The Art of Letting Go

10 Principles for Leaders Who Actually Want to Win

Most leaders these days won’t hesitate to tell you how busy they are, and that they couldn’t possibly have time to do anything else, because “there’s just too much to do.” If you’re one of those people, that’s okay, you’re normal. But you’re also probably not busy because the work is endless. You’re probably busy because you can’t let go of the things that you know you shouldn’t be doing. And then you wonder why you’re fried, the team’s disengaged, and success feels like pushing a boulder uphill.

But if you’re tired of being normal, and you want to be exceptional, your most underutilized superpower is: delegation.

Some people think that delegating is a cop-out. I don’t feel like doing this so you go do it. But that’s wrong. Delegation isn’t dumping work you don’t feel like doing. It’s a high-trust, high-performance move that frees you up to focus on what only you can do. And it gives your people the room to step up and grow. Do it well, and you build a self-sustaining team. Do it poorly (or not at all), and you’re stuck being the bottleneck forever.

Why Most Leaders Struggle to Let Go

The excuses are predictable:

  • “If I want it done right, I have to do it myself.”

  • “It’s faster if I just handle it.”

  • “They’re not ready yet.”

Translation: I don’t trust my team enough, and I’m scared of losing control.

The result? You’re drowning in meetings and to-do lists, working late to keep up, and ignoring the strategic work that actually moves the business forward. Meanwhile, your people are bored, under-utilized, and starting to wonder if they should take their talents somewhere they can actually grow.

Delegation isn’t letting go of responsibility. It’s about being a real leader, not just a boss.

10 Principles of Delegation That Actually Work

1. Protect Your Highest-Value Time
If it’s not something only you can do, it’s a candidate for delegation. Your time the most valuable resource you have. Stop burning it on $10-an-hour tasks when your real value is in making $1,000-an-hour decisions.

2. Do What Only You Can Do
Every leader has a unique lane - a superpower. Stay in it. Everything else? Pass it on.

3. Pick the Right Person
Handing the wrong job to the wrong person isn’t delegation, it’s sabotage. Match skills, experience, and interest to the task, otherwise you’re just setting your team up for failure.

4. Be Crystal Clear on the Outcome
“Handle the report” is vague. “Create a 10-page analysis on customer trends, with visuals, by Friday” is leadership.

5. Set Deadlines That Make Sense
Too short and you get sloppy results. Too long and it falls off the radar. Give them the right amount of runway.

6. Equip Them to Win
Make sure they have the resources, tools, information, and most importantly, the authority that they need to succeed. If they don’t, you’ve set them up to fail from the start.

7. Check In Without Hovering
Agree on milestones to track progress and provide feedback. Review the work EARLY, before it’s too late to course-correct. For something big, review their plan before they move on to execution.

8. Make the Stakes Clear
Explain why this matters in the context of the bigger picture, what the company will get out of it, and what happens if it doesn’t get done right. Purpose drives performance.

9. Put It in Writing
Clarity beats memory every time. After you have a conversation to align in person, a quick follow-up email locks in expectations.

10. Inspect What You Expect
Follow up on progress and outcomes. Offer constructive feedback throughout. Reinforce the standard.

In the Navy, as a leader, we’re taught that you can delegate authority but not responsibility. So if you get sub-par work back, odds are you didn’t do a good enough job on principles 3 through 10.

The Payoff

When you delegate well, you:

  • Empower your team to own results, not just tasks.

  • Multiply your capacity without multiplying your hours.

  • Get better ideas because more brains are engaged.

How to Start Today

  1. Audit your workload: circle the stuff someone else could do 80% as well as you.

  2. Match the right person to the job: skills, experience, and interest.

  3. Communicate like a pro: clear expectations, deadlines, and resources.

  4. Review and refine: tweak the process until delegation becomes your default.

Let Go to Level Up

Delegation isn’t “extra work.” It’s the most important work you do as a leader. It’s how you turn individuals into a team, and a team into a force that doesn’t need you micromanaging their every move.

So here’s your challenge: before today’s over, pick one task and hand it off. Don’t hover. Don’t snatch it back at the first sign of trouble. Trust the process.

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