job and in future career opportunities.

Some caveats before I jump into the advice:

  • I don’t know what the conversations and negotiation between the reader and his employers was like before being hired. The specific expectations from both sides may vary depending on the reasons both sides decided to invest in each other.
  • James Fallows says that the question that distinguishes tactics from strategy, when you consider any move, is “how does this end?” I don’t know what the reader wants for his life in the end. It may be short term income to transition into his own startup six months from now. I will dispense some ideas assuming that he wants to grow in the company.
  • I assume the company is average, with average employees. While most of this advice is universal, one may be spared a lot of office politics nonsense working for some great companies like Google.

So, how to grow in a company once you’re inside? Some thoughts:

  • You are an investment who was brought in to solve a problem. Your minimum obligation is to solve that problem without requiring additional investing (i.e., be problematic, lazy, etc.). Better yet to discover and solve other problems too, because you will be seen as a great investment. Clean the kitchen, fix the company’s website, bring clients, it all helps.
  • Ask about the vision and direction of your team and the company. Understand the intricacies of the problem the business is trying to solve, and why it’s doing it in its particular way. Work hard to understand the customers, because that’s what your bosses are thinking about: your customers’ needs. The sooner you join them in seeing the big picture, the faster you will join them in upper levels of the hierarchy.
  • Try to understand your bosses’ personal and professional goals inside and outside the company. Be subtle with personal questions! Help them achieve those goals. If you can be an ally for them as individuals, they will want to keep you close no matter what they do. That’s how you develop a network of allies.
  • Forget about trying to win arguments and proving people that you are smart. Fuck being right. You were not hired because of your wiseass skills.
  • It’s all about appearances. Be the first to come and last to leave, even if you are checking Twitter for the first and last hour.
  • It’s all about appearances. Don’t let people see your computer desktop if you are not working. Grab a bunch of papers and walk quickly around the office if necessary. Go relax where no one can see you, or relax when others are relaxing too. It’s all bullshit, obviously, but people’s judgements are emotional. If they see you alone in the bean bag chair, they will associate your face with bean bag chairs as opposed to hard work.
  • Be seen with different people, don’t hang out with the same coworkers all the time.
  • Try to understand what your coworkers like or care about, so you can find more ways to bond.
  • Put yourself in situations where you can play with others, or work hard and achieve milestones together, so people associate you with fun times or with achievement.
  • Shower and brush every morning, and put some perfume. Nothing worse than a smelly coworker. Make sure your clothes are clean too.
  • Ask your boss out for lunch and ask them about the industry, their experience, and career advice. People like to be heard and respected. Do the same with your coworkers (they have been in the company longer, so respect that).
  • Promise and deliver EVERY TIME. No excuses. You want to be seen as reliable, and more importantly, someone your superiors don’t have to worry about. Peace of mind and mental bandwith are the most precious gifts you can give to your bosses.
  • Think twice before going to your bosses with questions. Make sure it’s not a dumb question. If it’s not a dumb question, DON’T avoid asking it; it will make you look smart for asking a smart question, and you will avoid making mistakes out of stupid pride.
  • Leave your craziness and dramas at home. Act as if you have your shit together.
  • Take notes of everything, especially of advice someone gives you. Be seen as someone that writes down everything important. Don’t risk forgetting anything, since nothing is more annoying than having to tell someone something twice.
  • If someone gives you advice or tells you to read/watch something, follow up on it. Tell them how you applied it for last few days/weeks. Tell them about your impressions. Send them links related to what they told you. Show them that giving you advice is not a waste of their time.
  • Eliminate as much friction as possible and hand-hold people through every request you make. Tell your boss you will send him some ideas to bring more customers, how you will execute those ideas, and that the only thing you need is his permission. Don’t ask for him to sit down with you to think ideas together. Tell your coworkers that you will make a reservation for happy hour at the bar around the office at 6 pm. Don’t ask where everyone would like to go.
  • Don’t talk too much or dominate any conversation. If you want to be interesting, be interested. The more you listen, the more you can understand the dynamics, incentives and power plays within the organization.
  • The sooner you can understand “how we do things around here,” the better. You may modify the culture and create new habits eventually, but you can only do it once you’re seen as a member.
  • Always be aware of who else is listening. Should you be including them in your conversation? Should you not say certain things in front of them? People are unaware that most of life is a podium, not a 1-on-1 conversation. People talk to each other about what they hear. Take advantage of your audiences and be careful about who you may neglect or offend.
  • Praising others, working long hours, asking many questions, being playful in the office… Great attitudes to have, but if go too far, or display them in front of the wrong peoeple, you may be perceived as an ass-kisser, or a workaholic, or a threat, or a clown. Be conservative while you gauge people’s responses to your attitudes, so you can get closer to that culture’s sweet spots.
  • Don’t obsess about meritocracy or fairness. Other than being a hard worker, life comes down to how you make people feel. If you can combine competence and ambition with people’s trust and likeability, you will have a great career.
10 Confessions on Recruitment & Teamwork from my Start Up Life (a.k.a. “What NOT to do”)

