Comparing My Best With Their Last

“Why are you doing that?” he asked me.

“Doing what?” I replied…blind, oblivious, and completely missing his point.

“What you hired me to do.”

I quickly understood and handed off the task.

There’s a subtle sabotage lurking in the heart of even the most well-intentioned leaders: the inability — or perhaps unwillingness — to delegate. It starts innocently enough for me. I care about the work. I know how it should be done. In my early days with Horizon, I was an office of one. But over time, as the team grew, my own capability became a bottleneck. The ironic twist? What once made me valuable becomes a liability. I’m no longer scaling my impact — I’m capping it.

The Struggle: Letting Go Without Letting Down

Many leaders fall into the trap of comparing someone’s first day with their own last day. However, this mentality is a trap. Your own strong work ethic becomes a liability the higher you climb, particularly when you take on tasks that no longer belong to you. This leads to micromanagement, clumsy handovers, and underdeveloped teams.

It’s not just a personnel issue — it’s a growth inhibitor. Failing to delegate keeps leaders, and organizations, stuck in what Larry Greiner refers to as the “Crisis of Control” phase. Organizations that don’t evolve through delegation face burnout, apathy, dysfunction, and stalled progress.

Growth through delegation comes with a painful decision point: that’s the crisis of control. Leaders must shift from doers to enablers, and teams must be trusted with ownership and autonomy. This transition is necessary, but it’s rarely smooth.

Effective delegation isn’t just offloading tasks. It’s an intentional practice grounded in trust, alignment, and feedback loops. Here’s how to start doing it well:

1. Determine Where the Ownership Should Lie

First, ask yourself this simple question: “Is there anyone else on the team (or in the organization) who can do this?” If the answer is, “yes,” there’s your first indicator that it should likely be delegated. And if you happened to forget this first step, pray for courageous teammates who will speak up when you hold on.

2. Clarify Ownership, Not Just Tasks

Delegation is not assignment — it’s ownership. Clarify outcomes, boundaries, and authority. Help others see why the work matters, not just what needs to be done.

This decentralized approach allows for faster decision-making and more agile responses to changing circumstances, while empowering subordinates to make decisions and take initiative within the framework of your leader’s intent.

3. Accept Their First Day Won’t Look Like Your Best Day

You must resist the urge to critique early outputs as though they were final performances. Your job isn’t to replicate your standards immediately — but to coach others toward reaching them. They will struggle. They may even fail. But through both, they will grow.

“We often compare people’s first day with our best day,” and that mindset destroys initiative.

4. Use Feedback as a Development Engine

Delegation without feedback is abdication. Create a structure for assessment and course correction — an essential element for leader development.

Feedback should be bidirectional. Ask what support they need, what’s unclear, and where you can enable rather than evaluate.

5. Trust Doesn’t Mean Absence — It Means Presence with Purpose

A leader who spends too much time in direct decisions erodes initiative. But one who’s never present seems detached. Delegation still requires visibility. Your involvement signals engagement and priority — not micro-control.

Final Thought: Scale Through Others

Delegation isn’t about lightening your load — it’s about multiplying your impact. As your organization grows, your value is no longer what you can do, but what you can enable others to do.

Let them have their first day.

And don’t compare it to your best day — compare it to their last.

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Comparing My Best With Their Last was originally published in Horizon Performance on Medium, where people are continuing the conversation by highlighting and responding to this story.