Help Me Understand…

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How Great Leaders Use Questions to Build Trust, Uncover Risk, and Improve Decisions

After two back-to-back weeks of board meetings, I found myself reflecting on the train ride from New York back to Philadelphia. A few observations came to mind.

People want to be engaged.
When board members ask thoughtful questions, it energizes the room. It signals that the work matters and that leadership is paying attention.

Recognition matters.
Not empty praise, but authentic acknowledgment of meaningful results. Genuine recognition reinforces the behaviors and outcomes organizations want to repeat.

Boards bring perspective.
Because board members aren’t running the business day to day, they can often see patterns, risks, and opportunities through a different lens. Their greatest value isn’t having all the answers, it’s offering perspectives management may not yet have considered.

Tone matters as much as the question.
People don’t just want to be heard; they want to feel respected. Curiosity creates dialogue. Condescension shuts it down. Some of the best conversation starters I’ve heard are:

  • “Help me understand…”
  • “I may be missing something…”
  • “Walk me through your thinking…”
  • “What are we seeing…”
  • “What would make us change our minds…?”
  • “Where do you have the lowest confidence?”
  • “How is the team doing?”

Those simple phrases demonstrate both emotional intelligence and humility.

Be willing to share your failures.
Board members aren’t omniscient despite what some may think. We all learn through successes and mistakes. I’ve always found it more valuable when a board member shares where something didn’t work, what they learned, and how that experience shaped better decisions. That’s wisdom, and wisdom is one of the board’s greatest responsibilities.

It’s not enough to report on today’s weather. Great board members help management think through what might be coming next, why it may happen, and how to prepare for it.

Trust is built between meetings.
The board members I’ve valued most throughout my career are those who invest in establishing relationships outside the quarterly meeting cadence. They get to know the team. They ask questions. They stay engaged.

That trust becomes invaluable when the business inevitably hits turbulence.

No company wins forever. Even exceptional businesses eventually face market shifts, competitive pressure, or unexpected disruption. The strength of the board-management relationship is often tested most during those moments, not during the good quarters.

One final thought for management teams:

Know your business’s motion.
Know how the key drivers interact. When one variable changes, what typically happens next? That’s different from having all the answers. It’s understanding the dynamics of your business well enough to explain its expected behavior while remaining open to new information.

I call that controlled confidence…speaking with conviction while remaining intellectually curious. Confidence comes from experience. Experience grows through continuous learning.

And finally…

Be yourself.

It’s remarkable how often people change their personalities in boardrooms and executive meetings. Authentic confidence builds credibility. Manufactured confidence usually creates doubt.

People don’t expect perfection. They expect honesty, preparation, accountability, and a willingness to learn.

Those qualities earn trust with your team, your board, and ultimately, your customers.

Sales Teams Don’t Need More Research — They Need More Business Acumen

On By Joe DeRosaIn SalesLeave a comment

Recently I’ve had a few CEOs ask me a question that comes up often when discussing sales performance:

“How much research should a sales rep do before their first call with a prospect?”

It sounds like a straightforward question.

But in many ways, it’s a trick question.

Too often we try to solve sales performance issues with a formula:
“Spend at least an hour researching the prospect.”
“Know everything about their company before the call.”
“Come in with the answers.”

I tend to think about this differently.

The truth is, EQ paired with solid business acumen can carry most first conversations.

A first meeting shouldn’t be about showing up with a prescription. It should be about learning.

If a sales team is struggling, the answer isn’t a one-size-fits-all rule about research time. What matters far more is whether the salesperson has:

• Emotional intelligence
• Intellectual curiosity
• Strong business acumen
• A deep understanding of the product or service they represent
• Clarity on how that product or service is delivered
• A compelling sales story — why it matters to the customer

Too many salespeople become paralyzed by the belief they must have every answer before the conversation even begins.

When I see that, the first question I ask is simple:

Why can’t this person carry a thoughtful business conversation with limited information?