10 Confessions on Recruitment & Teamwork from my Start Up Life (a.k.a. “What NOT to do”)


Last week I was a guest speaker at Tallinn University of Technology for their “How to Start Up” program. Below is an edited version of my talk, and it’s one of the most vulnerable things I’ve written:

I don’t claim to know what you should do with your team and recruitment efforts in your startup. All I can share is things I’ve learned as an entrepreneur that one should NOT do. It is very costly for a business to get the people wrong, so now I work hard in trying to avoid these mistakes.

1) Don’t avoid a hierarchy (but don’t become a dictatorship either)

On my first business we were six co-founders. Decisions were slow, and everyone had their own agendas because there was no unifying direction. I liked having the “co-founder” title nonsense because I was young, naive and shallow, but I probably would have gotten more from the experience if I would have been answering to someone and working within a structure, however fragile it would have been. We romanticize democratic decision-making, but there are many good things about having a clear authority.

On the other hand, power reveals. In another startup, our CEO surrounded himself more and more with ass-kissers because they pampered him and didn’t clash with his decisions, which slowly transformed the business into a “dictatorship” of sorts. People realized that agreeing with him was the best way to grow and remain in the company. They would be rewarded with more responsibilities that their peers would notice they didn’t deserve. Those that wanted to challenge his ideas or his ethics, were punished. The sad thing, which I didn’t notice until it was too late, was that behind the back of this CEO and his closed circle of trust, everyone inside and outside the company would discuss the obvious: nod in agreement and act amazed about what he says, and you will thrive here.

Both structures limited our teams’ effectiveness and moral. Don’t take the easy way out and pick one or the other. Strive to create a structure that balances humility with confidence and allows for decision-making flexibility.

2) Don’t recruit “impressiveness” or skills

For the first time ever, we are all in charge of our own credentials. We decide what to put on our Linkedin, or our Twitter/Facebook stream, or our blog, or our resume. People get in the press or speaking events because they know the right people, not because they are the ones we should listen to. There’s nothing inherently wrong with this, but it does mean that we should be skeptical of most credentials because people have mastered the art of bullshit. A new critical skill to posess in a world where people control their own credentials is to be able to see through the bullshit.

There’s a famous cognitive bias called the “halo effect”, which says that our overall impression of a person can influence our feelings and thoughts about their character and other properties. We see someone that is attractive or knowledgeable or charismatic, and we make the mistake of thinking they are good people, or funny, or good leaders, etc. We give them attributes they don’t actually have.

Don’t recruit for impresiveness. It pains me to admit that I’ve made the mistake multiple times of partnering with someone because of how they presented themselves, as opposed to what their values, character, personality, and incentives were. I’ve been “charmed” by people that knew a lot of history, or people that wrote very well, or people that were a lot older, or people with many connections. Those reveal nothing about whether or not they are bad people, or lazy, or charlatans, or have integrity.

Similarly, don’t recruit or partner with someone just because they are a “programmer” or work in “sales.” These are just labels. While skills are obviously important, not having them is less risky for a startup than not having chemistry, a shared vision, or shared values. Don’t rush into professional relationships until you get the personal stuff right.

3) Don’t skip the dating phase

Since my last business, I’ve been telling people that I don’t care about WHAT I will work on in the future; any business idea will evolve as you move forward. I do care about WHERE I will work and WITH WHOM; the environment and the people don’t change. We have to explore and pick carefully.

I made the mistake of “marrying” to business partners too fast in the past. For example, in one my past businesses, I was naive enough to let discussions such as ownership percentages get pushed back over and over, until they never happened.

I no longer skip “dating” with potential partners. I find ways to test how they behave, and how many of their promises or beliefs about themselves actually become true. I ignore most of what people say about them, and I look at their actions. When I find a potential partner for new opportunity, I create low-risk experiments where we both work together but I get to see them in action before making a long term committment. If the experiment fails, no biggie, and I “cut” that person as an immediate ally. Like in dating, if you are going to have a bad relationship, better to end it after two months than two years.

We often hear that “co-founding a business is like a marriage” because, like a marriage, you need to work hard in the relationship to make it work. However, we often forget that, like a marriage, it only has to work once. If you’re looking for a business “life partner,” you are better off dating aggressively until you find the right one, instead of partnering with the wrong person and then hope that working hard will make it last.

No marriage is better than a bad marriage. No co-founder is better than bad co-founders.

