By Teaching, We Learn

“Docendo discimus.”
– Lucius Annaeus Seneca

Back to school: USACE engineer interns in Europe to mentor students on academic futures I often want to teach something I just learned. This may not be great for the people learning from me (sorry guys!). But I love to share the cool things I’ve learned from others.

For example, a year after I become a technical manager at a large corporation, I started offering management workshops to aspiring leaders on my team. This was the first time I had been formally managing people, though I had a strong passion for it. I consumed classes, breathed in books & blogs, and met with experienced managers to better learn this craft. I also made a lot of mistakes along the way, and took note of each painful lesson I learned.

Before each workshop, I crafted a lesson plan. I picked a central topic, researched various opinions & approachs for it, and related a personal story of how I’ve seen or tried to implement it. Feedback from the attendees shaped what I taught in subsequent classes, though I loosely followed an overall outline too.

My first few workshops probably sucked. I like to think that they got better over time. I hope they did. My management skills improved though, from both having to think about and explain various topics, to hearing suggestions from the attendees. Ironically, even though I was the one teaching, they ended up teaching me a lot too.

Later, I started offering general business workshops for my entire team. I thought I could make each software engineer more effective by helping them understand the motivations behind the actions of our business leaders.

At that time, I wasn’t formally in any kind of a business role. I was still a technical manager. But I dealt with product, buisness development, and marketing teams often enough to get a sense of their motivations and ways of thinking. That, and I consumed classes, breathed in books & blogs, and met with experienced managers too. This helped a lot when I took roles as a product manager and product director later in my career.

I may not have been the best teacher, but hopefully I imparted my teams with some useful knowledge. For myself, these experiences have been incredibly enlightening. I thought I was the teacher, when in reality, I was really the student.

Photo by: USACE Europe District

How to Determine an Effective Cofounder Match

Last month, I wrote about how to find a technical cofounder. Here is a follow-up.

Let’s say you have found a potential cofounder. Life is great, you got your cake!

But wait. Are you sure this is the right person?

Having a cofounder is like having a spouse. You both will be undertaking one of the most difficult activities a pair can do. So it is very important that you have the right partner.

How can you tell if this cofounder is the right one for you? It ultimately depends on your compatibility with each other, though here are a few personality traits to consider. Without these, your cofounder (or you, for that matter) may not survive the early stages of your startup.

Sometimes the exhilaration of finding a cofounder is so great that people don’t consider whether or not this person is compatible with you and will make an effective business partner.

Here are some questions you can ask to determine an effective cofounder:

Passion & personal interest
“Are you interested? Do you genuinely care about this market, these customers, and this solution? Will you still care about it in 2-5 years or more?”
Mental stamina
“Do you know the risks involved in starting a company from scratch? Have you done this before? How comfortable are you with risk? How comfortable are you working with no or little salary for the foreseeable future?”
“How comfortable are you with frequent change? Would you be willing to change the entire business model if we discover our current idea will not work?”
Communication, interpersonal & conflict resolution skills
“What is your communication style? Can you communicate effectively with a wide range of people? How do you resolve conflicts? How self-aware are you? Do you have leadership skills?”
Personal integrity
“Can I trust you? Do you trust me? How do we really know we can trust each other? Do you keep your word? Are you reliable? Are you a self-starter? Will you follow through on your responsibilities?”
Complementary talents & skills
“What talents and skills do you have that I don’t? Are your skills competent enough to help prove this business model and create a minimal viable product? Are your skills competent enough to hire great people?”
Complementary personalities
“Do we get along? Does your personality and communication style mesh with mine? Could we travel together on a 6-hour flight, then a week-long hotel stay, without strangling each other? How about working almost 24/7 for several years together?”

It is typically better to have worked together with this person before, so you have an idea of this person’s working style and temperament. It’s easy for someone to say, “Yes, I am comfortable with startup risk,” but much harder to demonstrate it if you haven’t seen it before.

Some of these traits, such as complementary personalities, are even harder to assess. Determining such a fit takes time. Social activities is one good method of doing so. Go get a meal together and chat about non-work topics. Then try to find an environment that may be stressful, like working on a paid contract or pet project together.

It’s hard enough to find someone willing to be a cofounder. Finding one that is a good match for you significantly narrows the pool. However, the wrong choice can be catastrophic. This is not a decision to be taken lightly, nor in desperation.

Finally, be aware that your first choice may be wrong. If so, and you truly believe your cofounder is not a good fit, it is my belief that you should part ways as quickly, yet respectfully, as possible. There is no room for the wrong people in a startup.

Build it Backwards

There’s this philosophical exercise where you write your own eulogy, then use that as a model of how to live your life. By laying out your life’s goals first, you can better structure your life to reach those goals.

For example, if you want to be remembered as a good parent, reconsider ditching your child’s baseball game for another hour in the office and prioritize your child first. If you want to be remembered as a generous person, give generously to charities and those in need. Etc etc.

