Bill Belichick and the Art of Winning: Lessons Beyond Football

On By Joe DeRosaIn LeadershipLeave a comment

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

On By Joe DeRosaIn LeadershipLeave a comment

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

On By Joe DeRosaIn LeadershipLeave a comment

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

On By Joe DeRosaIn LeadershipLeave a comment

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

On By Joe DeRosaIn LeadershipLeave a comment

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.

Customer Success:  5 Requirements to Creating Value in Every Client Interaction.

On By Joe DeRosaIn BusinessLeave a comment

 

Today’s buyers are overwhelmed with data points, reports, metrics, and an avalanche of nonstop news whether its from traditional networks, cable news, or social media.  Points-of-view are as infinite as the number of stars in the universe…or are they?  In a world dominated by countless Customer Success models I continue to observe just how complicated we’ve made some basic human interactions, and just how little value some of these interactions deliver.

 

Great Customer Success interactions require 5 crucial elements:

 

  1. It all starts with a clear customer success statement as articulated by the customer.  What does success look like?  When we meet 3 months from now, what would have to be true for you to say this engagement is a success?
  2. A strong understanding of general market conditions (macro), and the ability to connect those dots to your customer’s situation, this is what I call “pulling the thread all the way through”.  It requires solid structured thinking skills.  The ability to define a problem, understand the cause, and create a solution that reduces or eliminates the problem. 
  3. Ability to create insights – combining a fact with an implication or point-of-view,
  4. Strong EQ skills that allow you to connect/relate to your customer/buyer on an emotional level,
  5. Storytelling skills

 

I’m sure someone, somewhere is saying, “yeah, but what about…”, or “Customer Success is so much more than these 5 things…”, or “you don’t know my industry, it’s so different than any other industry…”

 

What does this look like in our daily lives?

 

Think of someone in your network you respect and learn something from every time you speak to him, or her, who would it be?  What characteristics does he/she possess? I’d suggest they made your list because they are proficient at all 5 of these competencies and perhaps expert at some of them.  Certainly, you wouldn’t offer me a name of someone boring who lacks details, confidence, or a clear point of view.  No.  Instead, you’d share a name of an individual that you hold in high regard, or perhaps even aspire to be like.

 

Once basic human needs – food, clothing, shelter, safety – are satisfied, you transition to next-level needs which include the need to be heard, understood, validated, and the ability to succeed.  These next-level human needs address both self-esteem and self-actualization.  Said differently, we all desire confidence and ultimately the need to be seen by others as being successful – that we’ve reached a position of respect, or sought-after expertise.

 

Tying it all together…

 

Customer Success Managers (CSM) are entrusted with managing, and growing client relationships.  The CSM has one of the most challenging roles in an organization as they walk the tight rope between Sales, Service, Marketing, Operations, IT, HR, Finance, and virtually any other functional area that touches the client with the potential of creating an experience be it positive or negative. Understanding macro-economic conditions does not mean going back to school to obtain an Econ degree.  As a result of the diversity of a CSMs interaction with a client it’s imperative for him/her to understand how macro conditions affect the customer’s business.   This doesn’t require an advanced education but rather some basic structured thinking, discipline and commitment.  This is the ability to define a problem, understand what causes the problem, and finally creating a solution(s) that addresses the problem.

 

Client Success Managers (CSM), need to have a general understanding of the market conditions.  What’s happening in the market?  How are interest rates moving?  What’s happening with employment numbers?  How is inflation trending?  Where is consumer confidence?  With one or two apps on your phone you can stay abreast of every major macro metric in real time…in less than the time it takes to sip a cup of coffee.  It requires the discipline to build that habit into your day.  According to an October 2023 survey by Statista, people on average spend 2.5 hours per day on social media.  Using 3 minutes of that time every day to understand market conditions doesn’t seem like a huge change in behavior…but it can be if you let it…you’ve got to commit.

 

I often use the phrase, “pulling the thread all the way through.”  This means, having the capability, or skill to understand these conditions and pull the thread all the way through to how these macro conditions affect your customer through storytelling.  Doing this allows you to clearly define the problem your customer is currently facing, or about to face, and be able to communicate this to them in a way that is both articulate and confident.  Storytelling is not fiction, nor is it fear mongering.  Storytelling involves understanding your client’s current situation, the inputs that affect the situation, and what possible outcomes may exist depending on the actions taken.  Effective storytelling can be summed up in the ability to take multiple inputs and synthesize them into a story that captivates, creates intrigue, and ultimately causes action.  Storytelling is not about scaring the client into taking the action you want, but instead is about causing the client to stop, think, ask questions, and genuinely ponder the possibilities the CSM has presented.

