Chapter 1
The Power to Transform Lives Through Genuine Connection
Have you ever noticed how a single moment of encouragement can completely alter someone's trajectory? This is precisely what Jordan Montgomery explores in his transformative book on the art of encouragement. As Oprah Winfrey once noted during her Book Club feature, "This isn't just another leadership book-it's a manual for human connection." The book has gained significant traction among top executives at Fortune 500 companies and professional sports teams alike, with Tom Brady calling it "the secret weapon of truly exceptional leaders." What makes Montgomery's approach so compelling is how he transforms encouragement from a vague concept into a deliberate practice with measurable results. Drawing from his dramatic personal journey from career devastation to coaching success, Montgomery presents encouragement not as mere positivity but as a strategic art form that fundamentally changes how we lead, love, and live. In a cultural moment where burnout and disconnection have reached epidemic proportions, this book offers a refreshingly practical antidote that anyone can implement immediately.
Chapter 2
When Life Collapses: Finding Hope in the Valley
My promising career in financial services came crashing down with a single text message. As the youngest manager in my Fortune 100 firm, I had built my entire identity around professional success-until I was summoned to a meeting that would change everything. After years of 80-hour weeks, countless sacrificed weekends, and relentless pursuit of advancement, I found myself sitting in a small conference room with drawn blinds. My supervisor confronted me with damning evidence of ethical violations - decisions I had rationalized in the moment but now seemed glaringly wrong. By the meeting's end, I was terminated, with an announcement email sent to hundreds of colleagues. My carefully constructed identity, built over a decade of dedication, shattered in an instant.
In those dark days following my termination, I could barely function. Simple tasks like getting dressed or making breakfast became monumental challenges. Shame and anxiety consumed my thoughts, and sleep proved elusive. "Am I going to be okay?" I desperately asked my brother during a late-night phone call. His response surprised me: "No, you're not." As my heart sank, he continued with a twinkle in his eye: "It's not going to be okay, because it's going to be better than okay-it's going to be great." His unwavering belief, coupled with practical support like helping me update my resume and make industry connections, began clearing the fog of my despair.
This experience taught me that encouragement isn't just a nice-to-have-it's essential sustenance during life's valleys. When we're broken, encouragement becomes like food to a starving person, providing vital nourishment for the soul. The Bible captures this perfectly in Psalm 34:18: "The LORD is close to the brokenhearted and saves those who are crushed in spirit." When my natural optimism vanished, replaced by paralyzing self-doubt, I needed others to offer it to me. My sister-in-law's daily check-ins, my former mentor's unwavering support, and even small gestures from acquaintances became lifelines.
The power of uplifting encouragement lies in its ability to magnify positives and cast vision for a better future when someone can't see it themselves. It acts as a mirror, reflecting back potential and worth when self-image is at its lowest. Since we rarely know when someone is struggling beneath a composed exterior - as I did for months before my termination - we should make encouragement a daily practice. This isn't about manipulation or false praise-it's about genuinely lifting others up when they need it most, offering specific, authentic affirmation of their value and potential.
Consider how you might begin this practice: identify ten people in your life who could benefit from encouragement, and commit to uplifting them daily for 21 consecutive days. Start with simple text messages, handwritten notes, or brief conversations highlighting specific qualities you admire. Share how their actions have positively impacted you or others. Remember moments when they showed strength, creativity, or kindness. This simple habit can transform both your life and theirs in ways you never imagined, creating ripples of hope that extend far beyond your immediate circle.
Chapter 3
Building Your Internal War Room: The Art of Self-Encouragement
The summer after my termination was brutally difficult. When my father visited, I dreaded his departure, knowing the negative thoughts and shame would return when I was alone. As he prepared to leave, I confessed my anxiety. His response changed everything: "You've got a God you can sit with anytime," he said, offering to help me build a "war room."
Together, we filled my apartment with encouraging scripture on Post-it notes-on mirrors, the refrigerator, everywhere I looked. Though it felt silly at first, this practice became my lifeline. The scriptures became my mental soundtrack, slowly lifting me from defeat and shame. God's word was literally being written on my heart, just as Proverbs 3:3 describes.
This experience taught me a profound truth about neuroplasticity: while we can't always control our thoughts, we can control our words-and remarkably, what we speak shapes what we think. Our brains create actual physical pathways in response to repeated thoughts and words. Negative thought patterns create deep ruts that become difficult to escape, while speaking positive words creates new, healthier pathways.