What’s missing?

Confidence?
Business context?
Curiosity?

Another important factor is how the meeting was positioned in the first place.

If a rep schedules a meeting saying, “We have the solution to your problem and only need 30 minutes to show you,” they’ve already painted themselves into a corner. Now the conversation becomes a rushed product pitch.

But if the expectation is set differently — “I’d like to learn more about your organization, what you’re trying to accomplish, and the challenges you’re navigating” — the entire dynamic changes.

Now the conversation becomes what it should be:

A dialogue.

One focused on understanding the problem deeply enough to eventually deliver a solution that brings predictability, consistency, and peace of mind.

The best salespeople I’ve ever worked with weren’t the ones who memorized the most information beforehand.

They were the ones who knew how to think, how to listen, and how to learn in real time.

Growth Still Comes Down to the Sales Engine

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I recently read BCG’s report “Private Equity’s Advantage Is Shifting, Not Shrinking.” One theme stood out clearly:

Performance improvements are shifting away from financial levers and toward operational excellence.

For years companies leaned heavily on two tools:

• Price increases
• Expense controls, and/or reductions

Both are important. Both are required to run a smart business.

But neither creates durable growth.

The real advantage comes from a well-run revenue engine.

That means mastering the fundamentals:

• Deep understanding of the market and buyer personas
• Clear value proposition tied directly to customer pain
• Pipeline health focused on quality and deal velocity
• Strong sales management and performance accountability

One of the most underrated leadership skills in sales is pattern recognition.

Where do deals stall?
Which personas convert?
Which messaging resonates?
Where is pipeline real — and where is it theater?

Great sales leaders see these patterns early and adjust quickly.

But even the best GTM infrastructure isn’t enough without the most important ingredient:

A sales growth culture.

I’ve seen companies with the right tools, processes, and talent — yet growth stalled because the broader organization didn’t rally around the sales engine.

Growth starts at the top.

When the CEO and leadership team clearly prioritize new revenue creation, the organization aligns.

A simple way to think about it:

Strong Sales → Hiring → Investment → Innovation → Growth

The reverse is also true:

Every positive outcome in a company ultimately traces back to new revenue.

Weak Sales → Cost Cuts → Layoffs → Retrenchment

Everything good flows from growth.

Nothing Is More Important Than Someone’s Own Problems

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One rule from What It Takes by Stephen A. Schwarzman, co-founder of Blackstone stands out:

There is nothing more important to someone than their own problems.

This applies everywhere — with executives, teammates, and clients.

If you speak directly to what’s on their mind — and have something thoughtful to offer — they will listen.

Too often we focus on:
• Our agenda
• Our priorities
• Our message

But real influence starts with understanding:

• What pressure they’re under
• What success looks like in their world
• What risks they’re trying to avoid

When you truly understand that, alignment becomes possible.

You stop pushing.
You start solving.

Because at the end of the day, everyone is asking the same question:

Do you understand my problem?

Bill Belichick and the Art of Winning: Lessons Beyond Football

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Few leaders in sports—or business—have demonstrated such consistent success as Bill Belichick. His six Super Bowl rings with the New England Patriots weren’t the result of luck, but of a philosophy rooted in discipline, accountability, and relentless improvement. While his field was football, his principles apply just as powerfully to business, leadership, and life.

Here are some key learnings I had from this amazing read:

Attitude and Productivity

Belichick’s view of people is stark but true: they fall into four categories. Productive with a good attitude, productive with a bad attitude, unproductive with a good attitude, and unproductive with a bad attitude. Only the first group sustains success. Talent alone is never enough—complacency from a skilled but disengaged teammate can be more damaging than an injury. Elite contributors don’t just show up for the “game”; they bring effort and intensity to every practice, meeting, and detail along the way.