 

Creating insights are something many CSMs struggle to do.  Keep in mind, an insight is combining a fact with an implication, or point-of-view.  A fact could be where current mortgage rates stand, or the current rate of inflation.  An insight would be how a change, up, or down, in that rate could affect your client and what the implication would be in either scenario.  This is a learned skill.  It doesn’t just happen.  Your CSMs need to study macro conditions, practice formulating insights, and role play with sales management in order to improve their effectiveness with their client engagements. 

 

The days of “objection handling” are done.  These old school sales tactics often rely on one’s ability to out-talk, or through smoke-and-mirrors, overwhelm the buyer.  I always disliked old-school objection handling.  Too much emphasis was placed upon having quick come backs, slick words, and one-liners.  Memorize these 3 responses and you’re golden.  Unfortunately, this approach is why Sales as a whole is often viewed in a negative light.  People are reluctant to meet with a salespeople and many salespeople don’t like to tell others they are salespeople.  How can we change this perception?

 

Being insightful is how you earn your customer’s time – their most precious resource.  People are only willing to invest their rarest of resources (time) with those that they can learn something from, and who make them feel validated.  So why is this so difficult?  Why do client engagement professionals still rely on old school objection handling?  Well, I’d suggest it’s because being able to provide real insights and value requires a full-out dedication to learning and understanding market conditions versus memorizing 3 great come-backs when a client raises an objection. 

 

Still today, too many salespeople subscribe to the nonsense of Sales ABC – Always Be Closing.   If this is happening in your company, I’d suggest this is a failure of leadership not leading…not teaching.  If leaders don’t raise the bar and expect a higher degree of business acumen, then their respective teams will fall back upon these ABC rules because they have nothing else.  Leaders need to lead.  This means leaders need to teach.  Further, this means leaders need to get more comfortable with being vulnerable.  Most people dislike role playing as much as they dislike public speaking, leaders included…perhaps more so.  However, role playing is a crucial element to improving your ability to take facts, formulate insights, and tell a story that leads to action, all in real-time.  Role playing for salespeople is the equivalent of a quarterback taking snaps under center at the line of scrimmage.  Defenses unfold in real-time.  We all know that good judgement comes from experience, and experience comes from bad judgement.  This is why professional sports teams practice, practice, practice.  The coach creates and environment that allows for real-time judgement based upon real-time changes to the scenario…all with the goal of making these bad judgements in the safety of a practice versus a real game.  As leaders it’s our job to create these types of learning environments for customer success managers to hone their skills.  It also means the leader must risk a wonky role play in front of the team.  No one has all the answers, but the best leaders, are okay with getting it right versus focusing on being right.

 

In conclusion, customer success is about having a clear success statement articulated by the customer.  Great CSMs will provide a blend of facts and insights that address their customers problems which result in earned trust and respect.  These CSMs take chances, formulate insights, role play their delivery, and embrace the outcomes as their own.  They are the game changers, the difference makers, in achieving outstanding customer success.

 

 

 

 

 

 

 

 

 

 

 

Choosing the right Chief Revenue Officer

On By Joe DeRosaIn Business, Leadership, SalesLeave a comment

Recently, I attended a webinar sponsored by Private Equity CXO.  The topic of the webinar was PE Strategy for Revenue Growth; CROs and Value Creation.  Presenting in the webinar were several Private Equity professionals sharing their insights on the impact that having the right Chief Revenue Officer (CRO) can have on an organization’s success.

Let me first say that the webinar overall reinforced my personal experiences and beliefs throughout my career as both a GTM consultant and a CRO with experience working with companies ranging in size from $50M to >$6B in annual revenue.  However, the webinar got me thinking about the challenges involved in finding the right CRO, the process that most private equity firms use to recruit CROs, and the end result…disappointingly low success rates as supported by comments in the webinar as well as in other datapoints I’ll present shortly.

While I could write pages summarizing the content of this webinar relating to how CROs should, or could create value, I will instead focus on one critical topic discussed by the group…finding the right CRO.