4) Don’t ignore your instincts

In a past business, my partner was a lot older and experienced than I was, and I felt lucky for the opportunity to work with her. However, as we moved forward, she started acting very rude and disrespecting me often. There was a little voice that told me “maybe I shouldn’t be working with her”, but I ignored it because I was naive enough to believe I had to endure assholes as long as they had the right credentials.

Boy, was I wrong. Not only I felt bad working with her, I also let her ideas influence my original vision for the business. Looking back, it was a disaster. We made some money, but the business ended quickly. What makes me mad is that I could have avoided the struggle if I would have trusted to my gut.

Paul Graham says that in startups you should never trust your intuition, except when it comes to people. Sometimes we don’t know why we should walk away from someone other than because it “feels wrong,” but that’s all you need.

5) Don’t punish nor expect vulnerability

If you create an environment where being vulnerable, honest and critical is ignored or punished, people will start hiding what they think or lying to you. I already gave the example of my past business where disagreeing was risky. In other cases disagreeing was simply a waste of time, because the founder would just rationalize and ignore all feedback. There was no backlash, but it was pointless to bring new ideas because the CEO would eventually put them aside.

A scary thing I saw once I announced I was leaving a business I co-founded was how many people involved with the company started being honest with me in private about how they felt about the organization, the leadership, the ways we disappointed them, and more. From clients, to employees, to partners, they all opened up. More importantly, they admitted that they didn’t say anything before because they didn’t think we would welcome the feedback well.

I got scared because I realized I’ve been deluded. People didn’t feel their honesty would be rewarded, so they didn’t give me access to the truth. And in business, nothing is more dangerous than living a lie. The worst part is that some of these people are involved with this company to this day and they still feel and think the same way but won’t say it out loud.

Another problem with a context that does not foster vulnerability is that people will start running their own agendas way before they tell you. By the time someone announces they are moving on a different direction, they have been thinking and planning their move for a while, and they think it’s better to a) extract as much value as possible before leaving, or b) minimize the value given. I’ve been on both sides of this equation. I’ve been shocked by people saying they didn’t want to work with me any longer, and I’ve shocked people that I’ve worked for when I told them I was done. In both cases, the environment didn’t foster true vulnerability, so remaining secretive made more sense.

This is a bad situation because when you don’t see what people are thinking or feeling, you risk investing more and more resources on a lost cause. I’m working hard in allowing people to be more open and honest with me about their doubts and unmet needs in our current projects, so if they do decide to do something else, I can help with their next endeavor without me being caught off guard.

6) Don’t ignore their past

A co-founder of mine had been sued by his former business partner, and I didn’t know about it. I was so young and naive that I never thought of asking. I learned about it once I left, because an old mentor researched him and informed me afterwards. Looking back, I feel stupid for not seeing that something was fishy. There was a gap in this person’s history. It was hard to find ties to his past professional projects, and that’s never a good sign.

If you’re thinking “but Carlos, there’s two sides to every conflict”, here’s a good heuristic to figure out who’s more risky to work with: Who has the most to hide and opens up the least in public? When people can’t say “talk to John and Mary about working with me in project X, they will tell you what I’m like”, watch out.

Let me be clear: things can go wrong, and we shouldn’t be always punished by our past. We must burn certain bridges sometimes, since some people are better to never see again. However, I would have prepared differently and taken smarter risks if I would have known. I know I would have saved myself many headaches if someone would have given me at least one more version of this person’s true colors, which I saw too late.

A lot of what people say about them, about what they did, and how they got to where they are is a fantasy. People invent a story they like about themselves. In most people’s cases, those stories involve a healthy amount of honesty and self-blame. But sometimes we work with people that would rather bury any non-flattering part of their past. It is because of these cases that we must always dig, so we know who we are dealing with.

There’s one caveat for asking people for recommendations: People will praise anyone if there’s no risk for them to do so. This is why we can’t trust most testimonials online anymore.* People will also praise anyone’s product or professional services if they are their friends, so they gain good will from them, even though they have never paid for them.* You can’t trust these recommedantions.

The only credential that matters is this: What do the people that invested their money or time in working with you as a client/partner/boss/employee have to say about you? Ignoring this question has been extremely costly for me in the past. Next to running short term experiments with people, asking for referrals from others that 1) invested in them in the past and 2) have both something to gain and to lose if they make the wrong recommendation to you, is the best way to know who you can trust.

7) Don’t promise more than you can give

My old business mentor taught me that every business has five parts: value created, marketing, sales, finance and value delivered. When I ask people what they think is the hardest to execute, they often say it’s sales. I disagree, I think it’s delivering the value that your promised them when you closed the sale. It’s easy to sell a product or a job if you tell people everything is going to be amazing. What’s hard is to be grounded in reality and sell only what you can deliver, so you don’t scam people.

