Understanding Is Our Problem

It’s so common for people to get frustrated with how often the people around them don’t understand them. It’s a boss that just doesn’t understand that we could be doing so much better if they just listened to me. A significant other that just can’t seem to remember that chore I have reminded them to do every other day. A sibling that just can’t get their life together and if only they followed my instructions, everything would work out for them.


Too often we are putting the responsibility onto the people in our lives and not paying close enough attention to our role in miscommunication. It makes sense. Everything is perfectly clear in our head. It’s a conclusion reached based 100% on your experiences, it’s laid out in a fashion that makes sense to your mind (whether that’s a logical structure or more emotionally based). The problem is that whoever we are talking to will have a completely different set of experiences and is unlikely to process information in the same way.

It’s not on the people around us make sure they understand what we are saying. We have to take responsibility for understanding who we are talking to and tailor our communication to how they process information. Your first try may not work but that is okay. Take a step back. Ask where you’re losing them. Adjust your message and try again. Eventually, we will find a way that lands for the person we are talking to.

If someone seems to be ignoring you, dismissing what you say, or are upset about what you are saying, it’s likely that you just aren’t communicating in the right way. It may not happen overnight but if you are communicating in an optimal way for the person you are talking to, we can start shifting their position. Eventually, aligning their position with ours. People don’t change their minds quickly and that’s okay. If people were easily swayed, not much progress would be made because people would give up too easily and we need someone to challenge our positions to make sure we have thought it out.


So far we have focused on our mindset in approaching communication. That is a vital first step but I don’t want to overlook the importance of our audience. We can only experiment with different styles and reach an optimal style if we are also listening to our audience. Without their feedback, we are adjusting based on our experiences and personality. This is no better than simply keep talking at someone and hoping repetition is the key to understanding. I promise, it’s not.

A technique that works for me is to divide my argument into smaller chunks. Not only is it easier for me to choose words wisely but it gives me the opportunity to ask my audience if they understand and if they agree with me up to this point. If they answer is yes to both, I can move on. If the answer no to either, that means I need to dig deeper into what they are thinking. I view this as progress. It means I’ve discovered a misunderstanding. Even if it’s not the only one, clearing this up means that I’m this much closer to building the foundation that my arguments need to be understood and agreed upon.

When I’ve discovered a roadblock, this is the point I turn over most of the talking to my audience. I need to ask the right questions and shut up. If they can’t get out whole answers, it’s unlikely that I’ll discover the miscommunication. An additional benefit of shutting up is that your audience feels listened to which relaxes them. No one want’s to be lectured to but if you are having a two-way conversation and it’s equitable then you’re a friend instead of a foe. That’s a much easier conversation to have.

Once I’ve discovered what the roadblock is, I can take a step back and readjust my communication to compensate. Then I check back in and repeat this process until I get a yes to understanding and agreeing and can move on to the next chunk. Even if I don’t get to the end of my argument, I can guarantee that I’ve made progress, either in understanding my audience better or shifting their position toward mine.


Success in communication isn’t winning an argument. It’s understanding. It’s being able to have empathy to the person you’re communicating with. In the end, you may find out you’re the one who was wrong in the beginning. You’re pulling from a limited number of experiences. Listening to someone else’s position will broaden that pool of experiences and will likely shift your positions to some measure.

If you’re not open to changing your mind, you are no longer communicating with someone you’re communicating at them. There is no easier way to shut down a channel of communication and frustrate both parties.


Be patient. Work with your audience. Be open to new ideas. Have empathy. Figure out what they need from you and deliver. Once you figure it out, things will get done much easier. It’s worth the investment upfront.


Be Better Faster

Trying to the absolute best in any one area is nearly a pointless pursuit. It’s naturally intriguing to our competitive nature. Trying to be the best satisfies our need for glory, adulation and a feeling of superiority.

The problem with trying to be the best is that you are probably not special. You will have to rely on passion to keep you motivated and out-work everyone else, especially the people who are more naturally inclined. Even that is way too simplistic of an equation. Of all the people that share your passion, the chance that you were born with:

  • A natural inclination toward your goal
  • You have the ability to outwork everyone
  • Have more time than everyone
  • The financial resources
  • The emotional support
  • The focus
  • The persistence
  • And every other factor that plays a role in being the best

It is highly unlikely that you have an advantage in enough areas to be the best. It’s just too many factors that need line up just right.On top of the odds of all these inputs lining up in your favor, you’re fighting the law of diminishing returns. In the long run, you will see less return on your effort. Getting to the 50th percentile is significantly easier than going from the 50th to 99th. Eventually, the amount of time you will have to put in to receive very marginal returns will start to feel like running in tar.

