The Leadership Habit

AI can give leaders answers in seconds. But getting an answer and making a good decision are two very different things.

As AI becomes part of how we research, solve problems, and evaluate options, leaders face an important question: Where does human judgment fit?

In this episode of The Leadership Habit Podcast, host Jenn DeWall sits down with decision-making expert Cheryl Strauss Einhorn, creator of the AREA Method and author of The Human Edge: Smarter Decisions in the Age of AI. Together, they explore decision-making in the age of AI, including why leaders need to think critically about the problems they are solving, recognize both human and AI biases, and resist the temptation to outsource their judgment to technology.

As Cheryl explains:

“The problem with AI is we now have this answer machine. So answers are pretty easy to come by. And so what that means is that human judgment actually becomes far more valuable.”

Meet Cheryl Strauss Einhorn

Cheryl Strauss Einhorn is a decision-making expert, creator of the AREA Method, and founder of the decision sciences company Decisive, where she helps leaders and organizations solve complex problems and make better decisions.

She is also an adjunct professor at Cornell University and the award-winning author of several books exploring decision-making, financial research, and the psychology behind how we make choices.

Cheryl’s approach to decision-making grew out of more than two decades in investigative journalism, including over a decade at Barron’s. Her reporting required her to evaluate complex information, question assumptions, weigh evidence, and make high-stakes judgments with significant consequences.

That experience ultimately led her to develop the AREA Method, a structured approach designed to help people recognize cognitive biases, expand their thinking, and make decisions with greater confidence and conviction.

AI Has Answers. Leaders Still Need Judgment.

AI has dramatically changed how quickly we can access information. But Cheryl argues that easier access to answers actually increases the value of human judgment.

AI does not inherently understand why you are solving a problem. It does not know your organization, your stakeholders, your priorities, your constraints, or what success looks like for you.

That is why Cheryl recommends turning to yourself before turning to AI.

“What is the problem that I am solving and why am I solving it?”

Without that clarity, leaders risk using AI to solve the wrong problem, even if they do it efficiently.

Cheryl points out that even experienced leaders sometimes assume they understand the problem in front of them without taking time to define it clearly. The result can be solving an adjacent problem, addressing only part of the issue, or eventually having to start over.

For leaders navigating decision-making in the age of AI, defining the problem is still a fundamentally human responsibility.

Know When a Decision Requires a Process

Leaders make countless decisions every day, and not every choice requires extensive analysis. But some decisions carry consequences that make a structured process especially valuable.

Cheryl recommends looking at three factors:

Is the outcome unknown?

Is the cost of getting it wrong high?

Will the decision have a long-term impact?

When all three are present, leaders should slow down and use a deliberate decision-making process.

Cheryl’s AREA Method stands for Absolute, Relative, Exploration and Exploitation, and Analysis. The process helps decision-makers examine different perspectives, challenge assumptions and judgments, gather evidence, and build greater confidence in their conclusions.

A process also creates something leaders often miss: an opportunity to learn from the decision afterward.

Instead of simply asking whether the outcome was good or bad, leaders can look back and evaluate the decision quality, whether they gathered the right information, considered the right perspectives, and followed a sound process.

Are You Using AI Like a Surgeon or a Lamborghini Driver?

One of Cheryl’s most useful distinctions is that leaders can approach AI and decision-making in two very different ways.

When you need one specific piece of information, Cheryl suggests thinking like a surgeon. You make a precise incision, extract what you need, and move on.

But many leadership challenges are not that simple.

When you are exploring a complicated problem and do not yet know exactly where you need to go, Cheryl suggests thinking of yourself as a Lamborghini driver.

AI may be an incredibly powerful and fast machine, but you are still behind the wheel.

“You need to direct it.”

In this mode, AI can help leaders research, analyze, explore, and refine their thinking. But the leader remains responsible for determining what they are trying to understand and where the process should go next.

The distinction matters because using the same approach for every interaction with AI can lead leaders to extract information without first understanding whether it is the right information for the problem they are trying to solve.

The Eight Human Moments That Matter in AI-Powered Decision-Making

In The Human Edge, Cheryl identifies eight pivotal moments where human thinking remains essential:

Defining the problem

Assessing motivations

Gathering context

Researching effectively

Analyzing options

Recognizing biases

Involving key stakeholders

Building conviction

These moments highlight an important limitation of AI: it cannot automatically know the context surrounding your decision.