On a past startup of mine, right before I would leave, I sold our product to +10 more customers. This was a very expensive product. It pains me to this day that some of those people, after their experience with the product, talked to me in private to let me know how it disappointed them. I hope I will make it up to the somehow someday, even I did not use their money.

Around that time, past team members of the same company told me that they were promised something which was never delivered. From money to responsibilities, these people felt betrayed. It may be tempting to exaggerate what the future holds in order to recruit more people, but you must avoid the temptation, because it will come back and bite you. If you’re in business for long enough, people will notice and spread the word about the gap between what you say and what you do. Like the boy who cried wolf, at some point people stop believing you, and if you lose people’s trust, you’re doomed in business.

Better to be humble and accurate than delusional and disappointing. Others may disagree, but I believe avoiding those rules makes success both harder and unethical.

8) Don’t blend the personal and the professional too much

One of the worst mistakes I’ve ever made was to get romantically involved with a client. Back in a lonely period of my life, I let someone manipulate me for her own interests. This woman lied to every organization involved in a government project, our company included, so she could inflate her personal brand. The result: her contract was canceled, many people got fired, and many clients were disappointed.

Side note: This woman is considered a “young leader in science” in her country by their media and other institutions that don’t know or care to uncover how she got ahead in her career.

Having a fling with this person clouded my judgement, and brought unnecesary stress to my team and my relationship with my partners. However, I believe I would have not made such a stupid mistake if myself and our company would have structured more room for personal space.

To be fully immersed in a professional project can stress us in our personal life. I remember a discussion with a partner I was living with where he told me he didn’t like that every time he came home I was working on the same table.

When there’s no space for a personal life, we judge people’s professional self because of how they behave outside of work. In my past company, people were criticized because they drank or did drugs in their free time, or because they kept working late at night when others were sleeping or having dinner, or because of who they wanted to hook up with, etc.

When there’s no space for a personal life, people risk making poor professional decisions. This is one of the things that I believe the corporate world to have gotten better than the startup world so far.

9) Don’t take communication for granted

A very successful business man once told me “trust has half-life of 12 days.” If one doesn’t nourish the relationship often, trust gets “cut by half” every 12 days. Sebastian and I had a similar revelation years ago when we said that good will lasts for about two weeks.

I’ve seen this effect in all my past startups. If my partners and I were too lax about the frequency and intensity of our communication when we had to spend a significant time away from each other, everything would go to hell. With every trip, we would lose some trust and good will.

*When communication is bad, it’s hard to have everyone on the same page. If they feel there is a gap in information or someone’s presence, they fill those gaps with their imagination. *People start assuming someone is no longer motivated, or is not working hard enough, or that important decisions are being made behind their back, etc. Eventually, everyone starts running different agendas.

If it’s not clear by now, I’m skeptical of remote teams for most startups. My suggestion is to see each other plenty and talk often, if for no other reason than fueling your trust in each other.

10) Don’t underestimate the complexity of a person’s life

People are more than a title or a set of skills. They are more than what you see and hear working next to you, debating projects and the future of the company. They think and feel more things that you will ever know. We are only allowed see a small portion of someone’s thoughts, values, relationships, and other elements that influence who they are and how they will act next. No matter how much you want to read people, some things will remain hidden from you, and you have to deal with it.

I’ve learned that you can’t control people with formulas or models. Leading with vulnerability, owning our mistakes, accepting the complexity of human relations, and being resilient when (inevitably) some partnerships don’t work out, are the only things I’ve seen work if we want to develop many long-lasting, mutually beneficial, and honest professional relationships.

Ask yourself these questions to know who is looking for you

Ask yourself these questions to know who is looking for you


Most people can answer questions such as “What kind of work would you like to do?” or “What’s missing from your career right now?” Responses usually range from concrete or perk-oriented, such as “I want a good salary” or “I want to launch a business”, to more abstract or purpose-driven, such as “I want to solve the problem of cancer” or “I want to learn how to become a good leader.”

Alas, people have a hard time describing WHO needs THEM NOW (each of those words is in caps for a good reason). Their answers to questions such as “What are you good at?” are rarely specific enough to be useful.

People struggle with these questions because they are personal. The answers are not published anywhere, and the only way to find them is through a personal exercise of both self-discovery and empathy with others. The good news is that for those that go down that path, the reward is a neverending string of opportunities because they constantly adapt their identities and services to what the world needs from them.

Balancing Ability and Ambition

While it would be exciting to help Elon Musk or Ban Ki-moon and work full-time directly with them, it’s not realistic for most people. Similarly, it would be nice to start the next Google or Amazon, but it’s also improbable that that is your next best step. A good way to start thinking about who we should help is to first think about who we CAN help.

