The Future of Business Belongs to the Wisdom Workers

An Interview with Chip Conley

The nature of leadership is undergoing a fundamental shift. As technology continues to revolutionize the business world, access to information has become ubiquitous. Yet, while knowledge is now widely available, wisdom—an irreplaceable asset rooted in experience and human insight—remains the defining trait of truly impactful leaders. I recently spoke with renowned entrepreneur and business mentor Chip Conley to explore how wisdom, not knowledge, is shaping the future of leadership.

If you don’t know Chip, he is on a mission. After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel, he co-founded MEA (Modern Elder Academy) . He’s also a New York Times best selling author and a leading voice on leadership having spent decades cultivating wisdom-driven approaches to business.

From Knowledge to Wisdom

To frame our conversion, Chip talks about 3 big forces at play when it comes to wisdom in the workplace today:?

1. We’re living longer, and working longer than ever before: Right now we have up to 5 generations in the workplace and many people are needing to stay in the workforce beyond the historically normal retirement age. It was normal to retire around the age of 55 in my grandparent’s generation. Today, many people in their 50s are starting new careers, hitting their stride, and finding a lot of success to build upon for years to come.
2. The average age of a person in a leadership position is getting younger and younger: Over 40% of people have a boss that’s younger than ever before due to our growing reliance on digital intelligence. Yet we expect them to embody the leadership skills and emotional intelligence that takes older leaders decades to learn.
3. We’re not training our leaders to lead: Leaders are often trained in the technocratic world- with a focus on accountability charts, business roadmaps, and endless OKRs and metrics. These are all important but need to be dosed with something else more human. Understanding the compelling mission and north star or how to get things done based on everyone’s diverse motivations are also critical and often missing in on-the-job leadership training.?

Management Theorist Peter Drucker coined the term Knowledge Worker in 1959. As Chip points out, it’s time we replace this term with Wisdom Worker- because our world is wildly different than it was in 1959 and wisdom is what we offer in our humanity to compliment the vast knowledge available through technology.?

“The people who are most important in the future of business will not be the knowledge workers, but the wisdom workers. In the age of AI, knowledge is a commodity, but wisdom is now the most valuable skill.”

The opportunity this creates is to build bridges across generations in the spirit of mutual mentorship and create an intergenerational flow of wisdom.?

“We accumulate knowledge, and we distill wisdom, so, arithmetically, knowledge is a plus symbol and wisdom is a division equation as a wise person gets to the root of something.”

In this view, wisdom is about understanding the essence of an issue, making it a far more valuable skill in decision-making.?

For leaders looking to continue their growth and impact, the key question is: How can we cultivate this wisdom?

Developing a Wisdom Practice

For Chip, developing wisdom is a continuous, lifelong journey. “Since age 28, I’ve followed a wisdom management practice of making a list of my top lessons of each week, what I learned from them, and how they would serve me in the future. This practice has helped me to metabolize my experience and accelerate my cultivation and harvesting of wisdom.”

This reflective process allows leaders to process their experiences, drawing meaningful lessons from both successes and failures. Chip emphasized that many of the most valuable insights come from life’s challenges: “Often, our painful life lessons are the raw material for our future wisdom.” By distilling experience into actionable insights, leaders can accelerate their ability to make wiser decisions in both business and life.

In addition to regular journaling and reflection, there are 4 critical mindset shifts that Chip believes wise leaders should practice:

1. Continue to evolve If you’re in midlife, you have to be able to reframe your mastery and be willing to shed parts of your historical and identity. It’s scary but actually beneficial to let go of old calcified identities in order to innovate and create new impactful things in laters stages of life. This requires right sizing your ego and realizing that you need to evolve your knowledge.
2. Be willing to learn Having a growth mindset, believing your potential is unlimited and that there is and endless see of things you don’t know, being a lifelong learner means breaking the conventional wisdom that as you get older you have less to learn. Blowing up this fixed mindset and deciding that you may in fact have more to learn in the next decade of life than you learned in decades past
3. Pursue effective collaboration Effective collaboration is essential for any company. You can have tons of meetings, but without a collaborative spirit and collaboration skills you won’t be as successful.
4. Listen to your council “Knowledge speaks and wisdom listens”. Wisdom is about listening not just to the story but for the story. Not just the literal takeaways but listening for the common threads in the story. The owl is perceived as the wisest animal in the forest because of it’s acute ability to hear.?

Wisdom doesn’t just serve leaders on a personal level—it directly impacts the success of their businesses. Chip famously mentored AirBnB CEO Brian Chesky for several years during the company’s meteoric rise. In a joint interview on intergenerational mentorship, Brian recalled a piece of advice he received from another mentor, Cheryl Sandberg:?