The same can be said about a startup.

I believe it was David McClure who I heard say the words, “build it backwards” during some startup conference. He talked about starting with a vision, then going backwards to build the business, the team, the offerings, etc.

That’s not quite the same as a eulogy, of course. Writing a eulogy for a company doesn’t make as much sense as for an individual. Instead, how about writing the About page for your company five, ten, twenty years from now? Or a Wall Street Journal article describing your company’s impact on the industry, your customers, and perhaps the world.

From that page or article, think about the steps needed to get you to that end goal, that vision. Then use that as the high-level steps for building your startup backwards.

And, as an extra bonus, consider writing your own eulogy too. It can be an intriguing and thought-provoking exercise.

Surrounded by The Unfamiliar

“How was your trip to Italy?”

I beamed. “It was amazing. We gave ourselves a schedule that had the right mix of relaxation, sight-seeing, and random wandering.”

“That sounds great. It’s good you guys had some time to relax too.”

“Hells yea,” I nodded. “I also stayed away from anything technology or business-related. It felt good to step away from all things Silicon Valley and take a break from for a while.”

“That must have been hard.”

“You know? It was at first. But after a few days, it was easy. We relied on paper guidebooks, advice from fellow travelers and people at the hotels, and some well-worn folding maps to get around. I’ll admit, I felt like pulling out my phone and looking at TripIt, TripAdvisor or Google Maps (GOOG) a few times, but I didn’t.”

“I would’ve been using those like crazy. I’ve grown so dependent on those apps.”

“Back in the States, me too. But I didn’t have an international SIM card and didn’t want to pay the roaming charges, so admittedly, the frugal side of me helped curb my app addiction too.”


“But you know what? I always enjoy being surrounded by the unfamiliar. Unfamiliar words, unfamiliar signs, unfamiliar cultures.” My hands waved around to punctuate each sentence. “I mean, Italy isn’t as foreign as, say, a village in rural China or the dunes of the Sahara desert. But it’s still exciting to be in a wholly different place than I normally am, then gradually learning enough of the language and customs to get around.”

“Hey, that could be a good analogy for a startup.”

“Oh yea? How so?”

“When you start a company, you’re doing something unfamiliar, right? Maybe it’s entering a new market or creating a new spin on something. Either way, it’s something new and unfamiliar. Then you gradually learn about the market, and as you do, you compete in it that much better. You navigate in it that much better.”

“Right, right. Traveling someplace unfamiliar involves some level of risk, just as entering a new market does. Some cities and countries have less risk than others, just as some markets have less potential than others. The companies that do well are the ones who have the ability to learn and understand their market. The people who enjoy their trips are the ones who have enough of an understanding to get around and not wander into a back alley somewhere and get robbed or something.”

“Yup, totally.”

“That IS a good analogy.”

“You should blog about this.”

“I think I will,” I smiled.

T-Shaped Skills, I-Shaped Skills and Dash-Shaped Skills

The term T-shaped skills – also known as T-shaped persons or simply, T-skills – is a metaphor for the depth and breadth of a person’s skills. What do they mean?

T-Shaped Skills
A person with a deep (vertical) expertise in one area, and a wide (horizontal) yet shallow knowledge in other areas. This person typically excels in one specific domain, and can also do a fair job in others.
I-Shaped Skills
A person with a deep (vertical) expertise in one area and practically no experience or knowledge in other areas. This person is typically known as a specialist. Their expertise is usually deeper than a T-shaped person in the same discipline.
Dash-Shaped Skills
A person with a wide (horizontal) yet shallow base of knowledge, and no discernible specialties. This person is typically known as a generalist. Or, more derisively, a jack-of-all-trades, master-of-none.

It is generally believed that T-shaped people are the most desirable, though this differs with the situation, environment and role. I tend to favor T-shaped people for startups and leadership positions. Some of the best managers I’ve known may not have a deep technical skill, but a deep leadership aptitude.

I avoid I-shaped people in startups because you need an organizational infrastructure in place before you can support I-shaped people well. But once you do, they tend to excel faster than T-shaped people in their particular roles.

I don’t find many people who are true dash-shaped people. Most have some kind of specialization in something, no matter how deep.

This skill metaphor unfortunately doesn’t map explicitly to one’s actual skills. Some of the most successful people I know have multiple vertical lines extending from their base of skills. In other words, they dominant in multiple areas while having a broad understanding of other disciplines. Too bad there’s no letter for that.

Photo by: TooFarNorth

Biz Vision: Social Engineering Prevention

Mask Social engineering is the act of manipulating people into performing actions or divulging confidential information. It is usually committed using technology.

Unlike hacking, which only uses technology to seek the weak points in a system, social engineering uses both technology and people. The belief is that people are the weak points in a system. And in many cases, that assertion is correct.

Two common examples of social engineering are phishing (the use of fraudulent emails or websites to acquire private information such as passwords or credit card details) and the Facebook Western Union scam (where someone chats you via Facebook saying they are in London and asks you to wire them some money).

