Article

The Visionary Evangelist

February 16, 2021

Their Superpowers and Their Dark Side

Elon musk and steve jobs are standing next to each other on a blue background.

Occasionally a leader comes along who not only develop this vision of the future, but also use their influencing skills to motivate others, by persuading them to join the cause. They are “pied pipers” who energize and inspire followers to get on board.  Their vision gives their followers a sense of purpose and direction for their team, their company, their industry or their nation. It inspires followers by giving them a vision of possibilities, a compelling sense of destiny and meaning.
Throughout history these visionaries have challenged their societies to think and act in new ways. They see what others have missed. They find opportunities others have ignored and challenge what others accept as given. They are pioneers. They are non-conformists. They are inventors. They open new vistas. You may not like them and think they are self-centered and narcissistic but, you have to admit, they have changed the organizations or societies in which they lived.
In our time, leaders such as Bill Gates, Elon Musk, and the late Steve Jobs have shared a common bond – they are Visionary Evangelists.
Some visionaries, like Thomas Edison, who invented the light bulb as well as the prototype systems and structures for distribution of electric power, are seen as heroes. Others, like Joan of Arc are burned at the stake. They influence business, politics, science, religion, the arts and economics and change the course of history. The Egyptian Pharaoh Akhenaton, Thomas Jefferson, Leonardo Da Vinci, Albert Einstein, Stephen Hawking, Martin Luther King, Pablo Picasso, Napoleon Bonaparte, and George Lucas, creator of the Star Wars and Indiana Jones movies, were all probably Visionary Evangelists.
Visionary Evangelists see the world differently. They see beyond the status quo and envision what might be. Perhaps they have a broader perspective or deeper level of insight. They are certainly much more creative than most of us. They dream up new products and new ways of doing things. They are independent risk takers who can’t help but challenge the status quo. As one business leader said, they “create a vision, articulate the vision, passionately own the vision, and relentlessly drive it to completion.”  [that was Jack Welch but we don’t have to say so.]
When the organization’s vision, strategy and goals need to motivate and influence employees, shareholders, or the investment community, it’s usually the Visionary Evangelist who stands up to do it. They know how to get people to follow their lead. They are filled with energy and drive, they hold up the flag and run forward; they take charge, push for action, and instill a sense of urgency to achieve the organization’s goals. It is difficult to imagine any organization succeeding without the creative vision, persuasive skill, and dynamic leadership of the Visionary Evangelist. 
Elon Musk
  • As a boy in his native South Africa with an insatiable thirst for knowledge, Elon Musk often read for 10 hours a day. He devoured two complete sets of encyclopedias, virtually memorizing them with his photographic memory.

  • In college, he declared that he “wanted to be involved in things that would change the world,” and after making his first fortune from the sale of PayPal, rather than stashing any of it away, he immediately sank the entirety of the $180 million he made into companies that are creating humanity’s future.

  • He’s CEO of Tesla, producing steadily more affordable, rechargeable electric cars to replace the pollution-generating vehicles most of us still drive. He is CEO of SpaceX, designing, building, testing, and now operating rockets that, among other things, bring supplies to the International Space Station. His vision for SpaceX: to transport 80,000 people to colonize Mars, making humanity a “multi-planetary species.”

  • He is also heavily involved in Solar City, which Tesla purchased in 2016, one of the largest installers of solar panels in North America, toward the goal of replacing the electrical grids currently in use with pollution-free, renewable solar energy. 
  • In 2012 Musk proposed what he called a Hyperloop system of high-speed ground transport, in which pressurized pods or capsules, containing either people or freight, would move through low-pressure or vacuum tubes either in tunnels or set above ground on stanchions. Speeds up to 760 mph would allow travelers, for example, to go between Los Angeles and San Francisco (approximately 350 miles) in little more than half an hour.

  • To facilitate the tunnel-creating aspect of Hyperloop travel, Musk started The Boring Company in 2016.   