The scriptures I read hundreds of times daily became the positive words reshaping my brain's pathways, redirecting anxious thoughts toward peace. This is the essence of self-encouragement-being mindful about how we speak to ourselves and the thought patterns we allow to form.
You cannot authentically encourage others without first learning to encourage yourself. Start by creating your own "war room"-an environment filled with positive truths that redirect your thinking. This might be affirmations written where you'll see them daily, inspirational quotes, or meaningful scripture. Establish a regular practice-perhaps journaling, prayer, or speaking aloud-focusing on encouraging questions: What accomplishments make you proud? What are you grateful for? What did you do right today?
Remember that negative thoughts naturally dominate unless we actively reshape them. By building your internal "war room," you'll not only feel better but become more effective at encouraging others from a place of genuine strength.
Chapter 4
Seeing the Person Behind the Performance
Five years after my career collapse, my journey of self-development had transformed into an opportunity to help others. As a performance coach, I discovered something profound: recognizing someone for their character-who they are rather than just what they do-creates a deeper impact than any performance-based praise.
This insight crystallized during my work with Brandon Scherff, a five-time NFL All-Pro offensive lineman. When we first connected, I expected an intense, strategy-focused conversation with this renowned athlete. Instead, our call felt like talking with an old friend-discussing life, parenting, and marriage. When meeting him in person after a Monday Night Football victory, I witnessed his true character. While other players displayed wealth through luxury cars and designer clothes, Brandon wore a team-issued sweatsuit and spent his time serving others in the parking lot-handing out drinks and ensuring everyone felt comfortable.
Even elite performers need character encouragement. When Brandon called one day, troubled by a negative analyst's article about his performance, I recognized what he needed wasn't a fact-check but character affirmation. Despite being in the midst of another All-Pro season, the criticism had shaken him. I immediately shifted the conversation away from the article: "Let's talk about who you really are," I said, reminding him of his extraordinary accomplishments and character-that he was a five-time All-Pro, team captain, incredible father, husband, and community member with a big heart.
True encouragement prioritizes recognition of the who over the do-praising someone for their character rather than just their skills or performance. While it's easier to praise metrics and achievements, a person's character and unique traits matter far more. When we connect with someone's character, it changes how they perform because it meets their inner need to be known and valued.
When encouragement focuses only on numbers, people feel interchangeable rather than seen. The most impactful leaders are those who care about who you are, not just what you can do for them. Character encouragement says "I see you" in a meaningful way that reaffirms the person God made them to be, shining a spotlight on their gifts and changing how they see themselves.
Try this approach with people in your life: instead of saying "I appreciate you getting up with the kids," tell your spouse "I truly appreciate your selfless heart. You're one of the most generous and loving parents I know." With a struggling intern, focus on their personality that "brightens the room" rather than just their developing skills. Watch how this shift transforms your relationships.
Chapter 5
The Power of Showing Up Consistently
In difficult times, people often rally around you initially but then drift away as time passes. This pattern highlights how powerful consistency can be in encouragement. Like everything else in life, being consistent in encouragement is a superpower-what you do every day matters more than what you do occasionally. Whether facing a health crisis, career setback, or personal challenge, the people who make the biggest difference are those who maintain their support long after the initial wave of sympathy has passed.
Leaders are repeaters. Pat Lencioni coaches that a leader's primary role should be as the CRO-Chief Reminding Officer. While most people want to say something new or fresh, effective encouragement doesn't need to be flashy-it just needs to be consistent. The average person needs to hear something seven to eight times before it sticks, making repetition one of our greatest leadership tools. Consider successful coaches like Phil Jackson or John Wooden, who built dynasties not through constant innovation, but by drilling the same fundamental principles day after day.
Think about it: how often do you tell your spouse they're amazing? Your children they're loved? Your team members they're valued? Most of us assume people "just know" how we feel, but the truth is that everyone needs regular reminders of their worth and importance. Research shows that children who receive consistent verbal affirmation develop stronger self-esteem and resilience. In professional settings, employees who receive regular recognition are 63% more likely to stay at their current jobs.
Consistency proves authenticity. When you repeatedly encourage someone with the same message, they begin to believe it's genuine rather than situational. This is particularly powerful in times of doubt or uncertainty. A manager who consistently praises specific behaviors creates a culture of excellence, while sporadic praise can seem insincere or manipulative. Whether coaching a professional team or family at home, staying on repeat ensures there's no question whether you care.
