As we close out a strong year for The Leadership Habit Podcast, we are revisiting three of the most impactful conversations from 2025. These episodes challenged conventional thinking, encouraged deeper reflection, and offered leaders practical insight for navigating change. Our Best of 2025 series brings these standout conversations back as we look ahead to new voices and ideas in 2026.

The second episode in this series features leadership strategist and author Caroline Stokes. In Emotional Intelligence Still Matters in the Age of AI, Caroline explores the mindset shifts leaders must make to remain effective in a world shaped by artificial intelligence, climate disruption, and societal change.

This conversation challenges outdated leadership models that prioritize speed and scale over emotional awareness. Caroline explains why emotional intelligence, radical listening, and trauma-aware leadership are not optional skills but core capabilities for leading in a polycrisis era. As technology reshapes work, leaders must focus just as much on how people experience change as on the change itself.

Revisiting this episode is a timely reminder that the most future-ready leaders are those who combine adaptability with empathy and clarity. Rather than resisting uncertainty, Caroline encourages leaders to meet it with curiosity, courage, and a willingness to rethink how leadership systems are designed.

We look forward to sharing more conversations with innovative and forward-thinking leaders in 2026. Until then, this episode remains one of the most important discussions of the year for leaders preparing for what comes next.

Listen to the Best of 2025 episode: Emotional Intelligence Still Matters in the Age of AI with Caroline Stokes

The post Best of 2025: Emotional Intelligence Still Matters in the Age of AI with Caroline Stokes appeared first on Crestcom International.

As we wrap up another incredible year on The Leadership Habit Podcast, we are revisiting three of our most impactful conversations from 2025. These episodes sparked reflection, inspired change, and created real momentum for leaders across industries. To celebrate the year, we are launching a short series called Best of 2025.

Our first featured episode returns to a listener favorite: How to Make a Purpose Pivot: Finding Balance and Fulfillment with Melissa Gonzalez. In this conversation, Melissa shares how leaders can step back, realign their energy, and redefine what meaningful success looks like. Her insights continue to resonate, especially during moments of transition and year-end reflection.

This replay is the perfect reminder that leadership growth often begins with a pause. As you prepare for the year ahead, Melissa Gonzalez offers a powerful guide for reconnecting with intention and building a more balanced approach to work and life.

We look forward to bringing even more innovative voices and fresh perspectives to The Leadership Habit Podcast in 2026. Until then, enjoy this standout episode and revisit the ideas that shaped our conversations this year.

The post Best of 2025: How to Make a Purpose Pivot with Melissa Gonzalez appeared first on Crestcom International.

Conflict is part of being human, but many leaders still struggle to approach difficult conversations in a healthy, productive way. Whether it shows up as tension on a team, discomfort around identity-based issues, or uncertainty about when to speak up, many professionals have never been given the tools to navigate conflict with confidence.

In this episode of The Leadership Habit Podcast, host Jenn DeWall speaks with Dr. Jen Fry, a social justice educator, speaker, and researcher who helps individuals and organizations understand how identity, communication, and power dynamics shape the way we engage with one another. Through her deeply practical and accessible approach, she shows leaders how to build stronger relationships, develop healthy boundaries, and embrace conflict as an opportunity for growth.

Dr. Jen Fry is the founder of JenFryTalks, a social justice education firm that works with organizations, teams, and leaders to help them better understand race, identity, conflict, and communication. With a background in collegiate athletics, a doctorate focused on social justice and higher education, and years of experience coaching leaders through difficult conversations, Dr. Fry brings a grounded and approachable style to complex topics. She has worked with companies, universities, and sports organizations across the country, helping people understand how identity shows up in everyday interactions and how to communicate compassionately, directly, and effectively. Her work has been featured in The New York Times, ESPN, NPR, and other major outlets.

Many professionals have been conditioned to think of conflict as something to avoid. Dr. Fry challenges this belief by explaining that conflict is not inherently harmful. It is simply a signal that something needs attention. When handled with clarity and care, conflict creates opportunities to repair, improve, and deepen relationships.

She explains that conflict avoidance often comes from fear. People fear being misunderstood, disliked, or labeled as difficult. As a result, they gloss over issues that need to be addressed, causing those small moments to grow into long-term resentment. Healthy conflict, on the other hand, creates space for honesty, accountability, and trust.

Dr. Fry emphasizes that leaders must get comfortable being uncomfortable. Growth requires willing participation in conversations that may feel awkward or tense. By learning to name what is happening, set appropriate boundaries, and stay present in the moment, leaders can strengthen their teams and reduce long-term friction.

Managing conflict requires understanding your own identity and how it shapes how you show up. Dr. Fry encourages leaders to consider how their lived experiences, cultural background, and social identity shape their lens.

For example, someone who grew up in a family that avoided conflict may naturally default to silence. Someone who learned early in life that speaking up had negative consequences may hesitate to voice concerns. Someone who carries marginalized identities may navigate conversations with stakes or risks different from those of colleagues who hold more privilege.

Recognizing these influences is not about judgment. It is about awareness. When leaders understand their own communication patterns, they can approach conflict more intentionally instead of reacting from old habits.