Process Over Results

Belichick insists that results cannot be mastered—only the process can. A disciplined process builds habits, habits create dependability, and dependability wins games. That same idea holds true in organizations: big wins are built from the thousands of small, consistent actions that precede them. Preparation must be predictable, repeatable, and designed to compound into excellence.

The Power of Improvement

If there is one theme Belichick returns to over-and-over, it is improvement. Improvement is not a temporary push or a seasonal theme—it’s the medium in which winning cultures live. It is about getting better every day, in every interaction. His three rules of improvement are simple yet profound:

  1. Don’t blame or make excuses.
  2. Understand what needs to be done.
  3. Take positive steps to change it.

Setbacks aren’t invitations to retreat. They’re opportunities to prepare harder, to adapt faster, and to re-commit to the standard.

Mental Toughness and Resilience

For Belichick, mental toughness means “doing the right thing for the team, especially when circumstances aren’t perfect for you personally”. Dwelling on mistakes wastes time; the only productive move is to reset and execute the next play. True competitors are measured not by comfort, but by their response to adversity.

“Do Your Job”

Perhaps his most famous phrase, “Do your job,” is deceptively simple. It’s not a one-time instruction but a continuous responsibility. Each person must focus on their role, execute it with excellence, and trust that teammates are doing the same. Trying to take on someone else’s responsibility dilutes accountability. A winning culture is built on clarity, dependability, and mutual trust.

Leadership and Team Culture

Belichick emphasizes that leaders provide tools and a plan, but it is the team that fills in the gaps with adaptability and determination. Culture is built by those who reject “not my job” mentalities. Role models, whether on the field or in the office, demonstrate that effort and attitude overflow downward, shaping the environment for everyone else.

Adaptability and Focus

Technology may level the playing field, but the differentiator is how teams use it. Belichick stresses redirecting saved time and energy into preparation and execution. And working hard isn’t about performative busyness; it’s about hitting the targets that matter, with accountability holding everyone to the standard.

A Daily Mindset

Belichick’s mindset can be summed up in one phrase: “Every day, you’re either building something, or you’re wasting time.” Winning, whether in football, business, or life, is improvement, one rep at a time. It’s about process over results, accountability without excuses, resilience in imperfection, and doing your job with unwavering focus.

Takeaway: The Art of Winning is not about trophies or titles. It’s about cultivating a culture where discipline, improvement, and accountability are woven into the fabric of daily work. That’s a playbook worth following in any field.

When the Ground Shifts Great Leaders Rise

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A leader’s mettle is tested not when things are going well, but when the ground beneath their team begins to shift. In times of uncertainty—when teammates feel unstable, insecure, or even afraid—a leader’s ability to show empathy is not a soft skill; it’s an essential one. Empathy calms fear. Clarity inspires action.

To lead effectively through uncertainty, leaders must remain steady while heightening their awareness. That means increasing observation, listening more intently, asking better questions, and keeping an eye not just on their own industry but on broader market dynamics. The best leaders resist the temptation to retreat inward; instead, they lean outward—with curiosity.

Whether you’re leading a small team or sitting in the C-suite, embracing a learner’s mindset is non-negotiable—especially in times of disruption.

For many of us, the Global Financial Crisis (GFC) was our first major test. The markets crashed. Unemployment surged. The very concept of “underemployment” became part of our daily lexicon. Household names like Bear Stearns and Lehman Brothers vanished. Confidence was shaken to the core. And yet, what helped steady the ship were leaders who had prepared for the unthinkable—people like Jamie Dimon and Warren Buffett—leaders who didn’t just react, but responded from a foundation built long before the storm.

Then came COVID-19, a global pandemic that affected not just our financial systems, but our health and our sense of safety. This time, the fear wasn’t of a market crash, but of mortality itself. People didn’t just worry about their retirement—they worried about whether they’d see another holiday with loved ones.

Since then, we’ve seen crisis after crisis: recessionary pressures, global supply chain disruptions, inflation driving up the cost of everyday goods, and now economic tension from shifting tariffs. Each wave has added more complexity to the leadership equation.