It does not know your budget unless you tell it. It does not know which stakeholders matter most. It does not know that you have until Tuesday to decide or that your organization is operating under a specific resource constraint.

As Cheryl explains:

“Something that looks plausible that doesn’t work for your context is something that can fail.”

Leaders bring the context. AI can help process information within it.

Human Bias Meets AI Bias

AI does not eliminate bias from decision-making. In fact, Cheryl points out that leaders now have to contend with two sources: their own cognitive biases and the biases in AI systems.

Human biases can include confirmation bias, where we look for information that supports what we already believe; liking bias, where we give greater weight to information from people we relate to or trust; and the planning fallacy, where we underestimate how much time or complexity a project will require.

AI can also bring its own imperfections into the process. Its answers may be incorrect, outdated, biased, or based on information that does not accurately represent the situation a leader is trying to solve.

But Cheryl also sees an opportunity.

Rather than asking AI for an answer and accepting the first response, leaders can use the tool to challenge their own thinking. They can ask for disconfirming evidence, explore opposing perspectives, question the credibility of information, and look for weaknesses in the decision they are considering.

The goal is not to have AI validate your thinking. Use it as one resource to strengthen your thinking.

Speed Is Not the Same as Quality

AI has made speed one of its biggest selling points. But faster decision-making does not automatically mean better decision-making.

“Speed and efficacy are often different. The speed of a decision says nothing about the quality of it.”

That distinction is especially important for leaders.

Our brains naturally develop shortcuts based on previous experiences. Those shortcuts help us move quickly, but they can also cause us to apply yesterday’s assumptions to today’s problem.

For high-stakes business decisions, Cheryl encourages leaders to create what she calls a “strategic stop,” a moment to evaluate whether the assumptions, information, and approaches that worked before still apply now.

AI may accelerate the process, but leaders still need to know when slowing down will ultimately lead to a better outcome.

Don’t Outsource Your Thinking

Perhaps the biggest takeaway from Cheryl’s conversation with Jenn is that the future of leadership is not about choosing between human expertise and artificial intelligence.

It is about knowing what each is good at.

AI can research, analyze, generate possibilities, and surface information at extraordinary speed. But leaders still have to define the problem, provide context, evaluate assumptions, consider stakeholders, recognize bias, and ultimately decide what to do.

Cheryl’s goal is to help leaders build the confidence and conviction to solve problems effectively, both with and without AI.

“I really hope that people gain confidence and conviction that they can solve problems well, both with and without the machine, and that they don’t ever sacrifice their thinking.”

As AI becomes more capable, protecting our ability to think critically is not rejecting technology. It is how leaders make better use of it.

Where to Find More From Cheryl Strauss Einhorn

To learn more about Cheryl Strauss Einhorn, the AREA Method, and her work on decision-making: 

Visit areamethod.com

Connect with Cheryl on LinkedIn 

Explore her latest book, The Human Edge: Smarter Decisions in the Age of AI.

Build the Leadership Skills AI Can’t Replace

AI can provide information. Leadership requires knowing what to do with it.

Crestcom helps leaders develop the practical skills they need to make better decisions, communicate effectively, navigate conflict, build emotional intelligence, and lead their teams with greater confidence.

Experience Crestcom’s approach firsthand with a complimentary leadership skills workshop. In just two hours, you’ll explore actionable strategies you can put to work immediately and create a personalized plan for addressing your leadership challenges.

Request your complimentary leadership skills workshop today.



The post The Human Edge in AI-Powered Decision-Making with Cheryl Strauss Einhorn appeared first on Crestcom International.

What is it Like to be Led by You?

Summary:  Do you know what it’s like to be led by you? Good intentions do not always translate into positive leadership impact. Ciarán Casey joins The Leadership Habit Podcast to explore why leadership is relational, how leaders can become more aware of the experience they create, and the six elements that help leaders get back “in tune.”

Most leaders have good intentions. They want their teams to feel trusted, supported, empowered, and valued. 

But good intentions do not always create a good experience.

You might give someone more autonomy because you trust them, only for them to walk away feeling abandoned. You might step in to help because you want to make their job easier, while they interpret your help as a sign that you do not trust them. You might send an email late at night simply to clear your inbox, while your team assumes they are expected to be available after hours.

That gap between what a leader intends and what others actually experience is at the heart of this episode of The Leadership Habit Podcast.

