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Truth's Ascent: Navigating the 3 Stages of Change
We are now well into the first quarter of 2026. By now, the polished slides of your annual kickoff have met the messy reality of daily operations. Are the "truths" you championed in January currently being embraced—or are they quietly being met with the friction of the status quo?
The transition from February to March is often the "make or break" window for digital transformation. It is the season where the novelty wears off and the discipline of leadership begins. If you find your initiatives facing headwinds, it may not be a sign of failure, but rather a sign that your strategy is moving through a predictable, necessary gauntlet.
There is a profound framework for this experience, famously articulated by the philosopher Arthur Schopenhauer in his preface to The World as Will and Representation (1818):
"All truth passes through three stages. First, it is ridiculed. Second, it is violently opposed. Third, it is accepted as self-evident."
For the C-suite leader, VP, or Principal Engineer, these stages aren't just philosophical observations; they are the strategic milestones of any significant change management initiative.
Stage One: The Ridicule of the Unfamiliar
In the fast-paced world of tech and Client Success, new truths often arrive looking like "extra work" or "unnecessary pivots." When you suggest a radical simplification of your tech stack or a shift in how you measure client health, the first response is often a dismissive laugh or a sarcastic comment in the hallway.
As a leader, your role here is not to take offense, but to practice high emotional IQ. Recognize that ridicule is often a mask for a lack of understanding or a fear of the unknown. Can you remain a steady, inquisitive force when your vision is being minimized during these late-winter months?
Stage Two: The Friction of Opposition
As your "truth" gains traction and begins to move from theory to implementation—the phase many of us find ourselves in right now—the opposition often turns from dismissive to defensive. This is the stage of "violent opposition"—not in a physical sense, but through bureaucratic roadblocks, passive-aggressive compliance, or vocal dissent.
In thermodynamics, we know that friction generates heat. In leadership, this heat is often a sign that you are finally touching the core of the problem. It is here that the biblical principle of "speaking the truth in love" (Ephesians 4:15) becomes a strategic imperative. Can you hold the line with authority and compassion, addressing the fear behind the opposition without compromising the integrity of the mission?
Stage Three: The Quiet Power of the Self-Evident
The most rewarding moment for a senior leader is the day the "radical idea" becomes "the way we’ve always done it." The opposition fades, the ridicule is forgotten, and the new system becomes the bedrock of your operational excellence.
However, the trap for the seasoned leader at this stage is pride. When the truth becomes self-evident, the focus should shift back to the team’s success. Your goal was never personal vindication; it was the flourishing of the people and the systems in your care. The goal of a transformative leader isn't to be proven right; it’s to ensure the right path becomes the common path.
Reflective Leadership Audit: The Q1 Check-in
As you evaluate your 2026 strategic initiatives this week, ask yourself:
Where am I in the cycle? Are you currently facing the "ridicule" of a new idea, or are you in the thick of February "opposition"? Identifying the stage helps you calibrate your emotional response.
How do I handle dissent? When a peer or direct report opposes a necessary truth, do you view them as an enemy to be defeated, or a partner who hasn't yet seen the self-evident conclusion?
Is my truth actually true? Before pushing through opposition, have you done the quiet work of self-examination? Does your plan align with the objective reality of your data and the well-being of your team?
Leading through these stages requires a rare blend of iron-clad conviction and humble empathy. By understanding this progression, you can lead your organization through the friction of today into the self-evident successes of tomorrow.
Strategic Stewardship: Redirecting Entropy through Purposeful Correction
In our recent discussions throughout this early part of 2026, we have utilized the laws of thermodynamics to frame the challenges of leadership. We examined the leader’s role as a stabilizing force against natural chaos and the necessity of sustained momentum to drive meaningful change. Yet, a more nuanced challenge often arises: What is the strategic response when the source of friction is internal—originating from a misalignment in attitude, a recurring lapse in judgment, or a detrimental habit within the team?
This is where leadership demands a more disciplined application of emotional intelligence: the shift from passive observation to firm, purposeful correction.
The Hidden Cost of Passive Management
It is tempting to adopt a posture of "passive kindness"—avoiding friction or delaying difficult conversations under the guise of maintaining morale. However, in complex Information Systems or Client Success environments, unchecked negative behavior acts as a catalyst for systemic entropy. By sidestepping the conflict, are you actually preserving the peace, or are you inadvertently subsidizing the erosion of your team’s standards?