So who is this man? “The thing that makes Elon Elon is his ability to make people believe in his vision,” said Dolly Singh, former SpaceX executive. Like most Visionary Evangelists, Musk is an eloquent speaker, “an incredibly compelling spokesman” for what he believes and aims to accomplish. Jim Cantrell, former SpaceX engineer, adds, “The guy is…three or four steps ahead.…Most of us can’t conceive these things working; he can’t conceive them failing.” They take what others see as big risks, but in their minds, they are sure they will succeed.
“People are drawn to his companies by his incredible vision, dedication, and perseverance,” said one writer. “Due to his work ethic and dedication, Musk inspired a generation of young engineers to work at his companies and believe in a shared vision.” [http://bradlm3.blogspot.com/2013/03/the-leadership-of-elon-musk.html]
Justine Musk, Elon’s first wife, said of visionary geniuses like her husband, “They don't think the way other people think. They see things from angles that unlock new ideas and insights…it’s this that allows them to open up windows to another, deeper reality in which transformation is possible and things of awe happen on a regular basis.” “They might make lousy husbands and terrible wives,” she said, “they might be the friend who never sends you a birthday present and forgets to show up for coffee, but they bring light to the dark, and they show us the universe.”
Musk has been described as pushy and confrontational, sometimes falling into “fits of rage.” Yet most people who work with him remain loyal, perhaps because they appreciate his world-changing vision. “If anyone in our generation has the chance of being remembered 200 years from now,” says an article in Fast Company, “it’s probably Elon Musk.”
Steve Jobs
If you wanted to create a poster child who exemplifies the qualities and characteristics, both positive and negative, of the Visionary Evangelist, you couldn’t do better than Steve Jobs, the co-founder and long-time public face of Apple.
On the plus side, he was a visionary and a driven perfectionist who played a key role in the development of the Macintosh computer, as well as iMac, iTunes, iTunes Store, Apple Store, iPod, iPhone, and the iPad. In addition, he helped to develop the visual effects industry when he helped create Pixar, which produced Toy Story, the first of many computer-animated films.
He was also an eloquent, charismatic, and persuasive speaker, which made him the perfect spokesperson for Apple products. Although he was not an engineer, he loved electronics, understood how things work, and could talk about them intelligently and convincingly.
According to his biographer, Walter Isaacson, “Steve was filled with contradictions. He was a counterculture rebel who became a billionaire. He eschewed material objects yet made objects of desire.” A student of Zen Buddhism as a result of a trip to India in his 20s, he lived very simply, preferred to sit on the floor, and was a vegan.
He had a formidable intellect. “He was very often the smartest guy in the room, and he would let people know that,” according to Atari cofounder Nolan Bushnell.
“Steve Jobs was not a great person,” commented a reader of his biography. He could be – and often was - dictatorial, vicious, ruthless, and so volatile as to be unpredictable. His interactions with people were often marked by harshness and nastiness. He had a violent temper. 
But there is no denying the enormous legacy he left behind for our generation and into the future.
Problem Children?
From a young age, Visionary Evangelists can be difficult, particularly with those in authority to try to get them to conform. Their inquisitive nature and proclivity for exploration often drives their parents crazy and sometimes endangers life and limb. Steve Jobs is typical. He had difficulty functioning in a traditional classroom, rebelled against authority figures, got in trouble, and was suspended a few times.
Visionary Evangelists have an unusually strong need for independence and autonomy and are overflowing with restless energy. This is precisely the spirit that is driving the present generation of young entrepreneurs, many of whom have the profile of the Visionary Evangelist.
These people are very bright, and they get bored easily by routine. They tend to get distracted by new, shiny objects. They are better starters than they are finishers. They want to move on before they’ve really nailed down the results. This is why they are not very interested in systems and processes, as Managers of Execution are. They see such things as restrictive and even boring. But this can cause problems, if they have not partnered with people who thrive on building processes and systems.
Kim Scott, author and executive coach, says that “while organizational design and management are probably not Elon Musk's chief interests," if he “could only put a fraction of the creativity and energy that he puts into building great products into thinking through his organizational design, he would find that his job as CEO and building cars is a lot less hellish." .
Both men and women with this personality profile have a lot of drive. Their energy and constantly bubbling creativity make them feel the need to be busy and on the move. When they are young, their refusal to sit still and submit to the routines of classroom education, and their tendency to challenge authority, often lands them in the principal’s office. Others, who are more socially skilled, press the limits but get away with it because of their personal charm.   They are bored with routine and seek out activities that require original thinking and creative expression. They are always building, tinkering and taking things apart. Even as children, their minds are open to multiple possibilities, beyond things as they are.
As they enter the workforce, these people have a hard time working for others – especially when there are a lot of rules to follow, or innovation is not highly prized. They are, says Prof. Gary A. Davis, author of Creativity is Forever, “naturally independent, unconventional, and bored by trivialities. Because rigid enforcement of rules will alienate creative people and squelch their creativeness, flexibility and rule-bending are necessary on occasion.” They will always see a better way to do it, and feel confident that they can do a better job. Often, they are right. That’s why the ranks of entrepreneurs around the world are filled with Visionary Evangelists. 
More than just independent-minded, they are nonconformists who question the beliefs, rules, and practices of the organizations in which they work. In the words of the poet William Blake, "I must create my own system, or be enslaved by another man's.” But if they are given enough freedom and not restricted in their creative expression, they love their jobs. 
They are comfortable being alone and working alone. But they are usually quite willing to seek advice from others when they run into something they can’t understand or manage on their own.
Despite their independence, VE’s like being around people and they handle their relationships with confidence. They are skillful at guiding conversations to influence and persuade others, though it is not beyond them to use their persuasive skills in ways that might be viewed as manipulation.
In one sentence, Visionary Evangelists “see” something that excites them, and they love to pursue their vision with passion and bring it to life.
The Secrets of Their Success
1 - Creative Visionary             In our research, the skill most correlated with the cluster of skills we have labeled the Visionary Evangelist is, not surprisingly, “Creating a Vision”. At their worst, they can be impractical dreamers who drift from one wild idea to another, living in their heads, rarely if ever bringing any of their ideas to fruition. At their best, they are the visionary geniuses who set new directions for organizations and for society as a whole. Metal birds that fly through the sky, self-propelled vehicles that make the horse unnecessary, a computer on every desk, an organization of nations dedicated to peace and global problem-solving – their innovative conceptions are without number.
One factor that fuels their creativity is an innate curiosity – think of Elon Musk reading for 10 hours a day and memorizing the encyclopedia – a desire to learn and to understand this complex world we live in. The mind of a Visionary Evangelist is a busy place. Innovative ideas bubble up at any time of the day or night. Some will be discarded, but many will lead to action. “Anyone vaguely familiar with Elon Musk,” said a recent article about him, “knows that he’s usually juggling tons of ideas at the same time.” And this is common for Visionary Evangelists.
 Here are some typical quotes from our 360 assessments of executives who may not be as well known as Jobs and Musk but who inspire their colleagues with their creativity and ideas:  “At times it seems that more good ideas are coming from Suzanne than from the rest of the management team put together, She is not afraid to step out of the box and try a new angle. She understands the power of creativity and provides all of us with the time to consider new ideas, thought patterns, and solutions.”
VE’s love work that requires original thinking and are always seeking new ways to look at things. Creativity researcher Davis notes that a creative person “looks at one thing, and sees modifications, new combinations, or new applications,” and “makes connections between one situation and another.”
Intellectually curious, Visionary Evangelists love exploring and learning about new ideas. They love to experiment. They take the time to study and reflect. Although they don’t have strong needs for companionship and most of them    enjoy periods of solitude, their creativity is fueled by lively discussions and philosophical debates with friends and coworkers. They are not afraid to surround themselves with people who have different beliefs, political views, and backgrounds, and who come from different cultures. They like nothing better than stretching their minds.    But because they tend to think they’re smarter than other people, they’re more likely to talk than to listen. This of course curtails their ability to learn.
2 – Translates the Vision into Strategy
Visionary Evangelists have a gift for making their ideas vivid and tangible, which draws support from others. Visionary Evangelists are strategic thinkers. Once they have conceived a vision, they find it natural to translate the vision into a strategy for the organization. Long-range plans need to be developed, and resources mustered to carry out the plans that will turn the vision into a reality. Not content just to dream, they may also excel at creating the plan which makes it happen.
While a lot of VE’s do have the capacity for strategic thinking, one of their weaknesses is that it often stays in their head: they don’t translate it enough into specific objectives. It’s very broad-brush, and when you poke at it a little, you find that it’s like a movie set: it looks good from the street, it enables them to pitch the venture capitalists and get funding, but the people within their companies almost invariably say that it’s not sufficiently meaty or detailed in translating the broad vision into priorities and actionable goals. 
Early-stage entrepreneurs, especially, tend to be more visionary than strategic. Those visionaries who succeed in growing their companies larger have figured out that they need to get it out of their heads and define it for others.   However, although they love putting together the master plan, they are relatively uninterested in the nitty gritty details of executing the plan. What’s important to them is the Big Picture. Once the design is in place, they are ready to move on to the next grand idea. 
3 – Sells the Vision
When the vision and strategy are in place, the time has come to rally followers and supporters. The dictionary defines an evangelist as “a person who crusades for, and builds support for a cause, and whose behavior is marked by evangelical enthusiasm.” When it comes to influencing others and finding just the right words to persuade and paint a powerful and inspirational picture, VE’s are the masters. 
Their superpower is their ability to sell their vision and influence people, and this differentiates the ones who get funded from those who don’t, because they have to be able to pitch skeptical venture capitalists who routinely listen to hundreds of pitches before they decide to fund just one. 
 Many shy or reserved individuals have a creative vision but lack persuasive skills to enlist the support of followers. They don’t know how to sell the thing they’ve created. Having a creative idea is only part of the equation. On fire with the compelling nature of their vision, leaders must also be able to paint it in glowing strokes and promote it like a preacher selling salvation.
This ability to pitch and influence people is one of the social skills that entrepreneurs possess, but you can’t say they have broad social skills, because they often do not read people or group dynamics well, and they tend to be insensitive. They are effective at what amounts to sales, but they need to develop better relationship skills and emotional intelligence (EQ) before they will be truly effective leaders. Often, they have high IQ and low EQ.   Bringing a vision to life involves not only the ability to inspire peers and employees to work hard together to make it a reality. The entrepreneur also – and crucially – has to persuade potential investors to get involved. They need to communicate their vision with a level of emotion, excitement, and passion that captures people’s hearts. VE’s bubble over with ideas, and they radiate enthusiasm. Unemotional, overcontrolled executives who only have access to their logical, rational side will have trouble generating excitement and inspiration.
Because they are so natural and so effective representing ideas, products, programs, or services that have meaning to them, as their companies evolve, they often take on the job of spokesperson. Poised and polished in front of groups, they make effective, high-impact presentations. Dynamic and socially confident, VE’s know how to make a strong and positive first impression. Many pay attention to cultivating their public image. They like to be the center of attention, with the spotlight on themselves. 
Every Visionary Evangelist begins with a dream. The most successful have the ability to communicate the dream with a passion and power that attracts followers whose combined strength transforms the vision into a reality.
Martin Luther King, Jr. was not a business leader, yet he is a perfect example of a Visionary Evangelist. A genius in his own right (he graduated high school at 15 and college at 19 before going on to his Ph.D. and Doctor of Divinity degrees) King was a passionate advocate not only for civil rights but for human rights for all. His vision of justice and equality drove him to campaign relentlessly, putting his life on the line day after day. In the eleven-year period between 1957 and 1968, he traveled over 6 million miles and spoke more than 2500 times. His famous “I have a dream” speech to 250,000 at the Lincoln Memorial in Washington, D.C. is known throughout the world. At 35, he was the youngest person to be awarded the Nobel Peace Prize.
4. Takes Initiative
When it comes to taking initiative and getting things moving, VE’s don’t have to be asked to take charge. If an opportunity presents itself, they feel impelled to take advantage of it. If they have a dream or an insight, they feel they must act on it. Conceiving the idea isn’t enough. They must turn it into something concrete. In fact, their vision consumes them and often takes over their lives, filling every waking and sleeping moment until it becomes a reality. They can’t help but take the lead.
The initiative of visionary leaders is recognized and appreciated by their peers and reports. “Hiroshi looks for things that need to be done, and takes action,” one person on his team said. “He is quick to take a leadership role. His initiative to grow the organization is an inspiration to the rest of us. Hiroshi leads by example.” Another person commented, “Ray is always the leader. He identifies problems, then attacks them. He has a solution for us most of the time before we even know it is a problem.” And another, in just a few words: “Very action oriented. Afraid of nothing.”
Their strong action orientation can be a double-edged sword. Yes, it gets things done, but as a result of their tendency to jump in and try to make something happen immediately, they often get involved in micromanaging. It doesn’t occur to them that they might delegate it, or who it should be delegated to. They tend to go around their managers and reports and go directly to employees. This is potentially undermining to the authority and decision-making independence of their directs. 
5. Creates Meaning – Shows Employees Why They Matter

