The modern workplace entered a new phase a few years ago. For the first time in history, we have five generations working together under the same roof:

• Traditionalists—born before 1946.
• Baby Boomers—born between 1946 and 1964.
• Generation X—born between 1965 and 1976.
• Generation Y, or Millennials—born between 1977 and 1997.
• Generation Z—born after 1997.

Nearly half of the Millenials (Gen-Y) and all of Gen-Z have never experienced the current level of uncertainty in the world. The early half of the Millenials experienced the beginnings and aftermath of 2008 as they were already adults and part of the workforce. The latter half was approximately 21-22 years old when the financial crisis hit. Their adulthood was born at the bottom of the crisis. Gen-Z may only have faint whispers in their memories of the previous period that challenged us.

In late 2019, the meme “OK, boomer” was birthed into existence. It was brought into the Internet’s consciousness to dismiss and mock the attitudes and perspectives that some Millenials and Gen-Zers felt were held by the baby boomer generation. Yet, it may have been cast on the Boomers, but it was meant more as a statement to every previous generation.

The meme is an expected response from the Millenials. Previous generations have always complained about the following generations. As a Gen-Xer, I remember being cast with the stereotype of being a rebel slacker. We were expected to be unmanageable, lazy, and entitled. The Millenials are no exception as “the generation that’s fun to hate.” As a generation born of the Internet era, a meme to express their feelings was not only expected. It was the most Millenial response.

The back and forth between the generations may seem unfair. Maybe it is. It is also familiar and relatively normal. George Orwell summed it up. “Every generation imagines itself to be more intelligent than theone that went before it, and wiser than the one that comes after it.”

What does all of this have to do with today and the current world situation?

It’s time to think about how much these generations need each other right now. The Millenials and Gen-Z need the Boomers and Traditionalists to share their experiences dealing with crises that seem insurmountable and destabilizing of the normal. The Gen-Xers have been through one crisis in 2008, but most of us were barely more than young adults.

The Traditionalists and Boomers are the most vulnerable to the novel coronavirus. They need the younger generations to sacrifice, realize our responsibility, and take precautions.

Ok, Boomer. We need you, and you need us.

 

In light of the recent CEO announcement for Contegix, I decided it was to resurrect this draft blog post. The post is surprisingly not about Leadville, ultramarathons, or even running despite the question. It is about knowing oneself and what one wants for a life well prioritized and planned.

Of all the questions around the Contegix equity investment, the most common was around why I stepped away as CEO of Contegix. It was asked by my team when we took the investment and has been asked by numerous friends and entrepreneurs since then.

It was asked in straightforward ways, “Hey, so why aren’t you CEO anymore?”

It was asked with innocence and timidness, “Everything good, man?”

It was asked with declarations and poor assumptions, “Dude, what the f* happened?”

Before getting to how I made this decision, it’s important to understand the context and a conversation with my mentor that happened almost two decades ago.

The conversation with my mentor about entrepreneurs started innocently and light-hearted. At this point in my life, I knew my path was one of entrepreneurship. I did not know precisely what that meant or how it would play out. Craig and I were about to start what eventually became Contegix after a few iterations. I had not yet learned a fundamental truth. The path of entrepreneurship is inevitably a path of risk and leadership.

I was yet again confronted with a question for an answer in response to mine. I had asked about entrepreneurs and their impact. I wanted to know how to be an entrepreneur that built a great company by facilitating and helping build incredible talent, even if the company ended up being an exporter of talent. Sensing the requirement of time to accomplish this truly, he pivoted to the core.

He repeated the question as I stared at him, “Do you know why Steve Jobs and Larry Ellison are so well known?”

I vaguely remember giving some remotely intelligent answer about how they had impacted the world and their stakeholders.

He repeated the question a third time, and this time he included an answer.

“Do you know why Steve Jobs and Larry Ellison are so well known? It is because their respective 100 miles is much longer than almost anyone else’s. Others have a 100 mile distance that sets up the next phase.”

He went on to explain what he meant by the cryptic statement.

The Mississippi River was filled with steamboat traffic not too long ago. While the traffic may have faded some, rivers remain vital to our country and economy. These boats have been and continue to be the heart of commerce and military transportation. Traversing these waterway has never been easy though. Rivers are like living, breathing organisms. Even today, the risk is inevitable and often unexpected because change is constant.