To allow a destructive pattern to persist is not an act of compassion; it is a failure of stewardship. In a technical ecosystem, this neglect allows "negative energy" to degrade the system’s integrity, eventually impacting output, client trust, and peer-level stability.
Correction as Strategic Redirection
True leadership in this context is an act of precision redirection. It is the process of intervening to ensure that a team member’s energy is not dissipated in friction, but channeled toward productive, high-value outcomes.
This approach requires a clear distinction between the individual’s inherent value and their current output or behavior. A seasoned leader recognizes the potential within the person while maintaining the authority to address the misalignment. The message is clear: “The current trajectory is inconsistent with the excellence we require. Because I am invested in your success, we must address this immediately.”
Operationalizing Firm Compassion
To implement this effectively within a high-stakes technical or SMB environment, consider these strategic pillars:
Clarity and Intentionality: Avoid the ambiguity of "dropping hints." Technical professionals and senior managers value precision. Address the behavior and its specific impact on system equilibrium directly. How often does a lack of clarity in your feedback lead to a recurrence of the very issue you hoped to resolve?
Alignment with Shared Objectives: Frame the correction within the context of the organization’s mission. If a Principal Engineer or Senior CSM is out of alignment, how does that impact the broader digital transformation roadmap? Positioning the conversation around shared goals reduces defensiveness and elevates the stakes.
The Partnership Model: Correction should not be a terminal event, but a transition. After identifying the misalignment, offer a collaborative path forward. This reinforces that your objective is to build capacity, not to assign blame. Are you providing the necessary scaffolding for your leaders to course-correct effectively?
By embracing the discipline of purposeful correction, you are not merely managing a team; you are actively resisting entropy. You become the force that transforms potential friction into the positive inertia required for significant, long-term success.
Bonus: The Passive Kindness Audit
A Strategic Self-Assessment for Senior Leaders
As we approach a new year of growth, reflect on your management style over the last quarter by auditing your recent interactions:
The Conflict Avoidance Check: Have I delayed a "difficult" conversation with a high-performing contributor because I feared it might disrupt a current project timeline?
Insight: Prioritizing short-term peace often subsidizes future systemic dysfunction.
The Clarity of Feedback Audit: When providing correction, do I use "soft" or ambiguous language to lessen the immediate discomfort of the recipient?
Insight: Precision is a form of respect. Does your team know exactly where they stand?
The "Culture of Exceptions" Analysis: Am I allowing a senior leader or architect to bypass organizational standards because their technical output is high?
Insight: When you make exceptions for behavior based on technical merit, you signal that system rules are negotiable.
The Non-Verbal Alignment Review: During meetings, do I remain silent when a team member displays a dismissive attitude or poor etiquette?
Insight: Silence from a leader is often interpreted as tacit approval.
The Partnership vs. Procrastination Test: When I notice a performance dip, is my first instinct to "wait and see" or to engage in a collaborative inquiry?
Insight: Real compassion is proactive. Waiting for a problem to become critical is a reactive failure.
Why Change Efforts Stall: The Cost of Systemic Inertia
How often do we allocate significant resources to organizational development (OD) and behavioral coaching, only to watch the resulting change efforts stall just short of impact?
Too often, these high-investment programs—especially those targeting mid-level management or Client Success teams—are at risk of not yielding sustained results. Why do we keep funding a change machine that seems to stall shortly after deployment?
The core challenge isn't a lack of commitment; it's often a profound misunderstanding of systemic inertia.
The Reality of the Flow: A Necessary Lag Time
I was recently struck by Dr. David M. Robertson's candid metaphor (Org/Ldr Development Is Piss In the River) regarding organizational development, which simplifies this complexity: The moment you stop the source of a problem, the system is still carrying what was already in motion.
In essence, stopping the undesired behaviour doesn't instantly deliver clean results. There is an unavoidable lag between the intervention (stopping the source) and the resolution (clearing the downstream effects).
It’s easy for leaders to mistake this crucial lag time for failure. They lose patience, overcorrect, or abandon the effort entirely, ensuring the system never fully flushes out the old, ineffective patterns. This impatience is the single greatest destroyer of strategic change initiatives.