Effective leaders make their followers feel that they are close to the source of something great.  Everyone feels that he or she makes a difference to the success of the organization. When that happens, people feel inspired because their work has meaning. One of the greatest sources of trouble in organizations today is the lack of connection employees feel to the company’s mission, vision and goals. Quarterly earnings, market share, and enhancing shareholder value, of vital concern to founders, investors, and upper management, don’t motivate many employees. The leader must touch their hearts as well as appeal to their intellects and pocketbooks.
Why? People have a deep need for meaning and purpose in their lives. Without meaning, work can easily become a chore, something you have to do rather than something you look forward to. This is fertile ground for apathy, lackadaisical performance and reduced productivity, as well as a discontented workforce.
The need for meaning and for a sense that what they do matters, seems to be especially crucial to members of the Millennial generation who have a strong desire to, in the words of Apple founder Steve Jobs, “make a dent in the universe.”   Visionary Evangelists are an effective antidote to this problem. Through their eloquence and passion, they help employees connect their jobs, and their lives, to the organization’s vision and strategy. They achieve employee buy-in and ratchet up motivation by showing people how to relate their day-to-day activities to a higher meaning and broader strategic priorities.  
Although “creating meaning” is not generally recognized on the 360-degree evaluations as having great importance, our research and consulting experience show that it is one of the vital components in promoting employee loyalty and building a strong corporate culture.
  6. Optimism
One employee said of her boss, “Bill never lacks for enthusiasm and optimism. He always looks for strategies to manage through tough times rather than hang his head.” Another put it slightly differently, “She works so hard despite the lagging numbers of the division, and always has a positive outlook on the future. It makes you want to work hard for her.” This is what Visionary Evangelists do for the people around them. They always assume that no matter how difficult things may appear to be, it will all work out just fine in the end. They tend to look on the bright side, seeing the glass as half full, and do not worry much about the future. 
Napoleon Bonaparte suggested that, “A leader is a dealer in hope.” Followers need leaders who give them hope and reassure them that they will succeed. One employee paid tribute to her boss’s optimism this way: “The positive morale in the department is directly and almost solely attributable to his leadership, mentorship, optimism, energy and enthusiasm.” Visionary Evangelists not only exude a confidence that things will work out – many of them also have an inherent trust in the good heartedness of people; they believe people can be trusted. This uplifts followers and inspires them to create a successful outcome.

7. Self-Confidence
If you met a Visionary Evangelist for the first time, you would almost certainly recognize their high level of self-confidence. They are sure of their capabilities, values, and judgments, believe in themselves and in their gift for leadership. Many of them truly feel that they were “born to be a leader.” They know they can almost always count on their ability to make a good impression on others. They are frequently “silver tongued devils” who have the self-assurance and persuasive power to win over the skeptical and ultimately get their way. A subordinate described his boss by saying, “Elaine has the power of persuasion through suggestion. Her confidence makes us want to follow her wherever she leads.”
Visionary Evangelists set high goals, often difficult to reach, and never question whether they can achieve them. They seem to be untroubled by self-doubt. They genuinely believe they are more talented than others, and their coworkers often agree with this self-assessment. 
They can also freely admit their shortcomings, if someone is willing to hold up a mirror and show them. They’re willing to acknowledge their mistakes and are ready to work to overcome them and to learn from them. However, it isn’t easy to convince them that they are wrong. 
Steve Jobs describes his growth of confidence in the following quote: “My father was a machinist by trade. He had a workbench in his garage, and when I was five or six years old, he sectioned off a little piece of it and said, ‘Steve, this is your workbench now.’ He spent a lot of time with me, teaching me how to build things, how to take things apart and put things back together. Inspired by a neighbor who worked at Hewlett Packard, I used to buy Heathkits to build radios and other electronic equipment. These kits came with detailed manuals and color-coded parts. Putting a piece of equipment together gave one the sense that one could build the things that one saw around oneself in the universe. These things were not mysteries any more…they were the results of human creation, not magical things that just appeared in the environment. It gave a tremendous sense of self-confidence, that through exploration and learning one could understand seemingly very complex things.”