At the same time, while one could probably put up a lemonade stand or get a job in McDonald’s right away, those moves provide little value for most people after a certain point in their careers. It’s a waste of their assets such as experience, skills, networks, etc.

The more standard the opportunity, the more competition there is, the harder it becomes to leverage our uniqueness, and the less value we can provide and receive. The more customized the opportunity, the bigger the rewards for both sides.

Our goal is to be able to answer this question:

“Right now, who can I help better than anybody, and how?”

If you figure that out, you have discovered your next career breakthrough opportunity. The more relevant the problems we can solve, and the more people we can help, the more value we receive exchange in the form of money, creative freedom, authority, autonomy, flexibility, joy, relationships, etc.

If we want to identify which are the best opportunities out there for us, we need to understand our specific circumstances. Below are some questions to help you with this process. The trick is to revisit these questions often because with every step we take in life, our conditions change, and what we can do for others changes too.

Problem Orientation

1) What problems spark your interest?
2) Who are people that you believe to be doing important work around those problems?
3) How are you investing in becoming a better ally around those problems?

Understanding and communicating the problems you care about will allow you to bond with others at a deeper level than simply transactional. This is the famous “start with why“, and it’s a major drive behind powerful collaborations. It will also provide the fuel you need to work on something or with someone for longer than you would otherwise. If you lack clarity about what problems you care about, that is the first problem you need to work on.


1) What assets do you have that could be valuable to others? Think free time, skills (soft and hard), wisdom, information, clarity, networks, reputation, money, technology, etc.
2) What assets are you pursuing that other people can help you get?

Here’s an example of asset leverage: I was invited on a speaking tour around US universities such as Harvard and Stanford because I had the relevant previous relationships, English fluency, speaking experience and location flexibility, plus I provided cultural diversity to the speakers lineup. In exchange, since I didn’t need to make money, the experience helped me improve my speaking skills and reputation, and sparked new connections all over the country. It was a perfect fit.


1) In what way are you unique?
2) How hard is it for others to acquire your current advantages?

*There’s room in the world for most people to monopolize certain opportunities. *The languages you know, the city you live in, your culture, the information trends you see before others, the people that trust you, the things you don’t care about… These are some neither-good-or-bad conditions that can make you uniquely qualified for certain opportunities. These factors can also act as barriers of entry for others to access those same opportunities.


1) Who do you have access to?
2) With whom should you be developing a relationship?
3) How well do you understand the different people that you think you can help?

On his must-read essay about his lessons working with Reid Hoffman, co-founder and chairman of Linkedin, Ben Casnocha explains the best way to reach successful people:

“As chief of staff, I reviewed thousands of requests for Reid’s time/attention/money. It was stunning how few requesters actually offered to help him on something. Amusingly, many requests were framed as if the asking party were doing Reid a favor by giving him the opportunity to help them: “It’d be fun to get your feedback on something I’m working on.” Reid’s so generous and so curious that sometimes it is fun for him to simply help you. But why not figure out what he’s working on and send an article of relevance? Or offer to share a perspective that could be useful? Help first. Help first. Help first. It’s key to building relationships – even with the ultra successful.”

As valuable as knowing many people can be, it’s equally important to do the work of understanding their needs. Think of it as your personal “market research.” The better you understand the people in your reach, the easier it will be to persuade them that you can help them.

It’s ok to not know the answers to all the questions above. They are simply meant to prompt you to discover new perspectives about your unique situation and what you can do next in your career. The point is to remember that, in a fast-paced networked age, there’s always some unique value we can provide someone, and we must exercise self-awareness and empathy periodically to uncover it.

What are the challenges and opportunities for people-centric professionals in a networked age?

What are the challenges and opportunities for people-centric professionals in a networked age?


If I were to ask what it takes to become a great architect, programmer or scientist, most people would agree: study a lot, prototype, stay updated with new discoveries, and constantly deploy your growing skills and knowledge in experimenting with opportunities, techniques, and ideas that interest you. Eventually, you may become a master in your profession or make new breakthroughs in your field.

In other words, it takes a lot of what Cal Newport, author and professor at Georgetown University, defines as “deep work”: professional activities performed in a state of distraction-free concentration that push your cognitive capabilities to their limit. Knowing what deep work looks like is important because, as Cal says, “the ability to perform deep work is becoming increasingly rare at exactly the same time it is becoming increasingly valuable in our economy. As a consequence, the few who cultivate this skill, and then make it the core of their working life, will thrive.”

Deep work has become increasingly rare because most people can’t concentrate anymore. We now have shorter attention spans than a goldfish. We live distracted due to the expansion of cheap technology and connectivity. Smart phones, social networks, blogs and funny websites… They all play a part in stopping us from working deeply.