Overcoming Organizational Inertia
To succeed, we must view behavior modification through the lens of Newton’s First Law: The Law of Inertia. Change requires a sustained force to overcome two critical sources of resistance:
1. The Inertia of Habit (Mass)
The "mass" of a team or individual is the deeply rooted strength of their existing habits and comfort levels. A ten-year-old process, even a poor one, has immense behavioral mass. Your coaching, new structure, or L&D program is the external force applied to overcome that mass. This force must be intense enough to start the movement, but more importantly, consistent enough to keep it moving. A one-day training seminar is merely a tap; a structured, perhaps a three-month accountability loop is the more likely, sustained force required.
2. The Inertia of the System (Momentum Transfer)
Once an individual or team accelerates into a new behavior, that momentum has a great chance of transfering to the adjacent systems—reporting, collaboration, approvals, and metrics. This is the ripple effect that takes time to clear the "downstream" effects of the old habits. For example, a client success manager using a new, proactive approach will inevitably expose flaws in the underlying ticketing system or billing process. This exposure is not a failure of the new behavior; it's a step in the successful transfer of momentum forcing the system to change.
The Mandate for Strategic Patience
The great differentiator for C-Suite leaders is not speed of intervention, but strategic patience—the discipline to wait for the effects to clear while maintaining a consistent force.
Leaders who rush to judgment—who "drink from the river too soon"—are likely to create instability. Their teams may learn that no plan will last long enough to matter, making future inertia even harder to overcome.
True success involves:
Locating the source of the problem and applying a measurable, sustained force (coaching/accountability).
Monitoring the system with objective data to verify the source has stopped.
Allowing sufficient time for the inherent inertia of the organization to dissipate the old effects.
Stop funding sprints for marathon races. Leadership in organizational development is less about heroic, one-time pushes and more about the quiet, disciplined application of consistent pressure.
What is one legacy habit in your organization where you have prematurely abandoned the force required to see the results clear downstream?
Executive Command: Mastering the Inner Operating System
If you lead a major Information Systems or Information Technology function, you understand the necessity of precise engineering. We spend careers optimizing systems, defining architecture, and enforcing rigorous execution protocols to ensure predictable results. Yet, how much deliberate focus do we apply to the most critical system we command: our own mind?
I've learned that even the most well-staffed digital transformation effort can be compromised not by a technological flaw, but by a flicker of irritation, a lapse in concentration, or an internal narrative gone astray. This recognition led me to Jim Murphy’s book, Inner Excellence, Train Your Mind for Extraordinary Performance and the Best Possible Life. It offers a framework for internal self-mastery that is as vital to executive performance as any strategic roadmap.
This isn't a book about corporate strategies; it's about optimizing your inner operating system to ensure your external leadership is consistently strategic, decisive, and focused.
The Greatest Opponents You Will Ever Face (Chapter 3)
The book posits that the most limiting forces threatening an executive’s focus and a team’s success are not market rivals or budget fluctuations, but internal adversaries. Recognizing these opponents and the systemic disorder they introduce is the first step toward containment.
The Critic: The persistent, often unhelpful internal voice focused on fear, doubt, and perceived inadequacy. In a leadership context, the Critic stifles strategic boldness, encouraging the safe, mediocre path rather than the challenging, innovative transformation.
Monkey Mind: The endless, fragmented chatter and distraction that erodes executive focus. This opponent guarantees a reactive leadership style, where a leader is perpetually driven by the inbox or the immediate operational incident, rather than the long-term strategic agenda.
The Trickster: The internal mechanism that rationalizes low-effort choices, excuses lapses in discipline, and justifies minor procedural deviations. This is the erosion of personal consistency that can lead to systemic risk.
When these internal opponents are unchecked, they make a leader unreliable and inconsistent, which inevitably introduces disorder into the organization. It reminds us of the principle: "A man without self-control is like a city broken into and left without walls." (ESV, Proverbs 25:28).
The Pillars of Self-Mastery: Unoffendable, Unembarrassable, Unirritatable (Chapter 4)
Murphy introduces the concept of mastering the ego as the foundation for true professional resilience. He distills this mastery into three key qualities, which are essential for navigating the complex political and relational landscape of enterprise-level technology leadership:
Unoffendable: The capacity to receive professional challenge, rigorous critique, or even personal slights without allowing it to compromise your strategic judgment or emotional equilibrium.
Unembarrassable: The willingness to be rigorously accountable, own setbacks transparently, and move forward without succumbing to paralyzing self-consciousness.
Unirritatable: The ability to remain centered and patient when faced with the inevitable operational delays, team friction, and shifting requirements of a major technology program.
