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:

1. 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.

2. 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?

3. 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"?