On top of the odds of all these inputs lining up in your favor, you’re fighting the law of diminishing returns. In the long run, you will see less return on your effort. Getting to the 50th percentile is significantly easier than going from the 50th to 99th. Eventually, the amount of time you will have to put in to receive very marginal returns will start to feel like running in tar.You will spend years of your life struggling toward a goal you may never achieve. There is a more efficient path to achieving great things. It is easier to become a top 1% performer by combining a strong grasp of several skills than to be excellent at one. My suggestion is to aim for the 80th percentile in a few areas that you’re interested in. You will have more fun if you get to work on different skills and aren’t pigeoned holed into one for the rest of your life and you won’t waste years trying to make a 1% leap.

You will spend years of your life struggling toward a goal you may never achieve. There is a more efficient path to achieving great things. It is easier to become a top 1% performer by combining a strong grasp of several skills than to be excellent at one. My suggestion is to aim for the 80th percentile in a few areas that you’re interested in. You will have more fun if you get to work on different skills. You aren’t pigeoned holed into one for the rest of your life and you won’t waste years trying to make a 1% leap.

Being in the 80th percentile in three skill sets makes you better than 99.2% of every human, on earth, at those three things. Adding a fourth skill where you are in the 80th percentile makes you better than 99.8% every human at those four things. For reference, out of the world’s roughly 7,475,000,000 people, that makes you better than 7,460,050,000 at those four skills. If that’s the case, you are in an unique position to be able to make a difference in your areas of expertise.


Be Explicit

Information about your company will be conveyed to all potential customers. Your sales staff or advertisements highlight your best aspects. They will naturally avoid talking about weaknesses because they don’t want potential customers to think about your weaknesses. That might work sometimes. Maybe your potential customers won’t care about the areas where you are weak.

There is an inherent risk with this strategy. If the customer does care at any level, they will either ask or, more dangerously, assume. The latter part is what can get you in trouble. If a customer is making an assumption, you have just lost control of your message. Whatever assumption the customer made now has become their reality, good or bad.

To avoid this situation, have honest conversations with your customers. Be honest about what you do well. Be honest about what you don’t do well. Be honest about what you are willing to do to overcome weaknesses. This radical honesty will set expectations accurately. Disqualify projects that have long term consequences. Such as projects don’t go the way that your client expects.

Artificial Ceiling

Artificial Ceilings

How do you keep your company from setting artificial ceilings?

It starts when we are hiring. Usually, we write a job description that details the tasks and responsibilities included in the position and defines where in the organizational chart the position falls. Short term, this is great. We set clear expectations. Clear lines of communication. Some forward facing managers might even account for employee growth. This is where the benefits end.

As time goes on, the original job description becomes rigid and limiting. Trapping your employee in a cycle. The same tasks day in and day out. Eventually, the tasks will be mastered. The employee will stop improving. The job description has set an artificial ceiling on the production.

Now that we understand the need for a fluid description. How do we do this without risking the underlying objectives? The answer is twofold:

1. Build a learning culture

As time goes on, the original job description becomes rigid and limiting. Trapping your employee in a cycle. The same tasks day in and day out. Eventually, the tasks will be mastered. The employee will stop improving. The job description has set an artificial ceiling on the production.

2. Give them the keys to the car

Allow your employees to determine their own fate. Give them the opportunity to explore anything they’re passionate about. As long as they can clearly define how it will have a positive impact on the business without hurting the bottom line. This forces them to bootstrap their passion. Some employees will give up but some will excel. Either way, they feel empowered to act.

The more you micromanage your team, the lower the artificial ceiling. Welcome diversity. Share ownership. Develop leadership. Your team will surpass your expectations if you remove artificial ceilings and allow them to do what they do best.


False Victories

Too often people aren’t willing to take the time to dissect why things are going right. It’s easy for to justify taking the time to solve issues that are immediately causing problems. This is being reactive instead of proactive.

