Which Do You Want To Be?

In four decades of coaching and training leaders, I’ve noticed some consistent trends in those who rise to the top: they ask thoughtful questions (frequently beginning with the words “Why” or “How”), they listen carefully to the answers, and they have voracious appetites for ideas. In other words, they are perpetual learners.

Damon Lembi certainly understands that mindset. He’s chief executive of Learnit, a global leader in corporate training solutions that has upskilled nearly two million professionals over the past 27 years. Prior to his business career, he played major league baseball. Lembi is author of The Learn-it-All Leader.

What, you may ask, are the characteristics of a Learn-it-All leader? And how does a Learn-it-All leader think and act differently from the Know-it-Alls?

Lembi defines Learn-it-All leaders as those who possess humility, curiosity, and courage. “Humility allows them to appreciate the collective intelligence of the team, nurturing a culture of respect and open communication,” he says. “They’re not always trying to be the smartest in the room but value the input of others. Curiosity drives them towards constant growth and learning. Unlike a Know-it-All, they refuse to settle, and are always looking for new ideas.”

Courage, Lembi says, equips Learn-it-All leaders to face challenges, fears, and self-doubt head-on. They understand that growth requires leaving their comfort zone, and they’re prepared for it. On the other hand, he explains, Know-it-All leaders often cling to an image of infallibility, fearing the unknown and missing the benefits of collective wisdom. Essentially, learn-it-all leaders recognize the limitless journey of learning, while know-it-alls believe they’ve already peaked, overlooking an expansive unexplored landscape of unexplored knowledge.

Lembi believes great leaders are neither born nor made, but are instead in the making.

“In the same way they’re more interested in questions than answers, I think great leaders tend to focus on improvement over completion,” Lembi says”. They don’t see knowledge or even mastery as a place you arrive and settle down. They value their achievements as milestones along the way, but they’re not interested in being done.”

He says great leaders view the ever-changing world not as a threat, but as an opportunity for continuous learning and improvement. They’re not content with simply coasting. They actively pursue new knowledge, ideas, and perspectives, recognizing their understanding is not exhaustive.

“Exceptional leaders aren’t deterred by the risk of failure,” he says. “They make decisions with courage, accepting that outcomes may not always match their expectations. Even when they stumble, they own their mistakes, learn from them, and push forward with resilience and steadfastness.

As an example, he offers Winston Churchill who famously opined that “Success is going from failure to failure without loss of enthusiasm.”

“Churchill’s own road to success was paved with failures,” Lembi says.” His relentless enthusiasm and eagerness to learn from setbacks formed the crux of his leadership during challenging times, like World War II. He viewed failures not as defining his character, but as learning opportunities.”

Imposter syndrome can slow or even stymie a person’s development as a leader. Lembi points out that feelings of doubt or insecurity can sneak up on even the most accomplished and capable people. “Those who deny experiencing imposer syndrome are either dishonest or out of touch with reality,” he says.

He offers a three-step approach to dealing with such self-doubt:

• Hard work. Consistent dedication to practice and improvement instills confidence. The knowledge that you’ve given your best effort reduces anxiety and boosts self-assurance, even if outcomes don’t always align with expectations.
• Focus. Scattered attention and external interruptions hinder progress and amplify self-doubt. When deliberately concentrating on objectives, especially when facing fears, people empower themselves to tackle challenges with determination.
• Continuous learning. Embracing a mindset of lifelong learning reinforces confidence. It’s essential not to take ourselves too seriously, and to acknowledge that impostor syndrome often gets amplified in our own minds.

Lembi says impostor syndrome provides opportunities for self-discovery and growth. “It pushes us to expand our limits and achieve new heights,” he says.

He notes that as Doris Kearns Goodwin observed in Team of Rivals, “Success is not final, failure is not fatal: It is the courage to continue that counts.”

“Embracing the journey, learning from experiences, and letting them fuel our growth,” Lembi says, “are the keys to overcoming impostor syndrome and reaching our true potential.”

Obtaining—and acting on—honest feedback is a critical element in a person’s development. Lembi offers insights on how to get the two-way communication flowing.

“Having come into business from baseball, where coaches don’t pull their punches, I’ve been very deliberate about encouraging equally frank (if less profane) feedback from my [business] teams,” he says. “But it’s not as easy to get as many leaders think. In fact, it’s a great litmus test. If you haven’t had someone tell you something at least a little hard to hear in the last six months, you’re probably not doing enough to breakdown the social, cultural, corporate, and financial barriers that keep people from speaking candidly.”

Lembi has found that by building trust and creating a safe space for open dialogue, a leader can establish an environment where feedback flows freely.

“When your team believes you won’t get defensive and that their opinions are valued, they will be more willing to share their honest thoughts,” he says.

One way he prompts people to offer candid feedback: he sends them a recording of a podcast he recently did and asks for their thoughts. He might specifically mention areas where he feels he could improve—such as his answer to a particular question—and then solicit their input on his overall performance.

Of course, receiving candid feedback in only part of the communication equation. A good leader must also be an effective listener.

“Many leaders over-estimate the quality of their own listening habits because they don’t understand what it actually means to be a great listener,” Lembi says. “They think they’re listening effectively, but in reality, they fall short.”

He says true listening goes beyond hearing words. It requires active engagement, attentiveness, and empathy. “Great leaders recognize that effective listening is not just about receiving information, but about making the person they’re speaking with feel valued and heard. It’s a win for both the listener and the speaker. By creating a safe space for open communication and genuinely listening, leaders can establish deeper connections, foster trust, and gain valuable insights. Listening is a tough skill to learn, as it takes mental energy and focus. But it’s without a doubt a must-have if you want to be considered a great leader.”

How can Learn-it-All leaders benefit from—rather than feel threatened by—technology advances like artificial intelligence? Lembi has given that a lot of thought.

“CHATGPT and other AI-related tech are making headlines everywhere,” he notes. “There are those who view it as doomsday, with robots taking over the world. Others believe AI will save the world. In my opinion, it’s too early to tell what the long-term implications will be on the workforce. I tend to lean towards the notion of increased productivity and job creation, drawing from what we’ve seen in previous industrial revolutions.”

Lembi believes the advantage that “Learn-it-All” leaders have lies in their ability to adapt to change, their innate curiosity, and their learning agility. “I’m confident,” he says, “that such leaders will leverage new technological advances to augment their capabilities and thus continue to thrive in the workforce.”