Herb Brooks, the famous coach of the United States 1980’s Men’s Gold Medal Olympic Hockey team, has one of the best all-time quotes and probably my personal favorite.  As he was assembling his team, he was asked why he didn’t choose this player or that player because “they were the best”.  Herb confidently, and with unwavering conviction replied, “I’m not looking for the best players, I’m looking for the right players.”  This philosophy will serve as my anchor for why the right CRO may look quite different from the best CRO. 

I believe Coach Brooks could not have been more spot-on.  While I’m sure this comment will strike a chord with some, I stand by the belief that skill is much easier to teach than attitude, let alone chemistry, as it relates to team dynamics.  A Harvard Business Review study showed that 44% of a company’s market value is attributable to its CEO’s reputation. This study further defines reputation as a combination of 3 key emotional intelligence characteristics including humility, visibility, and persuasiveness.  One may conclude that some portion of a CEO’s reputation is a direct extension of the CEO’s executive and senior executive leadership team if you believe that a company’s culture is the sum of its parts.

Throughout the webinar the conversation often returned to the importance of the CRO’s team building capabilities, and leadership skills required to build a sustainable high performing culture. 

From an operator point of view, I would say that while a new (and even existing) CRO certainly has the responsibility to lead and effect change in an organization, a new CRO especially needs to understand the existing culture that he/she is walking into, the runway in front of this them (timing expectations), and as mentioned in the webinar, a list of the “jobs to be done” – the critical items that must be completed within the next 12 months.  Measure twice, cut once, applies to walking into a new role for both sides of the relationship – CRO and private equity partners.  The greater clarity provided at the onset, the greater the likelihood of success and perhaps fewer missed expectations. 

I strongly believe that the “right” CRO has both a track record of successes and failures.  I’m always leery when I speak to any executive-level candidate who positions themselves as having made perfect decisions.  Perhaps I’ve been blessed to work for leaders like Scott Cook of Intuit, who famously pushed our management team to make more mistakes – fail fast – as a barometer for the speed of innovation.  If you’re not pushing boundaries, you’re not growing, you’re not evolving, you’re simply presiding over something that’s fairly vanilla, and hence replaceable.  Basic, or as I like to call them, cut-and-pasted tactics might work when the waters are smooth, but absolutely go out the window when faced with gale force winds that may include a tight job market, raging inflation, or a pandemic that shifted the norm on how we get things done in business. 

A status quo leader, not battle-tested by building and failing, decreases your probability of success and produces a lesser amount of value creation.  It’s just as important to know what not to do, then knowing what the right thing to do is, as both include countless variables, known and unknown.

Case studies or homework assignments are great, but here’s where I slightly divert from the consensus shared on the webinar.  In my own personal experience, focusing on the difficult questions to ask during an interview, combined with an Up-Down-Sideways reference check is another way to gauge the probability of success.  Some folks have a talent to write, research, and/or problem solve in a controlled environment, but rarely do we operate in controlled environments, and case studies and homework assignments are just that…controlled environments.   

In fact, I’d suggest that many sales leaders would have failed the case study in 2008-2009 during the GFC, or during the COVID pandemic.  The test of a strong leader lies in his/her ability to consume information quickly and being comfortable with operating in ambiguity.  According to Zippia, the average age of a Chief Revenue Officer is 49 years old.  When combined with a datapoint from Salesforce indicating the average tenure of a CRO is right at 2 years, you begin to understand why the concept of battle-testing is so important over a variety of different environmental factors relative to creating and sustaining high performing teams.   One could argue that even as case studies and homework assignments have become the norm for recruiting CROs, the success rates are discouragingly low at less than 2 years.  Why is that?  Here I’d suggest that what’s often missed is the softer, and perhaps more difficult skills to assess that include EQ (some of the items from the HBR study), charisma, and empathy, all of which are critical leadership qualities to establishing and maintaining high performing teams. 

As Stephen Covey famously said, “people don’t care how much you know until they know how much you care.”  A leader showing up as the smartest person in the room likely will result in a team that tries to distance itself rather than embrace.  Hence why EQ is so important when selecting a new CRO.  And, with the average tenure of a CRO being 2 years, one possible conclusion that might be drawn is that too many know-it-alls show up day one on the job versus showing up with a learners mindset. 

Of course, the right mix between EQ and IQ is critical.  And while I referenced the criticality of some of the softer skills above, I also want to be clear that an effective CRO must have the passion and capability to deliver tangible tools to the teams they lead.  I have written countless playbooks, personas, and ICPs for the teams I’ve led throughout my career as a CRO.  I study data, identify trends, create hypos to prove/disprove.  I spend a great deal of time in the field with sales professionals running these plays and adjusting them accordingly, perhaps another carry-over from my experience at Intuit with Noel Tichy’s famous “teach, learn, teach” model underpinned our day-to-day operating rhythm in the business.

