Tag: Personal development

The Miles Between the Decisions

On By Joe DeRosaIn LeadershipLeave a comment

The Miles Between the Decisions

The Miles Between the Decisions

I’m trying to have a little fun with Chat GPT’s caricature creation.

I’ve always been a runner.

For years, running was my reset button. It challenged me physically, cleared my head and gave me an outlet for stress. There was something wonderfully simple about it. Put on your shoes, head out the door and go.

Then, after three knee surgeries, my doctor gave me the news I didn’t want to hear.

No more running.

So what was left for cardio? The StairMaster? Elliptical machine? Walking?

All good forms of exercise. All sounded incredibly boring to me.

A few colleagues of mine cycled, but as a “runner,” I was skeptical. I had convinced myself that nothing could challenge me as much, make me sweat as much or leave me feeling as physically spent as a solid run.

Even my surgeon suggested cycling.

So there I was in June 2020, with COVID in full swing, walking into a local bike shop knowing absolutely nothing about bikes.

Road bikes. Gravel bikes. Carbon frames. Aluminum frames. Components. Gears. Price points that seemed to range from reasonable to “you want how much for a bicycle?”

It was intimidating.

Fortunately, the owner was incredibly gracious with his time and patience. He eventually guided me toward a road bike that was a step above entry level but still had an aluminum frame.

His advice was simple: Don’t get caught up in the cool-kid swirl of carbon frames and expensive equipment until you’ve ridden for a while and know you actually like it.

Good advice.

I bought the bike and got out on the road.

Looking back, it was easily one of the top five decisions I’ve made in my life.

It Started as Exercise. It Became Something Else.

I originally started riding to replace running.

What I discovered was something much bigger.

The freedom of riding. The wind. The resistance. The fresh air. The physical exertion. There’s something about the combination that invigorates me.

Over time, cycling became more than exercise. It became a total health habit for me — physically, mentally and, in many ways, spiritually.

Different strokes for different folks. I’m not suggesting everyone needs to buy a bike and start riding 25 miles.

But I do believe everyone needs to find their thing.

For me, cycling lifts my soul.

It gives me time to ponder, ideate, reflect, recharge and simply be present.

There is nothing quite like riding along the river in the quiet of the morning. No cars. Barely another person around. Six in the morning is my favorite time to ride — before the crazies get on the road.

My average outdoor ride these days is about 27 miles. My longest has been 50.

That means I regularly get two, three and sometimes four hours largely alone with my thoughts.

In today’s world, that is a gift.

Solitude Is Underrated

We spend much of our lives consuming information.

Emails. Texts. Meetings. Teams calls. News. Social media. Podcasts. Presentations. Dashboards.

Something is always coming at us.

But when do we actually have time to think?

Some of my best ideas have come to me on a bike.

Ideas for new sales plays. Articles I want to write. Problems I’ve been wrestling with at work. Conversations I need to have. Decisions I need to make.

Sometimes I solve something.

Sometimes I realize I’ve been thinking about something entirely wrong.

And sometimes nothing happens at all.

That may be the most important part.

There is value in giving your mind enough quiet that it doesn’t have to produce anything.

The Bike Has Taught Me About Myself, Too

There are stretches of a ride when everything feels effortless.

And then there are climbs.

Your legs start burning. Your heart rate rises. Your breathing gets shorter. Your brain starts negotiating with you.

Slow down.

Back off.

Maybe today isn’t the day.

Those moments have taught me something about how I respond to discomfort.

I’ve learned that I can push considerably further than my mind initially tells me. I’ve learned how changing my breathing under physical stress can calm both my body and my thoughts. I’ve learned the difference between genuine physical limits and the limits we sometimes manufacture in our own heads.

Those lessons don’t stay on the bike.

They show up in business, leadership and life.

Energy Changes How We Lead

I have always been a firm believer in fitness.

Not because everyone needs six-pack abs, run marathons or ride 50 miles.

Fitness matters because energy matters.

Our physical condition affects how we show up.

It affects our patience. Our confidence. Our resilience. Our ability to concentrate. Our ability to manage stress. And, ultimately, our ability to make good decisions.

It’s difficult to separate the mind from the body and the body from the spirit. They are connected.

When one is neglected long enough, the others eventually feel it.

And leadership requires energy.

The energy to remain engaged late in the day. The energy to listen instead of simply react. The emotional energy to deal with difficult people and difficult situations. The mental energy to distinguish the urgent from the important.

Good decision-making doesn’t only require intelligence.

It requires clarity.

And clarity is difficult to find when we are physically exhausted, mentally overloaded and never alone with our thoughts.

