After 15 years of working alongside leaders, we’ve noticed something — a pattern that shows up no matter the industry, team size, or title.
It’s not about strategy, vision, or even time management.
It’s something more subtle — a quiet habit that keeps even the most capable leaders stuck in the weeds, exhausted, and wondering why their team isn’t freeing them up the way they hoped.
We’ve seen it derail progress, stall growth, and burn out brilliant people.
So what is it?
It’s how they delegate — or more often, how they don’t.
Here’s the truth: The smartest leaders we know struggle to let go. And that single habit costs them more time, energy, effectiveness, and success than almost anything else.
1. Delegating Tasks Instead of Outcomes
Most leaders hand off assignments instead of ownership. They say, “Schedule this meeting,” instead of, “Help me protect time for what matters most.”
It’s well-intentioned, but it keeps you stuck as the bottleneck. Your assistant becomes a task-taker, not a problem-solver — and you never really get out of the weeds.
What to do instead: Explain the why behind the work, not just the what. When your assistant understands your goals, they can start anticipating what’s next — and that’s where real leverage begins.
2. Waiting Too Long to Let Go
You’d be surprised how often leaders say, “I’ll delegate this once I have time to train someone.” Spoiler alert: that day rarely comes.
By the time you’re drowning, you hand things off in a rush — and the experience feels chaotic instead of freeing.
What to do instead: Delegate earlier than you think you’re ready. Early handoff gives you space to teach, refine, and build trust before you’re in crisis mode.
3. Expecting Mind Reading
We hear this one all the time: “They should just know.”
Even the best assistants can’t anticipate what you’ve never shared. Leaders often skip the upfront investment of communicating preferences, priorities, and quirks — but that’s exactly what unlocks true support.
What to do instead: Over-communicate early on. Share your habits, pet peeves, and decision-making patterns. It’s not micromanaging — it’s setting your assistant up to read between the lines later.
4. Delegating But Not Releasing
Here’s the harsh truth: many leaders delegate, but few actually release. They pass something off — then hover, recheck, or quietly redo it.
It’s a comfort thing, not a competence thing. But it sends the message: “I don’t really trust you yet.”
What to do instead: Define what success looks like, then step back. You can’t lead and control every detail at the same time.
5. Treating Your Assistant Like an Extra Pair of Hands Instead of a Strategic Partner
The best leaders don’t just assign tasks — they build partnerships. When you see your assistant as an extension of your leadership, not just your calendar, everything changes.
What to do instead: Involve them in priorities and planning. Ask for their perspective. When they understand your world, they can help you protect it.
The Bottom Line
Leadership isn’t about doing it all. It’s about trusting, empowering, and creating space for what only you can do.
If you’re ready to step back, elevate your leadership, and finally let go — we can help.
👉 Download our free guide: Delegate to Elevate