And deep work has become increasingly valuable because any professional that wants to thrive in a hyper-connected market needs to 1) create outstanding value to beat the competition, and 2) learn new and hard things quickly. Both goals require a concentrated effort.

While difficult, the deep work “formula for success” is clear for architects, programmers and scientists… But what does deep work look like if you work with people?

What does concentration look like when you’re trying to understand humans and society? What does a “distraction-free” environment look like if your subject of work is a person, which is harder to control than a line of code or a set of chemicals? What is the networked age “formula for success” for the social butterfly, the connector, the teacher, the salesman, the social worker, the manager, the psychologist, the HR employee?

Side note: While deliberate practice is essential to master many crafts, Anders Ericsson explains that its principles are mainly applicable only to highly developed and studied fields like sports or music, but don’t work as well for professions like teachers, consultants, or business managers.

These questions matter to me for two reasons. First, because I’m a communicator. From selling, to teaching, to writing, all work I do revolves around making observations, understanding people, and bridging perspectives. If I want to thrive, I need to understand the deep work requirements for my profession.

Second, because to properly understand the present and imagine the future of employment and entrepreneurship, we must tackle people-centered skills and problems with the same level of focus and tinkering that we deploy in fields such as art, sports, science and technology.

Where technology fails

The main thesis behind my Sunday articles is that knowing with whom and how to collaborate, where to find them, and what to say to them, is the essence of a thriving career or business in a networked age. However, the wide availability of information and connectivity has actually made collaboration harder in unexpected ways because distractions, information “noise” and competition for our attention are at an all-time high.

To understand the intricacies of the problems and needs of the people we must collaborate with, now demands an unprecedented level of deep work. Like any previous revolutionary technology, the internet changed society and human behavior for good, but the difference is that it also accelerates the adoption of all subsequent technologies, triggering an exponential pace of behavioral changes for us to catch up.

This, I believe, is what scares and frustrates many inventors, entrepreneurs and technologists; they know that they don’t understand people, and that without people there are no users. They prefer the predictability of the laboratory or garage, where they can avoid the chaos and mystery of people’s emotions, habits and preferences. The amount of things they build that no one really wants is staggering, and it stems from ignoring the complexities of consumers’ behavior.

I’m glad those fears exist, because they remind us that people are still more important than technology, not just because they are the consumers, but also because they are the only ones that can do the deep work of empathizing with a market. The challenge is not to understand people in a philosophical or biological vacuum (anyone can do that by reading philosophy, psychology or biology), but rather understanding people’s changes in an evolving technological context. The former can be done in isolation, while the latter requires immersion and experimentation.

As Jaron Lanier, the popular pioneer of virtual reality and advocate against the utopian promises of artificial intelligence, wrote in You’re Not a Gadget: “the most important thing about technology is how it changes people.” He then pondered:

“‘What is a person?'” If I knew the answer to that, I might be able to program an artificial person in a computer. But I can’t. Being a person is a not a pat formula, but a quest, a mystery, a leap of faith.”

I see countless opportunities to thrive for those that take that leap.

The Hiring Equation

The Hiring Equation


Hiring is all the rage these days. There are thousands of companies worldwide trying to figure out how to update the hiring process for an Internet era, ranging from failure to moderate success. Even though Linkedin is the dominant player today, I often hear from friends about their bad experiences trying to hire through the platform.

I spent the majority of my “deep focus” energy of the past 18 months trying to understand the intricacies of how positive collaboration happens, mainly hiring. Traditional employment is only ONE form of career collaboration, but it’s the most popular, the one most people try to develop, and it’s vastly misunderstood.

In an effort to shed some light into the hiring process, I will share a “hiring equation,” a simple framework I came up with to explain the thinking of someone looking to fill a position. My hope is that it will help those trying to switch careers to better understand how to navigate the process, and also help recruiters do an honest self-assessment about their practices and how to improve them. Here it is:

Transference of trust + Solution orientation + Excitement for potential + Conservation of energy + Cultural fit + Assumption of visibility = Chosen candidate

Transference of Trust

Let’s say I want to buy a phone, but I don’t know much about phones. I can search on Google, explore different stores, read their specs, and learn what phone I need for myself… Or I can ask my friend to recommend me one, since he is an expert in technology, has no incentive to sell me a particular model, and knows my personality. I trust him, therefore, I trust his recommendation.

Hiring works the same way; employers need to trust the candidate. And if they don’t know him personally, they will look for sources they can trust and “transfer” that trust into the candidate. Friends in common, attending respected universities (ideally the same university of the employer), working at famous companies… These are all proxies of trust that help people decide between unknown candidates.