It is critically important to reserve time to look at the all of our processes. Especially the ones that are currently working. Without an in-depth knowledge of why it’s working, it will be impossible to detect false victories. Unless you like spending your day putting out fires and doing very little to push your organization forward, this is critically important.

It’s always easier to sail when you can detect incoming storms, correct course and navigate around the storm. Early detection not only allows you to avoid impending doom but it also gives your team a chance to learn. We need to peel back the layers of what processes seem to be working. 

  • Are we making any assumptions on why the process is working?
  • Can we test the assumptions?
  • What other factors affect the same outcome?
  • Are we misattributing the success of the outcome?
  • What can we do to rectify the situation?
  • How do we prevent ourselves from falling into the same trap?

The more often your team goes through this exercise the better they will be at it and the better they will be at preventing the situation in the future. Don’t limit your learning opportunities. Examining all of your processes on occasion can bring clarity to your team’s future decisions.  

Authentic Leadership

The Only Effective Type of Leadership

There is only one type of leadership that is truly effective and it’s different for everyone.

There are leaders who used different styles. I’m sure you can think of several prominent entrepreneurs who earned a reputation as loud, brash or charismatic. At the same time, Susan Cain, David Rock and others have written about the power of quiet leadership. Leaders have been tall and short, small and large and come from all different walks of life.

So with this great variance in styles, techniques, and backgrounds, what makes a truly effective leader? Authenticity. The only effective type of leader you can be is whatever authentic to your personality and experiences.

  • If you naturally loud, be thunderous.
  • If you are naturally reserved, actively listen.
  • If you are charismatic, be charming.
  • If you like to move fast, act early and often.
  • If you make lists, plan carefully.

The worse thing you can do is try to emulate someone else’s leadership styles when it doesn’t come naturally to you. It’s exhausting and your team will see straight through it. They may not notice the effort to emulate someone great but they will see the deceit and lose respect.

The road to recovery from a lost of trust is a long, uphill journey. Your job is hard enough as it is, be the type of leader you were meant to be.


The Real Cost of Education

Costs are hard to estimate because negative externalities are poorly understood.

With student debt rising far above inflation1, top students will be forced to chose the highest paying job. The idea of a flood of our most talented graduates moving into roles where they take on very little responsibility, have little passion and can possibly be invisible in the sea of drones will be economically crippling for decades to come.

Small business won’t have a chance at top tier talent. Startups without massive funding won’t have a chance at top tier talent. Nonprofits won’t have a chance at top tier talent.

These are the organizations that allow young talent to really make an impact. Take on responsibilities that stretch their capabilities. A position where they can constantly learn a new skill and have their voice heard is a powerful thing early in a career. It may not be the most prestigious but definitely more fulfilling.

Being one of the 118,000 Microsoft employees2, you can nearly guarantee that you don’t matter to Microsoft. You are replaceable. Your great ideas are likely to go unheard. Layers of a bureaucratic structure will stifle progress. None of this is Microsoft’s fault. It’s purely a statistics game. Think of all your Facebook friends. I am positive that you don’t keep in touch with every single one of them. There isn’t enough time in the day to keep up with 400 different people’s complex lives. Microsoft has 295 times as many employees as the average person has Facebook friends3.

While the global economy has evolved over time, our education system has not kept pace. School administrators are forced to be politicians. Teachers aren’t given the tools or freedom to succeed. Student’s incentives are not aligned with the proper outcomes. Our education system is too entrenched in bureaucracy to be able to adapt to the global economy. We need to create another outlet for our young people to gain the quality education without growing burden of debt.

The biggest obstacle will be the perception of quality. People fear what they do not know. The formula of getting good grades, to go to college, get a degree and get a job is what we have become comfortable with despite the growing proof that this is not the guarantee it once was. As we develop more options for students to learn inside and outside of schools, we need to get over our fear of breaking away from the past so students can pick the path that works best for them as an individual and we can succeed on as a whole.

Cars Destroy Communication

A Better Community: Series

Technology isn’t destroying our ability to communicate, cars are.

In most US cities, people rely on their car to get them where they need to go. Getting into our car cuts us off from people and our environment. We lose the luxury of random collisions. To interact with a diverse selection of people. These random collisions open our minds to new people, ideas, and perspectives.