One of the most powerful messages from Dr. Fry is that boundaries are not barriers. They are tools for clarity, safety, and mutual respect. Boundaries allow individuals to say what they need, articulate what is not acceptable, and protect their emotional and psychological well-being.

Dr. Fry explains that many people struggle with boundaries because they confuse them with ultimatums. Boundaries are not threats. They are statements about what you can and cannot manage. For example:

Healthy boundaries help teams function more effectively. They reduce assumptions, prevent miscommunication, and build trust.

Another key insight Dr. Fry highlights is the difference between intent and impact. Good intentions do not erase harm. Leaders often justify their actions by explaining what they meant rather than acknowledging the other person’s experience.

Dr. Fry recommends focusing on impact first. When someone is hurt, the priority is to understand the harm, take responsibility where appropriate, and repair the relationship. This approach builds credibility and strengthens team cohesion.

Throughout the episode, Dr. Fry shares practical strategies leaders can use to navigate challenging conversations with more skill and confidence. A few include:

These simple practices can shift even the most tense conversation into a constructive one.

Dr. Fry emphasizes that leaders must learn to regulate their emotions during conflict. This includes being aware of physiological responses such as tension, increased heart rate, or defensive body language. Emotional regulation allows leaders to stay present, think clearly, and communicate intentionally.

She encourages leaders to develop a toolkit of grounding strategies. These may include mindful breathing, taking a brief pause, writing down thoughts before responding, or seeking support from a trusted colleague. Emotional regulation is not about suppressing feelings. It is about creating enough space to respond thoughtfully instead of reacting automatically.

At Crestcom, effective leadership requires courage, clarity, and the ability to navigate conflict with compassion. Our leadership development programs help leaders build the self-awareness, communication skills, and emotional intelligence needed to create strong, inclusive teams. Participants learn how to have difficult conversations, set healthy boundaries, and build environments where people feel respected and heard.

These skills are essential for building trust and driving meaningful results. When leaders approach conflict with intention and care, they create cultures that are resilient, collaborative, and aligned.

Listen to the full episode with Dr. Jen Fry to learn how you can navigate conflict more confidently and strengthen your leadership presence.

To bring these concepts to your team, request a complimentary two-hour leadership workshop at crestcom.com/freeworkshop.

The post How to Navigate Conflict and Set Boundaries at Work with Dr. Jen Fry appeared first on Crestcom International.

The latest episode of The Leadership Habit Podcast welcomes globally recognized leadership coach Will Linssen to discuss how leaders can drive measurable results through better coaching. Hosted by Jenn DeWall, this conversation explores what separates good leaders from great ones and why sustainable leadership growth depends on one crucial shift: moving from know-how to show-how.

Leadership coaching has become one of the most effective ways to enhance results and strengthen teams, especially when paired with comprehensive leadership development programs.

Will Linssen is one of the world’s top executive coaches and the CEO of Global Coach Group. Named the world’s number one leadership coach by Global Gurus and the top coach trainer by Thinkers50, Will is also a Master Certified Coach through the International Coaching Federation (ICF), the highest professional designation in the field.

He is a number one Amazon international bestselling author and serves as an advisor to the Harvard Business Review, shaping global conversations around leadership development, coaching, and performance growth. Will’s work has influenced more than 100,000 leaders worldwide through data-driven coaching frameworks designed to deliver measurable impact for leaders, their teams, and their organizations.

Leadership today is harder than ever. Teams are stretched thin, priorities are constantly shifting, and leaders are expected to balance results, engagement, and well-being all at once. As Jenn DeWall noted during the episode, “Being a leader today is challenging. Being a coach is hard, especially if you’re unfamiliar with the tools or best practices within it.”

Will agrees—and he believes much of the problem starts with how we prepare people to lead. “Most people never got any education in people skills,” he explains. “They step into leadership roles without preparation, and organizations just say, ‘Now it’s up to you.’ It’s like becoming a parent with no manual.”

That gap between what leaders know and what they actually do creates frustration, burnout, and disengagement. It’s why many leaders, despite their best intentions, struggle to truly develop their teams or sustain results.

One of Will Linssen’s central insights is that most leaders don’t fail because they lack knowledge—they fail because they lack application.

“Most leaders we work with already know the right thing to do,” he says. “The challenge isn’t know-how. It’s show-how—doing the right things consistently so it impacts the people around them.”

When leaders are overwhelmed, buried in meetings, or constantly reacting to problems, their good intentions don’t translate into meaningful behavior. As Will puts it, “When things heat up, the show-how suffers, and that’s how leadership effectiveness suffers.”

This approach echoes the principles discussed in Crestcom’s Be the Coach They Need training module, which focuses on helping leaders turn awareness into consistent behavior. By choosing just two key areas to improve—and committing to practice those behaviors daily—leaders can make visible, lasting progress.

At the core of Will’s method is the idea of a Triple Win—helping leaders grow, improving team performance, and achieving better organizational results simultaneously.

He explains, “We reverse engineer success. We define what success looks like for the leader, the team, and the business, then build a plan to get there.” This data-backed approach has been tested with more than 100,000 leaders worldwide, achieving a remarkable 95% success rate in measurable improvement.