These moments trigger real, raw human emotion—and effective leaders don’t ignore them. They acknowledge them. They listen. They empathize. And most importantly, they act. Not with blind optimism, but with grounded confidence. They communicate a vision that’s both viable and realistic.

I still remember Jamie Dimon’s reference to JPMorgan’s “fortress balance sheet” during the GFC—a symbol of preparation and calm. I think of Warren Buffett investing in GE, a deliberate move to signal faith in the future.

But leadership isn’t limited to boardrooms or trading floors. It happens every day—in small businesses, city governments, classrooms, hospitals, and homes.

In uncertain times, the best leaders become anchors.

They don’t pretend to have all the answers. Instead, they stay steady, remain curious, and lead with conviction. They inspire trust not by avoiding reality, but by facing it—and showing others how to move forward, together.

The question for every leader today is not if another crisis will come, but when. The better question is:

When it does, who will you be for your team?

Leading from the Inside Out: My Journey from Misunderstood Introvert to Empowered Leader

On By Joe DeRosaIn Leadership1 Comment

Growing up in a large Italian family, I was surrounded by loud conversations, strong opinions, and lively weekend gatherings filled with singing and dancing. Yet, despite the joyful chaos, I often felt drained, exhausted, and at times even dreaded these events. Nearly everyone around me seemed effortlessly outgoing, boisterous, and gregarious. Then there was me.

Sure, I could keep up—and I often did. I knew how to step into the spotlight, to charm and engage, yet I felt profoundly uncomfortable inside. After every family gathering, I found myself utterly wiped out, craving solitude to recharge. Back in those days, there were no smartphones, iPads, or streaming services—just silence. And I loved it.

For years, I struggled to understand why I was wired differently from my extroverted parents and older sisters, who appeared so naturally comfortable being center stage. Despite my own ability to play that part when necessary, I always collapsed afterward, craving peace and quiet.

As I grew older, nothing changed. I could still “turn it on” whenever I needed to, yet afterward, I required immediate downtime to recover. Ironically, my career path led me into sales—a field traditionally dominated by outgoing personalities. Surprisingly, I excelled at it, yet constantly wondered how I, so different from the stereotypical, extroverted sales reps, was thriving.

Then in 2012, everything clicked. I came across Susan Cain’s TED Talk titled “The Power of Introverts.” Watching Cain speak was a revelation—I saw myself reflected clearly in her insights. I learned I was an introvert, deriving strength from my natural superpower: the ability to observe, reflect, problem-solve, and thoughtfully act. My greatest strengths flourished in quieter, low-key environments.

Moreover, I discovered that my deepest professional satisfaction came not from personal accolades or spotlight moments, but rather from seeing my team succeed through their own focused efforts. My leadership style evolved naturally—not from imposing force, but from Sua Sponte—through encouraging autonomy, creativity, and genuine collaboration. I found true joy in guiding, mentoring, and participating in the developmental successes of others.

Soon after watching Cain’s TED Talk, I eagerly read her book “Quiet,” deepening my understanding of my introverted wiring. Even more interesting, I learned I wasn’t purely an introvert but rather an ambivert, comfortably flexing between extroverted demands and introverted needs for solitude and reflection.

Society often misinterprets introversion as shyness or antisocial behavior. But the reality is far different: introversion is simply about how we energize and recharge ourselves. Harvard professor Francesca Gino’s research underscores this point: teams led by introverted leaders achieved 28% higher productivity when team members were proactive and independently motivated, thanks to the careful listening and thoughtful encouragement introverts naturally provide. Additionally, studies suggest introverted CEOs are 30-40% more likely to deliberate carefully when making critical strategic decisions, potentially reducing risky outcomes.

So, to my fellow introverts—and ambiverts—embrace your unique strengths. Your quiet power is not only valuable; it’s essential. In a world that often equates noise with strength, let your thoughtful voice lead, innovate, and inspire. After all, true leadership isn’t about being the loudest in the room; it’s about creating space for everyone else to thrive.