At this historic time, vessels lacked the current protections of GPS, sonar, and radar that help detect the changes in currents, debris, sandbanks, and many other factors. They lacked radio to communicate with other water-faring vessels about real-time changes in the river or to send a request for help. It was dangerous for the men who worked on these boats. It still is in many ways.

In lieu of the modern equipment, there were experts, specifically men who knew the most treacherous and dangerous sections of the river. These experts traveled up and down the river. Each would often focus on a specific segment, say 100 miles (or so). They would learn, re-learn, and memorize every change in the river with brain cells filled with the minute details.

Captains were generalists with a mission to traverse the entirety of the river. These men were specialists whose livelihood was based upon knowing a specific segment. No one knew it better, except for maybe another expert with more tenure or proficiency.

The captain, a man (unfortunately, it was almost always a male) appointed such by employment, tenure, rank, or direct ownership, is the last line of responsibility and authority for the boat during its voyage. When a ship would approach a treacherous or unknown section, the captain had a decision whether to hire the specialist who knew the next 100 miles better than he did or attempt the passage under his command. If the decision were made to hire one, the captain would hand over control of the boat and its precious cargo of souls and merchandise to the designated captain. The ship was his to command and his to relinquish when the 100 miles was over. He was the designated captain for that 100 miles.

Up and down the river, each designated captain went being hired and navigating the precarious waterways he knew. He stayed in the boundaries of those 100 miles.

Almost two decades later, I have yet to verify if the history is accurate. It perhaps may only be an analogy for which I could relate growing up in Saint Louis and living alongside the majestic Mississippi. Yet, I told this story to a friend a year ago who remarked he saw this in action on a European riverboat cruise in 2017.

Regardless, the insight for me was immediate. Jobs, Ellison, and many others since this conversation are known because they have a long 100 miles. They have had a long period to make an impact on their stakeholders and communities. They have gone from founders to tech icons, and they have evolved along the way. In the case of Jobs, it could be said that he had 2 sections at Apple and, perhaps, learned the second course during his time away from Apple navigating other waters. The cost of this is considerable sacrifices and prioritization of the essential mission.

This conversation left a mental mark with me that I carry to this day and have relied upon numerous times, including our transaction.

Craig and I decided to take an investment for numerous reasons. The most significant was our core value of Rapid Accelerated Growth. It was odd that most people never read the description of this core value. The growth was not in reference to the financials – the top or bottom line. It was in reference to our stakeholders, especially our talent, our team, and customers. We fundamentally believe that if these grow, the growth of the financials was a drag-along effect. It was a core reason we implemented the 20% pre-tax profit sharing.

We knew that the competitive landscape was shifting for both cloud and managed cloud services. An investment was the fastest path to be either fail or be prepared for the market shifts. It was contingent upon the right equity partner. We found that in Strattam Capital and its team. It was a relationship developed over years and one built on honest, regular discussions around expectations. These still continue to this day.

I flashbacked to the mentor conversation a few weeks ahead of completing the Contegix transaction in 2016. I realized that my 100 miles was coming to an end as CEO of Contegix if we went through with the transaction. I had navigated Contegix from an idea with the first servers in my basement. The transaction would mean Contegix would now by the combination of three companies and cultures.

Contegix’s CEO needed to be an expert at navigating the delicate waters of integrating these companies and their respective cultures. The CEO would need to spend more time with customers in this competitive landscape and time with our private equity partner.

I would need to expand my 100 miles if I wanted this journey whether through this transaction or another method. As the then-current CEO, my responsibility was to ensure the best talent for the journey ahead.

In the midst of this, I also realized there was a new role for me. I may have been relinquishing the role of captain. I was still on the boat and would continue the role I loved most – being the voice of our customer on the Board and the technology liaison between the business and the Board. For service companies, there should always be someone on the Board who loves the customer first and foremost (rather than the service, product, sales cycle, or anything else). For the executive team, that role is often the CEO.

As the new captain takes the next 100 miles, I relish in the fact that any change does not diminish the work and effort done by predecessors. These were absolutely foundational to get to this point. One cannot hire the designated captain if the boat fails to make it to the rendezvous point.

As a passenger on the boat, I appreciate that more than most.

A few weeks ago, I blogged about why I think people should spend less time on email.  I discussed some reasons why one could be spending too much time on email. I confessed my challenges with this at one point in my history. For me, it was about accomplishing something to demonstrate value and self-worth and needing breaks when dealing with complex challenges. I now check my emails less than five times per day.

