The Gift of Struggle

1. Struggle is a Gift in Disguise

Although it’s uncomfortable, it’s the most honest and revealing measure of progress toward becoming the leader you desire to be.

Reframing adversity. Herrera's upbringing as a migrant worker, though filled with hardship, ultimately became his greatest asset. He realized that the resilience, work ethic, and perspective he gained from those experiences gave him an advantage in facing new challenges. This reframing of struggle as a gift is a central theme, encouraging readers to view their own difficulties as opportunities for growth and self-discovery.

Perspective shift. Herrera's father, despite enduring brutal conditions as a bracero, viewed his experience as winning the lottery because it allowed him to provide opportunities for his children. This powerful perspective shift highlights the importance of finding meaning and purpose even in the face of adversity. It's about recognizing the potential for growth and the lessons that can be learned from challenging situations.

Turning point. Herrera's experience in Army boot camp, where his background prepared him better than his peers, solidified his understanding of struggle as a gift. This realization allowed him to approach challenges with confidence and gratitude, knowing that his past experiences had equipped him for success. It's a reminder that our struggles can shape us into stronger, more capable individuals.

2. Share Your Story to Inspire Others

Leaders share their gifts with others.

Authenticity and vulnerability. Herrera emphasizes the importance of leaders sharing their personal stories, including their struggles and vulnerabilities. By opening up and being authentic, leaders can connect with their teams on a deeper level, fostering empathy and trust. This creates a more human and relatable leadership style, inspiring others to share their own stories and connect with the company's mission.

Purpose and meaning. Sharing his "bus story" with his company, Populus Group (PG), transformed the workplace. Employees connected with his purpose for creating PG, which was to provide opportunities for those who started out like him. This gave their work greater meaning and aligned everyone around a common goal. It demonstrates the power of storytelling in creating a shared sense of purpose and driving engagement.

Overcoming reluctance. Herrera admits his reluctance to share his story stemmed from fear of rejection and vulnerability. However, he realized that it was his responsibility as a leader to share his narrative and allow it to inspire and give meaning to the work people do. This highlights the importance of overcoming personal fears and embracing vulnerability in order to connect with and inspire others.

3. Integrity and Trust are Foundational

The trust people have in you is the most important asset you will ever own.

Keeping your word. Herrera's father's insistence that he attend a friend's wedding, even when his father was near death, underscores the importance of honoring one's word. This principle, fiercely protected by his father, became a cornerstone of Herrera's leadership philosophy. It highlights the significance of integrity and keeping promises, no matter how small, in building trust.

Modeling trust. As a leader, Herrera realized that his actions, more than his words, set the tone for the company. He recognized that even small lapses in integrity, such as being late to meetings or failing to return calls, undermined trust and made it harder for people to follow his lead. This emphasizes the importance of modeling the behaviors you want to see in your team.

Building trust daily. Herrera incorporated trust-building signals into his interactions, such as scheduling calls at unusual times to demonstrate his commitment to keeping his word. He also emphasized the importance of daily behaviors like candor, listening, and transparency. These practices transformed PG into a community built on trust and collaboration.

4. Vision Guides Culture

Culture is the feeling people get when they interact with your company.

Defining culture. Herrera defines culture as the feeling people get when they interact with your company, emphasizing that it's experiential and the hook that keeps people coming back. He argues that successful organizations are intentional about what they cultivate, citing examples like Nordstrom's customer service and Southwest Airlines' business recipe. This highlights the importance of consciously shaping the culture to align with your company's values and goals.

Building identity. To execute the culture you envision, you must focus on building identity, guiding behavior, and speaking a common language. This involves making sure everyone knows the vision of the culture, its purpose, and what it means to be a community member. It also requires overcommunicating how you expect everyone to behave and using common vernacular to reinforce the message.

Guiding principles. At PG, the guiding principles are:

• Give more than you take
• Speak from the heart
• Go off the beaten path

These principles reinforce the belief that collaboration, honesty, and innovation ground and sustain culture. By stating boundaries in the positive case, they are expansive, not restrictive.

5. Continuous Learning is Essential

If you want to be a wise leader someday, you must fiercely apply what you learn.

Application over theory. Herrera emphasizes that true transformation comes from applying what you learn, not just reading or studying. He shares his experience with Dr. Joe, who pushed him to not only read books but also to actively change his behavior based on the lessons he learned. This highlights the importance of putting knowledge into practice and continuously seeking ways to improve.

Seeking mentors. Herrera sought out mentors like Bill, who reinforced the necessity of being a real student. Bill's guidance helped him realize that his inconsistent approach would never work and that he needed to commit to continuous learning. This emphasizes the importance of finding experienced leaders who can provide guidance and accountability.

Building on strengths. Herrera learned that his job as a leader isn't to have all the answers but to know his strengths and work rigorously to sharpen them. Building on your strengths also highlights your weaknesses, allowing you to surround yourself with a team whose strengths complement your own. This emphasizes the importance of self-awareness and building a team that can compensate for your weaknesses.

6. Ask Questions to Understand

Your role as a leader is to give people confidence every time you give direction.

The "why" behind the question. Herrera learned that every question contains two parts: the "what" (the words) and the "why" (the reason for asking). He realized that most leaders don't respond to questions with discerning follow-up questions to better understand why the question was asked in the first place. This emphasizes the importance of getting to the root of the issue and understanding the underlying concerns.

