The Art of Encouragement

The Art of Encouragement Plot Summary

Introduction

In a world where negativity often dominates headlines and division seems to be the norm, the simple act of encouragement stands as a powerful antidote. Though we all inherently understand the value of uplifting words, there exists a striking gap between knowing and doing. Most people recognize that encouragement matters, but few consistently put it into intentional practice. This disconnect represents one of the greatest missed opportunities in our relationships, workplaces, and communities. The pages ahead explore a transformative truth: encouragement is not merely a nice addition to our interactions—it's essential oxygen for the human soul. Everyone speaks and understands this universal language, yet too few people actively speak it. Whether you're leading a team, nurturing a family, or simply moving through your day among strangers, mastering the art of authentic encouragement will profoundly impact both your life and the lives of those around you. The principles may seem simple, but their application requires intention, practice, and heart—elements that, when combined, create ripple effects of positive change that extend far beyond what you might imagine.

Chapter 1: Recognize Character Over Accomplishment

At the heart of genuine encouragement lies a simple but profound distinction: recognizing who someone is rather than merely what they do. When we praise character—the innate attributes, moral qualities, principles, and personality traits that make someone uniquely themselves—we acknowledge their intrinsic value as a human being. This form of encouragement runs deeper than congratulating achievements or skills, which anyone could potentially acquire. Brandon Scherff, a five-time NFL All-Pro offensive lineman, demonstrates how even elite performers need character-based encouragement. Despite his tremendous success on the field, Brandon experienced a moment of insecurity after reading a critical article about his performance. When he called his performance coach Jordan feeling "sideways" about the criticism, Jordan responded not by analyzing the football critique but by reminding Brandon of his character: "You're an incredible, loving father. You are a great husband. You are surrounded by a community who loves you and who you love back. You have one of the biggest hearts of anyone I have ever met, and you have this inspiring ability to remain humble, sincere, and down-to-earth, despite your incredible success." This shift in focus—from the critique of his performance to the affirmation of his character—completely transformed Brandon's perspective. The conversation ended with laughter and renewed confidence, demonstrating how powerful it can be to remind someone of who they truly are, especially in moments of doubt. When encouraging others, we often default to performance-based praise because it's easier and more observable. We notice the team member who exceeded their sales goal and naturally congratulate them on the achievement. While acknowledging results has its place, connecting with someone's character activates their deeper potential and makes them feel irreplaceable rather than interchangeable. To practice character-focused encouragement, take time to truly understand the people around you. Notice their unique traits, values, and what drives them. When you offer praise, specifically mention qualities like integrity, creativity, perseverance, or compassion. For example, instead of saying "Great job on that presentation," try "Your thoughtfulness and dedication really shone through in how well-prepared you were. I've always admired your commitment to excellence." Remember that everyone possesses valuable character traits, even those who might struggle with performance in certain areas. By consistently recognizing these qualities, you help others see themselves more clearly and feel valued for who they are, not just what they produce.

Chapter 2: Practice Consistent Encouragement Daily

Consistency transforms encouragement from a momentary boost into a life-changing force. The difference between occasional and consistent encouragement is like the difference between a single rainfall and steady irrigation—one briefly refreshes while the other sustains growth over time. Rob Victor demonstrated this principle powerfully when his friend Jordan experienced a public career setback. While many people initially reached out with support, most eventually faded away as time passed. Rob, however, called Jordan every single day, often receiving no answer. When Jordan finally picked up, intending to politely ask for space, Rob simply said: "Dude... it's all good. I'm just calling to tell you that I love you, and I'm going to call you every single day to check on you, and remind you that I am thinking of you. When you're ready to talk, we can talk." True to his word, Rob continued his daily calls, eventually becoming a trusted confidant during a critical healing period. This persistence created a profound realization for Jordan: "You're getting a gift at 27 years old that most people won't get until they're older—it's the gift of finding out who your real friends are. Who loves you because of who you are, and who loves you because of your status, your position, and your work." The consistency of Rob's encouragement revealed its authenticity and transformed a difficult season into one of valuable perspective. Many leaders understand the importance of communication but underestimate the need for repetition. Andy Stanley wisely observed that "the cost of under-communicating will be far more significant than the cost of over-communicating." Most people need to hear something seven to eight times before it truly registers. This is why effective leaders embrace the role of "Chief Reminding Officer"—consistently reinforcing important messages and encouragement. To implement consistent encouragement in your daily life, establish simple habits. Perhaps send a brief encouraging text to someone different each morning, or end team meetings by recognizing someone's contribution. Make notes about important events in people's lives so you can follow up consistently. The key is regularity—even small encouragements delivered consistently create a powerful cumulative effect. When you feel reluctant to repeat encouragement, remember that most people are starving for affirmation. Your words might be the only positive message they hear that day. By making encouragement a daily practice rather than a rare occasion, you create an environment where people feel consistently valued and supported.