Here’s how the framework works in practice:

This process not only creates accountability but also builds shared ownership of the change. “Leadership,” Will emphasizes, “is about co-creating change with coworkers. When the leader and the team work together, performance must increase. It always works.”

Even with a solid process, many organizations struggle with one key challenge—getting honest feedback. Employees often hold back from sharing candid observations out of fear of retaliation or hierarchy.

Will’s advice is simple but powerful: create psychological safety from the start. “Before sending out a 360-degree survey, ask the leader to send an email inviting open and honest feedback,” he says. “When leaders show humility and curiosity, people respond with candor.”

This step transforms a typical evaluation into a collaborative experience. Will adds, “When coworkers see that the leader is serious about improving and that their input is valued, they become part of the change process.”

He also emphasizes combining quantitative data from surveys with qualitative insights from behavioral interviews. This two-part approach provides a complete picture of a leader’s strengths and development opportunities—and helps avoid blind spots that pure numbers can miss.

Will’s approach also reinforces the value of building a coaching culture, where feedback, accountability, and trust fuel performance improvement at every level.

Of course, insight alone doesn’t drive change—action does. Will recommends that leaders invest about 2% of their monthly work time—roughly four hours—into reflection and implementation. “Five minutes a day and a little discipline go a long way,” he explains.

This consistent, focused effort turns new behaviors into habits that eventually shape culture. Over time, leaders move from conscious practice to automatic execution, and their teams begin to mirror that growth.

Jenn DeWall summarizes it well: “Leadership isn’t about grand gestures. It’s about small, consistent actions that improve how we think, behave, and interact.”

Even the best coaching plans face resistance. Some leaders struggle to control emotions, others lose focus or motivation. Will stresses the importance of addressing these issues directly through honest conversation and self-reflection.

“When something goes wrong, ask: what was the impact of my behavior?” he says. “You always have the right to be upset—but it comes with consequences. If you want better results, you have to choose different behavior.”

That mindset—taking responsibility for one’s influence—is what separates average leaders from exceptional ones. As Will notes, “It’s not about perfection. It’s about progress. Pick two things you’re excited to improve, involve your team, and stick with it.”

Perhaps the most powerful message from the episode is Will’s reminder that leadership is not a solo journey. “Leadership coaching for leaders getting better is actually simple,” he says. “It’s not about more know-how. It’s about show-how. And the coworkers are the holy grail of creating forward momentum—because now it becomes a we movement, not a me movement.”

That shift—from self-improvement to collective growth—is what creates lasting cultural change. When leaders model vulnerability, consistency, and collaboration, their teams follow.

Listen to the full episode for all the great insights Will and Jenn have to offer! Then, to explore Will Linssen’s proven approach in greater depth, check out his book, Triple Win Leadership Coaching, available on Amazon and major booksellers.

And if this episode inspires you to strengthen your own leadership skills, Crestcom offers a powerful next step. You can request a complimentary two-hour leadership workshop designed to help your team enhance decision-making, build trust, and increase accountability. Visit crestcom.com/freeworkshop to get started.

The post How to Drive Results as a Leadership Coach with Will Linssen appeared first on Crestcom International.

Every leader faces those moments that can make or break an opportunity. It may be asking for a raise, pitching a big idea, or addressing a room full of decision-makers. These high-stakes conversations require the ability to communicate with confidence!

In this episode of The Leadership Habit Podcast, host Jenn DeWall sits down with Dia Bondi, a communications catalyst and author of Ask Like an Auctioneer: How to Ask for More and Get It. Together, they explore what it takes to prepare for those defining conversations where trust, influence, and outcomes are on the line.

Whether you’re negotiating resources, inspiring your team, or advocating for change, Dia’s frameworks and insights reveal how to speak powerfully and how to be “absolutely clutch in clutch moments.”

Dia Bondi is a keynote speaker, coach, and communications expert who helps leaders and changemakers speak with authenticity and authority when it matters most. Her clients include global brands like Nike, Meta, Salesforce, and Dropbox, as well as entrepreneurs, executives, and athletes seeking to elevate their presence in high-pressure situations.

As the author of Ask Like an Auctioneer: How to Ask for More and Get It, Dia combines storytelling, neuroscience, and negotiation strategy to help people push past fear and unlock their boldest communication potential. Her work has been featured on CNBC, NPR, and Forbes, and she’s known for helping professionals deliver messages that move audiences to action.

As Bondi explains, high-stakes moments aren’t just about closing a deal or landing a promotion; they’re about leadership itself. These are the situations where your communication can unlock decisions, resources, or opportunities that move your business and career forward.

A high-stakes conversation could be a one-on-one with your boss, a pitch to a major client, or a keynote at a conference. What makes it high stakes is the combination of risk, visibility, and impact. These moments require you to build trust quickly, communicate with purpose, and guide others toward a decision.

“Every high-stakes moment,” Bondi says, “is really an ask. You’re asking for engagement, for a decision, or for action, and how you prepare for that ask determines the outcome.”

In her two decades of coaching executives, startup founders, and leaders, Dia has seen several recurring missteps that undermine even the most talented professionals.