Find Your Ride

Cycling started because my knees took running away from me.

At the time, that felt like losing something I loved.

Instead, it forced me to discover something I probably never would have tried otherwise.

Today, when I head out early in the morning, I’m not trying to outrun anyone. I’m not chasing a podium. Most of the time, I’m not even chasing a personal record.

I’m chasing something much more valuable.

Energy.

Clarity.

Perspective.

And a few quiet miles where nobody needs anything from me.

We spend enormous amounts of time trying to become better executives, better leaders, better decision-makers, better spouses, better parents and better people. We read books, attend meetings, study data and seek advice.

All of that matters.

But sometimes becoming better at everything we do begins with taking better care of the person doing it.

Find the thing that challenges your body, quiets your mind and restores your spirit.

For me, it happens to have two wheels.

And some of the best decisions I make aren’t made sitting behind a desk.

They’re made somewhere around mile 20, with tired legs, a clear head and nothing in front of me but the road.

 

Help Me Understand…

On By Joe DeRosaIn LeadershipLeave a comment

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.

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.

Birds of a feather

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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

20 Objectives For All Chief Revenue Officers

On By Joe DeRosaIn LeadershipLeave a comment
  1. Be a continuous learner – what got you into the CRO role won’t keep you there.
  2. Create a culture of innovation – willingness to try new things without the fear of failure.
  3. Demonstrate teamwork and camaraderie – people will watch and observe your behavior before they act.
  4. Focus on the people – this means getting to know your colleagues beyond their quotas.
  5. Be authentic – this equals consistency and predictability. Wild mood swings are often due to people transitioning from their “real” self to their created façade.
  6. Be vulnerable – show you’re human, it’s okay.
  7. Confront reality – denial wrecks your credibility. Quotas are huge, don’t act like they’re no big deal.
  8. Provide a path to success – it may be a difficult path but a path none the less. Remember, the leader’s job is to provide the vision…the possibilities.
  9. Be honest – shoot straight, share what you can, not only what you must.
  10. Always have an active ear – listen…actively. People want to know how much you care before caring about how much you know.
  11. Never surprise your boss – understand what’s important to the CEO and how/when to best communicate.
  12. Be deliberate in your actions – an environment of uncertainty is a byproduct of hedging bets. Your team will know if you’re not all in.
  13. Be kind – nothing in this job should justify taking someone’s dignity.
  14. Be gracious – say thank you. Give credit and recognize people consistently.
  15. Look for the good – every day find a good deed, or success from a colleague, and then share it.
  16. Know your numbers – where are you this month to quota, next month, and quarter standings.
  17. Know your business – what external factors may arise to get in the way of achieving your goals and those of your colleagues?
  18. Always be planning – “In preparing for battle I have always found plans are useless, but planning is indispensable.” ~ Dwight D. Eisenhower
  19. Stay fit – CROs tend to be the heartbeat of a company. Work hard to have and maintain a healthy heartbeat.
  20. Always, always, remember (and thank) those who helped you arrive – family, friends, former bosses, mentors. No one gets to where they’re going totally alone

Growth Through Adversity

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Our lives are filled with crucible moments.  Situations that shape and mold who we become as people, workers, managers, and leaders.  These moments, whether we face them in our personal lives, or professional life, shape the core of who we become.  They inform, and direct our future beliefs, habits, and behaviors.  They can strengthen or weaken, improve, or deteriorate.  

Most of these moments are unplanned.  They sneak up on us and force our hand.  They force us to buckle, retreat, or forge ahead.  These moments-in-time, although difficult to persevere, help strengthen our constitution…or weaken us.  The choice really is our own.  How we react to adversity is in fact a choice.  Famous, U.S. Men’s Hockey Coach, Herb Brooks, said, “Great moments are born from great opportunities”.  First let me say I have great admiration for Herb Brooks and his legacy. That said, if I may be so bold, I’d make a minor change to his quote and add that great moments are born from either a great opportunity, or adversity.  After all, it’s friction that creates the most beautiful, and valuable diamonds in the world.  The same can be said about our greatest leaders – past, present, and future.  While not always pretty, the world’s great leaders have experienced their share of friction, adversity, and disappointment.  From Washington to Reagan, from Henry Ford to Steve Jobs, from Sam Walton to Elon Musk, each of these leaders experienced their share of hardships and challenges…crucible moments that shaped their views, perspectives, ideas, and leadership styles. 