8. Risk Taker and Agent of Change One of the problems with VE’s is that they can be overly confident, overly optimistic risk-takers. As a result, they will not validate their conclusions and insights with facts. And they can be impulsive. Being a change agent is different. Being an agent of change is about challenging the status quo and coming up with new ideas. That is highly correlated with VEs. But risk-taking is a double-edged sword. Being a risk-taker and not grounded in seasoned judgment is foolhardy.
“I witnessed Karen coming in and ripping apart a process that was outdated, inefficient, and meaningless. It was a beautiful thing.” Visionary Evangelists can’t help but be agents of change. Their willingness to try something new, coupled with their creativity and vision, makes them fearless in trying out new approaches and challenging the status quo. “Leaders,” said Dr. Robert Jarvik, inventor of the first permanently implantable artificial heart, “are visionaries with a poorly developed sense of fear and no concept at all of the odds against them. They make the impossible happen.” 
This is not always a walk in the park. “There is nothing more difficult to take in hand, more perilous to conduct, or more uncertain in its success, than to take the lead in the introduction of a new order of things,” said Niccolo Machiavelli. Yet they are willing – even eager – to challenge the system in order to make things better. “Bruce challenges departments to constantly re-evaluate the processes and priorities they set.” They are simply not satisfied with tradition or “the way we have always done it” if it doesn’t move the organization forward.   
Independent thinkers, Visionary Evangelists are not susceptible to social pressure. If they believe in something, they are willing to take an unpopular position. Says one coworker, “Aimee will confidently and readily buck the status quo if she believes it impedes getting results. She is tenacious and sticks to her guns if she feels very strongly about an issue.”
Visionary Evangelists like Steve Jobs are not plagued by fear and appear to worry less than others. They are not foolhardy, but they are willing to take a risk on an idea or a venture if they believe it might pay off. When they really want something – when the potential reward or return is great enough – they are willing to go out on a limb. In fact, they seem to enjoy taking chances.
Jeff Bezos has combined his skills as a Visionary Evangelist with his ability to be a Manager of Execution and has become the richest man in the world. He was also a classic risk taker who challenged the status quo. Long before the Internet became the center of commerce that it is today, Jeff Bezos saw the future and decided to play a role in making it happen. In 1994, he told a reporter, “I came across a startling statistic, that web usage was going up at 2,300% a year. I decided I would make a business plan in the context of that growth.” So, he quit a good job at a Wall Street hedge fund and started a small company, selling college textbooks online.
Of course, that company, Amazon, has become one of the world’s largest mega-corporations, “a place where people can come to find and discover anything they might want to buy online,” according to the Amazon mission statement, and Bezos became the world’s wealthiest man.
In 1997, when he took Amazon public, Bezos said, “We’re at the Kitty Hawk stage of ecommerce, “referring to the small town in North Carolina where the Wright brothers flew the world’s very first airplanes in 1903.
 9. Achievement Driven and Socially Competitive
Competitiveness is one of the most highly regarded and highly rewarded qualities in the American character. From Little League to the Olympics and the Super Bowl, and in virtually all educational institutions, we are trained to compete and rewarded for coming out on top. The drive to be the best leads to high achievements as well as personal gratification. In the business world, most people would agree that the best thing that ever happened to Detroit – and for the driving public – was competition from Japanese automakers. The competitive spirit has contributed greatly to America’s strength at home and abroad.
Visionary Evangelists are highly motivated individuals whose drive to succeed is legendary. The literature of successful entrepreneurs, from Thomas Edison to Bill Gates, is full of stories of men who hardly slept, ate, or changed their clothes while working to achieve their goals. These days, Tesla employees report that when production gets behind schedule, CEO Elon Musk stays at the plant and sleeps a few hours on a narrow couch right on the factory floor. These people feel, from an early age, that they are destined to accomplish great things in their lives, and they are willing to work hard to do so and to make a difference
However, it is important to distinguish between the need or drive for achievement, and competitiveness. Competitiveness can be destructive if it’s a matter of winning and being right, no matter what. Sales reps, for example, are very competitive with their peers, but they are poor team players and don’t make good sales managers. Competition with other people, characteristic of many entrepreneurs, works against collaborating and being good team players.
Achievement drive is different; it’s a desire to attain goals. Competitiveness is a desire to be better than others, to be Number One, to dominate.   This drive for dominance is a double-edged sword. On a personal level, an obsession with success at all costs often results in neglected marriages and children, poor health and heart attacks. It poisons the marketplace by turning competitors – who, after all, are also legitimate business enterprises – into symbols of evil. At its worst – especially if the entrepreneur’s path is blocked and the achievement of their vision is threatened – it breeds a kind of self-centered callousness toward “the enemy” that can bring out ruthless behavior, where the end justifies any means no matter how illegal or unethical.
Many VE’s are notorious for the fierceness of their competitive nature. A Web biography of Microsoft founder Bill Gates, who has a strong Visionary Evangelist profile, tells us that his family upbringing taught him competitiveness from an early age. “His great-grandfather had been a state legislator and mayor, his grandfather was the vice president of a national bank, and his father was a prominent lawyer. Early on in life, it was apparent that Bill Gates inherited the ambition, intelligence, and competitive spirit that had helped his progenitors rise to the top in their chosen professions.” Combative and hard-driving, Gates has been called “a brilliant and ruthless businessman who single-mindedly pursues not only his own success but also the annihilation of his foes.” 
Their Dark Side
Like all of us mortals, Visionary Evangelists also have their weaknesses and challenges. “Exasperated parents, teachers, colleagues, and supervisors are all familiar with some negative traits of creative people,” says creativity expert Gary Davis. “They can be stubborn, uncooperative, indifferent to conventions and courtesies…careless and disorganized, especially with matters they consider trivial.”
 As in our discussion of competitiveness above, many of these “weaknesses” can best be understood either as the “shadow” or dark side of one of their strengths, or as less developed or immature aspects of essentially positive qualities:
Their rebelliousness is the other side of their willingness to challenge the status quo.
Their indomitable optimism, so inspirational to others, easily leads to a kind of cavalier attitude about deadlines and commitments – “It’s okay, it’ll all work out.”
The self-confidence and love of being center stage that make them such charismatic presenters has an element of narcissism and can lead them to believe they are “special” and are therefore entitled to special privileges and exemptions from rules everyone else has to follow.
1. Self-Centered and Egocentric
Many leaders are self-centered. But the Visionary Evangelists are more narcissistic than others. This is one of their biggest Achilles’ heels. It prevents them from being the kind of outstanding leader who puts the needs of the organization ahead of themselves. It prevents them from thinking they could be wrong, and from listening to input, whether critical or intended to be helpful. They think they are always right and are the center of the universe. 
Visionary Evangelists are well aware that they are highly intelligent, creative, charismatic, charming and natural leaders. All too often, this breeds arrogance. As one manager’s colleague put it on his 360-degree assessment, “He displays a negative form of confidence that sends the message, ‘I am smarter and better than you.’ His self-importance and huge ego comes at other’s expense.” For most Visionary Evangelists, humility is not their strong suit.
Sure that they will achieve their vision, VE’s often see only opportunities and possibilities and fail to consider that they might fail. This is an outgrowth of their ego and can be dangerous to their organizations. “I think Justin’s confidence in the team’s ability to make miracles happen is unrealistic and more than a little arrogant. We cannot blindly assume that ‘if we can think it, we can do it.’”
They would much rather talk and expound their own ideas than hear what others have to say. They become so wrapped up in their own ideas that they don’t leave much room for other’s opinions. On personality self-assessments, VE’s tend to see themselves as tolerant and open. Very often, they are not.
They are also not very sensitive to the needs and concerns of others. This is another blind spot. They frequently describe themselves as affectionate and aware of others’ feelings, but in fact they tend to be self-absorbed and insensitive.
As we have seen, Visionary Evangelists are independent non-conformists. Because by nature they question beliefs, rules, and practices that others take for granted, they are often able to see a new and better way. But their need for autonomy and their tendency toward non-conformity can create friction when they have to work in a group. They are not natural team players. They don’t want to be bound by confining rules or the necessity for compromise. In fact, they don’t like restrictions of any kind. They want to do it the way they want to do it.
This may seem fine when the Visionary Evangelist is an entrepreneur, running his or her own company. But as the company grows larger, in order to function efficiently it must develop rules, policies, and procedures, which the entrepreneurs often violate, resisting these curbs on their freedom. They can actually do the organization harm at this point, and indeed, sometimes have to step down for the good of the organization they helped to create.