Perhaps the reasons why one excessively clings to email did not resonate. Perhaps a belief that immediate responses are critical when dealing with clients and employees, and perhaps that belief trumps the causes. Perhaps one did not finish reading the post due to an audible ding indicating the arrival of a new email. I heard similar feedback when I gave this advice to the aforementioned panel.

Regardless of the reasons why one is always on email, there are numerous reasons to change. The financial and productivity reasons should be enough. Yet, it is not the most prominent reason to change.

It can destroy relationships. Period. I am not talking about reading email while at dinner with loved ones. I am talking about the relationships with the people on the other side of the email.

It comes down to reality, expectations, and commitments.

Imagine someone wants to send a package via FedEx. The package is not needed until Christmas which is more than two weeks away. She steps into a FedEx store and decides to send it via FedEx Ground. The package should get there within four days which is more than enough time.

After leaving the store, the agent and the entirety of the FedEx team size up the situation. They unanimously decide to send the package FedEx SameDay after seeing the holiday wrapping paper. FedEx never notifies the customer of the priority change. The package is getting there today, and they are not charging the customer for this upgraded delivery. The customer is ecstatic when she receives a call saying her package arrived the same day!

This happens repeatedly for every package the customer ships with FedEx. It continues through the holidays and for weeks afterward. The customer always chooses FedEx Ground. She always pays the price of FedEx Ground. Yet, packages are repeatedly delivered FedEx SameDay.

The customer eventually discovers this happening, and she is ecstatic. It is a deal for the customer, and FedEx never waivers or complains.

It’s reasonable to believe the customer would no longer select the truly needed priority when sending a package. FedEx never committed to anything other than four-day delivery. Regardless, it has always delivered same day. The customer has been trained to expect SameDay service.

That is the case until the one time FedEx a package must get there tomorrow. The customer now has a decision. Should she send it next day or ship it ground?

If she choses next day, she is now paying additional for the same service that has always been delivered at no extra cost. She may feel this is outrageous because she knows FedEx can do it for the same price as four-day. She may have the opposite reaction and feel this is acceptable as an insurance policy. Yet, I question if this is the feeling one wants a customer to have.

She may consider it financially foolish since packages have always arrived the same day. FedEx has never let her down – SameDay, every day.  So, she ships it ground and takes the risk. FedEx is not aware of the imbalanced expectation or the risk. If the package doesn’t arrive on time, the customer is upset and probably realizes she is at fault. It still negatively impacts the relationship because her expectations have not been met.

How did the situation get here? It was a relationship created with initial good intentions by the vendor. It devolved. The misalignment between services purchased and services delivered has created a relationship no longer based on honest expectations. That’s where the problem crept in and began to eat away at the core of the relationship.

Instant Replies == SameDay Service

As a format, email does not innately convey a priority or expected reply time. It does not even contain a requirement to reply. It needs to be explicitly stated.

If a recipient instantly reads and replied to an email, the tone and expectations are potentially being set for the conversation. When it repeatedly occurs over multiple conversations and is not based on committed priorities and time requirements, the expectations on the relationship between the parties is altered.

People are being trained to expect replies not aligned with committed response times. In customer service, clients are being trained to expect this level of service regardless of the contract or service level agreement. As a leader, teams are being trained this is the expectation of each other and from their leader. This is also the expectation when a customer emails.

Are you training your customers to expect messages read and replies faster than the commitment? Are you training your team that this is the modus operandi for customer emails? For your emails? Are you training your spouse that replies must be instant?

Each day is an Instant Replay
They say what we display is symptomatic of addict behavior
– Eminem “Love Song”

Relationships, Expectations, and Commitments

Respect in a relationship is built on met expectations and commitments. Unmet and unreal expectations are critically harmful to relationships. There is no need to create additional ones that will inevitably fail.

Finally, it is potentially insulting. It is about saying that you will set the priority regardless of the sender sending it via a mechanism that implicitly has no real priority. It is about you saying that you are smarter than the sender and will be the one to protect everything by setting this priority and replying immediately.

All of this adds up to being destructive. It can be destructive of your relationships with your team, your customers, your friends, and your family.

I recently wrote about how I was a panelist for EO Accelerator. In that post, I discussed how there are times to share experience, and there are times to give advice. I finished the blog post with the advice I gave the audience that day – Get off your fucking email. I want to take a moment to explain why this direct and intentionally vulgar statement is subtle and critical.

