Why Pencils Have a Rubber End

A leadership reflection on imperfection, patience, and purpose

In the world of software engineering and technical leadership, it's easy to get swept up in systems, structures, and sprint goals. But leadership isn't about managing architecture diagrams or burn-down charts. It's about managing people. And managing people is messy—beautifully, inevitably messy.

That’s why I keep coming back to the humble pencil.

Pencils have erasers because humans make mistakes. It's not a design flaw. It's a design feature. It quietly acknowledges that perfection is not the expectation—and that correction, reflection, and second chances are part of how we create.

When we forget this simple truth in management, we risk doing more harm than good.

Mistakes Will Happen—What Happens Next Is Leadership

Too often, organizations treat mistakes as verdicts. A failed deployment becomes a narrative about a person's competence. A missed deadline becomes a warning flag rather than a coaching opportunity.

But good leaders know: we don’t hire perfect people. We hire capable people. People with ambition, resilience, values—and yes, flaws. The job of a leader isn’t to expect flawlessness. It’s to create conditions where people can learn from their missteps, grow, and try again. Just like you did. Just like I did.

I’ve made hiring decisions not on resumes, but on values. I've delegated critical work not because someone was fully ready—but because I believed they could grow into it. And I’ve seen those bets pay off more times than not. Not because of talent alone, but because of trust.

Leadership is a pencil, not a pen.

Perfection Is the Enemy of Good

There’s an old adage in software: Premature optimization is the root of all evil. I believe that.

When engineers try to make a system perfect from day one, they often end up building brittle, over-complicated solutions that don’t serve the actual business need. The right approach is iterative—build something valuable, learn from how it performs, and improve it over time. That same thinking applies to people and teams.

Expecting perfection, either from systems or from humans, is not just unrealistic—it’s damaging. It stifles innovation. It breeds fear. And worst of all, it prevents people from taking the very risks that fuel their growth.

Instead of optimizing for theoretical perfection, we should optimize for business value. For learning loops. For psychological safety. For teams that reflect on what went wrong not with blame, but with curiosity. Because only then do we evolve—not just our products, but our people.

Before You Replace the Pencil, Use the Eraser

In leadership, the temptation to “replace” people who don’t perform instantly is strong. Especially in high-pressure environments. But performance is rarely a binary trait—it’s a product of context, clarity, coaching, and trust.

I’ve led teams where the “underperformers” became star contributors—after they were given context and confidence. And I’ve also seen top performers falter—when they weren’t treated with humanity.

Of course, there are times when parting ways is necessary. But those should come after support, feedback, and honest conversation—not before.

Because management is not about maximum efficiency. It’s about long-term effectiveness. About enabling others to build, fail, reflect, and build again—stronger.

Final Thoughts

Leadership is the quiet discipline of believing in people—even when they haven’t yet fully believed in themselves. It’s about replacing judgment with curiosity, and impatience with perspective.

So next time someone on your team makes a mistake, pause before reaching for the permanent marker of blame. Pick up the pencil. Use the eraser. Then ask them what they’ve learned—and what they want to try next.

That’s how people grow. That’s how trust is built. That’s how leadership leaves a legacy.

Because in the end, a pencil is only useful if you’re willing to write with it. And rewrite.