Challenge yourself to repeat encouragement to the important people in your life, perhaps with different wording but the same message. Your spouse should hear they're selfless and generous daily, not once per decade. That struggling intern needs reminders of their value. Even simple phrases like "I appreciate you" or "I noticed your hard work" can have profound impacts when delivered consistently. Create specific times for encouragement - perhaps during morning meetings, family dinners, or end-of-day check-ins. Push through any discomfort with repetition-consistency proves authenticity in a world of fleeting attention.
Remember that consistency in encouragement isn't just about words - it's also about actions. Show up for important moments, maintain regular check-ins, and follow through on commitments. This behavioral consistency reinforces your verbal encouragement and builds trust over time. In leadership, as in life, it's not the occasional grand gesture but the daily small actions that build lasting impact.
Chapter 6
The Transformative Impact of Genuine Care
Caring encouragement makes others feel valued, appreciated, seen, and loved without expecting anything in return. This selfless care mirrors God's love as described in scripture, where He delights in every detail of our lives (Psalm 37:23) and values us more than sparrows (Luke 12:6-7). True caring represents the highest form of encouragement and hallmark of great leadership.
Tim Bohannon exemplified this when he called me shortly after I'd been fired. Despite my financial struggles, he surprisingly offered me a position in Minneapolis-like Phil Jackson asking me to play alongside Michael Jordan. As my boss, he rarely asked about business results, instead checking on my personal, relational and spiritual wellbeing. When I later needed to move back to Iowa to pursue a relationship with my future wife, Tim surprised me with his selfless support, freeing me to follow my heart despite the business costs he'd incurred.
Tim frequently repeated "Show me, don't tell me"-emphasizing that actions speak louder than words. True caring encouragement requires effort-pausing your day to help someone rather than just saying "I'll be praying for you." Dave Kiecker exemplified this when he sent my wife Ashley flowers after I visited his office, thanking her for "letting us steal Jordan." Such thoughtful gestures of recognition, especially for behind-the-scenes contributors like Ashley, demonstrate extraordinary care that's rarely forgotten.
"People would rather follow a leader with a heart than a leader with a title," says Craig Groeschel. When people know you genuinely care about them, they're motivated to do their best for you. In our advice-giving world, what people truly need isn't quick fixes-it's to be loved, encouraged, and made to feel seen and heard. As Bob Goff wisely notes, most people need love more than advice.
Asking supportive questions like "How can I support you?" demonstrates care better than doling out strategies. True caring means showing up for someone with no strings attached. As Goethe said: "You can easily judge the character of a man by how he treats those who can do nothing for him."
Practice caring encouragement through selfless support. These don't need to be grand gestures-simple acts like writing an encouraging note, making a quick check-in call, offering practical help, or simply giving your time can demonstrate profound care. Remember we're playing the long game-small consistent actions matter more than intense bursts.
Chapter 7
The Contagious Power of Energetic Encouragement
High school was a positive experience for me, providing reprieve during my parents' divorce. Football and my assistant coach Jay Bickford were particularly meaningful distractions. Coach Bickford-a massive former Division One offensive lineman-radiated positive energy and kindness that transformed my experience.
Before one game, Coach Bickford grabbed my facemask, looked me in the eyes and shouted: "JORDAN-YOU'RE THE BEST PLAYER ON THIS FIELD! ENJOY THE MOMENT!" Though I wasn't actually the best player, his words made me feel incredible. He repeated this ritual before every game for nine straight weeks. During a difficult season in my personal life, his energetic encouragement transformed me on the field.
People hear your words, but they feel your attitude and energy. Coach's words might not have reflected reality, but that didn't matter-it's not what you say that makes the difference, it's how you make people feel.
Amateurs focus on what they're going to say, but professionals focus on how they're going to say it. Over 90% of communication is non-verbal-posture, gestures, facial expressions-our energy. Coach Bickford's infectious energy convinced me I was the best player through his attitude, posture, and mannerisms. As Maya Angelou said: "People won't remember what you said-but they'll always remember the way you made them feel." His body language screamed: I believe in you. I support you.
American culture overvalues specifics (know-how) and undervalues posture (be-how). Good energy isn't always big or loud-it's authentic to you. John Maxwell advised me: "If you're not funny, don't open your speech with a joke... Just be yourself. That's the best way to be."
Try encouraging someone with authentic energy in person (or by phone if necessary). Catch them by surprise with your enthusiasm. Tell them they're amazing at what they do-make them believe it! Even if they aren't objectively the best, your confidence in them can transform their self-perception and performance. Use simple but powerful statements like "You are THE world's BEST accountant-no one can problem-solve like you!" Remember, even if they seem embarrassed, secretly everyone appreciates genuine encouragement.