Too often, leaders jump straight to the solution, listing features, metrics, or data, without slowing down to paint a compelling picture of why it matters.

“The most powerful communicators,” Bondi explains, “don’t just describe a product or proposal. They invite the audience into a vision of what’s possible.”

By taking time to describe the problem, future, and stakes, leaders create emotional engagement and tension that make the solution more valuable.

Nerves and pressure can cause people to over-focus on their own objectives, like what they need, want, or fear. But as Bondi reminds us, “communication isn’t just about information transfer. It’s about connection.”

Compelling storytelling shifts attention to the audience: their desires, frustrations, and motivations. When people feel seen and understood, they’re more likely to say yes.

Many professionals limit themselves by asking for too little. Bondi challenges leaders to “ask big enough that you might get a no.”

This approach, inspired by her experience as an auctioneer, helps leaders stretch beyond comfort zones and uncover what’s truly possible. If you get a no, you’ve found the boundary. If you get a yes, you’ve just achieved more than you thought possible.

Behind every effective communicator is a strategic ask,  a clear understanding of what you’re requesting, who you’re asking, and when the timing is right.

Bondi encourages leaders to check three elements before entering any high-stakes moment:

When you align these three factors, your message lands with far greater impact and credibility.

Dia Bondi’s genius lies in turning complex communication strategies into simple, repeatable frameworks. Two of her most powerful tools are the Blocker Buster and the Mirror Effect. These tools help leaders craft messages that resonate, persuade, and inspire.

This four-part model is ideal for product pitches or team presentations where you need to frame a challenge and position your solution.

This structure builds logical and emotional momentum, helping your audience see you as the solution to their challenge.

For more personal, one-on-one conversations, such as asking for a promotion, budget approval, or collaboration, the Mirror Effect emphasizes empathy and connection.

This framework transforms a transactional request into a collaborative partnership. It’s not manipulation, it’s alignment. As Bondi notes, “When you slow down, reflect back what you see in the other person, and connect it to your purpose, you create trust in real time.”

Fear is one of the most significant barriers to confident communication. The fear of rejection or being perceived as too assertive prevents many professionals from speaking up.

Bondi’s advice? Stop waiting to feel neutral.

“The most compelling leaders I’ve coached aren’t fearless,” she says. “They simply accept the intensity that comes with high-stakes moments and choose to show up big anyway.”

Courage doesn’t mean calm; it means conviction. The goal isn’t to eliminate nerves but to channel them into focus and authenticity.

At the heart of Bondi’s message is a reminder that technical skill isn’t enough. Accurate leadership communication requires finding your unique voice through the combination of values, tone, and presence that makes you memorable.

“It takes a lifetime to sound like yourself,” she says. “You can master every framework, but your voice is what brings those tools to life.”

Developing that voice takes practice, reflection, and feedback, the same ingredients that make effective leaders.

Want to learn more from Dia or explore her work on high-stakes communication? Connect with her and discover her latest projects at the links below:

At Crestcom, we understand that communication is the cornerstone of leadership. Our leadership training programs help leaders develop the emotional intelligence and influence skills needed to succeed in high-stakes situations.

Just as Dia Bondi teaches, powerful communication starts with preparation, awareness, and confidence in your own voice. Crestcom participants learn to translate those principles into action and drive measurable results for themselves and their teams.

Every leader faces moments that test their communication and courage. The key is preparation, empathy, and a willingness to ask big.

Listen to The Leadership Habit Podcast featuring Dia Bondi to discover how you can prepare for your next high-stakes moment and speak with clarity, confidence, and impact.

From handling difficult conversations to inspiring organizational change, Crestcom’s leadership training provides the tools, practice, and accountability leaders need to communicate with purpose and clarity.

Ready to strengthen your leadership voice? Request a complimentary 2-hour workshop to discover how Crestcom can help you and your team master confident communication.

The post How to Prepare for High Stakes Conversations with Dia Bondi appeared first on Crestcom International.

In this episode of The Leadership Habit Podcast, host Jenn DeWall talks with Melissa Gonzalez, retail strategist, experiential designer, and author of The Purpose Pivot. Together, they explore how professionals and leaders can reconnect with what truly drives them—realigning their work, energy, and values to create a more fulfilling life.

Gonzalez’s insights go beyond traditional career advice. She challenges the belief that constant busyness equals success and offers a practical roadmap for creating balance, purpose, and sustainable growth. Whether you’re leading a team or navigating your own next chapter, this conversation invites reflection on what it means to live and lead with intention.

Many leaders are running on autopilot—meeting after meeting, day after day—without pausing to ask if their actions truly align with their goals. In the podcast, Melissa Gonzalez explains that a purpose pivot is about stepping back, taking inventory, and asking: Am I creating the life I want to lead?

Her inspiration for The Purpose Pivot came after a personal health crisis that forced her to slow down and reassess her priorities. Through that experience, she realized that wellbeing isn’t something to fit in “after work”—it must be part of how we lead and live every day.

“Wellbeing shouldn’t be a side project,” Gonzalez says. “It deserves equal importance to your career growth.”

The purpose pivot is about moving from busyness to impact—recognizing that filling your calendar isn’t the same as creating value. For leaders, this often means shifting from the mindset of doing more to doing what matters most.