For senior leaders, this self-mastery is the ultimate force multiplier. It allows you to maintain strategic composure and clarity of thought, even during high-stakes executive negotiations or when confronting a critical project derailment. It embodies the wisdom to be: "quick to hear, slow to speak, slow to anger." (ESV, James 1:19).
How much collective organizational time is currently being consumed by reactions stemming from undefended egos or unnecessary leadership irritation?
The Code of the Leader (Chapter 5)
The book links self-mastery directly to a personal and professional code of conduct, much like the discipline of the Samurai. This code is built upon a continuous investment in three areas:
Self-Awareness: Understanding your own biases, triggers, and authentic professional strengths. This allows you to delegate wisely and ensures you are managing processes and strategy, not reacting to personal impulses.
Self-Discipline: The consistent, focused execution of high-leverage activities, even when immediate motivation is absent. This is the sustainable fuel that successfully combats professional entropy.
Personal Growth: The commitment to continuous learning and skill evolution, recognizing that leadership is a daily practice of becoming, not a static state of being.
Successful digital transformation requires this consistent, disciplined effort, not merely periodic bursts of inspiration. Rituals, practices, and routines, as detailed by the author, are the tactical mechanisms we use to focus on what is most important—ensuring our internal state is always aligned with the external demands of our strategic role.
What specific daily routines have you implemented to ensure your inner state is optimized for the strategic challenges you will face in the next 90 days?
Call to Action
The greatest project an executive will ever manage is the development of their own internal operating system. If you are serious about refining your executive performance and increasing your strategic impact, I strongly recommend you pick up a copy of Jim Murphy's Inner Excellence. It’s a compelling resource for any leader seeking to move beyond technical competence toward genuine professional mastery.
Strategic Leadership: The Engine of Organizational Order
In the demanding environment of Information Systems and Client Success, inaction is not a stable state; it is systemic drift. A high-performing team, left without intentional guidance, gradually trends toward organizational disorder. Priorities can quietly diverge, knowledge transfer slows, and processes begin to accrue systemic risk.
For senior leaders—the C-Suite, SVP, and VP—your fundamental, strategic role is to function as a Thermodynamic Engine. You are the conscious, deliberate force that expends focused energy to convert raw organizational resources and effort into predictable, high-order business outcomes.
This is not about being a directive manager; it is about maintaining and increasing systemic order through strategic influence and design. Is your executive energy focused on fire-fighting immediate issues, or on defining the strategic architecture that prevents them?
Organizational Drift: The Systemic Tax on Performance
Organizational drift is the silent, incremental increase in systemic complexity and drag on efficiency. As a leader, you must skillfully manage its key forms:
Strategic Misalignment: The energy dissipation that occurs when departmental efforts are not precisely synchronized with the overarching corporate objectives. This often results in IT prioritizing non-essential projects or Client Success investing effort in low-value accounts.
Process and Technical Decay: The natural accumulation of technical debt and operational overhead. This forces high-value talent to dedicate cycles to low-value maintenance and reactive support, reducing capacity for innovation.
Talent Stagnation: The risk that capable team members become comfortable with routine, leading to a gap between current skills and the emerging requirements of digital transformation.
You are not tasked with achieving perfect, permanent order. Your mandate is the intentional, continuous management of this systemic disorder.
The Strategic Leader’s Mandate: Directing the Force
The mandate of the strategic leader is to maximize high-order output while systematically mitigating organizational friction. This requires three professional levers:
1. Injecting High-Quality, Directed Energy
As the executive, you are the primary source of strategic clarity. You must deliver a vision that is not just motivating, but fundamentally directive—a filter that clearly validates every team priority and investment. The clarity of your input determines the potential clarity of your team's output.
Does your team's current mission actively guide resource allocation, or is it a conceptual statement decoupled from daily execution?
2. Designing for Predictable Flow
The efficiency of any system is defined by its design. Your leadership energy is best spent creating the high-flow operational architecture (communication standards, decision protocols, performance metrics) that enables talented people to execute autonomously, without unnecessary friction. This demands an astute understanding of team dynamics and non-verbal cues to identify and resolve systemic bottlenecks before they impact client delivery or project timelines.
How much time is your most experienced talent spending navigating internal procedural barriers that you, as a leader, could strategically eliminate?