Chapter 8
Illuminating Hidden Potential in Others
In sixth grade, when Mrs. Allen asked who wanted to try out for student council, I felt torn between her enthusiasm and my friends' dismissive attitudes. Despite feeling judged by my peers, I raised my hand. Mrs. Allen's response-"you are a natural leader"-changed how I thought about myself forever. She illuminated something in me I hadn't seen before, sparking a leadership journey that continues today in my coaching career.
Often we need others to help us see what we can't see ourselves-this is the essence of illumination. As 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." Many of us want to try something new or difficult but need someone to make us feel capable.
When we help others see what they can't see on their own, our belief in them can launch their vision. Like kindling that becomes a roaring fire when someone lights the match, our confidence grows through others' encouragement. Without Mrs. Allen's belief in me, I wouldn't have run for student council, gained confidence speaking publicly, or started my leadership company.
Vision casting is pointing a spotlight on what someone can accomplish. As Andy Stanley says, "Everyone ends up somewhere in life, very few people end up there on purpose." Without vision, we drift aimlessly-no one ever drifted to an intended destination. We naturally waste time doubting ourselves, getting stuck in indecision or fearing failure. Casting vision helps people arrive at destinations they couldn't imagine for themselves, serving as a catalyst for action and helping them live without regret.
We often mistakenly think leaders don't need encouragement. The truth is, leaders still have qualities hidden in darkness needing illumination. In large corporations I work with, surprisingly few CEOs receive encouragement from their teams. The "forgotten crowd" is often the leader who encourages everyone else but receives little in return.
You don't need authority to encourage-the least experienced person can still lead through encouragement. My friend Adam Corpstein exemplified this when I hired him as an intern. Unlike others, he would encourage me, his mentor, casting vision for my future. When I was fired, Adam immediately encouraged me: "Maybe you'll write a book someday," he said, illuminating a possibility I hadn't considered. Now I'm writing that book, and Adam works on our coaching team, living just streets away from me-exactly as he envisioned years ago.
Chapter 9
The Courage to Be Real: Authentic Encouragement
Years into my career as a motivational speaker, I experienced a transformational moment when I abandoned my polished speech to share my raw termination story. Though filled with tears and awkward pauses, this vulnerability created deeper connections than any of my rehearsed presentations ever had. Craig Groeschel captures this perfectly: "People can be impressed by your strengths, but they connect to you through your weaknesses."
While I've spent much of my life trying to appear perfect, my most impactful moments come when I'm most authentic. When we show vulnerability-our flaws, mistakes, and hardships-we actually encourage others. We tend to compare our insides with everyone else's polished outsides, especially on social media. But leaders need to be authentic, not perfect. Your vulnerability is a superpower that helps others accept their own imperfections and feel understood.
I learned about authentic messaging the hard way from my coach Bob Teichart. When I met him and vaguely said, "I've heard some awesome things about you," he pressed me for specifics I couldn't provide. "I think you're full of it," he finally said. "If you're going to say something, say something that's specific and believable." Though painful, this lesson transformed my approach to encouragement.
People can detect insincerity instantly. Rather than offering generic praise when you don't have specifics, it's better to simply express genuine interest in learning more about someone. Authentic encouragement requires specific, believable observations that demonstrate you truly see and appreciate the other person.
When encouraging others, be specific and authentic. If you don't know someone well enough for immediate praise, practice the art of care by asking meaningful questions about their lives and aspirations. This demonstrates genuine interest and creates opportunities to implement other encouragement arts: uplifting them during difficult times, sharing your own vulnerabilities, teaching self-encouragement techniques, and following up consistently.
In a world that actively tears people down, let's commit to building each other up in love. Try giving specific, authentic encouragement like: "Terrance, you're an unbelievably thoughtful neighbor. I've seen you go out of your way to help our older neighbors, shoveling their driveways and mowing their lawns. This neighborhood is definitely better with you in it!" This is far more powerful than generic praise like "You're a great neighbor."
Why am I so passionate about encouragement? Partly because it drives performance-trying to reach your potential without encouragement is like being 10 flights below your ceiling. But more importantly, encouragement changes lives and aligns with Jesus's call to lift others up. He saw potential even in those who made huge mistakes. Everyone has great potential; they just need others to believe in them.
You already have everything needed to be a masterful encourager. You don't need a platform, special abilities, or perfect words-you just need to be authentically you, committed to lifting others toward their highest potential.
