Delegation Lessons From My Toddler: Why Most Teams Fail Up the Chain

Laith Khoury
Jun 24
3 min read

We often wonder why our teams underperform—why tasks slip through the cracks, why things are messier than they should be. But rarely do we start with the harder question:

“Did I give them clear instructions, expectations, and support?”

In my experience, the biggest blind spot for most managers—myself included—is forgetting to engage in self-reflection. Too many leaders separate themselves from the outcomes of their teams. But like it or not, you’re always part of the result.

Lessons From a 1.5-Year-Old CEO

As a father to a one-and-a-half-year-old, I’ve learned that toddlers, like employees, need guidance, not just supervision.

Toddlers will test everything: boundaries, patience, and safety rails. You have two choices:

Treat them as incapable and work around them, while also chasing them off furniture…
Or, give them small, meaningful tasks that engage them, contribute to your workflow, and build their confidence.

Here’s the trick: you can’t ask a toddler to do something beyond their current level of understanding. That’s not fair to them—or to your expectations. You give them jobs that match their capabilities, while supporting your broader objectives.

That’s Also Management.

Too many managers do the opposite—they delegate without context, set unrealistic expectations, or simply offload what they don’t want to deal with.

Every employee arrives with a different background, exposure, and speed of learning. You can't hand someone a spreadsheet or a job title and expect mastery.

This is why I always advise: pair new hires with senior team members who have both competence and the emotional maturity to coach others.

Recruitment ≠ Perfect Fit

There’s no such thing as a “100% perfect hire.” And if a recruitment agency promises you one, feel free to quote me when you say:

“Leo Khoury called BS—liar liar pants on fire.”

What you can do is build clarity:

Map the skills and knowledge your department needs
Audit the existing talent against those skills
Identify gaps and plan Learning & Development (L&D) accordingly

From there, you’ll know:

🟢 What to train

🟢 What to hire

🟢 What to stop expecting

Learning Starts On the Job

Formal training is fine, but study after study shows that the most effective form of adult learning is experiential—also known as on-the-job learning (70:20:10 model). That’s:

70% learning from real experiences
20% from peer or mentor coaching
10% from formal education

That means if you want mastery, your best bet is structured shadowing, mentoring, and feedback loops—not just sending someone to a course.

Skills Without Process = Talent Without Direction

You can have all the right people in all the right roles—but without process, you have chaos in a sharper suit.

Clear, documented processes matter everywhere:

From the boardroom to the break room
Across every department and hand-off
Especially in roles where confusion breeds micromanagement

When a process breaks down, people get labeled “bad managers” when they’re actually stuck without a map.

So don’t rush to add headcount or overhead. Start with this:

✅ Vision
✅ Mission
✅ Values
✅ Process Mapping
✅ Skills Inventory

One last note: A prioritized to-do list doesn’t always reflect what’s most important. Start with what supports structure, not just what screams loudest.

Why Staffing is My Obsession

As a Fractional COO, I focus obsessively on staffing because:

It represents 50% or more of most organizational costs
Bad staffing decisions are the fastest way to burn cash, morale, and momentum

We all love the quote: “Hire slow, fire fast.”Sure, it sounds cool—but real businesses need structure, not slogans. If you ever want to exit your business or take a vacation without a breakdown, then the process is king.