Host Jenn DeWall sits down with leadership practitioner, coach, and author Ciarán Casey to explore why leadership impact matters more than good intentions and how leaders can become more conscious of what it is actually like to be led by them.

Meet Ciarán Casey, Leadership Coach and Author

Ciarán Casey is a leadership practitioner and coach with more than three decades of senior leadership experience across sectors and international environments. His work focuses on organizational transformation, culture, high-performing teams, and complex human dynamics.

More recently, Ciarán has focused on leadership development, working with individuals, leadership teams, senior civil servants, and executive teams to strengthen trust and collaboration.

His book, Leadership in Tune, grew out of a question he kept encountering throughout his career: Why do some highly capable, intelligent, confident leaders struggle to connect with the people around them, while others seem to create environments where people naturally flourish?

For Ciarán, part of the answer lies in the difference between leadership intent and leadership impact.

Your Intentions Are Only Half the Story

Leaders rarely set out to frustrate, disengage, or demotivate their teams. The problem is that employees cannot experience a leader’s intentions. They experience their behaviors and interactions.

As Ciarán explains:

“The intention isn’t the problem. What we need to focus on is the experience.”

That distinction can be uncomfortable, especially when we know our intentions were good. But it also gives leaders a more useful way to evaluate their effectiveness.

Instead of asking, “What was I trying to do?” effective leaders can ask, “How might that have been experienced?”

That shift matters because leadership behaviors carry more weight than we may realize.

Ciarán points out that leaders are constantly being observed. A delayed response can be interpreted as a lack of interest. Silence can make people wonder if something is wrong. A rushed conversation can leave someone feeling like their time or contribution does not matter.

As he puts it, a leader’s impact is amplified.

Becoming more aware of that leadership impact is not about overanalyzing every interaction. It is about recognizing that the meaning we intend to communicate and the meaning someone receives are not always the same.

Leadership Does Not Happen in Isolation

One of the central ideas in Ciarán’s work is that leadership is relational.

We often think of leadership as something an individual possesses. We describe someone as confident, charismatic, decisive, or a strong communicator and conclude that those characteristics make them a good leader.

Ciarán challenges that idea.

He argues that leadership emerges in the space between people. A leader can offer direction, guidance, or support, but leadership only takes shape when another person is willing to engage with and follow that direction.

“Leadership is a relational practice that doesn’t reside within an individual, but emerges between people.”

That changes the way we think about leadership development.

Instead of focusing exclusively on the leader’s characteristics, we can pay more attention to the quality of their interactions. Are people willing to speak openly? Do they feel trusted? Do they feel heard? Does the leader create the conditions for people to contribute?

Those everyday interactions are where leadership impact becomes real.

The Six Strings of Leadership

In Leadership in Tune, Ciarán introduces his Conscious Relational Impact Model, built around six elements of leadership.

As a guitarist, he compares these elements to the guitar’s six strings. A guitar does not need every string to be completely wrong to sound off. One string that is out of tune can change the sound of the entire instrument.

Leadership can work the same way.

The six strings are organized across three stages:

The Connected Self: Authenticity and Emotional Intelligence

Effective leadership starts with understanding yourself. That means knowing your values and how they influence your behavior while also having the emotional intelligence to understand and regulate the impact you have on others.

Authenticity without emotional intelligence can become an excuse to behave however you feel in the moment. Emotional intelligence without authenticity can feel performative.

Leaders need both.

The Bridge: Presence and Trust

From there, leaders have to create the conditions for connection.

Ciarán describes presence and trust as the two spans of a bridge between people. Trust determines whether it feels safe to cross. Presence determines what it feels like to cross.

One of the simplest ways leaders can strengthen that bridge is by giving people their undivided attention.

Phones, emails, meetings, and competing priorities make genuine presence difficult. But when a leader is distracted during a conversation, that distraction can communicate something they never intended: You are not important enough for my full attention.

Shared Impact: Co-Creation and Influence

Once leaders have built that connection, they can create shared impact through co-creation and influence.

Ciarán describes co-creation as one of the most underused leadership skills. Leaders do not need to have every idea, solve every problem, or provide every answer themselves.

Instead, they can involve capable people in designing solutions, processes, products, and outcomes.

Influence also changes depending on the situation. Sometimes leaders need to be direct. Other times, they can draw ideas and creativity from the people around them.

The key is that shared impact becomes much easier when trust and connection already exist.

Which Leadership String Is Out of Tune?