Despite knowing the importance of rest and reflection, many high achievers still struggle to prioritize themselves. Gonzalez explains that this difficulty stems from how success is often measured—by how much we accomplish, not by how intentionally we live.

She encourages professionals to ask key questions:

In her book, Gonzalez includes an exercise where readers list what energizes them versus what drains them. This simple reflection often reveals patterns—time spent on tasks that deplete energy far outweighs the time spent on what brings joy or motivation.

Taking time to reflect doesn’t slow progress—it fuels it. By giving yourself permission to pause, you create mental clarity, emotional balance, and stronger decision-making capacity.

As Gonzalez explains, purpose-driven leadership is rooted in trust—trust in others and trust in yourself.

Many leaders resist delegating because they fear losing control or worry others won’t deliver at the same level. This lack of trust leads to burnout and exhaustion. True leadership, Gonzalez says, involves trusting your team to rise to the occasion while also trusting that you don’t have to carry everything alone.

Jenn and Melissa also discuss self-trust, which can be even harder to cultivate. Self-trust means believing that you’ve prepared enough, done enough, and can let go when necessary. It’s recognizing when additional effort will no longer change the outcome and giving yourself grace to rest.

Learning to delegate and release control not only improves wellbeing—it helps leaders model healthy behavior for their teams. When leaders demonstrate balance and confidence, others feel permission to do the same.

Making a purpose pivot isn’t about quitting your job or overhauling your life overnight. It’s about intentionally adjusting how you spend your time and energy so that your daily actions reflect your long-term goals.

Melissa Gonzalez outlines several strategies to begin this journey:

A purpose pivot is not about doing everything—it’s about focusing on what’s most meaningful.

One of the most powerful lessons from The Purpose Pivot is the importance of reflection. Gonzalez reminds us that most leaders don’t stop long enough to acknowledge how far they’ve come. Without reflection, progress can feel invisible, leaving even accomplished professionals feeling stuck or unfulfilled.

By pausing to celebrate small achievements, you reinforce your sense of purpose and prevent burnout. Gonzalez also emphasizes that transitions are recalibration moments—opportunities to reassess what’s working and what needs to change. Whether you’re starting a new role, leading a new team, or entering a new phase of life, these transitions offer a chance to adjust, grow, and realign.

At Crestcom, we believe that the most effective leaders combine professional competence with personal awareness. Leadership isn’t just about achieving results—it’s about understanding yourself and guiding others with purpose, empathy, and authenticity.

Crestcom’s leadership training programs are designed to help leaders make their own purpose pivot. Through monthly learning experiences, practical action plans, and accountability coaching, participants learn to balance ambition with wellbeing—creating teams that thrive on trust, collaboration, and continuous growth.

Like Melissa Gonzalez’s message, Crestcom’s approach to leadership development centers on reflection and application. Leaders are encouraged to identify what energizes them, build emotional intelligence, and focus on meaningful impact instead of mere activity. The result is not just better leaders—but stronger organizations and healthier workplace cultures.

A purpose pivot isn’t a one-time event—it’s an ongoing practice of alignment between your values, goals, and actions. As Melissa Gonzalez reminds us, success isn’t about how much you do, but about how intentionally you live and lead.

Listen to the full episode of The Leadership Habit Podcast featuring Melissa Gonzalez to discover how to make your own purpose pivot and begin leading with clarity and confidence.

Ready to explore your own leadership journey? Visit crestcom.com/freeworkshop and request a complimentary leadership workshop for your team! 

What is a purpose pivot?

How can leaders balance success and wellbeing?

Why does self-trust matter in leadership?

How can Crestcom help me grow as a purpose-driven leader?

The post How to Make a Purpose Pivot: Finding Balance and Fulfillment with Melissa Gonzalez appeared first on Crestcom International.

On the latest episode of The Leadership Habit Podcast, Jenn DeWall sat down with aviation executive, trailblazer, and author Stephanie Chung to discuss one of the biggest challenges leaders face today: how to lead people who are not like them.

Stephanie is the author of the new book Ally Leadership: How to Lead People Who Are Not Like You, which provides a practical framework for leaders who want to get the best results from diverse teams. In this episode, she shares her philosophy of Ally Leadership and explains why learning how to lead people across differences is not just about diversity, equity, and inclusion—it is about return on investment.

Stephanie Chung began her aviation career working at Boston Logan Airport, parking planes and handling luggage. From there, she rose through the ranks, becoming a top sales executive, then moving into private aviation, where she eventually sold and oversaw the sales of private jets.

Her career milestones include becoming the first Black person in U.S. history to lead a major private aviation company as President of JetSuite. She later became the founding Chief Growth Officer at Wheels Up, helping take the company public—the first private jet company in the United States to do so. Today, she is an international bestselling author, keynote speaker, board member, and coach to Fortune 500 executives.

Stephanie has also been named to the Ebony Power 100 list and recognized as one of the top 500 CEOs by the respected consultancy YPO. Her journey reflects not only professional success but also resilience, courage, and a commitment to helping leaders everywhere learn how to lead people across differences through the practice of Ally Leadership.