I gave this advice because I used to be this person. I regularly answered emails within minutes of receiving them.

Email me asking to review a proposal due in 30 minutes? I replied within minutes.

Email me asking about plans for the weekend? I replied within minutes.

Email me asking if I have thought much about where our kids will go to college in 5 years? I replied within minutes. OK, maybe that took an hour. We are talking about a life decision. It deserves that extra time.

I would walk out of meetings with my phone in hand and digest emails. There was no time to process the meeting and its takeaways. There was no time to socialize and express gratitude for those in attendance. I thought I was doing well and fully present by not being on email in the meetings.

This behavior led people to email a second time if they had not heard from me within hours of the first email. They would ask if everything was ok. They would ask if I was ok. The answer is no because this is insane. This is majoring in minor things.

“A key point to bear in mind: The value of attentiveness varies in proportion to its object. You’re better off not giving the small things more time than they deserve.”
– Marcus Aurelius

Before discussing the causes and impact of this behavior, it’s critical to understand the concept around the size of challenges and an organization.

As an entity grows, the challenges become more substantial.  Previously conquered difficulties are later done with ease. Most of us can walk across the room and perform basic mathematics. We engage our muscle memory and do not need to exhaust much mental capacity. The oddity is that very few of us can explain how we do these tasks with ease.

Watch an infant learn to walk or a child learn addition and subtraction. The struggle is visible and palpable.

The same growth of challenges and opportunities occur within organizations. The smaller problems are solved and create growth. As the organization grows, the quantity and volume of opportunities and challenges grow. Each takes longer to solve. For example, a buddy recently closed his 90+-year-old family business and opened a franchise in the same industry. That process took more than 20 months with tremendous challenges and opportunities along the way.

Leaders must grow to tackle these problems. They need to learn new skills and amplify current strengths. The Director of a 50 person company often requires different skills and capabilities to be a Director of a 500 person company. If a leader does not grow, the organization will outgrow him. If the leaders do not grow, the organization will cease growth and probably wither.

Let’s break this down regarding the potential causes of this mindset including what drove this behavior in me.

Procrastination

Procrastination is not inherently bad. It is sometimes the result of needing space for diffuse thinking. In Barbara Oakley’s course “Learning How to Learn“, she discusses how our brains need to step away from problems, especially when learning new skills. This is diffuse thinking mode. It allows our brains to create new connections and solve new problems.

Email can be the opportunity to step away and be effective procrastination. That’s not what I was doing.

I would often jump on email because I did not want to address the significant tasks at hand. They seemed daunting. I was afraid of where to start and being unable to tackle the challenges at hand.

The most likely cause of this feeling was a failure to manage my energy that day. I just didn’t reserve enough horsepower and capabilities to tackle the tasks.

The reality is that almost all work is like math problems. You often have to start and figure it out along the way. Yet, you have to actually start the work.

Self-Worth

I was most guilty of wanting to accomplish something by the end of the day. Considerable challenges often take a long time. I became acutely aware of this as a driving force of being on email during our transaction. It was not because there was a need for instant communication with the lawyers, accountants, and private equity teams.

We began our discussions with private equity in March. Our transaction concluded in November. I worked on the transaction every day. It consumed most of my time. We were merging three companies with similar but different cultures. We were bringing in a CEO. We wanted our PE firm to understand our customers.

Many of those days I felt I had done nothing as I walked out. There was no task crossed out that day. Many of our team probably thought I did nothing the same thing since most did not know about the transaction.

In the midst of a monumental moment, I would jump into email threads with replies. I was often included as a courtesy or by accident. I would reply to a customer would accidentally email me instead of their sales rep.

I later realized I engaged because it feels good to accomplish something. I wanted to walk out with a checkbox receiving a beautiful mark that screams “Done.” This was short-sighted and more about my needs than what our talent and organization needed. It was about my self-worth and feeling I had done something.

Self-Confidence

This is the nasty one. There are multiple ways this could be an issue of self-confidence.

Email is 7% as effective as talking. (We won’t even cover the social impact of other forms of text-heavy and non-verbal communication, such as SMS and Snapchat.) Email does not implicitly convey emotions. It also does not implicitly convey time sensitiveness. These need to be explicitly stated by the sender. In the case of time sensitivity, this would be with phrases such as “This is needed by tomorrow at noon”, “ASAP”, or “Oh, shit. I needed this yesterday.”