3. Managing Systemic Friction
The conversion of organizational potential into realized order inevitably generates friction—the natural resistance to change, the challenge of resource trade-offs, and the labor of holding people accountable. The high-EQ leader does not ignore this systemic friction, but effectively channels it. You must create professional environments for candid communication, measured accountability, and structured conflict resolution, ensuring organizational energy is efficiently directed toward shared goals.
Are you creating the structured space for necessary strategic debates that will result in a higher, more sustainable state of operational order?
By embracing this thermodynamic mindset, you move beyond merely managing activity. You position yourself as the essential strategic function—the conscious, deliberate force that creates and sustains a powerful, ordered system capable of driving superior client outcomes and successful digital transformation.
The Physics of Professional Entropy: Defying the Drift toward Mediocrity
Have you ever observed how quickly a highly optimized system can degrade without vigilant intervention? A perfectly tuned data center slowly accrues technical debt. A streamlined process becomes clogged with exceptions. A high-performing team begins to tolerate small inefficiencies. This isn't a moral failing; it is the Second Law of Thermodynamics at work.
This fundamental principle of physics states that the entropy, or disorder, of an isolated system will always increase. In the vacuum of a closed environment, complexity naturally spirals toward chaos. For the seasoned professional—in Information Technology, Information Systems, or Client Success—this manifests as professional entropy: the natural drift toward skill obsolescence, process decay, and strategic stagnation.
The critical insight is this: Your professional life, your team, and your organization are NOT isolated systems.
Your Organization as an Open System
To defy this natural, downward pull toward mediocrity, we must view our organizations as open systems—entities that exchange matter, energy, and information with their environment. The fuel for battling professional entropy is not just budget, but high-quality, directed energy:
Directed Information: Strategic market intelligence, customer feedback loops, and advanced technical knowledge.
Directed Action: Rigorous process re-engineering, intentional skill development, and purposeful relationship building.
Directed Investment: Focused allocation of resources (time, capital, and talent) that yields sustainable order.
The ability to successfully defy this natural drift toward chaos lies in purposeful strategic leadership and execution.
The C-Suite's Guide to Entropy Management
How does a strategic leader systematically combat the decay of professional and organizational excellence?
1. Acknowledge the Default State
Accept that complacency and technical debt are the path of least resistance. The moment you remove focused effort, degradation begins. This is not a failure of morale; it is a law of nature. Where is your organization currently allowing disorder to become the norm, and what is the cost of that neglect?
2. Define the High-Order Architecture
Disorder can only be fought with a clearly defined structure of order. In a technical or client-facing environment, this means defining a Desired State Architecture for your team, your technology stack, and your client relationships. What are the key performance indicators (KPIs) of an optimally "ordered" system, and what is the strategic value of that order?
3. Invest in High-Leverage Energy Inputs
Not all effort yields equal results. Low-leverage activities—reactive troubleshooting, repetitive administrative tasks, and participation in non-strategic meetings—consume energy while only minimally reducing entropy. High-leverage inputs are those that inject powerful, directed energy into the system:
Strategic Automation: Eliminating routine disorder by converting it into predictable, automated processes.
Deep Skill Development: Focusing development on future-proof capabilities that enhance intellectual capital.
Client Relationship Rigor: Transforming reactive service into proactive, strategic partnership and value delivery.
Are your teams confusing activity with output, and are you optimizing for effort or for results?
4. Practice Intentional Redirection of Force
A great leader does not waste energy fighting every small force of resistance; they redirect the most powerful forces to a productive end. Think of an enterprise-wide transformation. The inherent resistance (the 'energy' of entropy) can be redirected by anchoring the change to a clear, undeniable business objective, thereby converting resistance into momentum. Which existing organizational forces—be it the pressure of quarterly results or a major client initiative—can you redirect to drive your most critical strategic objectives?
By embracing the reality of professional entropy, you move beyond simply reacting to problems. You position yourself as the intelligent force of order, systematically investing energy to build and maintain a beautiful, highly-ordered system of professional and organizational excellence. The purposeful life is not a gift; it is a meticulously engineered defiance of chaos.
Principle Over Privilege: Eisenhower's Maxim for Modern Tech Leadership
Consider this: What's the true cost of convenience, efficiency, or even profit when it comes at the expense of our guiding beliefs?