Spend some time taking inventory of your crucible moments.  I was first exposed to the concept of life journey lines when working for Lorrie Norrington who at the time was the EVP with Intuit in the early 2000’s.  In fact, Journey Mapping is still very much a part of Intuit’s culture.  Looking back, Lorrie is still one of the most influential leaders in my career.  She taught me the importance of quantifying my capabilities and having the confidence to embrace them and act.  Creating a life journey line is an effective way to identify one’s crucible moments, and more importantly understand how those moments shaped us and the new skills and capabilities we acquired because of those moments.  Taking the time to think about these critical moments in life helps to provide clarity on your capabilities.  Steve Jobs famously said, “You can’t connect the dots looking forward, you can only connect them looking backward.”  That’s not to say, or suggest, we should live in the past, but rather to understand our ability to endure, preserve, learn, adjust, and succeed.

What are your crucible moments?  How did they shape you?  What changes did you endure?  Positive or negative?  

Every person we encounter on a day-to-day basis has gone through, or is currently going through, a crucible moment.  Our ability to empathize is critical.  How we assess these moments, and learn to adjust and adapt, based on this new knowledge and experience, is what enables our future success…and the success of the teams we lead.

Leaders are not born, they’re developed

On By Joe DeRosaIn Leadership1 Comment

I recently had dinner with one of my top sales people in San Diego this week and the conversation got around to whether people are born as natural sales people, or leaders.

I’ve never been a believer that people are born into a specific life path. What I believe is that each of us is born with a set of talents, capabilities, and competencies. We are all born with a specific attitude as well. A mindset, a glass half full, versus half empty thinking. A skeptic, an optimist, or pragmatist.

Here’s where the conversation gets fun. Believe it or not there was an interesting life lesson that has stuck with me for years from a rather unexpected movie – RAMBO III. In the movie the character of Colonel Troutman gives a pep talk to John Rambo. He tells the story of a sculpture who finds a perfect stone. He drags it back to his workshop and creates an incredible statue. When his friends compliment him on his creation, he says, he didn’t create anything. The statue was always there…he just chipped away the small pieces.

We are all born with natural talents. Some are blessed with athletic abilities, others with analytical strengths, others with caregiver strengths. The difference between those that achieve their full potential versus those who don’t, is finding a mentor(s) who helps validate and provide direction for your unique set of skills.

What if there was no Earl to Tiger Woods? What if no Joe to Michael Jackson? What if no Kurt to Michael Douglas? There are thousands more of these examples of folks who are not in the limelight but succeeded because they benefited from someone who recognized their talents and provided direction and encouragement. I’ve been incredibly blessed to have had a number of bosses throughout my career who have guided, counseled, and encouraged me to embrace my skills, take chances, and stretch. Without them, I am certain I would not have accomplished what I have thus far. And while I’m now considered “middle age”, my need for their input, guidance, and counsel still remains strong. Being a continuous learner never stops…until the heart does.

So what if you don’t feel like you have a person like this in your life? What do you do to find someone to fill this gap? The answer is easy. Look around. That person is probably closer to you than you think. It could be a spouse, partner, boss, friend, someone at the gym, someone sitting next to you on a plane. In fact, my love for American history was born on a flight I was on in 2004 when I met a gentlemen who asked me what types of books were my favorite to read. Foolishly I said none. He said, how can you spend so much time on a plane and not read. He told me I was missing all kinds of opportunities to expand my thinking. When we landed he gave me a book that became the catalyst for creating my voracious appetite for reading. That book was called His Excellency on George Washington. I can’t count the number of books I’ve given away over the years to people who I just met in similar situations. You never know who, or how you can impact the life of a stranger for the better. It’s incredibly heartwarming and fulfilling.

Life lessons are everywhere. Sometimes you just need to put down your phone, take out your ear buds, and just be…be present. Take an inventory of all the things you’re good at. Jot down what you like to do. Assess the crowd you hang with and identify a few people to approach to help you clear away those stones. Remember, the statue is always there…it’s just how badly you want to chip away at the stones to show your uniqueness and value to the world.

Growing Through Adversity

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Positive growth can happen even under the toughest of conditions. Perseverance, determination, and the ability to adapt are what’s needed to push through the challenges and capture the growth that’s yours. New skills, new perspectives, new ideas.

As I walked around our property today I saw this beautiful petunia growing in-between some pavers. Oddly this is not a flower we have planted anywhere on our property, yet here it is. With temperatures in the high 90’s this past week, and no rain or water, seeing this thing of beauty grow in the most difficult conditions made me realize how possible growth is in any environment.

It reminds me of the line in Jurassic Park – “Life will find a way.” You really can do anything you set your mind to.