How is this related to self-confidence?

Being the person in the know is powerful. Being the person who solves problems is powerful. People express gratitude and encouragement to keep doing this. If the problem is smaller than one’s position, it’s can often be easy because it’s been done a thousand times. It’s a situation of minimal effort with maximum reward.  All of this demonstrates one is valuable and can boost self-confidence.

Yet, it’s also extremely selfish and destructive. It’s the concept of being the one-eyed man on an island of blind people. It tells others that one needs to step in because only she can do it. It tells the team that one can do their jobs with part-time effort and partial knowledge. It might be more subtle to send an email to the team saying, “Hey, I know you do the job full-time and consider yourself an expert, but I know best after studying the situation for a few minutes. It’s due to my infinite intellectual capabilities. All of that says here is what you should do.”

The harder and selfless option is delegation. When one does know more, delegation can be an incredible opportunity for development. Instead of replying to the customer who accidentally emailed, delegate to the sales rep and ensured her manager knows in case it is a development opportunity.

Frankly, I never struggled with this as a reason; however, watching people grow always provided a confidence boost. And that is the long game.

FOMO

Fear of Missing Out.

I struggle to understand this one. Logic overrides my emotions regarding FOMO. Perhaps it is my opinion that Facebook is the curated trophy case of one’s life and Twitter is a steam of people’s current context with minimal character. Perhaps it is the reality that human knowledge is doubling every 12 months. It could soon be every 12 hours.

There is no possible way to know everything that is happening – on email, on Facebook, on SMS. There is no possible way to care about everything that is happening. Regularly checking these is akin to hitting one’s head against a wall. (Pun intended.)

It’s exciting, causes an emotional reaction, and potentially creates brain damage.

Today

“Everybody wants to change the world.
But one thing’s clear
No one ever wants to change themselves.”
– “Do You Really Want It?” by Nothing More

Today, I mainly check my email 3-5 times per day. I never check it as soon as I wake up. I set reminders to check it. That is time for preparing for the day ahead.

All of this was a significant change. It’s made me a better person and a better leader of my family and the organizations in which I lead. I get more done with less distraction.

I changed because of the pain and destruction I was causing. I intend to discuss those in an upcoming post.

Last month, the New York Times published an op-ed by Thomas Friedman titled “How to Get a Job at Google“. The premise of the article is that Google has reduced its dependency for candidate evaluation around traditional measurements of academic success and traditional leadership.

It’s interesting to see Google change their interview approach over time. Originally, you had to attend the best university. You had to have the best grades. The interviews were notoriously grilling. You had to be the best of the best. (Note, there was never any definition of what “the best” was.) According to the article, their core areas of focus are now around general cognitive/learning abilities, emergent leadership, humility, and ownership.

This shift is the difference between “what you know” vs. “who you are” as a candidate. At Contegix, we have spent the last 5 years placing more emphasis on the “who” than the “what”. We learned a few lessons along the way that experientially highlight and predict the long-term success of a team member based around who they were. An example I often give is our support engineers.

We have absolutely brilliant engineers as part of our team. They manage, monitor, and maintain our customers’ infrastructure everyday. They ensure systems are performing and respond to technical challenges. This work is based upon what they know. The “who” aspect of our engineers is around their ability to deliver passionate customer service while performing this work. We cannot lose sight that this infrastructure can and does have an impact on customers’ livelihoods. Being the best engineer, but then being insensitive to the customer, leads to failure.

Furthermore, in the world of evolving technology, the “who” of an engineer will guide how she/he will be able to grow, adapt, and rethink. We need people who are excited by and able to build the technology. They should be able to deliver technology to our customers while not being overwhelmed by it.

Of all the candidate attributes, I would take this a step further and state that (true) leadership is the core attribute. It is the critical, all-inclusive “who” trait for which every company must evaluate candidates. This is regardless of the position or role in the company. True leadership shows itself in every place, from small team settings to times of challenge.

It takes true leaders to take ownership of challenges. It takes true leaders to be humble and allow a more qualified or experienced team member to temporarily lead a team. This is the truly open minded approach. Can one truly lead if they ignore new facts and drive their team off the cliff due to ego?

Leadership has been the trait most critical to growing Contegix. Building and adding great leaders has had a profound positive impact on the culture. Having folks who are willing to be humble leaders, who are open minded, and are willing to take ownership, significantly increases our capacity for progress, innovation, and, most important, customer service.