Feature
The conventional wisdom about how to successfully run large companies is wrong. At least according to AirBnB founder Brian Chesky, who shared his thoughts at a recent Y Combinator event.
The speech, which Paul Graham wrote about on his blog, covered Chesky’s journey as he worked to grow his company from a small startup in 2008 to the mega-company it is today, valued at more than $72 billion.
The big mistake all these leaders are getting wrong, according to Chesky? Not tapping into founder mode.
Founder Mode vs. Manager Mode
There are two effective ways to run a company, wrote Graham: founder mode and manager mode.
Graham defined manager mode as when managers treat subtrees of the organizational chart as black boxes — they tell direct reports what to do and leave them to figure out how. They don’t get involved in the details. What this often looks like, according to Graham, is “hire professional fakers and let them drive the company into the ground.”
Founder mode is more involved. Not micromanagement, per-se, but some amount of delegation while being more active in the various aspects of the company.
Graham pointed to Steve Jobs as one founder who seems to have perfected the technique. For instance, Jobs would run an annual retreat for who he considered to be the 100 most important people at Apple (and not the 100 people highest in the organization’s hierarchy). “Steve presumably wouldn't have kept having these retreats if they didn't work,” wrote Graham.
Related Article: How to Identify Your Leadership Style
Is Founder Mode the Path to Success?
While Graham and Chesky posit that founder mode is what leaders need to find success, the issue isn't so black and white.
“Founder mode and manager mode are not necessarily mutually exclusive; they can coexist,” said Chou-Yu Tsai, professor at Binghamton University's School of Management, State University of New York. While a hierarchy provides stability, he explained, it’s the founders’ leadership that empowers and motivates employees to perform beyond expectations.
“By setting an example, founders reinforce the company’s core values, ensuring they resonate with all employees. It is also crucial for founders to establish personalized, one-on-one mentorships to encourage individual growth, inspiring employees to exceed or redefine their roles.”
While hierarchical structures enforce routines through top-down control, Tsai added, it’s equally important to cultivate a foundation that encourages the bottom-up emergence of new ideas and practices from every member of the company. Structure helps maintain routine, but it is leadership that drives synergy among people and cultivates the capabilities to fuel innovation.
What Skills Do Leaders Really Need to Succeed?
To truly succeed as a leader, you need a wide range of skills. But what do those skills actually look like in the workplace?
Strategic Agility
Today’s leaders need strategic agility, the ability to see ahead clearly into the future — or at least see patterns that give a sense of clarity and direction, said Loren Margolis, faculty of leadership at Stony Brook University and founder and chief executive coach at TLS Leaders LLC. With this skill, you can anticipate future consequences and trends well.
“Strategic agility also means that you are future-oriented and can paint credible pictures and visions of what is possible for your company and what will likely happen,” she explained. “You have knowledge of the marketplace, your competitors and can guide the company through breakthrough strategies that enable the company to win against your competitors and thrive.”
Adaptability
Leaders need to be adaptable to thrive in both founder mode and manager mode, said Valeriana Colón, learning scientist and strategic growth leader at Connect Centric.
In a 2024 leadership study from Harvard Business Publishing, 62% of L&D professionals surveyed said it’s important that leaders develop greater openness to adapting their behaviors to meet current and future business needs. And more than half said it’s important for leaders to improve their ability to function long-term in an environment of constant change, uncertainty and stress.
“This flexibility helps them navigate the strategic vision of a founder and the day-to-day operational needs of a manager,” said Colón.
Emotional Intelligence
High emotional intelligence (EQ) is linked to better leadership effectiveness, explained Colón. In fact, according to Dr. Travis Bradberry, a leader’s emotional intelligence is responsible for 58% of his or her job performance — and more than 90% of top performers in leadership positions possess a high degree of EQ.
“This trait helps leaders manage their own and others' emotions, which is essential in balancing visionary and managerial tasks,” Colón said.
Margolis added that having empathy means you can understand peoples’ worldviews, concerns and joys — and thus, influence them effectively. “So, having strong EQ also means that you are an influencer. It means that you know how to get them to do what you want them to do in order to make the business thrive. Emotional intelligence impacts everything that you do as a leader.”
Influential Communication
Another top skill for leaders, said Margolis, is influential communication — listening well and asking the right questions. Something you need emotional intelligence to get right, she explained.
Conference
Sep
16
HR Tech Conference Las Vegas 2025
Register
Conference
Oct
27
Gartner HR Symposium/Xpo Orlando 2025
Register
“As a leader you must listen well to get the right data so you can make high stakes decisions,” Margolis noted. “You must also listen well to show others that you care. You motivate others by getting them to produce their own answers by asking the right questions, otherwise known as taking a coaching approach.”
Plus, she added, influential communication includes picking up on the communication styles of others and using their words and motivators to move them and achieve results. “I call this a form of benevolent brainwashing.”
Systemic Thinking
One big skill successful leaders have, according to Margolis? Systemic thinking. “This trait means that you are not wedded to thinking or working in one area of the company,” she explained.
Instead, she added, you see the organization as the sum of its parts and you see its inter-connectivity. “You work systemically, integrating every part of the company to produce results.”
Standing Alone
Leadership often means having to go things alone, even if it seems challenging. Margolis said she also calls this trait “leadership courage.”
As a leader, she explained, you encounter difficult decisions on a daily basis. And while you hope to have others on your side when you make decisions that impact lives and livelihoods, you sometimes must stand alone.
“Sometimes you must make difficult decisions that will make you unlikable for the sake of the company. It means that you don't shirk personal responsibility and you are willing to be the only champion for an idea or a position.”
Situational Leadership
Situational leadership, according to researchers, is an approach that embraces adaptation and adjustment of leadership style to the situational factors at hand, such as the type of employees one is trying to lead.
“It means that you understand how much ‘rope’ your employees require,” said Margolis. “You understand how closely you should supervise them vs. how much independence they should have.”
That same research report added, “... there is not only one leadership style [that] works for all followers, and a leader needs to change and adapt his/her leadership style according to the followers.”
Related Article: What Is Participative Leadership?
Navigating the New Leadership Landscape
Leadership dynamics have been undergoing significant changes, especially with the rise of hybrid and remote work. “This shift has made it more challenging to balance visionary and managerial roles because leaders must now also focus on maintaining team cohesion and productivity in a virtual environment,” noted Colón.
To navigate these challenges, she added, leaders must implement a structured approach: scheduling dedicated time for both strategic and operational tasks, conducting regular check-ins with remote teams to maintain connections and alignment and leveraging project management tools to streamline operations and enhance collaboration.
