When “Helping” Becomes Enabling: A Leadership Lesson in Boundaries

In leadership — especially in community-based work — we walk a tightrope. Every day, we face heartbreaking stories, urgent needs, and desperate voices. The calling is real. But so is the danger: the danger of enabling instead of empowering.

Recently, I received an email that perfectly illustrated this tension. A community member demanded that we break our own policies to pay a client’s rent a second time — even though they had signed an acknowledgment that assistance is one-time only. The email was laced with entitlement, mischaracterizations, and even attacks on our staff and my late mother’s legacy.

It was a bold display of audacity, but also of a deeper truth: when boundaries are tested, leaders must hold the line.

Boundaries Are Leadership

Kent Hays once wrote that “the leader who blurs boundaries for sympathy destroys systems for everyone.” The purpose of boundaries is not cruelty — it’s fairness, sustainability, and truth-telling.

If one client receives repeat assistance outside the rules, another — perhaps one on hospice or facing certain eviction — is left out. As Peter Drucker reminded us, “Management is doing things right; leadership is doing the right things.” In this context, the right thing is to protect the integrity of the program.

Enabling vs. Empowering

John Maxwell said, “A leader is one who knows the way, goes the way, and shows the way.” Showing the way means guiding people to real, lasting solutions — county programs, disability benefits, charitable supports — not providing unsustainable bailouts.

Enabling says: “I’ll fix this for you, again.”

Empowering says: “Here are the doors to walk through — let’s walk together.”

One leads to dependence. The other leads to dignity.

The Audacity of Entitlement

When someone suggests that their friend should receive special treatment above hundreds of others, it is selfish. It ignores the reality that staff members are human beings too — juggling families, cancer diagnoses, grief, and financial burdens of their own. Leadership means protecting those staff members from abuse while still standing strong for the mission.

Angela Duckworth, author of Grit, reminds us that “enthusiasm is common, but endurance is rare.” Real endurance for a client comes not from another emergency check, but from building systems of support that last.

Marcus Aurelius said it simply: “You have power over your mind — not outside events. Realize this, and you will find strength.” That’s as true for clients as it is for leaders.

A Leader’s Charge

To my fellow leaders in social services and healthcare:

• Do not apologize for boundaries.

• Do not let entitlement dictate your decisions.

• Do not confuse sympathy with strategy.

Our role is to stand in the gap — but not to be the gap forever. We provide the hand up, not the handout. And we must call out enabling for what it is: a betrayal of long-term justice.

Final Thought

The writer of that email thought attacking my staff, my company, and even my mother’s name would bend our decision. It did not. Because leadership rooted in principle does not bow to pressure — it stands firm in truth.

As Kent Hays taught and as experience confirms: leaders must refuse to enable, even when it hurts, because the long-term good outweighs the short-term relief.

🎙️ Want more on real leadership?

I dive into topics like this every week on The Giovanne Show — where we confront hard truths about leadership, social services, and building systems that actually work. Follow along if you want leadership that is bold, unfiltered, and committed to solutions — not enabling.