Want Them to Win. Prepare Them to Win Without You.

by Sep 10, 2026Leadership, T.R.I.P.

Here’s a question for you this morning.

If you’re leading people, do you really want them to become good enough that they don’t need you anymore?

I mean really don’t need you.

They can make the decision.

They can deal with the problem.

They can lead the meeting.

They can handle the customer.

They can make a mistake, figure out what happened, correct it, and keep moving without waiting for you to come rescue them.

Because I think one of the real tests of leadership is this:

Want your people to win. And prepare them to win without you.

My name is Henry Chidgey, and welcome to this week’s blog.

I’ve been thinking about this because there’s a strange thing that happens with leadership sometimes.

A person gets put in charge.

Pretty soon, being needed starts to feel pretty good.

Everybody comes to them for an answer.

Everybody asks permission.

Every important decision runs through them.

And before long, they can begin to confuse being needed with being a good leader.

Those aren’t necessarily the same thing.

In fact, sometimes they’re exactly the opposite.

If everybody still needs you to solve the same problems you were solving for them three years ago, I’d have to ask:

What have you been developing?

Maybe you’ve developed a pretty good dependency system.

But have you developed people?

I don’t think the purpose of leadership is to keep people dependent on the leader.

I think part of our responsibility is to help people develop the judgment, confidence, experience, and ability to eventually do things they once needed us to do for them.

That’s success.

And I’ve believed something else for a long, long time that goes right alongside this.

I used to tell people:

I am committed to your success, but I am not one ounce more committed to your success than you are.

That’s an important distinction.

Because I can help you.

I can mentor you.

I can tell you what I’ve learned.

I can tell you where I’ve screwed it up myself, and maybe help you avoid doing the same thing.

I can ask you questions.

I can challenge your thinking.

I can give you responsibility.

I can open a door occasionally.

And I can certainly tell you the truth when I think you’re headed in the wrong direction.

But I can’t do your part.

And I can’t want your success more than you want it.

I’ve learned over the years that this makes a tremendous difference in where I invest my time.

You give me somebody who’s hungry to learn—even if they aren’t particularly good yet—and I’ll spend a lot of time with that person.

They don’t have to have all the answers.

Heck, if they had all the answers, they probably wouldn’t need me.

What I’m looking for is something else.

Do they listen?

Do they think?

Do they come back having done something with the last conversation?

When they make a mistake, do they own it?

Do they learn from it?

Are they willing to try something that’s uncomfortable because they know they need to grow?

If that’s what I’m seeing, I’m probably going to invest pretty heavily in that person.

Because they’re investing too.

But let’s take the other case.

We’ve had the same conversation four or five times.

Nothing changes.

There’s always a reason.

There’s always somebody else responsible.

There’s always some explanation for why this particular time it couldn’t be done.

And I’m doing all the work trying to create somebody else’s success.

Well, somewhere along the way I need to recognize what has happened.

I’ve become more committed to their success than they are.

That’s not a good place for either one of us.

Now, if these Wednesday Morning Memos are helping you think about your own leadership, subscribe and stay with me. That’s what I’m trying to do here each week—not hand out a bunch of simple answers, but give you something worth thinking about and maybe something worth talking about with your own people.

And while you’re at it, I’d like to hear your answer to this:

Have you ever worked for somebody who was genuinely trying to prepare you to succeed without them?

If you have, tell me what that leader did.

Because somebody else reading your comment may learn something from it.

Now, there’s another part of this that’s worth talking about.

Don’t confuse somebody’s present ability with their commitment.

Those are two different things.

I’ve had people who weren’t ready yet, but they were absolutely committed to getting there.

Those people are worth investing in.

Give me somebody who says, “I don’t know how to do this, but I’ll learn,” and we’ve got something to work with.

I’ll take that person over somebody who’s got enormous natural ability but doesn’t particularly care whether they get any better.

You can help somebody develop skills.

Experience comes with time.

Judgment gets better when people are allowed to exercise it and then think about what happened.

Confidence grows when you’ve actually done difficult things.

But I can’t reach inside somebody and manufacture desire.

Sooner or later, they’ve got to decide what they want badly enough to work for.

That’s their responsibility.

And I think this is where leadership sometimes gets confused.

Supporting somebody does not mean carrying them.

Believing in somebody does not mean lowering the standard for them.

And wanting somebody to succeed doesn’t mean keeping them forever in a position where they’re not succeeding.

Sometimes, after you’ve done the work, you realize you’ve got the wrong person in the seat.

That doesn’t necessarily make them a bad person.

They may be a perfectly good person in the wrong job.

Or maybe they simply aren’t willing to do what’s required.

But once you know that, you’ve got another leadership responsibility.

You’ve got to deal with it.

Because everybody else is watching.

The person who’s doing their job is watching.

The person who’s carrying extra weight because somebody else isn’t doing theirs is watching.

Your best people are watching to see whether the standards you talk about actually mean anything.

So there are times when I’m 100 percent committed to helping somebody succeed.

And there are other times when, after enough evidence, I’m 100 percent committed to making a change.

Both can come from the same place.

Stewardship.

I’m responsible for that individual, but I’m also responsible for everybody else who’s depending on me to lead.

So here’s what I’d like you to think about this week.

Look at the people you’re leading.

Pick one person.

And ask yourself:

Am I helping this person become more capable—or am I helping them become more dependent on me?

Then ask the harder question:

Who is more committed to their success right now—me or them?

You may like the answer.

You may not.

But you’ll probably learn something from asking it.

And if you’ve got somebody who’s fully committed to becoming better, don’t hold back.

Teach them.

Challenge them.

Give them something that’s a little bigger than they’re comfortable with.

Let them make some decisions.

Let them struggle a little.

Don’t jump in every time you know the answer.

Sometimes the best thing you can do as a leader is keep your mouth shut long enough for somebody else to figure it out.

That’s how judgment gets built.

That’s how people become leaders themselves.

And one day, if you’ve done your job well, they may not need you anymore.

Good.

That’s not a loss.

That’s part of the job.

Want them to win.

Prepare them to win without you.

And be completely committed to their success—but never one ounce more committed than they are.

If you’re leading a business and this hits close to home—maybe you’ve got somebody you’re trying to develop, or somebody you’ve spent a long time trying to develop and you’re beginning to wonder whether you’re carrying more of it than they are—reach out to me.

That’s exactly the kind of leadership conversation I enjoy.

We may not find an easy answer.

But we can probably ask some better questions.

And better questions have helped me find a lot of better answers over the years.

Want to Become a Calmer, Clearer Leader?

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P.S. I also offer a 1-on-1 session where you bring a real leadership issue and we work through it together. No pitch, no slides, just clear thinking applied to your actual situation.

henrychidgey.com

Thanks for spending a few minutes with me this morning.

Now go out there and be the leader—the one your team deserves, the one your business needs, and the one you were built to be.

Leadership does matter.

About Henry:
Henry is a Leadership Coach and Mentor. He helps Owners and Executive Leaders develop their teams to grow their business so they can have more time, more results and more money. To learn more, Henry offers a FREE clarity call  check out the details on this website.