Dwight D. Eisenhower’s warning—"A people that values its privileges above its principles soon loses both"—is more than just historical counsel; it's a strategic maxim for modern technology leadership. In the relentless, high-stakes environment of Information Systems, we are constantly making trade-offs. The "privileges" we enjoy—market dominance, access to user data, operational autonomy, and even our high-level job titles—can become powerful distractions. As leaders, our gravest error would be to let the pursuit of these advantages overshadow the foundational "principles" that grant us the public trust and internal cohesion necessary to sustain them.
Principles as Strategic Pillars in Technology
In the technology sector, our principles aren't merely abstract ethics; they are non-negotiable strategic assets. They define how we handle user privacy, the integrity of our algorithms, the security of our systems, and the culture of accountability within our teams. When a team or organization prioritizes the privilege of a rapid deployment schedule over the principle of rigorous security and quality assurance, the result is predictable: a breach of trust, a system failure, and ultimately, the loss of the market position (the privilege) that was so aggressively pursued. Our commitment to security-by-design, transparent data governance, and ethical AI development are not hurdles to innovation; they are the principles that ensure our continued license to innovate.
Leading with Principle Over Position
For those of us leading major IS/Tech departments, the principle-over-privilege dynamic manifests daily. It's the moment we must decide whether to use our position (the privilege) to push through a short-sighted solution or to leverage our influence (earned by principle) to advocate for the harder, but ultimately more resilient, strategic architecture. Authentic leadership means consistently modeling the behavior we expect. When we see a colleague or a team chasing a fleeting advantage—a quick fix, a manipulative growth hack, or a corner cut—it's our duty to step in and reset the compass. Our ultimate privilege is not the title we hold, but the trust we inspire.
Applying the Maxim to Your Career and Life
The core of Eisenhower's message is a call for a profound, personal commitment to values. As you navigate your career and life, apply this litmus test to your own actions. To ensure your long-term success isn't undermined by short-term gains, consider how you can apply this principle right now:
Define Your Non-Negotiables: Explicitly write down the top three professional and three personal principles you refuse to violate. Do you value intellectual honesty over being right? Do you value work-life integration over mere work-life balance? Knowing these makes critical decisions clearer.
Audit Your Trade-Offs: Whenever a major decision arises (e.g., a job change, a product pivot, a resource allocation), assess whether you are optimizing for a temporary privilege (higher salary, quicker win, reduced effort) or a lasting principle (long-term professional reputation, organizational health, ethical use of technology).
Mentor Through Principles: Use your leadership position not just to delegate tasks, but to embed principles. When coaching a team member, focus less on how they completed the task and more on the integrity and diligence (the principle) with which they approached it. This develops the next generation of principled leaders.
Guard Your Personal Trust Bank: Recognize that the privileges you have in your relationships—the assumption of loyalty, the access to your partner's time, the respect of your children—are only sustained by the principles you embody, such as integrity, presence, and kindness.
Commit to a Principled Exit: Ensure your legacy is built on the principles you stood for, not just the systems you delivered. The end of a project, a job, or even a career should reflect the integrity you maintained throughout.
Ultimately, the most successful and enduring technology organizations—and careers—are those built on bedrock principles. The moment we mistake a temporary advantage for a permanent right, we set ourselves on a path to losing everything. Your strategic advantage in the next decade will not be the technology you master, but the ethics you uphold.
The True North of Leadership: Are Your Actions Telling the Right Story?
In the demanding world of Client Success and Information Systems, we often operate under the conviction that our Strategic Action Plan or our KPI dashboard defines our success. We push our teams to do more, implement faster, and achieve higher numbers. But what if the most powerful force shaping your leadership legacy—and the loyalty of your team—isn’t what you do, but something far more foundational? Are you leading your organization based on what you love more than what you know?
The Unseen Anchor of Leadership
The technical marketplace is a crucible of urgency. Whether rolling out a complex digital transformation initiative or fighting to preserve a critical client relationship, the pressure to execute is immense. We rightfully focus on metrics, governance, and effective workflow. Yet, for leaders operating at the VP and C-Suite levels in SMB and mid-market companies, the difference between transactional management and transformative leadership often comes down to an internal, often neglected quality.
Centuries ago, Augustine Aurelius distilled a profound truth about human character that holds immense resonance for today’s executive:
“We are shaped most by what we think, not by what we do, but by what we love. For when we ask whether somebody is a good person, we are not asking what he believes or hopes for, but what he loves.” (Augustine Aurelius, De Trinitate, Book IX)
This statement is not merely philosophical; it is a critical strategic insight. In the context of leadership, what you love—what you value, prioritize, and genuinely care about—serves as the unseen anchor that determines your decisions, your relational style, and the ultimate health of your organization.