The goal of Ciarán’s model is not leadership perfection.

It is awareness.

A leader may be authentic and emotionally intelligent but struggle to be fully present. Another may care deeply about their team but fail to build trust. Someone else may build strong relationships but rarely give others enough opportunity to co-create solutions.

When something is not landing the way you intended, Ciarán’s six strings offer a framework for asking why.

“We’re not going for perfection here. We’re just going for improvement.”

That can start with small moments of reflection.

Think about a recent conversation that did not go as planned. A piece of feedback someone did not respond to well. Or, a meeting where the energy suddenly changed. Maybe a team member who has started pulling back.

Rather than immediately focusing on what is wrong with the other person, consider the interaction itself.

What might they have experienced? Which leadership string may have been out of tune? What could you adjust the next time?

What Is It Like to Be Led by You?

Toward the end of the conversation, Ciarán offers a question that captures the central idea of the episode:

“What’s it like to be on the receiving end of me?”

It is a very different question from “Am I a good leader?”

Being a strong leader is an evaluation we can make about ourselves. Understanding how people feel and what it is like to be led by us requires considering someone else’s experience.

That is where leadership impacts lives.

You will not always get it right. Your intentions and someone else’s experience will not always align. But becoming curious about that gap can help you build stronger relationships, strengthen trust, and create an environment where people are more willing to contribute their best over the long term.

Listen to the full episode of The Leadership Habit Podcast to hear Jenn and Ciarán explore the Conscious Relational Impact Model, the six strings of leadership, and how you can become more intentional about the experience you create for the people you lead.

Where to Find More From Ciarán Casey

Want to learn more from Ciarán Casey?

Check out his book, Leadership in Tune

Explore his self-evaluation resources

Connect on LinkedIn

Ready to Strengthen Your Leadership Impact?

Understanding how your leadership is experienced is one thing. Building the skills to adapt, communicate, build trust, and lead more effectively takes practice.

Crestcom’s award-winning leadership development programs help leaders turn leadership concepts into behaviors they can apply in their everyday interactions with their teams.

Experience Crestcom for yourself with a complimentary Leadership Skills Workshop and discover practical tools you can begin using right away.



The post Why Leadership Impact Matters More Than Intentions with Ciarán Casey appeared first on Crestcom International.

Summary: What makes people want to follow a leader? In this episode of The Leadership Habit Podcast, Crestcom Business Owner John Lentini introduces his Six-Dial Framework for character-driven leadership. Learn how discipline, mindset, resilience, integrity, empathy, and influence work together to help leaders build trust, inspire others, and lead with greater confidence.

Leadership isn’t defined by a title. It’s defined by character.

The most effective leaders don’t earn trust because of their position. They earn it through the decisions they make, the values they demonstrate, and the consistency they show every day. That’s the foundation of character-driven leadership.

In the latest episode of The Leadership Habit Podcast, host Jenn DeWall sits down with John Lentini, President of Bold Training Corp. and a licensed Crestcom Business Owner serving organizations throughout New York, New Jersey, Connecticut, Rhode Island, and Delaware. John is also a TEDx speaker with more than 235,000 views on his TEDx talk, where he first shared his practical framework behind his upcoming book, Engineering Character: Six Dials to Build Better Leaders, and explains why becoming a better leader starts with becoming a better version of yourself.

Meet John Lentini

John Lentini knows that great leadership isn’t about having all the answers. It’s about continually developing the character and habits that earn trust. As President of Bold Training Corp. and a Crestcom Business Owner, John draws on more than two decades of executive leadership experience to help leaders become more resilient, influential, and effective. His perspective is shaped by leading global teams through 9/11, the Fukushima nuclear disaster, and choosing to start a business during the COVID-19 pandemic.

What Is Character-Driven Leadership?

Character-driven leadership is the intentional practice of developing the habits, values, and behaviors that inspire others to trust and follow you.

Rather than focusing solely on technical skills or authority, character-driven leaders cultivate self-awareness, resilience, integrity, empathy, and influence. These qualities allow them to navigate uncertainty, build stronger relationships, and create lasting impact.

As John explains:

“You must learn to lead yourself effectively before you can really lead others well.”

That simple idea forms the foundation of his Six-Dial Framework.

Great Leadership Starts with Leading Yourself

According to John, every leader must first master three personal leadership habits:

Discipline

Mindset

Resilience

These three “dials” represent the internal habits that determine how consistently leaders perform, especially during difficult times.