Often, I see CROs rely much too heavily on outside consultants (I was one of those), to do this type of work.  Why?  Because they either are not close enough to the business to know, or in the worst cases feel that the level of in-the-weeds work is beneath them.  This, however, is exactly the work that moves the needle by building sales effectiveness, team spirit, and a high performing culture where teams recognize that their Sales leader is sleeves-rolled-up, capable, competent, and credible. 

It was mentioned several times during the webinar private equity’s desire for predictability.  Delivering a “flash-in-a-pan” result is easier than producing consistent results over time.  Again, this is why it’s critical to be clear about what is required within the first 12-month period and what resources are available to accomplish those requirements.  The resource discussion is yet another topic that is deserving of its own thought leadership piece.  For now, here’s a simple way to illustrate the importance of having the right resources…

As someone raised in a musical family, and having played drums for many years, I consider Neil Peart to be arguably the best drummer of all time.  So, was it the 54-piece drum kit that made Neil sound so incredible?  Or was Neil’s raw talent such that he’d sound good no matter how many drums he had at his disposal?  While I’d seen Peart amaze enthusiasts on a regular 4-piece Jazz set, the sounds and complex rhythms he played on 54 pieces simply amped things up a notch.  He had the resources to transcend being great to being the greatest.  Now, drop in Phil Collins behind Peart’s 54 pieces.  Would Collins, another great, sound equally impressive?  Or does it suggest that resourcing wouldn’t matter, and that Collins would just “know” how to play, what to play, and when to play it?  As a reference point, Phil’s typical set is (was) a 10-piece kit.  Regardless, it’s clear that talent, plus resourcing, equals output.  The key to success is understanding what that specific talent requires, relative to resourcing, to produce the expected or desired results.

Back to the CRO thing, a CRO must also have the ability to look at data and make inferences…quick assessments of a situation.  Deductions usually come when deeper analysis is done, and oftentimes, the ability to do a deep dive is limited by a company’s systems, platforms, access to the data itself (perhaps it’s never been captured historically), or not having the analysts (talent) available to do such work.  This leaves the CRO in the position of either taking no action as they become paralyzed by fear of making the wrong decision, or the opposite extreme, making knee-jerk decisions as they quickly fire from the hip.  This area of CRO skill must also be contemplated when thinking about culture, timeframes, and expectations.

Finally, the relationship the CRO has with his/her owners/investors cannot be underestimated relative to performance.  Are the company’s owner enthusiastic supporters?  Are they impatient investors who have gone through a series of failed CROs leading them to bring high levels of doubt or skepticism into any new relationship?  Does the CRO have solid chemistry with both the CEO and CFO?  It has always struck me as odd that I’ve personally never interviewed with a CFO while being recruited for the top Sales chair, yet my personal relationship with a CFO, as a CRO, is perhaps equally important if not more important than the relationship between a CEO and CRO.  There’s a ton there to unpack as a topic – the relationship between CRO and CFO – that opens the door for future thought leadership content.

In summary, finding the right CRO begins with an accurate assessment of the future of the asset.  Where are we in the hold period?  What has the last 3-5 years of organic growth looked like for the company?  What’s the tenure of the team?  Is it a complete build, or rebuild?  Is there a VP of Rev Ops in place, and further, how strong is that person relative to all aspects of analysis and GTM tech platforms?  Do any of the CROs previously-built-teams still exist?  Can the CRO demonstrate an example where he/she groomed and promoted their replacement, and where and how is that replacement fairing today?  With the average age of a CRO being 49, what was he/she doing during the dotcom bust, the GFC, the pandemic, and most recently our current period of high inflation and stifling borrowing rates?  Can the CRO candidate comfortably articulate key learnings from each of these periods and demonstrate how those learnings enabled them to better navigate through the subsequent challenges or crises?  What tangible examples can the CRO point to as evidence of something they built new, as a response to their own evolution of thought due to their experiences?    

In choosing the right Chief Revenue Officer, it’s essential to recognize that leadership is not just about past successes, but about the ability to adapt, evolve, and thrive in an ever-changing business landscape. The true measure of a CRO lies in their capacity to turn challenges into opportunities, ensuring that their experiences become the cornerstone for future growth and innovation.