Chapter 3: Show Genuine Care Through Action

Authentic encouragement transcends words and manifests through tangible care. When someone knows you genuinely care about them as a person—not for what they can do for you—your encouragement carries transformative power. This type of caring encouragement prioritizes making others feel valued, appreciated, seen, and loved, without requiring anything in return. Tim Bohannon exemplified this principle after Jordan's public firing from a financial services firm. As a managing partner at another branch, Tim unexpectedly called Jordan during this difficult period and offered him a position in Minneapolis. What followed wasn't just a job offer but a demonstration of extraordinary care: Tim showed Jordan around the city, rolled out the metaphorical red carpet, and consistently prioritized Jordan's wellbeing over business metrics. During their two years working together, Tim regularly checked in with questions like: "How are you doing? In your personal life, relationally, spiritually? Do you feel valued? Appreciated? What could be done better?" This caring approach continued even when Jordan needed to move back to Iowa to pursue a relationship with his future wife. Despite the financial investment Tim had made in relocating Jordan, his response was simple and supportive: "Well then, you should move back to Iowa... You can do anything you want to do." Tim demonstrated that Jordan mattered to him as a person, not just as an employee. To implement caring encouragement, remember that actions speak louder than words. Instead of just saying "I'll be thinking of you" when someone faces difficulties, take concrete steps to help. This might mean writing a handwritten note, making a personal phone call, running an errand, or preparing a meal. Dave Kiecker demonstrated this by sending flowers to Jordan's wife Ashley after Jordan spent time consulting with Dave's firm, with a note saying: "Ashley—thank you for letting us steal Jordan the last twenty-four hours. God bless." The key to caring encouragement is asking questions that help you understand how to best support others: "How can I support you? What do you need from me? What can I help you with?" This approach is more powerful than offering unsolicited advice. As Bob Goff wisely notes, most people need to be loved more than they need advice. Remember that true caring means showing up because you value the person for who they are, with no strings attached. The measure of your character, as Goethe observed, can be judged by how you treat those who can do nothing for you.

Chapter 4: Bring Authentic Energy to Your Interactions

The energy we bring to our encouragement often matters more than the words we choose. People hear what we say, but they feel our attitude, enthusiasm, and presence. This dynamic plays a crucial role in how our encouragement lands and transforms others. Jay Bickford, a high school football assistant coach, demonstrated this principle powerfully for a young player going through his parents' divorce. Before each game, Coach Bickford would grab the player's face mask, look him directly in the eyes, and enthusiastically declare: "JORDAN—YOU'RE THE BEST PLAYER ON THIS FIELD! ENJOY THE MOMENT!" While the objective truth of this statement might have been questionable, the energy and conviction behind it transformed the player's self-perception and performance. For nine consecutive games, Coach Bickford repeated this energetic encouragement ritual. His presence, posture, tonality, and body language communicated a powerful message: I believe in you. I support you. This wasn't merely about football performance—it provided essential emotional support during a difficult family situation, offering a temporary transformation into someone who felt capable and confident. Maya Angelou captured this phenomenon perfectly: "People won't always remember what you said—but they'll always remember the way you made them feel." Coach Bickford's energy transferred belief, which is why basketball coach John Calipari reminds coaches that "Your body language never whispers—it screams." To bring authentic energy to your encouragement, focus less on crafting perfect words and more on how you deliver them. Be fully present and undistracted when encouraging others. Maintain eye contact, use appropriate physical touch like a handshake or high-five when appropriate, and adjust your tone to match the significance of your message. Importantly, authentic energy doesn't mean you need to be loud or extroverted. Your energy should align with your natural personality—you're most effective when you're most authentic. As John Maxwell advised a nervous public speaker: "If you're not funny, don't open your speech with a joke... Just be yourself. That's the best way to be." Avoid trying to match someone else's style or energy when encouraging others. Instead, bring your unique energy signature to each interaction. Whether you're naturally exuberant, calmly reassuring, thoughtfully attentive, or warmly engaging, your authentic energy will resonate more deeply than any forced enthusiasm ever could.