Changing communication. Herrera shared his experience with his son, Santino, to illustrate the impact of "Stop" versus "Go" commands. This inspired him to evaluate how he was communicating with his team and to shift his approach to be more encouraging and supportive. It highlights the importance of being mindful of your tone and nonverbal communication.

Building confidence. Herrera emphasizes that your role as a leader is to give people confidence every time you give direction. They must feel that you understand their reasoning, and you must question "why" until you do. This requires keeping your powerful and unconscious body language in check and not leaving the discussion until that individual has a sense of optimism that they can get the job done.

7. Speak Openly and Honestly

One of the best compliments a leader will ever receive is to be told by their team that they are wrong.

Creating a safe space. Herrera realized that his team was afraid to challenge him, even though he encouraged them to be transparent. This was because he had reacted defensively in the past, creating a culture of fear. This highlights the importance of creating a safe space where people feel comfortable speaking their minds, even when they disagree with the leader.

Acknowledging feedback. Herrera learned to acknowledge opposing opinions with a simple "Thank you for saying that." This simple act of appreciation made his team more transparent and rewarded him with the gift of challenging him, making him a better leader. It emphasizes the importance of being open to feedback and not taking criticism personally.

Walking into fear. Herrera emphasizes that we need to walk right into the fear together and make it an opportunity to build trust. This requires being vulnerable and sharing your own fears, as well as creating an environment where people feel understood and supported. It highlights the importance of building trust as the most valuable currency you have as a leader.

8. Embrace Exploration and Innovation

We go off the beaten path!

Challenging the status quo. Herrera encourages people to challenge the company status quo and to view innovation as an everyday occurrence rather than an aberration. He uses the term "insultant" to describe someone who "consults from the inside," constantly looking for ways to improve processes and challenge assumptions. This emphasizes the importance of fostering a culture of curiosity and continuous improvement.

Service mapping. Herrera introduced the concept of "service mapping," which looks at every process through the customer's experience rather than the company's. This exercise helped to identify "pain points" that annoyed customers and ignited awareness about nonessential steps to remove, making things easier for the client. It highlights the importance of putting the customer first and constantly seeking ways to improve their experience.

After-action reviews. Herrera adapted after-action reviews from the Army to spark reflective conversations and make performance stronger the next time around. These reviews encourage open dialogue and procedural changes, fostering a culture of learning from mistakes and continuously improving. It emphasizes the importance of structured reflection and continuous improvement.

9. Resourcefulness Drives Creativity

The essence of resourcefulness is courage.

Doing more with less. Herrera learned from his upbringing and his time in the Army that resourcefulness is about doing more with less. He encourages leaders to challenge the way they're currently doing things and to focus on eliminating unnecessary work. This emphasizes the importance of creativity and finding innovative solutions to challenges.

Time horizon. Herrera uses a "Flush List" to categorize problems and opportunities based on their time horizon. This helps leaders prioritize their time and energy, focusing on the "big bets" that will have the greatest impact on the business. It highlights the importance of strategic thinking and prioritizing long-term goals.

The "gray conversation." Herrera encourages leaders to get comfortable with the "gray area" between saying yes or no to requests for more resources. This means stretching their teams, editing their processes, and applying energy and creativity to every problem. It highlights the importance of finding balance and not always relying on adding more resources to solve problems.

10. Accept Attrition with Grace

Everyone you hire started their career climb before you met them, and they will likely continue climbing for a long time after their tenure with your company is over.

Climbing different mountains. Herrera uses the metaphor of climbing Mount Rainier to illustrate that everyone is climbing their own mountains and that their goals and aspirations may not always align with the company's. This helps him to accept attrition with grace and to appreciate the contributions of those who choose to leave. It emphasizes the importance of honoring people's dreams and recognizing that their journey may take them in different directions.

Celebrating contributions. Herrera encourages leaders to celebrate the time they shared with those who leave and to maintain the connection. He views former team members as alumni of the company and recognizes that they may still make surprising contributions in the future. It highlights the importance of building relationships and maintaining a positive network.

Focusing on the present. Herrera emphasizes the importance of focusing on the team you have with you on the mountain, rather than being disheartened by those who have left. This helps him to stay present and to guide his teams as best he can for as far as they are willing to climb with him. It highlights the importance of being grateful for the present and not dwelling on the past.

11. Work Together Towards a Common Goal

Life Is Better Together.

Eliminating silos. Herrera realized that a lack of clarity around the company's top priority had created silos across teams, leading to rework and redundancy. To address this, he implemented a thematic goal model, crafting a single rally cry for a specified time period. This helped to unite the teams and eliminate the infighting that had been unintentionally encouraged.

Thematic goal model. The thematic goal model involves identifying the single most important priority for the organization and aligning everyone around it. This requires candid assessment, open communication, and a willingness to own your part in the problem. It emphasizes the importance of clarity and alignment in achieving common goals.

Building a united organization. Herrera emphasizes that it's far more productive to slow down and ask a clear and direct question: "What's our single most important priority?" By demanding that our people do more, we leave everyone irritated and pushing back on each other. If you want to build anything worthwhile, do it together.

Last updated: March 3, 2025