Birds of a feather

On By Joe DeRosaIn LeadershipLeave a comment

Today’s article in the WSJ, “Buffett and Munger on Success…” got me thinking…

Success is about surrounding yourself with other high-achievers with whom you share common values. Many people surround themselves with like-minded people. This approach becomes self-limiting as it’s easy to fall into group-think when the focus is to associate with other like-minded folks. Sure, it may feel comfortable, or safer to align with others that think like you do, but that approach is a growth limiter.

Instead, focus on surrounding yourself with people who share similar values, and morals, and you’ll end up with a network of positive, diverse thinkers who can stretch and grow your perspectives.

Another important filter when thinking about your network that resonated with me came from the WSJ interview with Charlie Munger. Success comes from steering clear of toxic people. “The great lesson of life is get them the hell out of your life—and do it fast,” Mr. Munger said. 

Find those that lift you up, challenge you, teach you, coach you, and are courageous enough to be real with you. Those are the folks that will help you grow and become a better human being.

https://www.wsj.com/articles/warren-buffett-on-finding-success-at-work-and-what-matters-in-hiring-43da47c3?mod=business_lead_pos1

Leading Through Fear, Uncertainty and Doubt

On By Joe DeRosaIn LeadershipLeave a comment

From What’s In It for Me (WIFM), to Keep It Simple Stupid (KISS), there are countless acronyms we’ve all heard, and used, throughout our careers. Given today’s challenging climate, a leader’s mettle is tested in times of (FUD) fear, uncertainty and doubt. Leading from the front when the wind is at your back is far easier than walking into gale force winds in your face. Said differently, any average leader can lead with tailwinds, but high performing leaders are those that can advance the cause in the face of the strongest headwinds…in the face of fear, uncertainty and doubt.

Many of us are having to do just that today – lean into the headwinds. Macro conditions are reeking havoc on buyers and accelerating the FUD factor. As buyer behavior changes, FUD spills over into our teams…how can it not? As I spend time self-reflecting on the leadership behaviors and attributes that I have experienced during other times of fear, uncertainty and doubt, including Y2K, the dot-com bust, 9/11, and the Great Recession to name a few, it became evident to me that:

  • Leaders must balance confidence and reality with empathy. Too much confidence makes you appear disconnected. Too much reality can create more fear. Empathy makes you human…relatable.
  • Leaders need to be curious. In times of FUD, leaders need to ask questions. Go deep. Get under the covers. Learn first hand what’s going on. Your curiosity is responsible for identifying new paths forward for your team thereby calming the troops.
  • Leaders need to have courage. Not every decision will be right. In fact, many will be flat out wrong…once you have hindsight. You make the best decisions you can, in the moment, with the best available data…and own it.
  • Leaders need to have conviction. The decision is your decision. Right or wrong, you own it. There’s no escape. The art of decision making is knowing when to lean in, and knowing when to admit that a course correction is necessary.
  • Leaders are responsible for identifying and communicating the silver lining. Economic cycles come and go. History tells us that there are bull markets, and there are bear markets. Markets move. Every rain storm is preceded by sunny skies, as well as being followed by sunny skies. It’s the leaders job to reassure their teams that while it may be raining at the moment, the sun will in fact shine again…that’s a fact.
  • Finally, leaders need to be visible, in the trenches, shoulder to shoulder with their teams. Great leaders don’t hide behind Zoom, or a curtain, (we used to refer to the ivory tower), but instead face the same heat/fire their people face with customers, vendors, suppliers, investors, etc. After all, as Stephen Covey said, “people don’t care about how much you know until they know how much you care”. Great leaders demonstrate this by being present.

Recently I had a conversation with a colleague. Story telling, analogies, and metaphors have always been my go-to communication style. I got to thinking about our role as leaders as it relates to a ship’s captain…

The waters are rough…it’s beyond your control…

The ship is creaking and rocking…you can’t control that…

As captain you’re not sure whether the boat will stay together or start breaking apart…you can’t control that either…

You embrace the storm knowing you’ve sailed through storms before and made it through…this experience gives you conviction…

You’ve carried your crew through rough waters before and they’re counting on you to get them to solid ground…

You chart your course and sail into the wind…this is your decision…

While your internal doubts may be high, you push those doubts into a corner of your brain and lock them there while you focus on sailing through the storm and delivering your crew to solid ground…

You never give up fighting for your crew. That’s the captain’s job.