Discipline is often the least glamorous but most essential.

“It is the boring, tedious, mundane stuff that we would all love to avoid… But when you start to appreciate the medium-term rewards that can be gained through regular discipline, you’re going to see a difference.”

Mindset is the unwavering belief that your vision is achievable, even when progress feels slow. Resilience allows leaders to adapt, recover, and continue moving forward, whether that means persevering through challenges or changing course entirely.

Together, these qualities create what John calls a determined leader.

Character Is Built Through Integrity, Empathy, and Influence

Once leaders learn to lead themselves, they can begin leading others more effectively.

John’s second set of leadership dials focuses on:

Integrity

Empathy

Influence

Together, these create the trust every high-performing team depends on.

One of the episode’s most memorable insights is John’s definition of integrity:

“If discipline is consistency in your activity, then integrity is consistency in your values.”

Character-driven leadership requires leaders to consistently act according to their values, even when it’s difficult. When actions align with words, trust grows. When they don’t, credibility quickly disappears.

Why Empathy Is a Leadership Strength

Empathy is often misunderstood as being too soft or avoiding difficult conversations.

John challenges that misconception.

“Empathy is understanding what someone wants, but not necessarily catering or executing on it.”

Character-driven leaders don’t avoid accountability. Instead, they make difficult decisions with compassion, communicate openly, and consider how those decisions affect others.

That combination of empathy and accountability builds stronger relationships and healthier workplace cultures.

Character Requires Continuous Reflection

One of the most practical aspects of John’s framework is that it encourages leaders to assess themselves regularly.

Rather than assuming growth happens automatically, character-driven leaders intentionally reflect on where they need to improve and actively seek feedback from others.

John recommends using tools such as 360-degree feedback or anonymous surveys to better understand how others experience your leadership.

As he reminds listeners:

“Always focus on where you are at the moment and why it’s changed… understanding we’re never done. It’s just the journey.”

Leadership isn’t about reaching perfection. It’s about continually becoming a better leader.

The Future of Leadership Is Character-Driven

Today’s leaders face constant change, increasing complexity, and growing expectations from their teams. Technical expertise alone is no longer enough.

Character-driven leadership provides a framework for earning trust, navigating uncertainty, and helping others succeed.

John’s Six-Dial Framework reminds us that leadership begins within. By intentionally developing discipline, mindset, resilience, integrity, empathy, and influence, leaders create the kind of character that inspires others to follow.

Listen to the Full Episode

Want to learn more about John’s Six-Dial Framework and discover practical ways to strengthen your own leadership character?

Listen to the full episode of The Leadership Habit Podcast featuring Crestcom Business Owner John Lentini for actionable insights you can begin applying today.

Ready to Build Character-Driven Leaders?

Strong organizations are built by leaders who inspire trust, communicate with integrity, and lead with purpose. Crestcom’s leadership development programs help leaders build these essential skills through practical learning, coaching, and real-world application.

Request a complimentary Leadership Skills Workshop to experience Crestcom’s approach firsthand. In this interactive session, your team will explore practical leadership strategies that improve communication, strengthen accountability, and develop the habits that drive long-term success.



The post Why Character-Driven Leadership Matters More Than Ever with John Lentini appeared first on Crestcom International.

Summer Leadership Rewind: Staying “Forever Human” in the Age of AI with Sylvie di Giusto

Artificial intelligence has changed dramatically over the past year. New tools arrive almost weekly. Organizations are experimenting faster than ever. And leaders everywhere are asking the same question:

How do you embrace AI without losing what makes great leadership human?

This week, we’re taking a summer break, so we’re revisiting one of our most impactful conversations on The Leadership Habit Podcast. Jenn DeWall sits down with leadership expert and Crestcom faculty member Sylvie di Giusto to explore why the leaders who thrive in the age of AI won’t be the ones who know the most about technology. They’ll be the ones who remain unmistakably human.

If you missed this episode the first time, or if your relationship with AI has changed since then, now is the perfect time to listen again.

Meet Sylvie di Giusto

Sylvie di Giusto is an international keynote speaker, author, Certified Speaking Professional (CSP), and Hall of Fame speaker who helps organizations improve leadership, influence, and communication. For years, her expertise has been part of Crestcom’s leadership curriculum, helping leaders around the world strengthen emotional intelligence, executive presence, and decision-making.