Why Empathy Is the Secret to Leading Through Tough Decisions

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Leadership isn’t for the faint of heart. It’s difficult by design. At its core, leadership is about making decisions—many of them difficult, and some of them unpopular. A leader must often choose a path that not everyone agrees with, weighing what’s best for the organization against how it might impact individuals. And that’s part of the job: to make the tough calls even when others might not fully understand or support them.

But here’s where great leaders distinguish themselves. While decisions must be made, and action must be taken, how those decisions are made—and how people are treated along the way—defines the legacy of a leader. This is where empathy comes in, not as a soft skill, but as a strategic advantage.

The Case for Empathy in Leadership

Empathy is the ability to see the world through someone else’s eyes. In leadership, it means taking the time to understand what your people are experiencing—even when you can’t change the outcome. It doesn’t mean avoiding hard decisions. It means making them with humanity.

Empathy builds trust, and trust builds alignment. And alignment is what allows an organization to move forward, even when times are uncertain.

When I think about leaders I admire, either through reading about them, and in many cases having had the privilege of working for many great leaders I’ve observed the following commonalities:

  • Average leaders make decisions and get results.
  • Great leaders do the same—but in a way that brings people along with them.

An average leader explains the “what.” A great leader also explains the “why.”
An average leader gets compliance. A great leader inspires commitment.
An average leader operates with authority. A great leader operates with authenticity.

Few would argue the impact of Abraham Lincoln’s leadership during the Civil War. He made some of the most difficult, divisive decisions in American history. But he led with deep empathy—even toward those who opposed him. Lincoln’s famous quote, “Do I not destroy my enemies when I make them my friends?” reflects his belief in finding common ground in the face of division. That demonstrates incredible empathy capabilities which in turn became the mark of his greatness.

The Leader’s Critical Obligations

Whether you lead a handful of people or thousands, leadership brings obligations—not just to your business, but to your people. Each day I do my best to:

  1. See People, Not Just Roles
    Behind every title is a human being with dreams, fears, and stories. A leader’s job is to understand what makes people tick, and to help them thrive—not just produce.
  2. Create Psychological Safety
    Innovation, honesty, and growth all begin with safety. People must feel safe to speak up, take risks, and be vulnerable without fear of blame or retribution. When teammates act fearlessly and with vulnerability, not afraid to make a mistake, you know you’ve done this well. Fail fast, fail forward.
  3. Champion Common Ground
    When opinions differ—and they will—a leader must become the bridge. Finding shared values and uniting people around a common mission is a leader’s superpower.

Empathy Is Not Weakness—It’s Strength

Empathy doesn’t mean avoiding hard truths. It doesn’t mean being a push-over, or weak. It means being able to deliver difficult decisions with care. It doesn’t mean pleasing everyone. It means respecting everyone—especially when decisions don’t go their way.

We’ve all heard it—people might forget what you said, but they’ll remember how you made them feel, especially when things get tough. I’m definitely not perfect at this, but I try to keep it front of mind every time I make a decision. It’s what I strive for every day—even when I don’t get it perfectly right.

Harnessing Focus; What Shackleton’s Antarctic Expedition Taught Me

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I believe success in any endeavor—business, personal growth, or leadership—begins with a singular element: focus. Without it, energy is scattered, priorities drift, and progress stalls. But focus is more than simply paying attention; it’s the discipline of aligning your habits, behaviors, and determination toward a well-defined goal.