The Strategic Alignment of Affection
For the leader in Client Success (CSM) or Information Systems (IS/IT), what does it mean to be judged by what you love?
1. The Love of the Mission Over the Method
Many experienced technical leaders know they should prioritize the client experience or system reliability. But if your deepest affection is rooted in the perfection of the method (e.g., maintaining rigid legacy processes, proving the technical superiority of a chosen stack, or protecting a departmental budget), your leadership will be rigid.
Challenge for You: When facing a critical decision—be it a system overhaul or a client escalation—where does your attention land first? On preserving your operational comfort, or on the success of the outcome for the organization and the client? Your genuine love for the mission (delivering value, enabling the business, upholding integrity) must supersede your attachment to the process.
2. The Love of People Over Productivity
In technology, it is easy to view engineers, CSMs, and specialists as highly effective resources to be managed for optimal output. While performance is non-negotiable, a leader whose core love is the well-being and development of the individual will naturally inspire profound commitment.
This is not a soft approach; it is strategic wisdom. When you genuinely love to see your people grow and succeed, you invest time in mentoring, you offer constructive correction, and you advocate for their future. This leadership style is felt—it creates loyalty, reduces costly churn in specialized roles, and fosters a culture of mutual respect where people give their best, not just their obligated minimum.
3. The Love of Clarity Over Control
For leaders operating at the top of an organization, the temptation to hoard information and maintain tight control is a constant challenge. However, true strength lies in a love for Clarity—the commitment to transparent, unambiguous communication, even when the news is difficult.
When your primary desire is to maintain Control, you create bottlenecks and breed suspicion. When your true love is for Clarity, you empower your seasoned individual contributors and managers with the context they need to make intelligent, localized decisions. You trust the individuals you hired and align your team to the strategic intent of the organization, freeing your own time for higher-level thinking and external engagement.
The Call to Examine Your Heart’s Motives
The complexity of the SMB and mid-market landscape demands leaders who are not only competent in action but sound in character. Your success is not merely a reflection of the latest quarterly numbers, but a reflection of the deep-seated values you carry into every meeting, negotiation, and one-on-one conversation.
As you step into your next strategic challenge, take a moment to pause and consider the truth of Augustine’s words. Ask yourself: What does my leadership truly love?
The answer will be clearly demonstrated not through your email signature or your formal job description, but through the non-verbal cues your team reads, the decisions you make under pressure, and the loyalty you command when times are difficult. Lead with strategic affection, and watch your organization thrive.
The Unexpected Power of Unseen Kindness
"No act of kindness, no matter how small, is ever wasted."
These words from Aesop, the ancient Greek fabulist, hold a profound truth. In a world that often celebrates grand gestures, it can be easy to dismiss the smaller, quieter moments of kindness. We might wonder if a brief smile to a stranger or a quick word of encouragement really makes a difference. But the wisdom of this old saying suggests that these small acts carry a power far beyond their apparent size.
The Ripple Effect: How Small Acts Create Big Waves
Think of a small pebble dropped into a vast, still lake. The initial splash is tiny, but the ripples it creates travel outward, touching the entire surface of the water. This is the ripple effect of kindness. When you hold a door for someone, you aren't just performing a single, isolated act. You're creating a moment of connection that can subtly shift the recipient's mood. They might, in turn, be more patient with a cashier, or offer a helpful tip to a coworker. Your small act becomes the starting point of a chain reaction of positivity. You may never see the full extent of this effect, but that doesn't mean it isn't there, spreading its energy far and wide.
Kindness as Self-Care: A Benefit for Both Giver and Receiver
We often think of kindness as something we do for others, a selfless act of generosity. But true kindness is also a powerful form of self-care. When we practice compassion and generosity, we reinforce our own character. It builds our empathy, strengthens our sense of purpose, and can even counter feelings of helplessness. Spending a few minutes to help a friend study for a test or volunteering to water a neighbor's plants while they're away isn't a waste of your time. It’s an investment in your own well-being—a reminder of your capability to make a positive impact, which in turn boosts your confidence and sense of worth.