In this conversation, she offers a refreshing perspective on AI that replaces fear with curiosity and competition with collaboration.

The Best Leaders Won’t Compete with AI

Many professionals still think of AI as something they have to outwork or outperform.

Sylvie challenges that mindset.

“The goal was never to beat the machine. It is to build with it.”

AI will always process information faster, remember more data, and complete repetitive tasks more efficiently than people. Rather than trying to compete in those areas, leaders should focus on the capabilities that technology cannot replicate.

Judgment. Empathy. Trust. Context. Ethics.

These are the qualities that separate management from leadership—and they become even more valuable as AI becomes more capable.

Why Being “Forever Human” Matters More Than Ever

As AI-generated content becomes increasingly difficult to distinguish from human-created work, authenticity becomes a competitive advantage.

People don’t simply want information. They want confidence that someone understands their challenges, considers context, and genuinely cares about the outcome.

That’s why Sylvie believes leaders should intentionally cultivate the uniquely human skills AI cannot replace.

She explains that while AI can generate answers, leaders ask better questions. AI can analyze information, but leaders interpret meaning. AI can suggest actions, but only people can weigh ethics, relationships, and long-term consequences.

In other words, AI can assist leadership, but it cannot replace it.

Soft Skills Are Becoming Power Skills

For years, organizations emphasized technical expertise and productivity. Ironically, AI is now making those skills easier to automate.

The result?

Communication, emotional intelligence, adaptability, critical thinking, and relationship-building have become even more valuable.

As Sylvie notes:

“There will be a big comeback for soft skills because those are the skills that AI cannot replicate.”

Organizations investing in leadership development today aren’t preparing people for yesterday’s workplace. They’re building the capabilities that will matter most tomorrow.

Leadership Still Means Accountability

One of the episode’s most powerful reminders is that AI cannot own the consequences of a decision.

Leaders still carry that responsibility.

AI can recommend hiring decisions, summarize employee performance, or suggest business strategies. But it cannot understand every human circumstance, organizational nuance, or ethical consideration.

As Sylvie points out, leaders cannot blame technology for decisions they choose to make.

Accountability remains a human responsibility.

A Conversation That’s Even More Relevant Today

When this episode originally aired, many organizations were just beginning to explore generative AI.

Today, AI has become part of everyday work.

That makes this conversation even more valuable.

Rather than focusing on specific tools or trends that quickly become outdated, Sylvie shares timeless leadership principles that help leaders navigate any technological change. Her message isn’t about resisting AI or blindly embracing it. It’s about learning how to use it wisely while protecting the qualities that make leadership meaningful.

Key Takeaways

If there’s one message to carry forward from this Summer Leadership Rewind, it’s this:

AI will continue to evolve.

Great leadership will continue to depend on people.

The leaders who succeed won’t be those who simply adopt the newest technology. They’ll be the ones who combine technology with empathy, sound judgment, authentic communication, creativity, and accountability.

Or, as Sylvie says best:

“Don’t compete with AI. Focus on what you do in the moments that matter most as a human being.”

Listen to the Episode

Catch this Summer Leadership Rewind episode of The Leadership Habit Podcast with Sylvie di Giusto and discover why staying “Forever Human” may be the most important leadership strategy of the AI era.

Where to Find More from Sylvie di Giusto

To learn more from Sylvie: 

Visit sylviedigiusto.com

Connect with her on LinkedIn

Buy her books

Develop the Human Skills That Matter Most

Technology will keep changing, but leadership fundamentals endure. Developing stronger communication, critical thinking, emotional intelligence, and decision-making skills helps leaders succeed regardless of what’s next.

To learn how Crestcom helps organizations build these essential leadership capabilities, request a complimentary two-hour leadership workshop at crestcom.com/freeworkshop.



The post Summer Leadership Rewind: Staying “Forever Human” in the Age of AI with Sylvie di Giusto appeared first on Crestcom International.

Effective leadership communication isn’t just about delivering information. It’s about creating connection, inspiring action, and ensuring people remember what matters long after the conversation ends.

On the latest episode of The Leadership Habit Podcast, host Jenn DeWall speaks with communications expert Andy Freed. Andy shares his insights from an unexpected source of leadership inspiration: Bruce Springsteen.

Andy draws from more than 95 Springsteen concerts and decades of leadership experience. Through this lens, he shares how great leaders can communicate with greater purpose, prepare more intentionally, and create lasting impact through every interaction.