“Your biggest challenge is people stop telling you the truth- and it’s probably already happened and you just don’t know it yet.”?

Brian shared this to emphasize Chip’s guidance around creating an open culture of listening. He continued, “the truth means that you’re willing to tell people things regardless of how they will feel about you– because they care about you.”

As Chip noted, wisdom helps leaders avoid the trap of repeating past mistakes: “We’ve heard the famous Einstein quote that ‘insanity is doing the same thing over and over again and expecting different results.’

Well, wisdom is learning from our mistakes and creating new results based upon what we’ve learned.”

In this way, wisdom cultivates a growth mindset, enabling leaders to continuously evolve and improve their strategies. By learning from past experiences, wise leaders can create better results over time, fostering both personal and organizational growth.

Baking A Human Needs Hierarchy Into Business

For many CEOs and executives, one of the greatest challenges is balancing the pressure to perform in the short term with the need to make long-term, strategic decisions. When asked how leaders can cultivate wisdom in such high-pressure environments, Chip responded candidly: “How can they not? In a competitive world in which the same knowledge is accessible to all of us, why not tap into our ‘wisdom fingerprints’ based upon our own unique experiences?”

According to Chip, wisdom is the differentiator that sets exceptional leaders apart. With the same knowledge available to everyone, it’s the insights drawn from personal experiences—what Chip calls our "wisdom fingerprints"—that give leaders a unique edge.

Chip shared a practical example of how he brings wisdom into his leadership approach:?

“Once per quarter, I sit down with my leadership team and each of us explains our biggest lesson of the quarter, what we learned, and how it’ll serve us in the future, and we also discuss our biggest team lesson. By focusing on our learning process and being candid enough about our lessons, we’re teaching vulnerability and we’re learning from each other.”

“Wisdom is not taught, it’s shared.”

This practice not only fosters openness but also reinforces the importance of continuous learning and vulnerability within leadership teams.

Another key part of Chip’s wisdom-based approach to leadership is his PEAK model , which applies Maslow’s hierarchy of needs to both employees and customers. You can read more about it in his critically acclaimed book PEAK: How Great Leaders Get Their Mojo From Maslow .

“The key to this model is recognizing that an employee, a customer, and an investor have survival needs at the base of the pyramid, success needs in the middle, and transformational needs at the peak,” Chip explained.

For executives looking to embed these insights into their organizations, Chip offered practical advice: “You need to address them in this order which means you need to be patient in satisfying the peak employee and customer needs of meaning and satisfying unrecognized needs.”

In other words, wise leaders understand that long-term success stems from fulfilling not just the functional needs of employees and customers, but also their deeper, more meaningful desires that they may not even be aware of.

Wisdom Leaders, Start Here:

When asked how leaders can apply wisdom in their day-to-day roles, Chip offered the following recommendations: emphasized the importance of small but consistent practices.

• Free yourself from perfection: Many leaders fall into the trap of believing they must appear flawless. “So many leaders aren’t willing to be vulnerable enough to share their lessons. They believe they have to be perfect,” Chip warned. Wise leaders embrace vulnerability, knowing it fosters a culture of learning and improvement.
• Unleash the power of gratitude in leadership: “The middle level of the employee pyramid is about recognition and great leaders realize that ‘catching people doing things right’ is an essential talent for a great leader.”
• Understanding motivation at every level: What motivates employees at different levels of the organization can vary tremendously. “Meaning can vary based upon the individual or job classification. In my boutique hotel company, what gave housekeepers meaning was different than what brought bartenders meaning, so it’s essential that you sit down with your various types of employees and create a PEAK pyramid for each job classification.”
• Leverage wisdom in the team: Ask your employees: “Other than your boss, who at the company do you look to for advice and wisdom?” These people can scope down their work and focus on internal mentorship, join other teams to mentor and share institutional knowledge and wisdom. By doing this, you’re leveraging an often untapped resource and making other people and teams more productive.

Ready to dive deeper into cultivating wisdom in your leadership? To discover how you can integrate these transformative practices into your own leadership, I highly recommend Chip’s books PEAK , and Wisdom at Work , as well as his excellent blog Wisdom Well as a starting point.

If you’d like to go deeper on what wisdom means in your own leadership practice, schedule a consultation with me to learn more about my 3 month Mindful Leadership program and Corporate Advisory services.?

Original Article: https://www.jessicalynnmacleod.com/blog/the-future-of-business-belongs-to-the-wisdom-workers