By getting in cars we are essentially stepping into our robot suits. No longer do we have an emotional connection with the people around us. This plays out in several ways. First, when we pull up to a stoplight with and make eye contact with someone asking for money on the corner, our car makes us feel like we can hide and pretend we didn’t notice. Allowing us to have no emotional connection to this person who needs help. If we walk past the same person, we are forced to either help or say no. This creates a situation we can’t ignore. Even if we say no, we are emotionally affected by the experience and more likely to act next time.

Second, getting into our car helps remove any emotional connection to the drivers around us. Bad driving can put even the most even tempered person into a rage. Being in a car makes it easy to forget that. By and large, most cases of reckless driving are caused by people doing their best. Maybe they had an extremely long day. Maybe they are going through a difficult personal issue. Maybe it’s one of a million different circumstances that could cause someone to be distracted at any given moment. If a person bumps into you on the street and immediately apologizes, I highly doubt you will be thrown into a yelling rage because you’re connected on an emotional level.

Cars becoming commonplace offered people more options for living. Now you can live well outside of a city and commute to work. On the surface, it seems like a benefit but it drastically changes how cities are built and more importantly expand.

Instead of designing cities to be thriving communities, incorporating the natural environment and increasing health, we are building concrete mazes that no living creature can thrive in. We decrease the beauty of our cities, which has major implications on our happiness. As more jobs come to a city, more people want to work there. Developers have one of two options. Tear down current buildings and rebuild higher (which is expensive upfront) or build outward (much more common). As these suburbs are built and filled, shops and restaurants move into serve customers who live outside the city, decreasing the incentive to travel to the city’s core.

This is the downward spiral of urban sprawl. Pretty soon the local identity is split into factions. There are significantly fewer interactions of people from diverse backgrounds. The city begins to lose its energy and heart.

Now the question becomes how do we reverse this trend? How do we get people out of their cars and rebuild cities that thrive on emotional connection?

Human Connection

The Personal Economy

Over the last decade, our world has moved to a digital world. Shopping, social lives, and working relationships are almost entirely digital. This switch has driven a rise in demand for a matching skill set. If you can write software, build a website, write social media copy that drives interactions, you are valuable. We as a society have adapted. Spending our time perfecting a digital life.

This new digital world has opened many doors. Connecting old friends and new acquaintances. Reaching previously unreachable lands. This is powerful but comes at a cost. Now that we have adapted and everyone has this ability to connect digitally, the focus is digital relationships. How does someone separate themselves from the noise?

Personal connection.

It has never been easier to send in an application for a job. So, everyone from anywhere sends in their application, hoping for the best.

To see how this changes the hiring process, think about HR’s point of view. Hundreds of resumes for each position. Each one only gets a few seconds of their attention, if you’re lucky. Instead of adding to the overload, find a way to reach the decision maker personally. Show that you are the type of person to go above and beyond. Stop by the office. Ask informed questions. Get to know people in-person. Help them understand what working with you is like. It makes the decision easy for them.

This is relevant in so many aspects of our life. So many people wish their friends a happy birthday on Facebook and nothing more. Even a text makes you stand out. With minimal effort, you can stand out from the noise. Make a real connection with a real person. Be remarkable. You just have to go the extra step and literally meet someone halfway.

Whenever society has gotten too enthralled with an innovation, we shift our focus away from what really matters. There is always a correction. The next generation of impactful people will thrive because they have mastered personal connection. This next decade will be the decade of the Personal Economy.

Countdown Clock

What is the value of your time?

If you don’t know the answer to that question, you need to spend some time and really nail down a number. Knowing an exact number will save you lots of time down the road.

It’s is very common for us to search the internet (sometimes for hours at a time) trying to find the best possible price. The internet has given us a lot of power in that regard but it can easily get out of hand. It’s easy to feel good about the $10 you saved on your new gadget because we can easily visualize $10. It’s much harder to visualize the value of the time you spent.

The solution is to know exactly what your time is worth to you. Not what your time is worth to your employer. What it’s worth to you. If you value your time at $20 an hour and you spent an hour to find a deal that was $10 cheaper, you just lost $10. That’s easy to visualize. By having your number figured out, saying no becomes a lot easier and your life less overwhelming.