2. Managerially Challenged
Visionary Evangelists are great at starting projects, not so great at following through and driving to completion. They need to have Managers of Execution around them, to translate their vision into strategy and ultimately into the tactics and operational disciplines that are going to make the company successful.
A successful entrepreneurial startup has to figure out how to become a culture of discipline. That means systems and processes, and it means disciplined approaches to solving problems, making decisions, analyses of unsuccessful initiatives, and the management of things that the Visionary thinks are boring and routine. Every organization needs processes, policies, playbooks, procedures that help people be efficient and maintain quality.
Put simply, VEs are bored with such things. With their minds on their Grand Vision, they just can’t be bothered with such mundane matters, and they badly need Managers of Execution to partner with them. The problem is that most often they are loners and not good partners, so even if they do bring in some expert MEs, they don’t listen to them.
What they need is sufficient awareness of their weaknesses and shortcomings so that they will bring people in to complement them and shore up their weaknesses. If they are too narcissistic they don’t recognize this need.
Skillful managers are organized, good at planning, and disciplined in carrying out the plan. Visionary Evangelists are often undisciplined, undependable, and uninterested in bothering with the nuts and bolts of execution.
On their own, it may not matter much that they are not organized or disciplined but as leader of an organization, it is fatal to the culture. Why? Because they are good starters but not good finishers, because they fail to follow through and meet commitments, they are poor role models for others in the organization. Then they find that the organization doesn’t have discipline and others don’t show up for meetings on time, or take product deadlines seriously, and so on, because the leader doesn’t.
Why would leaders who are so driven to achieve their vision and so action-oriented fail to follow through and meet their commitments? Because they are seers of vast unbounded possibilities, dreamers and creators of what might be brought to life; they are enamored of the big picture and simply bored with the details. Furthermore, they hate to be restricted by boundaries such as deadlines, budgets and systematic processes.
Their native optimism also works against them. People who are not so certain “it will all work out” tend to see the value in tactical planning and disciplined project management. The optimistic Visionary Evangelists don’t sweat the details; as a result, they may miss deadlines and fail to deliver on their commitments. The result is that their grand vision goes unfulfilled.  
Our research has shown that being a visionary is negatively correlated with orderliness and thoroughness, and our observations of leaders’ behavior bear this out. As leaders, Visionaries don’t tend to establish the structures, systems and processes that are needed to implement their vision. 
Although they may set broad goals for themselves, when it comes to managing their own teams, they may fail to clarify objectives, roles, and priorities. They understand the vision and are confident that they can work their way toward achieving it, and they assume that other people will know what to do – that others will be able to act independently, too. Once the design phase is complete, they often lose interest and leave subordinates to figure out what to do next. 
3. Poor Team Players Who Don’t Empower Others
Leadership is about leverage. Unless you empower other people, you put yourself in a situation where you are making too many decisions. That doesn’t scale. Hub and spoke management and leader-centric organizations have trouble scaling efficiently.
When there are eight people outside your door waiting for a decision, and you are working longer and longer hours, these are signs that you haven’t pushed decision making down. You have to empower people, based of course on their capabilities and their track record of having good judgment and making good decisions. But if you don’t empower people, the company will stall and you will burn out. You can’t do it all.
As entrepreneurs, the Visionary Evangelists’ independence, creativity and habit of taking decisive action work in their favor. But when it comes to building teams and working through others, these identical qualities can become an obstacle.
 An effective leader must learn to leverage the input and efforts of followers. This is one of the key factors that enables them to grow their organizations and multiply themselves. Headquartered in Silicon Valley for nearly 40 years, I have seen numerous Visionary Evangelist entrepreneurs hit the wall when they don’t figure out how to fully utilize the capabilities of their team.
So, what prevents them from benefiting from the diverse experience and skills of those who work for them? First of all, they don’t delegate well and don’t empower others. They are fundamentally loners who are accustomed to succeeding by individual initiative and action. They are also certain that they are smarter than the people around them, and don’t really value the input of others. They prefer to maintain control and make the calls. Consequently, they fail to harvest the full potential of their team. 
In addition, Visionary Evangelists don’t want to give up their special status and the ego gratification that comes from being center stage. After a lifetime of following their dreams, getting their own way and flying solo, they don’t play well with others. Team play requires you to subordinate your own individual agenda for the good of the team. This isn’t easy for Visionary Evangelists.             4. Unreflective Over-confidence
What is the difference between a high degree of confidence and sense of self-worth that allows leaders (and really, anyone) to undertake difficult challenges with the belief that they can overcome any and all obstacles and achieve their goals successfully – and the kind of blind over-confidence that ignores weaknesses and potential problems and may lead to disastrous results? Where is the line between confident boldness, and foolhardiness?
Visionary Evangelists are very confident individuals. And they are not self-reflective. They are so confident that they don’t think about what could go wrong. When this combines with their native optimism, they will oversimplify. They tend to be afflicted with what is called “confirmation bias” – they only listen to evidence that supports their ideas. They don’t think they need critical input! They don’t take the time to think that they might be wrong. They’re just sure they are right. This faulty thinking easily leads to bad judgment and mistakes. 
For example, entrepreneurs are often so self-confident that they don’t pay enough attention to their business competition. They think their stuff, whatever it is, whether product or service, is the best, and they may not even have done their homework to discover whether they do have significant competition or whether somebody else, some other company, may have gotten there first. Obviously, this is a formula for disaster.
This “overconfidence effect” is a well-known phenomenon, in which a person’s sense of confidence in their judgments is higher than is merited by the actual accuracy of those judgements. As Nobel laureate Daniel Kahneman said, “Overconfident professionals sincerely believe they have expertise, act as experts and look like experts. You will have to struggle to remind yourself that they may be in the grip of an illusion.”
It is a bit tricky to sort out, as some of the greatest leaders, such as Steve Jobs, had this kind of self-confidence and self-assurance and was often proved correct by the results.
Conclusion   Creativity, and the ability to inspire and to motivate people with a compelling vision, are not skills that are easily learned. Indeed, our research indicates that Visionary Evangelists are a rare breed – even though there are a lot of them heading up fledgling companies in Silicon Valley and elsewhere, there appear to be significantly fewer of them walking the planet than there are Relationship Builders and Managers of Execution.
It would not be overwhelmingly difficult for Visionary Evangelists to warm up their people skills or to add some of the disciplined behavior characteristic of effective executors. Doing so would surely add balance and completeness to their leadership. Learning to be a better listener, making an effort to reply to emails and requests and to get to meetings on time, to honor deadlines that they themselves set or agree to meet – doing a few of these things will add to their effectiveness and elicit greater support and buy-in from others.
But our primary advice to Visionary Evangelists is: Leverage your God-given assets! Don’t try to become something you are not. Your gifts are relatively rare and are vital for the success of any enterprise. Use them with energy and passion. At the same time, admit that you are not perfect and can’t do it all. Some aspects of your personality are less-well developed, so you’ll need to find effective managers and relationship builders to complement your strengths and fill out your team.
Development, for you, is more about facing yourself honestly and dealing with the natural weaknesses that go with this leadership style. Observe your attitudes and your behavior – not just once but consistently! – and be alert for signs of arrogance, self-importance, failure to empower others, manipulativeness, and the other “negative” characteristics mentioned above.