Meet Andy Freed, Author and Chairman of Virtual Inc.

Andy Freed is Chairman of Virtual Inc., where he has spent more than three decades helping organizations navigate growth, change, and strategic communication. Throughout his career, he has worked with global organizations like Microsoft, Google, and Meta. He also helps leaders become more intentional communicators. 

His newest book, How to Lead Like a Boss, explores leadership communication in an unconventional way. It looks at the habits and behaviors that made Bruce Springsteen a respected performer and leader.

While the setting may be a concert stage rather than a boardroom, the leadership lessons translate directly to today’s workplace.

Great Leadership Communication Starts with Intention

One of Andy’s most important messages is that effective communication begins long before a meeting starts.

Rather than simply creating slides or gathering updates, leaders should first ask themselves three questions:

What do I want people to think?

How do I want them to feel?

What do I want them to do?

This simple framework shifts communication from information sharing to intentional leadership.

Whether you’re announcing organizational change, leading a team meeting, or having a one-on-one conversation, understanding the desired outcome before speaking dramatically improves clarity and impact.

Preparation Is a Leadership Skill

Bruce Springsteen doesn’t walk onto the stage and hope for the best.

Before every concert, he carefully builds a set list that creates an emotional journey for the audience. Every song has a purpose. Every transition is intentional.

Leaders should prepare the same way.

Instead of opening yesterday’s PowerPoint presentation and making minor edits, Andy encourages leaders to think first about the experience they want their audience to have.

Preparation isn’t about creating more slides. It’s about creating a message people will remember.

If They Can’t Repeat the Message, It Didn’t Land

One of the most memorable ideas from the conversation is that communication isn’t measured by how many times you’ve delivered a message.

It’s measured by whether your audience can repeat it back to you.

Leaders often become frustrated after explaining something once or twice, assuming everyone understands. In reality, people frequently need to hear important messages multiple times before they truly retain them.

Instead of asking, “How many times have I said this?” leaders should ask:

“Can my team say it back to me?”

That shift in perspective can transform the way leaders communicate organizational priorities, strategic initiatives, and change.

Leadership Is Always a Performance

Leadership doesn’t end when the presentation is over.

Andy explains that leaders are constantly communicating through their behavior, energy, and presence, even when they aren’t speaking.

Employees notice whether leaders are engaged during meetings. They notice body language, enthusiasm, and consistency. Your energy sets the tone for everyone around you.

The most effective leaders recognize that every interaction communicates something, whether intentional or not.

Never Underestimate the Power of Appreciation

At the end of every Bruce Springsteen concert, he personally thanks each member of the E Street Band before leaving the stage.

For just a few seconds, every musician receives their full attention and appreciation. That simple ritual offers an important reminder for leaders. Recognition doesn’t have to be elaborate to be meaningful.

Consistently acknowledging effort, celebrating contributions, and expressing genuine appreciation helps people feel valued. Those small moments often leave a lasting impression.

As Andy notes, one of our deepest human needs is simply to feel appreciated.

Leadership Communication Creates Lasting Influence

Strong leadership communication isn’t about being the loudest voice in the room.

It’s about preparing with intention, connecting with people, reinforcing important messages, and creating experiences employees remember.

Whether you’re leading organizational change, facilitating a meeting, or simply thanking someone for their contribution, every interaction shapes trust and influence.

The best communicators understand that leadership isn’t measured by what they say.

It’s measured by what others hear, remember, and ultimately do.

Where to Find More From Andy Freed

To learn more about Andy Freed, his leadership philosophy, and his book How to Lead Like a Boss, visit andyfreed.com. There you’ll find additional resources on leadership communication, speaking, and practical strategies for becoming a more intentional leader.

Develop Leadership Communication Skills with Crestcom

Leadership communication is one of the most important skills leaders can develop, yet it’s also one of the most challenging to master. From communicating change to building trust and influencing performance, effective communication shapes every aspect of leadership.

At Crestcom, communication isn’t treated as a standalone topic. It’s integrated throughout our leadership development programs, providing leaders with practical tools they can apply immediately in conversations, meetings, coaching sessions, and organizational change initiatives.

Listen to the full episode of The Leadership Habit Podcast for even more insights from Andy Freed, and discover how intentional communication can strengthen your leadership influence every day.



The post Leadership Communication and The Boss with Andy Freed appeared first on Crestcom International.