Modern workplaces are changing faster than ever. Stephanie explains that today’s leaders face challenges never seen before. “If you are a leader worth your salt, your job is to make sure that you get the best people in the best position to get the best result. That’s the job of a leader.”

What makes that more challenging now is the sheer range of diversity within the workforce. As Stephanie describes, six generations are now working side by side—from Boomers to Gen Z. Gender dynamics have shifted, and ethnic and cultural diversity is increasing. Organizations are more aware of the contributions from LGBTQ+ professionals and neurodiverse employees.

This variety of backgrounds and perspectives can lead to misunderstandings if leaders rely on a one-size-fits-all approach. But when leaders embrace differences, the benefits are measurable. “Diverse teams are 35% more productive, diverse teams have a 70%… more likely to actually be more innovative, and diverse teams are 36% more profitable.”

The takeaway is clear: learning how to lead people who are not like you is no longer optional. It is a requirement for leaders who want to deliver results.

At the heart of Stephanie’s philosophy is her book Ally Leadership: How to Lead People Who Are Not Like You. She defines Ally Leadership as the ability to create trust, curiosity, and action in diverse environments.

The ALLY framework is simple but powerful:

“That’s the secret sauce here to getting the result out of your people”, Stephanie explained.

By practicing Ally Leadership, leaders build stronger relationships, create safe environments for contribution, and encourage teams to innovate.

In addition to the ALLY framework, Stephanie developed the EARN system, a step-by-step approach to building high-performing teams:

Stephanie notes that misalignment is expensive and disengaged employees are costly. The EARN system gives leaders practical tools to align teams and build momentum toward shared goals.

Leadership is never easy, but Stephanie believes it does not have to be overly complicated. “When you have to have an honest conversation about it… it’s not as hard or as complicated as people have told you it is. Utilize the talents that you have around you because they too have gifts and talents”.

Her advice is clear: stop trying to do it all yourself. By becoming an ally leader, you can unleash the potential of your entire team.

To hear more from Stephanie Chung, including her insights on curiosity in leadership and building psychologically safe teams, listen to the full episode of The Leadership Habit Podcast.

At Crestcom, we believe leadership is a journey, not a destination. That’s why we offer a complimentary leadership skills workshop for organizations that want to sharpen their leadership practices. In just two hours, you will walk away with tools to improve decision-making, build trust, and create accountability across your team.

The post How to Lead People Who Are Not Like You with Stephanie Chung appeared first on Crestcom International.

What will it take to lead in the year 2030?

In this episode of The Leadership Habit Podcast, Crestcom’s Jenn DeWall speaks with leadership strategist and author Caroline Stokes about the critical mindset shifts leaders must make to stay relevant in a world defined by artificial intelligence, climate disruption, and societal transformation.

From emotional intelligence to radical listening and future-ready leadership systems, this conversation challenges old paradigms and offers a practical path forward. Caroline invites leaders to step into the uncertainty—not with fear, but with curiosity, courage, and the willingness to reinvent themselves and their organizations.

Caroline Stokes is an executive recruiter, leadership coach, futurist, and the founder of Workplace EQ. She is the author of Elephants Before Unicorns: Emotionally Intelligent HR Strategies to Save Your Company and her most recent book, AfterShock to 2030: A CEO’s Guide to Reinvention in the Age of AI, Climate, and Societal Collapse.

Drawing on decades of experience at companies like Sony and Disney, Caroline now works with founders, boards, and executives to build emotionally intelligent, trauma-aware, and adaptive leadership systems. She has spoken at the World Bank and the United Nations, and her insights appear in Harvard Business Review, Fast Company, and other leading publications.

Caroline begins by identifying the defining feature of our current moment: we’re living in a polycrisis era—an interconnected web of challenges that include AI disruption, climate change, economic instability, and societal unrest.

“We all have to reinvent our nervous system to be able to evolve in this particular age,” she explains. “It means doing it at a much faster pace than ever before.”

This isn’t just about learning new technology. It’s about changing the way leaders show up emotionally, psychologically, and strategically. Traditional models of top-down leadership are no longer effective in an environment where employees are under unprecedented levels of stress.

Many leaders today are navigating exhaustion, outrage, and anxiety—right alongside their teams. Caroline explains that many people are stuck in a stress response: fight, flight, freeze, or fawn. She says: 

“We’re all pretty much paralyzed in some way to understand and comprehend the challenging environment that we see ourselves in.”

This emotional context cannot be ignored. Whether it’s burnout, distrust, or the rising cost of living, Caroline emphasizes that leadership is emotional and psychological. CEOs can no longer separate performance from well-being. Caroline asks: 

“If you haven’t got the basics satisfied, how can you expect people to perform at a high level?”

This is a direct challenge to leaders who try to motivate with perks or platitudes. A free yoga class won’t matter if your employees are worried about putting food on the table.

Even in the age of artificial intelligence, emotional intelligence remains the most human and most powerful leadership skill.

“AI is not emotionally intelligent. It can’t show empathy. It doesn’t care. That’s still our job.”

Caroline urges leaders to go beyond performative empathy and instead practice radical listening—a deliberate effort to create space for honest feedback, without judgment or fear.