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When Should a Founder Bring in a COO? And why choosing the right type of COO could save or sink your
By Rich Hagberg September 28, 2025
One of the biggest dilemmas that founders face knowing when and why to bring in a Chief Operating Officer (COO) . Too early, and you risk creating bureaucracy before the business finds its footing. Too late, and the founder becomes a bottleneck, throttling growth and burning out teams. Get the wrong type of COO, and you’ll spark culture clashes or stifle innovation. I have had 4 COOs over my career. Their styles and capabilities were very different and the role I needed them to play differed dramatically based on the stage of the company. Some of them worked out beautifully and were the perfect complement to my founder tendencies and limitations. Some were a disaster. Here is what I learned. The COO is the most variable role in the C-suite. Some founders never hire one. Others go through three or four before finding the right fit. In many cases, the question isn’t if you need a COO—it’s what type of COO your company and your leadership style demand at this stage of growth. Let’s break this down. Why COOs Matter Founders are visionaries. They are idea machines, market spotters, and force-of-nature storytellers who rally talent and investors around a dream. But those same strengths often come paired with weaknesses: disorganization, impatience, lack of systems, and difficulty letting go of control. A strong COO is the counterweight. They turn vision into execution. They stabilize culture. They keep promises made to customers and investors. And, at the right time, they free the founder to do what only the founder can do—set direction, evangelize the mission, and keep the spark alive. But “COO” isn’t one job. It’s a category. And picking the wrong type is like forcing a square peg into a round hole. The Seven Archetypes of COOs 1. The Executor The backbone of day-to-day operations. They build systems, enforce discipline, and make the trains run on time. Best fit: Visionary founders who thrive on ideas but leave chaos in their wake. Stage: Early scaling, when the business needs process without killing momentum. Examples: Sheryl Sandberg at Facebook (balancing Zuckerberg’s vision), Gwynne Shotwell at SpaceX (stabilizing Musk’s whirlwind). 2. The Change Agent The fixer. Brought in when transformation is urgent—scaling fast, restructuring, or pulling out of crisis. Best fit: Founders who know the business has outgrown their own operational grip. Stage: Scaling into hypergrowth, or turnaround scenarios. Examples: Daniel Alegre at Activision Blizzard, leading cultural and operational overhaul. 3. The Mentor/Partner The grown-up in the room. A seasoned leader who steadies a first-time or young founder, often more coach than operator. Best fit: Visionary but inexperienced founders, often in the earliest stages of institutional growth. Stage: Transition from startup scrappiness to formal organization. Examples: Eric Schmidt at Google—while not COO by title, he played this role for Page and Brin. 4. The Heir Apparent The COO as CEO-in-waiting. They take on broad P&L responsibility, often shadowing the founder before succession. Best fit: Companies preparing for leadership transition. Stage: Later scaling into maturit Examples: Tim Cook at Apple before succeeding Steve Jobs. 5. The MVP Functionalist The specialist. A COO with deep expertise in one critical area—finance, product, supply chain, or sales. Best fit: Founders strong in vision but weak in a single domain essential to scaling. Stage: Startup to early scale. Examples: Prabir Adarkar at DoorDash, covering finance and operations. 6. The Complement to the CEO’s Gaps A tailor-made role. If the founder is a disorganized visionary, the COO is structured and disciplined. If the founder is technical but introverted, the COO is outward-facing and people-savvy. Best fit: Any founder aware enough to know their own blind spots. Stage: Anywhere, but especially scaling. Examples: Sandberg balancing Zuckerberg’s lack of operational rigor; Shotwell countering Musk’s volatility. 7. The Integrator/Hybrid The most complex type. They unify strategy, execution, culture, and talent at once—bridging across multiple functions. Best fit: Complex, multi-line businesses with global teams. Stage: Scaling into maturity. Examples: Angela Ahrendts at Burberry, integrating brand, culture, and operations before moving to Apple. Why Founder–COO Relationships Fail So Often If the COO role is so valuable, why do so many founder–COO relationships crash and burn? Boards are often gun-shy about hiring COOs because they’ve seen these partnerships implode. The reasons fall into several predictable buckets. 1. Lack of Role Clarity The fastest way to sabotage the relationship is leaving the COO’s job undefined. Who owns what decisions? Where does accountability lie? If the COO’s role overlaps with the founder’s, or isn’t communicated to the rest of the team, the COO quickly becomes either a glorified project manager or a powerless deputy. Both end badly. 2. Founder’s Inability to Let Go Many founders simply can’t let go. They want to approve every detail, revisit every decision, and undermine the very autonomy they hired the COO to exercise. A COO who feels second-guessed or constantly overruled either disengages or quits. 3. Misaligned Vision and Values Operational excellence isn’t enough if the COO doesn’t fully buy into the founder’s vision and cultural values. When the COO wants to optimize for stability while the founder is pushing disruption—or vice versa—the two end up pulling the company in opposite directions. 4. Trust and Emotional Reactivity Trust is fragile. If the founder is volatile under stress, or the COO isn’t skilled at navigating the founder’s personality, the relationship becomes brittle. Outbursts, defensiveness, or miscommunications erode psychological safety between them and ripple across the organization. 5. Succession Ambiguity and Power Tensions Is the COO being groomed as the future CEO—or not? Few questions create more tension. If expectations aren’t clarified up front, the COO may feel misled and the founder may feel threatened. Meanwhile, employees begin to compare the two and pick sides. Boards have seen this movie before, and it rarely ends well. 6. Unrealistic Expectations Founders and boards often expect the COO to “fix everything yesterday.” In reality, operational improvements take time—learning systems, culture, and people. When results don’t appear overnight, frustration builds. On the flip side, some COOs expect to make sweeping changes immediately, without respecting the founder’s legacy or the team’s tolerance for disruption. 7. Culture and Communication Breakdowns The founder and COO need structured ways to align—weekly check-ins, clear communication norms, and mechanisms to resolve disagreements. Without them, minor irritations accumulate into major grievances. Worse, the team sees open conflict at the top and begins to question who’s really in charge. 8. Identity and Ego Issues Let’s name the elephant in the room: many founders see hiring a COO as an admission of weakness. They sabotage the hire by bypassing the COO or contradicting them in front of the team. On the other side, ambitious COOs often chafe at being “Number Two.” If the relationship isn’t anchored in humility and respect, egos will clash. How Founders Can Prevent the Breakdown Knowing the pitfalls is only half the battle. Preventing them takes deliberate work: Define the COO’s mandate explicitly —what they own, what’s shared, and what stays with the CEO. Set up trust rituals early —regular one-on-one check-ins to surface tension before it festers. Align on vision and values —not just what you’re building, but how you’ll build it and why it matters. Clarify succession expectations —is this person a partner, a long-term No. 2, or a potential future CEO? Say it. Set realistic timelines —agree on milestones, but don’t expect magic overnight. Communicate clearly to the org —so employees understand who does what and aren’t caught in the crossfire. Hire for complementarity —choose a COO who fills your blind spots, not one who duplicates your strengths. The founder–COO relationship is like a marriage with the pressure of Wall Street, venture capital, and 200 employees watching. When it works, it’s transformative. When it doesn’t, it’s messy, public, and expensive. The Founder × Stage × COO Fit So how do you know when and which type of COO to bring in? Here’s the decision logic: Startup + Visionary Founder Needs an Executor or Mentor/Partner. Someone to turn chaos into motion without killing energy. Startup + Operator Founder May not need a COO yet. If they do, it’s usually a domain specialist (MVP Functionalist) to cover blind spots. Scaling + Visionary Founder Needs an Integrator or a Complement to gaps. Execution and people issues become bottlenecks. Scaling + Operator Founder May need a Change Agent or Heir Apparent. The role becomes about transformation or succession. Mature Company + Visionary CEO The COO role is succession-oriented (Heir Apparent) or complex integration (Hybrid). Mature Company + Operator CEO Sometimes no COO is needed; the CEO already runs operations. In other cases, the COO is simply the next CEO waiting in line. Takeaway Hiring a COO isn’t about “offloading work.” It’s about admitting what kind of company you’re really building, and what kind of leader you are. If you’re the spark but not the engine, you need an Executor. If you’re a force of change but leave wreckage behind, you need a Relationship-Builder complement. If you’re building for the long haul, sooner or later you need an Heir Apparent. The best founders aren’t the ones who try to do it all. They’re the ones who know when to step aside—just enough—to let someone else make the company stronger. Closing Thought In Founders Keepers, I often say: what got you here won’t get you there. The founder’s job is to create possibility. The COO’s job is to turn possibility into performance. The only real mistake is waiting until your company is already fraying before you decide which kind of COO you need. By then, the cost of waiting may be higher than you can afford. 