Last year, Thomas Ryan, co-founder of Provide Security, was able to get a fair bit of sensitive information from information security, military and intelligence personnel using a fake profile of an attractive & flirty young woman named Robin Sage. Although a few people realized her profiles (on Facebook, LinkedIn and Twitter) were fake, there was no central place for them to warn others.

More recently, the hacker group Anonymous made headlines by breaking into the HBGary Federal website and (now former) CEO Aaron Barr’s email account. They did this using a combination of social engineering and hacking. Despite HBGary’s high profile in the security industry, they were undermined by fairly basic psychological and technical exploits. If a professional security firm had such leaks, imagine how many security vulnerabilities exist with the average Internet user.

In this age of social media, I can only imagine this kind of social engineering occurring more and more frequently. Anyone armed with Robert Cialdini’s book Influence, an Internet connection, a little ingenuity, a lot of time, and an insidious motive could craft a social media scam nowadays. People are falling for them all the time.

This tells me the need for social engineering prevention is going to emerge and grow. How such prevention will take place, I don’t know. Here are some preliminary ideas:

  • Formal classes held at schools and education centers
  • A central website (Snopes for social media, perhaps?)
  • A new breed of social media security consultants
  • Social media security software that verifies websites & people to you

The last option could be turned into a viable business too (wink wink), if implemented reliably. That’s perhaps easier written than done though.

There’s no question that social media is becoming more pervasive. In such an open society, there will certainly be people who will try to take advantage of others. And hopefully, there will be organizations (for- and not-for-profit) that will protect the people from such predators.

Photo by: Ben Fredericson

An Example of Critical Thinking

Homer Simpson's Brain At the heart of critical thinking is Why? To examine a topic critically means to examine and understand the currently-held beliefs and challenge them in an objective manner. Are the beliefs based on facts or opinions? Where did the beliefs originate? Why are these beliefs in place today? Does modern research and knowledge refute any of these beliefs?

Let’s look at the task of organizing a new conference in the Internet industry. We can start with a single problem statement and go from there.

  • It is difficult to get a lot of people to a new conference.
  • Why?
    Some don’t know about it, some can’t pay for it, and some don’t want to pay for it.
  • Why don’t some know about it?
    There are a lot of conferences in this industry and we haven’t been able to distinguish ourselves yet.
  • Why haven’t we been able to distinguish ourselves?
    Our topics and speakers are not unique or famous enough.
  • Why are our topics and speakers not unique or famous enough?
    We have chosen common topics that our immediate friends and colleagues can speak about.
  • Why have we chosen common topics by our immediate friends and colleagues?
    Those are the topics we thought mass audiences would want to hear, and we don’t know any famous speakers ourselves, so we chose our friends and colleagues.
  • Why do we think those are the topics mass audiences want to hear?
    We assumed those are mass appeal topics, but aren’t sure exactly.

Ah ha, our first insight! With the power of Why?, we’ve drilled down to a fundamental assumption that was made. This assumption could be true or false, but it is nevertheless an unproven assumption.

Let’s say it is not true. The topics chosen for this make-believe conference aren’t the only ones with mass appeal. With that in mind, we do some brainstorming and come up with a list of topics not commonly covered by other conferences. Our list includes somewhat obscure or difficult – yet unique – topics.

And voila, with critical thinking, we have a potential differentiator. Go through this exercise a few more times, perhaps with the questions, “Why can’t some pay for it?” and “Why don’t some want to pay for it?” as starting points, and we may uncover additional insights. With enough effective insights, we may be able to make this conference a success.

It’s All About Asking Questions

Curious Perhaps the most important question in the world is: Why? This question leads to all kinds of insight, and occasionally, innovation & invention.

Why? Because questioning the reasons behind “the way things are” allows you the opportunity to usurp the status quo and find interconnections that you otherwise may not have realized. This curiosity digs deep into the foundations of assumptions and beliefs. Armed with such a tool, you can unearth some very interesting artifacts.

It’s also one of the main tools I use in my Serenity Philosophy of Entrepreneurship. This philosophy is all about accepting what cannot be changed, changing what can, and knowing the difference between the two.

Why do we have to carry all these heavy books around? Think: Amazon Kindle.

Why do the screens on electronic devices have to break if we accidentally bend them? Think: Electronic paper.

Why do I have to worry about losing all of my data if my computer is stolen? Think: Dropbox.

These example questions are perhaps a little too specific, but you get the point. Start with a why and keep on asking it until you get to the foundation of the issue. Ask it relentlessly, like a wide-eyed seven-year-old. You may end up with a dead end, more questions, or perhaps some ingenious insight.

Such curiosity is the impetus for two types of thinking: critical thinking and lateral thinking. As an entrepreneur, these modes of thinking give birth to creativity and can separate the boring & useless businesses from the delightful & useful businesses.

Photo by: re-ality