Chapter 5: Illuminate Hidden Potential in Others

Some of the most powerful encouragement occurs when we help others see qualities in themselves they hadn't recognized. This illuminating encouragement serves as a catalyst, highlighting potential that might otherwise remain dormant. Mrs. Allen, a sixth-grade teacher, demonstrated this transformative power when she asked her class who wanted to try out for student council. As young Jordan hesitantly raised his hand, feeling the judgment of his peers, Mrs. Allen enthusiastically declared: "I think that's a great decision, Jordan! You are a natural leader." This simple statement—recognizing a quality Jordan hadn't seen in himself—changed his life trajectory. It began a leadership journey that continued through middle school, high school, college, and eventually into his career as a leadership coach. Where energetic encouragement fans existing flames, illuminating encouragement strikes new matches in areas yet to light up. As Jon Gordon observes, leadership involves transferring both energy and belief. Mrs. Allen transferred belief in Jordan's leadership capabilities before he saw them himself, creating a cascading effect that shaped his entire future. This principle of illumination acknowledges that we often need others to help us see what we can't recognize ourselves. As legendary football coach Tom Landry said, "A coach is someone who tells you what you don't want to hear, who has you see what you don't want to see, so you can be who you have always known you could be." The reality is that we are all moments away from becoming better versions of ourselves—we just need someone to believe in us and illuminate the path. To practice illuminating encouragement, first observe others carefully. Notice their natural gifts, interests, and potential that they might overlook. Then, find specific opportunities to point these out. For example, after witnessing someone peacefully resolve a conflict, you might say: "Have you ever considered a role in mediation? You have a natural gift for helping people find common ground." Illuminating encouragement extends beyond peer relationships. Remember to "lead up" by encouraging those in authority positions above you. Adam Corpstein demonstrated this when encouraging his former supervisor Jordan after a professional setback: "This doesn't change anything about your gifts, man, or my level of respect for you. One day this will all make sense. Maybe you will write a book about what you've been through." By intentionally choosing to see, amplify, and project the good in others—especially qualities they don't yet recognize in themselves—you become a catalyst for their growth and development.

Chapter 6: Elevate Others Through Strategic Connections

One of the most powerful forms of encouragement involves elevating others—helping them receive the recognition they deserve and creating new opportunities through strategic connections. This practice of elevation puts your social capital to work for someone else's benefit. David Nurse, a former NBA shooting coach turned speaker and entrepreneur, exemplifies this art of elevation. When Jordan first invited David to speak in Iowa, David arrived with an enthusiastic greeting that made Jordan feel like a longtime friend, despite never having met in person. Throughout their time together, David asked countless questions, offered generous compliments, and showed genuine interest in everyone he encountered. This wasn't a one-time performance but David's consistent approach to relationships. He regularly reaches out with messages like: "Hey Jordan, just thinking of you, brother; I want to connect you with this person..." or "Jordan, I have an amazing idea for you..." Through these ongoing connections, David has introduced Jordan to influential thought leaders who have become mentors and friends, including Brad Lomenick, who in turn connected Jordan to others like John Maxwell and Patrick Lencioni. The formula for becoming a natural "elevator" like David is surprisingly simple: ask more questions than everyone else, see the good in people, point it out to others, and find ways to help those people. This approach makes someone a "people magnet" and a catalyst for others' success. To practice the art of elevation in your own life, look for opportunities to publicly praise others. Use your "megaphone"—whether literal or figurative—to highlight someone else's contributions. This could mean introducing them to someone who might benefit from their services, writing a review for their business, endorsing them on LinkedIn, promoting them on social media, or nominating them for recognition. When giving speeches or presentations, prepare by learning about people in the audience who deserve recognition but might be overlooked. Rather than highlighting top performers, focus on those who quietly hold teams together. When you elevate these individuals publicly, it creates a wave of gratitude that benefits both the recipient and everyone witnessing the recognition. The beauty of elevation is that it demonstrates vulnerability and authenticity. Using your own moment in the spotlight to praise others catches people by surprise and draws them in. It creates meaningful connections and fosters a culture where people feel valued not just for what they do, but for who they are.