The important thing to remember about trust is that it’s emotional and primal. This is why referrals often get hired over better qualified people that the employer doesn’t know. In a traditional hiring process, companies take the most risk with a new hire, and the main question they want answered is “How can I trust this person to fulfill my expectations?” Turns out that “she’s a friend of my brother” is a better answer than “she has an MBA.”

In a world where where people switch jobs every 2.2 years, trust is the best currency one can amass to open up new collaboration opportunities. Instead of obsessing about having a lot of impersonal credentials, focus on making more friends, smiling more, and showing interest in everyone’s lives and careers. They will like you and trust you more.

Solution orientation

Last year, a woman called Nina Mufleh decided to do whatever it takes to get a job at Airbnb. After trying the “normal way” and coming up empty, she created, with the purpose of persuading Airbnb that she was the right person to add to their company. The website explained her fascination with Airbnb, what business opportunities she saw, how she would pursue them if hired, and how her values aligned with the company’s.

Nina’s innovative resume-like proposal was a remarkable showcase of her drive, discipline, creativity and other intangibles that companies want in their candidates. She caught the eye of the media and was invited to be interviewed by companies like Uber, Dropbox, Linkedin, and yes, Airbnb. Finally she would be interviewed by her dream company that she was so perfectly suited for!

And she didn’t get the job.

No need to be sad for Nina; her campaign was a career success however you look at it, and she found a great position at Upwork thanks to her PR efforts. It’s worth going above and beyond to stand out in a crowded job market. But an equal important lesson is that it doesn’t matter how great you are if you don’t solve the need the customer/employer has. I don’t know what Airbnb was looking for, but it wasn’t her, no matter her remarkability, or how polished her presentation was. If I need a programmer, I don’t have an use for the best salesperson in the world.

It’s similar to having a job that gives you all the good perks but no salary. It’s hard to take it, isn’t it? When looking to get hired, make sure you cover the baseline needs, and then find ways to exploit your other skills and ideas.

Excitement for potential

One of the biggest mistakes people make in their resumes, Linkedin profiles and live answers to the ubiquitous “What do you do?” question, is to list past accomplishments and credentials. They say things like “I have a degree in economics from university X, worked four years in industry Y running their program Z to to help our clients get more ABC.”

This is cold information. It lacks context.

Competence visibility is asymmetric; you talk about those four years and remember all the things you did day to accomplish X and Y (often polishing details that would take away prestige from the narrative), but I wasn’t there. I can’t relate or assess your full personality and capabilities from your story.

Talking about past accomplishments or credentials doesn’t generate excitement for what we can build together for the future, which is where we are headed, and the reason we are having this interview. When imagining the future of any collaboration opportunity, showing potential is (slightly) more important than experience.

However, the kind of potential you need to show depends on the people and organization you may work with. Different cultures may want to see potential that you will…

…be diligent, quiet and obedient.

…grow into a leader in the organization.

…question the status quo and be an agent of innovation and improvement.

…wear multiple hats and cover many different needs.

…put your network connections at the disposal of the organization.

…not leave the company.

…not be a pain in the ass.

…repeat the results of your experience.

Don’t get me wrong: your experience matters. But 1) you must frame it in a way that relates to what is going to come, and 2) between two-equally (in)experienced individuals, potential tends to tip the scale.

Conservation of energy

Monica Anderson, of the Stanford Transhumanist Association, and founder of several A.I. initiatives, says that 0.0001% of our daily decisions are conscious. This is what she calls the “reasoning” process. The other 99.9999% is what she calls “understanding”, which is unconscious and always “on”. We can’t help to understand that a table is a table when we see one, that we need a sweater when we are cold, or to interpret English once we’ve learned it.

The problem with asking people to “reason” what they should do is that reasoning requires a lot of energy and focus. Humans try to avoid reasoning as much as possible, and let their unconscious mind do the work of going through daily life. We are wired to be “lazy” and conserve energy because our ancestors didn’t know how long they would be without finding food, or when they would have to run from a threat. Back then, if you didn’t save energy, you risked dying,

While the world has changed and it’s much safer to reason through most things, our biology has not changed.

What does this have to do with hiring?

For most companies and employers, hiring people does not make the “reasoning” cut. They make most decisions unconsciously following what they “understand” to be right and prioritize what’s less demanding. A big problem with how people want to make their way into a new job is to hope/expect/push for people to “reason” why they should be selected. They wish that quality or talent (whatever that means) decides who gets picked.

However, while employers believe that they are dedicated to quality, in reality they want “good enough.” They want to NOT think. This does not mean they will hire whoever comes through the door first, but rather that between two hypothetically equal candidates, they will hire the one that demands less reasoning.

In business, I call this “hand-holding the sale”: do your best to predict the exact series of questions and decisions of your potential customer (in this case the potential employer) and find a way to make their thinking process and subsequent decisions easier until you “close the sale.”