The Unseen Impact: Finding Value Beyond the Obvious
The most meaningful acts of kindness are often those whose impact is invisible to us. A kind word to someone who is having a bad day might not change their situation instantly, but it could plant a seed of hope. It could be the one positive thing they remember from a difficult week, a flicker of light in a period of darkness. The quote asks us to trust that even if the result isn’t obvious, it is still there. We must have faith that our actions matter, even when we don't see the return on our investment. The value of kindness is not measured in immediate, tangible results but in its quiet, persistent ability to leave the world a little brighter.
The Paradox of Kindness: When "Tough" Is the Most Compassionate Choice
Kindness isn't always gentle or agreeable. Sometimes, the most compassionate choice is a firm one. This is especially true when someone you care about is heading down a difficult or destructive path. Firmly, yet caringly, confronting a loved one about a harmful habit, or a team member about a negative behavior, can feel uncomfortable. It can be a very hard conversation. But allowing a bad decision to continue out of a desire to avoid conflict is not kindness—it’s negligence. True kindness in these moments means being brave enough to provide honest feedback and loving correction. It's the act of showing someone that their well-being matters to you so much that you're willing to have an uncomfortable conversation for their sake. This form of "tough kindness" is a difficult but essential way to show that no act of kindness, no matter how hard, is ever wasted.
The Scarred Face of Leadership: Why We Must Step Into the Arena
How often have you been in a meeting—maybe about a failed digital transformation project, a major system outage, or a key client churn—where the loudest voices belonged to those who were never actually accountable for the outcome? You know the scenario: the armchair quarterback ready to dissect every mistake, having never been under fire themselves. It's a frustrating dynamic that poisons the growth and strategic daring essential for any scaling SMB or mid-market organization. As leaders in Client Success and Information Systems, we are constantly faced with immense complexity, finite resources, and the relentless pressure to deliver. The question isn't whether we'll fail, but how we'll respond when we do.
The True Measure of Professional Leadership
For those of us working at the nexus of technology (IT/IS) and customer retention (Client Success), our daily reality is the high-stakes 'arena.' We don't get the luxury of theoretical debates; we are focused on deploying systems, protecting data, securing adoption, and ensuring our technology directly translates into client value and operational efficiency. When the network goes down or a key integration fails, it's our team's face that is marred by the proverbial dust and sweat.
In this environment, success isn't defined by the absence of problems, but by the relentless commitment to solving them. We must deliberately cultivate a culture where the effort—the striving—is honored above the outcome alone, and where strategic risk-taking is encouraged, not penalized.
Escaping the Critic's Circle
The biggest threat to high-performing teams isn't technical debt; it's leadership cowardice—the retreat into process paralysis or a fear of making the difficult, often unpopular, decision. Strategic leaders understand that significant achievement requires significant exposure to risk. They also recognize that fostering a climate of external critique without internal support stifles innovation and trust.
When a major initiative stalls, the focus of strategic leadership should not be on assigning blame, but on deconstructing the failure for maximal learning and rapid correction.
This mindset is perfectly captured by Theodore Roosevelt in his famous 1910 address, "Citizenship in a Republic":
"It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best, knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat." (Theodore Roosevelt, "Citizenship in a Republic," delivered at the Sorbonne, Paris, April 23, 1910)
Moving from Manager to Arena Leader
As senior managers and leaders in technology and client-facing roles, this quote is our professional mandate. To lead strategically and build enduring relationships, you must:
Prioritize Action Over Perfection: Recognize that the IT landscape in scaling businesses is too dynamic for perfect planning. You must empower your people to make high-quality, high-velocity decisions, even if they occasionally lead to a misstep. The strategic cost of inaction always outweighs the cost of an informed mistake.
Model Resilience and Vulnerability: Your team needs to see you in the arena, too—not just observing from the skybox. When a project goes sideways, your emotional intelligence and non-verbal cues matter most. Do you convey panic and frustration, or do you convey calm resolve and an unshakeable focus on the next step?
Build Professional Trust through Support: The highest form of professional relationship building is the unwavering commitment to supporting your team after a failure. Strategic leaders absorb the organizational pressure and shield their doers, ensuring that the necessary post-mortem learning is conducted without the distraction of punitive scrutiny.
In the fast-moving, high-pressure world of mid-market technology and client success, we must be the people who "spend themselves in a worthy cause." Our strategic value is determined by our willingness to step into the fray, face the complexity, and stand beside our teams when they are striving valiantly—dust, sweat, and blood included.
What's Your Arena?
What critical, high-stakes project is your team currently tackling, and how are you ensuring they feel supported enough to "fail while daring greatly"?