From Vision to Reality: How Founders Can Ensure Their Ideas Get Implemented
By Rich Hagberg September 21, 2025
The Founder’s Dilemma Founders are fountains of ideas. You see possibilities everywhere, you connect dots others can’t, and you can sell a vision with enough energy to light up a room. But there’s a problem: ideas don’t implement themselves. They need systems, people, and execution discipline. In my coaching of more than a hundred startup founders—and backed by data from 122 founder assessments—the same challenge comes up again and again: founders are world-class at generating ideas, but their companies stumble when those ideas aren’t translated into action. I have struggled with this tendency for my entire career. My creative ideas just keep bubbling up and my execution discipline and focus can’t keep up. I have the classic “shiny object” distraction problem shared by many founders. The irony? The very traits that made me a classic visionary evangelist—creativity, independence, impatience, and risk tolerance—are the same traits that made execution difficult. If you want your ideas to live beyond a brainstorming session, you must learn to do what feels unnatural: offload execution, delegate real authority, and empower others to carry your vision forward. Why Great Ideas Die Without Execution Most failed ideas don’t die because they weren’t brilliant. They die because: 1. The founder keeps ownership too long, trying to do everything personally instead of empowering others. 2. Delegation is fake, with tasks assigned but no real authority granted, leaving the founder still in control. 3. Priorities aren’t clear, so teams are overwhelmed by too many initiatives and unsure of what matters most. 4. Accountability is weak, with no consistent follow-up or consequences when commitments slip. 5. Founders love possibilities but resist discipline, avoiding the planning, sequencing, and focus execution requires. 6. Ideas are left open-ended, because founders generate endlessly but fail to converge on closure and completion. 7. Optimism turns unrealistic, as founders overestimate what’s possible and ignore what could go wrong. 8. Expectations aren’t communicated, leaving teams uncertain about roles, outcomes, and next steps. 9. They rush ahead without buy-in, moving too fast to bring others along and win their commitment. 10. They undervalue operators, failing to leverage managers of execution who can turn vision into systems. This is what I call the founder time bomb. Early success convinces you that your personal hustle is the engine of growth. But as the company scales, hustle becomes a bottleneck. Unless you shift, your best ideas will choke on lack of oxygen. Step 1: Translate Vision Into Tangible Priorities Your job as a founder isn’t to hand down a 37-slide vision deck and hope for the best. Your team needs clarity. That means breaking down your big idea into concrete, winnable battles. Set the “critical few” : Define 3–5 top priorities for the quarter. Outcome > activity : Don’t assign tasks, define the result (e.g., “Increase retention by 5%”). Overcommunicate : If you feel like you’re repeating yourself, you’re doing it right. One founder I coached changed his company trajectory by beginning every weekly meeting with just three priorities. The noise vanished. His team finally knew what mattered. Step 2: Practice Real Delegation, Not Fake Delegation Too many founders think delegation means assigning a task and then hovering over the person doing it. That’s not delegation—that’s micromanagement with extra steps. Real delegation means: Handing over ownership, not just chores. Giving the decision rights along with the responsibility. Accepting that “80% their way” may be better than “100% your way.” Here’s a phrase worth practicing: “You own this. You don’t need my approval.” Few sentences are harder for founders to say. Few sentences build more trust. Step 3: Build a Culture of Accountability Without Becoming a Tyrant Accountability is where many founders stumble. They either avoid conflict (hoping problems fix themselves) or they overreact when deadlines slip. Both extremes poison execution. Healthy accountability requires: Clear expectations : No hidden rules or shifting targets. Visible commitments : Public goals build peer pressure to deliver. Rhythms of review : Regular check-ins that aren’t nagging but structured. Consequences : Underperformance addressed quickly, not ignored. Accountability isn’t punishment—it’s support. It says, “I expect the best from you because I believe in you.” Step 4: Share Information Like Oxygen Execution thrives on information. Yet many founders hoard knowledge—sometimes out of habit, sometimes out of insecurity. Teams can’t execute if they don’t understand the why behind the what. Empowered teams need: Transparent dashboards : Everyone sees progress metrics. Context, not just orders : Explain reasoning, not just results. Accessible strategy docs : Kill the “founder black box.” When people understand the big picture, they stop running back to you for every decision. They start acting like owners. Step 5: Invest in Second-Line Leaders Scaling execution isn’t about having 50 great individual contributors—it’s about having 5 managers who can each lead 10 people effectively. Yet many founders neglect their managers, focusing instead on product or fundraising. Strong second-line leaders can: Translate your vision into plans. Coach their teams instead of doing the work themselves. Spot and develop talent below them. Your leverage point is not how many people you personally manage, but how many leaders you multiply. Step 6: Watch Out for Founder Autopilot Your instincts—boldness, independence, impatience—got you this far. But they can sabotage you at scale. I call this founder autopilot. It looks like: Jumping back into execution “just to speed things up.” Overloading the team with new initiatives before finishing the old ones. Cutting around your managers and making unilateral calls. The cure is self-awareness. Tools like 360 feedback and coaching help you notice when you’ve slipped back into heroic founder mode instead of scalable leader mode. Step 7: Celebrate Execution, Not Just Ideas Most founders glorify the spark of ideation but forget to recognize the grind of implementation. If you only celebrate creativity, you’ll get lots of brainstorming but little delivery. Shift the culture: Spotlight the team that launched, shipped, or solved—not just the one that dreamed. Tell stories of execution at all-hands meetings. Publicly recognize “builders,” not just “visionaries.” What you celebrate becomes what your team repeats. The Founder’s Evolution: From Genius to Builder of Builders The founder who can’t offload execution ends up as the bottleneck, exhausted and surrounded by frustrated employees. The founder who masters delegation and empowerment evolves into something much more powerful: a builder of builders. In my research, the difference between founders who scaled 10x and those who flatlined wasn’t idea quality. It was execution quality. The 10x founders learned to empower others, create accountability systems, and step back from doing everything themselves. The founder who shifts from “I’ll do it” to “I’ll ensure it gets done” makes the leap from fragile startup to durable company. Closing Thoughts Ideas ignite companies, but execution sustains them. If you want your vision to shape reality, you must resist the temptation to hold the reins too tightly. Translate vision into priorities. Delegate real authority. Build accountability and transparency. Develop leaders beneath you. And above all, celebrate execution as much as you celebrate ideation. That’s how founders ensure their ideas don’t die in the brainstorm stage but live on as products, services, and companies that change the world. 
When Loyalty Becomes a Liability: Why Founders Must Confront Team Obsolescence
By Rich Hagberg September 14, 2025
