You already know how to delegate

He was doing everything himself.

Responding to every investor email.
Scheduling appointments.
Commenting on LinkedIn.
Sending newsletters.
Making pitch decks.
Underwriting deals.
Booking webinars.
Meeting brokers.
Filing paperwork.

All of it.

He knew he needed to delegate. In fact, it was one of the first things he said on the call.

He had read the books. He knew what to do. If you put him on stage, he could teach a delegation framework better than most speakers.

But he wasn’t doing it.

And here’s what he said that stopped me.
“I know what needs to be done. But whether I do it or not is a different question.”

That’s the moment where books end and real psychology begins.

Research calls this the intention-behavior gap.

Your brain forms clear intentions - but only about 1/2 become real behaviors.
You can intend to delegate, want to delegate, tell a dude on Zoom you need to delegate - and still never do it.

This gap isn’t about information (almost none of them are).
It’s about your fears.

For syndicators who love numbers and deals, delegation feels especially risky.

You can underwrite faster than anyone.
You know the markets cold.
Your deals are solid.

But growing means leading people - not just analyzing spreadsheets.

And that uses a completely different part of your brain.

MIT research found that leaders with technical backgrounds struggle most with delegation. When your identity is tied to execution, letting go feels like losing yourself.

Let’s peek behind the curtain to see what’s really going on.

Fear of losing control.
“Nobody can do this as good as me.”
Research shows 49 percent of managers are uncomfortable delegating because they doubt their team can match their standards.

Identity threat.
“But I’m the face of this company.”
You’re the numbers person. The deal junkie. If someone else does your work, who are you? Studies show leaders often tie their value to personal accomplishment instead of team achievement.

The belief that the boss must work hardest.
“I don’t want them to walk all over me.”
One syndicator I coach was working 70 hours a week even with a team of 12. He believed if he wasn’t working the most, his team wouldn’t respect him.

The research is clear. These aren’t character flaws.
They’re psychological barriers. And we know how to break them.

Start absurdly small.
Don’t try to delegate your underwriting tasks right away.
Hand off one tiny task this week.
Scheduling. Inbox sorting. LinkedIn commenting.
Small wins build trust faster than big gambles.

Delegate outcomes, not tasks.
Don’t tell people how to do it. Tell them what success looks like.
Research shows this builds their confidence and reduces your urge to micromanage.

Name your identity shift.
You’re moving from deal executor to team builder.
That’s not a demotion.
It’s the next level of your career.
And the only way you’ll scale to $50M.

When you begin delegating, 3 things happen.

1) You get time to focus on your zone of genius.
2) Your team grows because they have ownership.
3) You stop being the bottleneck that limits your own growth.

The syndicator I mentioned at the beginning is still sitting with the gap between knowing and doing.
But he’s closer than he was a week ago.

Because now he knows the gap isn’t about knowing what to do.
It is about his psychology.

And psychology is something you can work with.

Chris

Johnson, E. (2024). The delegation dilemma. MIT Sloan Management Review.
Sheeran, P., and Webb, T. L. (2016). The intention behavior gap. Social and Personality Psychology Compass.
Harvard Business Review. (2023). Survey on delegation comfort among managers.
Gallup. (2022). CEO delegation and revenue growth study.