“We’re trying to understand where the themes are, where the gaps are, where the opportunities are… and to put everybody’s ego on the line.”

This shift isn’t about being soft. It’s about being real, responsive, and ready to act on what your team actually needs.

To lead through disruption, CEOs must embrace what Caroline calls a “blank slate” mindset. That means letting go of outdated goals and assumptions—especially those tied to unbridled growth. She explains: 

“We have left the old paradigm. The past is firmly in the past. We’re in a new paradigm, and it requires us to have a different mindset.”

Caroline explains that growth targets and OKRs rooted in pre-pandemic expectations are no longer realistic—or responsible.

“We’re not going to achieve growth right now. The world that we had previously experienced in previous decades just isn’t happening anymore.”

Instead, leaders should build future-ready leadership systems that reflect current realities. That includes involving employees in shaping new goals, acknowledging the emotional toll of change, and aligning strategies with both performance and sustainability.

With all the uncertainty ahead, is there still room for hope? Caroline says yes—but it must be grounded in reflection, not toxic positivity.

“Hope can only be found once you’ve actually done the work.”

In her book, AfterShock to 2030, she provides CEOs with tools to reflect, reset, and reimagine their leadership approach. The goal is to create transformation—not just for the organization, but for the individuals within it.

“If we don’t have that hope, how are we… It’s very hard for people to get out of bed in the morning.”

Leadership today demands resilience, self-awareness, and a willingness to change. And for those willing to do the work, Caroline believes there is a real opportunity to lead with purpose and make a meaningful impact.

Want to learn more from Caroline? Here’s where to find her:

At Crestcom, we help organizations develop the soft skills that drive hard results. Our interactive leadership development programs empower managers to lead with curiosity, compassion, and confidence. If you are interested in learning more, get started with a free, live-facilitated leadership skills workshop for you and your team. Click here to learn more: crestcom.com/freeworkshop

This episode of The Leadership Habit is packed with insight, strategy, and a fresh perspective on what leadership must look like to thrive in the future!

🎧 Listen now: The Leadership Habit Podcast 

If you found this conversation valuable, share it with someone ready to lead with purpose in the face of change.

The post Emotional Intelligence Still Matters in the Age of AI with Caroline Stokes appeared first on Crestcom International.

Managing a multigenerational workforce is one of the biggest challenges facing leaders today. With five generations working side by side, the workplace is more diverse than ever. From Traditionalists to Gen Z, there are significant differences in terms of values, communication preferences, and expectations.

In this episode, host Jenn DeWall interviews generational expert and keynote speaker Karen McCullough to explore how leaders can build stronger, more connected teams across generations. If you’re looking for insights on leading Gen Z employees, adapting leadership styles, and building trust across age groups, this episode is a must-listen.

Karen McCullough is a conference keynote speaker and a generational expert and workplace strategist who helps leaders and teams navigate today’s fast-changing workplace. Her signature message, “It’s Not Personal, It’s Generational,” blends humor, research, and real-world stories to unpack what drives each generation. 

With a background in branding and business, Karen shares practical insights that help organizations break down barriers, spark connections, and build cultures that work. She’s worked with top companies across North America, including Procter & Gamble, McDonald’s, and MD Anderson.

Karen offers a snapshot of the five generations currently shaping today’s workforce:

“Every generation brings change,” Karen says. “But Gen Z? They’ve been coached by their parents, their podcasts, and their peers. They’re forming their own opinions—and they’re not afraid to expect more from work.”

Karen emphasizes that today’s leaders can’t rely on old-school management tactics. Gen Z enters the workplace with strong values and high expectations—but not always the soft skills or organizational experience leaders assume.

Leaders need to shift from managing to coaching. Instead of giving someone a deadline and walking away, Karen explains, leaders must guide their team through the process, ask good questions, and provide developmental support.

“To be a leader today, you have to be a therapist.”

Companies that invest in coaching skills for managers are more likely to retain Gen Z talent and build resilient, productive teams.

Forget free snacks and trendy office spaces. Gen Z is focused on:

Karen shared examples of Gen Z employees who leave jobs for small pay increases—or pursue multiple side hustles, including with competitors. These behaviors reflect a desire for flexibility and fulfillment, not just compensation.

One company in Houston that Karen interviewed stands out for retaining young talent. During interviews, they tell candidates:

“We want you here for a lifetime.”

That kind of clarity and commitment from the start sets the tone for long-term success.

Trust is foundational in leading across generations. Karen notes that both sides—leaders and younger employees—often hold skepticism about one another.

Some leaders worry Gen Z will quit after lunch. Meanwhile, young professionals often hesitate to ask questions for fear of looking unqualified. This creates a communication gap that hinders productivity and connection.

Jenn offers a practical reminder:

“When you’re furious, get curious.”

Karen agrees, emphasizing that curiosity and compassion are key to understanding and retaining talent.

If you want openness and engagement from your team, you must create a culture where it’s safe to be honest—without fear of judgment.

Balancing the needs of Baby Boomers, Gen X, Millennials, and Gen Z in one workplace can feel overwhelming. Each group has different communication styles, career expectations, and values. For example, Boomers often value loyalty and structure, while Millennials and Gen Z want flexibility, purpose, and continuous feedback. Without a thoughtful approach, these differences can lead to tension, misunderstandings, and increased turnover. 