Chapter 7: Serve Without Expectation of Return

The highest form of encouragement comes through selfless service—making someone else's goals and agenda your priority without expectation of return. This serving encouragement demonstrates authentic care in its purest form. Mark Cole, CEO of Maxwell Leadership enterprises, captured this principle perfectly when asked what advice he would give emerging leaders: "Find out what the leader's agenda is and make that your agenda for a season." This wisdom inspired Jordan to reach out to Jon Gordon, a respected leadership author and speaker, with an unusual proposal: "I'd love to make your agenda my agenda for a year. I know there are things you care about that I would love an opportunity to help you with. I don't expect you to respond right this moment, and I don't need anything in return, but if I can serve you for this year, you can count me in." Gordon accepted this offer, and Jordan began serving by helping organize events, handling logistics, recruiting sponsors, and promoting Jon's work. This service wasn't performed for payment or recognition—it was simply about learning from Jon and supporting his mission. After a successful event in Iowa, Jon asked, "Don't you want anything out of this? I want to make sure I'm helping you," to which Jordan replied that valuing Jon's mentorship was enough. This selfless approach ultimately led Jon to become deeply invested in Jordan's growth: "Look, I'm all in on you. Anything to help you grow." This experience illustrates what Patrick Lencioni calls the counterintuitive "personal economics" of service: "When the personal economics don't make sense, when you're not keeping score, when you're focused on bringing value without any strings attached, that's usually when you receive the most value in return." Mike O'Connell, pastor of Love Church and former college football team captain, exemplifies this principle. Despite being a gifted communicator, Mike left a successful medical sales career for an entry-level church position, driven by a deeper purpose. At a leadership event where he could have been a featured speaker, Mike instead arrived early to help set up, stayed late to clean up, and encouraged the actual speakers afterward—all without seeking recognition. To implement serving encouragement in your life, first identify who you want to serve. Choose someone whose mission aligns with your values—someone you feel excited about supporting. Then, seek to understand what truly matters to them by asking thoughtful questions. The key is to go beyond surface-level inquiry with "second questions" that dig deeper. For example, after learning someone enjoys painting, rather than shifting to your own experience with art, ask: "Do you have a favorite painting that you've done, and if so, what did you love about it?" Remember that time is our most valuable resource to give. As Dale Mullikin demonstrated through his regular Bible study meetings with Jordan, consistent investment of time in others without expectation of return creates profound encouragement that can shape lives for years to come.

Summary

Throughout these pages, we've explored how encouragement transcends simple positivity to become a transformative force in relationships, workplaces, and communities. The arts of recognizing character, practicing consistency, showing genuine care, bringing authentic energy, illuminating potential, elevating others, and serving selflessly work together to create meaningful connections that can literally change lives. As Jordan Montgomery discovered through his own journey, "We are all just moments away from being the best version of ourselves. Everyone around us is moments away from their best life, as well. They just need someone to believe in them." Your challenge now is to become fluent in this universal language of encouragement. Begin today by identifying one person in your life who could benefit from authentic encouragement. Rather than offering generic praise, recognize a specific character quality, show consistent support, demonstrate genuine care through action, bring your authentic energy, illuminate potential they may not see, connect them with opportunities, or serve their needs without expectation of return. Remember that in a world actively seeking to tear us down, your choice to build others up becomes not just a kind gesture but a revolutionary act of love.

About Author

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Jordan Montgomery

Jordan Montgomery is a performance coach, keynote speaker, and the founder of Montgomery Companies. He specializes in helping sales professionals and leaders achieve high performance. Montgomery is known for his high-energy speaking style and his focus on the importance of trusted relationships in business.\n\nHe is the author of The Art of Encouragement: How to Lead Teams, Spread Love, and Serve from the Heart. Montgomery argues that the most underrated leadership tool is encouragement. He distinguishes between empty flattery and genuine, specific affirmation that builds confidence. His work encourages leaders to be "dealers of hope," fostering environments where people feel seen and valued.

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