Every founder eventually faces a moment of reckoning. It doesn’t arrive with a clear announcement. It creeps in gradually, often disguised as small frustrations: projects slipping, team members complaining, or investors quietly losing confidence. And at the center of it all is a painful truth: The people who carried you through the chaos of the early days, the ones who slept on office couches, pulled all-nighters, and took pay cuts to bet on your dream—can no longer keep up. The company has grown. The stakes are higher. And the job has outgrown them. This is one of the hardest truths in entrepreneurship, and one most founders struggle to face. Instead of acting, they convince themselves: “She’ll grow into the role.” “He’s been with me since day one—I can’t let him go.” “Loyalty matters more than resumes.” But here’s the hard truth that separates founders who scale from those who stall: loyalty doesn’t scale. Competence does. The Startup Version of the Peter Principle The Peter Principle tells us that in large corporations, people rise to their level of incompetence. In startups, this principle plays out in hyper-speed. What made someone a hero in a five-person company, improvisation, raw hustle, and the willingness to do anything becomes a liability in a 50- or 500-person company. Think about the hacker who was indispensable in the garage. Brilliant at rapid problem-solving, he could patch servers at 3am and crank out features in a weekend. But leading a team of 50 engineers requires a totally different skill set: planning, delegation, recruiting, building processes. His improvisation becomes chaos. His genius turns into bottlenecks. Or the co-founder who thrived on energy and vision. In the early days, charisma and instinct were enough. But scaling requires a discipline around metrics, process, and accountability. What once looked like bold leadership now looks like reckless improvisation. Even the beloved “culture carrier”—the person who organized team offsites, boosted morale, and made the company feel like family—can become a roadblock. When decisions stack up and complexity explodes, loyalty and good vibes aren’t enough. What the company needs is a strategic operator, not just a glue person. This is what I call team obsolescence : the brutal, recurring reality that many early employees get outgrown by the job. The Head vs. Heart Conflict Why do founders struggle so much with this? It’s not because they’re blind. It’s because they’re human. The tension isn’t just intellectual—it’s emotional. Guilt and Indebtedness : Early employees bet on you before anyone else did. They turned down safer jobs, endured lower salaries, and staked their careers on your vision. Cutting them loose feels like betrayal. Psychologists call this the principle of reciprocity: the human drive to repay sacrifices. Founders feel they owe these people more than just a paycheck. Fear of Losing the Magic : Founders often worry that bringing in “outsiders” will ruin the scrappy, intimate culture that made the company special. This is a classic case of in-group bias. We trust the familiar, even when it’s no longer fit for purpose. Many founders cling to the idea that culture is fragile and must be protected from “corporate types.” Conflict Avoidance : Few people relish difficult conversations. Founders, especially those wired to inspire rather than confront, often procrastinate on hard personnel decisions. This is loss aversion at work: the immediate pain of conflict feels worse than the long-term risk of stagnation. Blind Loyalty Bias : Founders frequently overestimate an early employee’s ability to “grow into” a scaled role. This is the halo effect: past loyalty and past performance cast a glow that blinds you to current shortcomings. This is the founder’s head-versus-heart struggle. Rationally, you know the company has outgrown someone. Emotionally, you can’t let go. A Founder’s Story: When Friendship Meets Reality One founder I coached built his company with a close college friend. This friend was the first engineer, working nights and weekends to bring the product alive. He coded nonstop, patched outages at all hours, and was the reason the company survived its early chaos. By Series B, the company had 80 employees. Suddenly the role wasn’t about heroic coding; it was about systems, processes, and leading dozens of engineers. The founder knew his friend was drowning. Deadlines slipped. Senior engineers were frustrated. Investors raised eyebrows. But he kept saying, “He’s been with me since the beginning. I owe him.” Eventually, he faced reality. With coaching, he had the hard conversation: “You’re invaluable to this company, but the role has outgrown your strengths. Let’s find a place where you can thrive without being set up to fail.” The friend transitioned into a specialist role where his brilliance could shine without the weight of leadership. The company brought in a seasoned VP of Engineering. Painful as it was, the decision saved both the company and the friendship. This is the essence of true leadership: honoring loyalty without letting it sink the ship. The High Price of Avoidance The costs of avoidance aren’t abstract—they’re devastating. Execution Bottlenecks : An underqualified leader slows everything down. Projects drag, opportunities slip, and customers churn. It’s like trying to scale a skyscraper on a foundation built for a cottage. A-Players Walk : The best people won’t stay if forced to work under weak leaders. They leave, taking ambition and excellence with them. The company becomes a place where mediocrity thrives. Culture Corrodes : Protecting underperformers sends a loud signal: politics matter more than performance. Over time, resentment builds. High performers check out. Trust erodes. Investor Mistrust : Boards and investors notice quickly when execution falters. They start asking tough questions—not just about your team, but about your judgment as a founder. Founder Burnout : Perhaps the greatest cost: you, the founder, pick up the slack. Instead of scaling your vision, you spend nights fixing problems others should solve. Exhaustion sets in. Your energy, the one resource no one else can replace, gets depleted. What feels like an act of loyalty today can quietly strangle the company’s future. Another Case: The Culture Carrier I once worked with a founder whose operations manager was beloved by the team. She organized payroll, ordered office supplies, and planned offsites. She was the glue. But when the company hit 150 employees, the demands shifted. The job required scalable systems, compliance expertise, and strategic HR planning. She was still running things on spreadsheets and memory. People loved her, but they were increasingly frustrated with the chaos. The founder feared that replacing her would “destroy the culture.” Eventually, he hired a Head of People. But instead of cutting her out, he redeployed her into an employee experience role. She continued to be the cultural heartbeat of the company while freeing leadership to professionalize operations. The lesson: redeployment, when done thoughtfully, preserves loyalty without sacrificing competence. What Great Founders Do Differently The best founders I’ve studied don’t avoid this problem. They approach it with discipline and compassion. 1. They Diagnose Early They don’t wait until the crisis is obvious. They ask themselves, “If I were hiring for this role today, at this stage, would I choose this person?” If the answer is no, they don’t kick the can—they act. 2. They Separate Potential from Plateau Some people can grow. With coaching, training, and mentorship, they can rise to the next level. Others plateau quickly. Great founders don’t confuse the two. They invest in growth where it’s possible and cut losses where it’s not. 3. They Redeploy with Respect This isn’t about discarding people. The best founders move loyal employees into roles where their strengths shine—special projects, advisory positions, cultural leadership. Redeployment preserves respect and institutional knowledge while freeing the company to grow. 4. They Upgrade Before Crisis They don’t wait until the engine fails. They hire seasoned executives early, before execution falters. And they communicate clearly: every stage requires different skills. Honoring the past doesn’t mean guaranteeing the future. Leadership with Compassion The real test of a founder isn’t whether you can attract capital or inspire a team. It’s whether you can make the painful calls that protect the company’s future while respecting the people who got you started. True leadership is not about cold detachment. It’s about balancing head and heart: Gratitude means honoring contributions, celebrating sacrifices, and rewarding loyalty. Governance means making clear-eyed decisions about whether someone can perform at the next level. When founders confuse the two, they put sentiment ahead of survival. But when they balance both, they create companies that endure. One founder I know addresses this directly with his team: “Every stage requires new skills. Some of us will grow into them. Others will contribute in different ways. What matters is building a company that lasts.” That’s leadership with compassion—telling the truth while honoring the past. Why This Matters More Than Ever The startup environment today is more unforgiving than ever. Capital is tighter. Investors are quicker to act. The margin for error is smaller. In this climate, founders who delay tough calls are at greater risk than ever. Execution failures and cultural corrosion are spotted instantly by boards and competitors. The founders who scale are those who balance loyalty with realism—who act before the cracks widen into chasms. The Founder’s Real Test It’s easy to celebrate early wins and bask in loyalty. The real test is whether you can honor that loyalty without being trapped by it. Because here’s the paradox: The only way to truly honor early sacrifices is to build a company that endures. And that means making the call when loyalty becomes liability. Call to Action If you’re a founder facing this dilemma, don’t wait for the board to force your hand. Don’t wait for top talent to walk or investors to lose confidence. Confront it now. Diagnose honestly. Redeploy with respect. Upgrade before crisis. Be compassionate. Be decisive. Be clear-eyed.  Your team—and your company—will thank you later.
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