That’s why multigenerational leadership training is becoming a priority for many organizations. By learning to adapt their style, today’s leaders can bridge the gap, improve collaboration, and create cultures where every generation feels valued.

With AI accelerating change, coaching and emotional intelligence are more critical than ever. Karen’s final message is clear: the future belongs to those who adapt and keep learning.

“If we keep learning, if we become better coaches, if we tap into our emotional intelligence—what harm can it do? It can only do good.”

Whether you’re a CEO, middle manager, or HR leader, embracing generational differences at work isn’t just about retention—it’s about creating a workplace where everyone can thrive.

And, of course, listen to the full episode to hear all of Karen’s insights!

How Can Crestcom Help You Lead a Multigenerational Workplace?

Crestcom can help leaders manage the challenges of a multigenerational workforce! Our leadership training programs equip managers with the tools and techniques necessary to build strong teams, understand generational differences, and create an inclusive culture that works for everyone. Request a complimentary leadership skills workshop to learn how to coach, connect, and retain talent from every generation.

The post Leading the Multigenerational Workforce with Karen McCullough appeared first on Crestcom International.

Leaders know that keeping a team innovative is easier said than done. The pressure to deliver results, stick to timelines, and avoid mistakes can stifle the very creativity that sparks breakthrough ideas. But what if leaders could borrow a proven process from one of the most successful creative teams in entertainment history?

In a recent episode of The Leadership Habit Podcast, Rob Kutner and John Krewson shared how the Saturday Night Live (SNL) approach to creating sketches can inspire leaders to spark creativity, embrace iteration, and launch winning ideas.

John Krewson is the founder and CEO of Sketch Development Services, a two-time member of the Inc. 5000 list, and a former comedian who even appeared on an episode of SNL in 1997. With a background in both entertainment and software development, John has a unique perspective on how to blend creativity and business strategy.

Rob Kutner is an award-winning comedy writer for The Daily Show with Jon Stewart, Conan, and more. For the past six years, he has taught sketch comedy writing at Loyola Marymount University’s School of Film and Television. Together, John and Rob co-authored Pitch, Sketch, Launch, a book that applies the principles of sketch comedy to team innovation.

On SNL, the week kicks off with a high-energy pitch session where anything goes. As John described, “This is a no-holds-barred, no ideas are bad ideas brainstorming session.” Around 100 ideas are generated, knowing that only a handful will make it to air.

Leaders can use this approach by creating safe spaces for idea generation where quantity comes before quality. Removing judgment in the early stages gives your team the freedom to think bigger.

Try this: Schedule a weekly 30-minute “idea jam” with no evaluation—just contribution.

John emphasized that creativity is rarely instant perfection: “The best solutions do not emerge fully formed from the thigh of a great leader.” Instead, they’re the product of steady, incremental improvement.

In business, this is an essential creative leadership strategy. Keep projects small and self-contained so you can evaluate, adjust, and move forward without being bogged down by weeks of sunk effort.

Try this: Break projects into two-week sprints with a review session at the end of each cycle.

Rob pointed out that in comedy, mistakes are part of the process: “Freedom to make bad pitches” is a core value. Even seasoned professionals start with “not this, but something like it” ideas to spark the right solution.

For leaders, encouraging failure in early stages prevents fear from killing creativity. Make it clear that less-than-perfect ideas are stepping stones to the winning concept.

Try this: Reward contributions to the process, not just final results. Publicly acknowledge when a “bad” idea inspired a breakthrough.

Reflecting on his own career, Rob shared that hierarchy can unintentionally stifle creativity: “We couldn’t really pitch when Conan was in the room.” Even with a supportive leader, the pressure to impress can limit bold thinking.

Leaders should step back in the early creative phases, then rejoin when ideas are ready for refinement and alignment with business goals.

Try this: Assign a peer facilitator for brainstorming sessions and review ideas as a group later.

Rob also stressed the importance of keeping the audience—or in business, the end user—front and center: “Is this enhancing the desired end user value?” On SNL, the metric is simple: did it make people laugh? In business, your “laugh” is the value your customer receives.

Try this: Define your team’s “end-user value” and revisit it during every project review.

You can connect with John Krewson on LinkedIn, or learn more about John’s work at sketchdev.io and find Pitch, Sketch, Launch on Amazon in print, e-book, and audiobook formats. In the audiobook, you’ll hear sketches performed by a comedy team—bringing their concepts to life in a fun and memorable way. Rob can be found on LinkedIn and at robkutner.com, where he shares his comedy and writing projects.

Crestcom’s leadership training programs are designed to help leaders apply practical strategies—like the ones shared here—to inspire innovation, strengthen teams, and achieve results. In our interactive workshops, you’ll learn proven techniques to foster leadership and creativity, build trust, and adapt quickly to change. Discover how you and your team can unlock your creative potential—request a complimentary leadership skills workshop today.

The post Pitch, Sketch, Launch Your Team’s Creativity with John Krewson and Rob Kutner appeared first on Crestcom International.