Why Delegation Breaks Down in Growing Businesses

Welcome back to the Mid Market Insider!

Today, we’re discussing one of the biggest mistakes bosses make when delegating, and how you can set your team up for success instead of frustration.

Before we dive in…

I read a recent Wall Street Journal article that hit on something I’ve seen repeatedly inside growing businesses.

Most leaders don’t actually struggle with delegating.

They struggle with how they delegate.

Here’s the common pattern:

An owner or manager finally hands something off.

Then they disappear completely.

And when the outcome isn’t what they expected, frustration sets in on both sides.

The leader thinks, “See? This is why I just do it myself.”

The employee thinks, “I was set up to fail.”

And trust erodes.

The Real Problem Isn’t Delegation, It’s the Gap in Between

In the lower and middle market, delegation is often treated as an on/off switch.

Either:

• I do it myself, or

• I hand it off and hope for the best

That works early on when the business is small and speed matters more than scale.

But as companies grow, this approach quietly becomes a bottleneck.

What actually works is recognizing that delegation exists on a spectrum, not a binary choice.

Some tasks require:

• Walking through the process together

• Explaining why decisions are made, not just what to do

• Periodic check-ins before things go off the rails

Others truly can be handed off with minimal oversight, but only after someone has proven they’re ready.

Why This Matters More Than People Realize

From a buyer’s perspective, poor delegation shows up fast.

If everything still flows through one or two people:

• Decision-making slows

• Leaders burn out

• Teams stop developing

And that creates risk.

Buyers aren’t just evaluating whether a business is profitable today.

They’re evaluating whether it can function without heroic effort from the owner.

A team that’s been developed through thoughtful delegation is a huge signal of maturity.

Delegation Is a Development Tool, Not a Shortcut

The goal of delegation isn’t to get things off your plate.

It’s to:

• Build capability in others

• Reduce dependency on a few individuals

• Create repeatable outcomes

That takes more effort upfront, not less.

But the payoff is real:

• Fewer fire drills

• Stronger leaders beneath you

• A business that can actually scale and eventually transfer

If delegation keeps “not working” in your business, the issue probably isn’t your team.

It’s the assumption that delegation means disappearing.

The best leaders I’ve worked with don’t just hand things off.

They stay involved just long enough to make sure the person on the other side can succeed, and then they step back.

That’s how teams grow.

And that’s how businesses stop being owner-dependent.

That’s all for today’s newsletter! Thanks for reading!

📅 Next Week:

In next week’s edition, I’ll break down the different private equity playbooks buyers run from “strip and flip” to growth-focused strategies, and why understanding which one you’re signing up for matters more than most owners realize.

Keep building,
Nick