Throughout my leadership career, I’ve emphasized to my teams the critical importance of focus. Establishing clear goals, cultivating the right habits to achieve them, and, most importantly, developing the inner fortitude to stay on course when the unexpected happens and threatens to derail our plans, are essential components of effective leadership.  And, since all leaders face unexpected surprises, improving your focus capabilities will help you become a better leader. Focus pertains to our ability to concentrate, while inner fortitude reflects our resilience when unforeseen obstacles arise—a scenario all leaders inevitably face.​

One of the greatest testaments to focus and inner fortitude is Ernest Shackleton’s legendary Antarctic expedition, chronicled in Endurance. When his ship became trapped in the ice, Shackleton didn’t waver. He shifted his focus from exploration to survival, leading his crew across arguably the most remote and hostile part of the Earth for nearly two years. His ability to set a new goal and maintain unwavering determination saved their lives. Shackleton’s leadership exemplifies the power of focus combined with tenacity, perseverance, and an unrelenting will to succeed.​

In our daily lives, achieving focus requires more than motivation, it requires habits and behaviors that reinforce discipline. Start with a clear goal. Define it with specificity. Then, create triggers or routines that support it. Whether it’s blocking time for critical meetings, conducting follow-up, eliminating distractions , or maintaining physical and mental strength, your behaviors must align with your objective. As an example, for years, I’ve laid out my workout clothes at the bottom of the bed. When I wake up, the first thing I see is my gear, which acts as a trigger that drives my behavior to immediately get to my work out. A work-related habit I’ve used over the years is to create my “next-day” priorities that start with the most difficult actions first thing in the morning when I’m at my sharpest. The list has clear and specified goals or priorities for the day, and serves as my trigger when I arrive at my desk in the morning. It is a focus-enabler.

Determination fuels focus, but tenacity sustains it. I’ve observed these traits in great leaders because they have the ability to push forward when motivation fades. This is why Shackleton’s journey resonated so much with me as a leadership lesson: Set your goal, adapt when necessary, but never lose focus. Whether in business, fitness, or personal development, success is reserved for those who define their purpose and relentlessly pursue it. Start today, stay locked in, and stay tenacious.

Why Every Leader Needs a “Swim Buddy” for Success

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You might be curious about the connection between a “swim buddy” and leadership. At its most basic definition, a swim buddy is someone who swims alongside you, ensuring safety and offering encouragement. In broader terms, a swim buddy represents a person who supports you unconditionally, regardless of the situation. In the military, particularly among Navy SEALs, the swim buddy system is essential. It emphasizes safety, accountability, and motivation, especially during challenging times. Essentially, a swim buddy’s role is to keep you alive and moving forward.

Over the years, I’ve immersed myself in numerous military-themed books, gaining insights, picking up new skills, and expanding my leadership capabilities by applying the practices and attitudes I was reading about from these frontline operators to Commanders in Chief.

While I’ve extensively read about Navy SEALs—arguably among our premier military operators—the profound connection between a swim buddy and leadership crystallized for me when I recently read Admiral William H. McRaven’s book, The Wisdom of the Bullfrog. McRaven describes a swim buddy as “someone who could bail you out of a tough situation.” He emphasizes that no leader is capable or strong enough to withstand the daily pressures of leadership alone.

This perspective prompted me to reflect on the significance of my own swim buddies throughout my career. A common thread among them is trust. This trust fosters an environment where complete, and sometimes brutally honest, feedback is possible, which is essential for personal and professional growth. It allows one to “accept both their support and criticism with equal grace.” Simply said, career swim buddies are there to push you forward and stop you from wallowing in self-pity when times are tough. Ultimately, your swim buddy will help you make better decisions as a leader.

Every leader faces challenges such as missed deadlines, economic downturns, unmet sales targets, or declining employee morale. I’ve encountered these adversities, often simultaneously. Reflecting on my career, I recognize that my achievements would have been significantly diminished without the invaluable support of my swim buddies over the years. Their presence provided not only practical assistance but also the emotional resilience needed to navigate complex situations which only become more common as your leadership level rises.

​In leadership, having a trusted partner—a “swim buddy”—is invaluable. These individuals offer safety, accountability, and motivation, helping improve your decision making capabilities and drive better outcomes.