Those who can think ahead of their employers and save them the effort of reasoning have the best chance of getting picked.

Side note: This is why the best jobs, with the least competition, are often “co-imagined” by the employer and potential employee, and never published online. Instead of waiting for the busy person with the problem (employer) to make the time to reason what he needs and how to find it, proactive professionals help them figure it out and how they can help them. The employer is now thankful for both finding a person with the solution, and for saving himself time and energy of having to decipher his situation.

Cultural fit

Culture is a fancy word for “how we do things around here.” The great Clayton Christensen defines it as “a way of working together toward common goals that have been followed so frequently and so successfully that people don’t even think about trying to do things another way.” The bigger the organization, the longer some “rules” have been around.

A good friend of mine that runs a very successful startup says that the number one question he tries to answer when interviewing a potential hire is “Can they work within our team?” A case could be made for this question to be the most important thing an employer needs to get right with each new member. When looking for a job, it’s not a good idea to try to fight or cheat the culture fit filter, but rather evaluate it to the best of our ability in order to avoid suboptimal collaborations.

Culture is important to get right because it automates countless daily decisions for those that share its values. It allows for tacit agreements between team members about what’s right and what’s wrong. It doesn’t matter how talented a person is, the odds that one individual is able to bring more value to an organization than a cohesive team are almost zero. Any organization, even with a shitty culture, will accomplish more than one person with the best principles and work ethic.

It follows that a strong culture is often also why companies fail. Doing things differently sometimes is necessary for survival, but hard to execute after a culture has endured long enough. I believe this is what Peter Thiel refers to when he says “a startup messed up at its foundation cannot be fixed.”

No one can be a great candidate for every organization. To be a great fit for one team means being a bad fit for another. For example, myself and many of my entrepreneur friends don’t care much about partnering with people who invest heavily on credentials such as degrees, press mentions, awards, etc. Credentials are easier to invent/manipulate than building useful products or services, which is why most people choose to accumulate credentials over building stuff. Paul Graham likes to say starting a startup is hard because it’s where gaming the system stops working. Most people prefer to play with rules where they can game the system because it allows them to get respect and rewards without being evaluated exclusively by their output.

Many organizations reward pretense over results, ass-kissing over merit, novelty and controversy over quality, the status-quo over ambition, etc. Most would agree those are not ideal values, and yet most people still prefer those cultures as long as they don’t have to deal with the pressure of building useful stuff. Arnold Kling, from the Library of Economics and Liberty gives the example of people that don’t go to college:

“Sometimes you have to do something that doesn’t make sense to you but we do it because we do it in the organization, and it needs to get done because the organization demands it, and if you won’t do it, that’s gonna cause problems. […] Right now, not going to college sends a negative signal. You’ve demonstrated clearly that you’re a non-conformist in a world where in many organizations you need some level of conformity.”

If you are a good fit to work with my entrepreneur friends, chances are you would be a bad fit for working in academia, media, the public sector, non-profits, big corporations, etc., since they reward persuasion and pretense over proven value. And viceversa.

We’re better off identifying the organizations that share our values, and demonstrating that match to the employers, instead of trying to convince them that we are someone we are not.

Side note: There is something to be said about the process of not knowing your own values and principles and figuring them out by experimenting with different organizations and cultures in the early stages of your career. The hope is that, as you grow older, you get better at avoiding poor cultural fits.

Assumption of visibility

It amazes me when I hear employers say that there’s a “skills gap”: the notion that there are not enough skilled people in the job market for the positions they want to fill. As if they had full visibility of all the talent out there.

Maybe the right people never heard that the company was looking. Or maybe people don’t want to work for that company because it’s not attractive enough (but don’t tell the company). Or maybe they would be great fits but the company has outdated talent filters, and ignore the best person because they didn’t present themselves in a particular way. Or maybe the company doesn’t foster a dialogue with outsiders so they can help think of an ideal collaboration.

When employers talk about a skills gap, they are describing their hiring struggles as an external problem. They ignore that a bigger reason behind their struggles is their poor understanding of their own incentives, shortcomings and biases.

Is there competition for great talent and experience? Of course. Is there a shortage of trained talent in certain industries? Yes. But is this why most companies and people have trouble finding the person or career opportunity they are looking for? Not at all. Before we talk about a skills gap, we need to improve how individuals’ and companies’ can find each other.

If you are someone looking for a new career opportunity, show up in more places more often, so you can be seen by those looking for someone like you.

Improving visibility of potential professional allies is where I see the biggest opportunity for improvement among all the hiring factors. Millions of people, from both sides of the hiring table, are looking for someone that would like to join them. They just haven’t had a chance to meet or imagine their future together yet.

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