How To Effectively Delegate To Executive Peers

When a CEO tells me their leadership team lacks ownership, they are usually describing something real, but they have often misread where it started. They work alongside executives who escalate instead of deciding, who show up with neatly organized problems instead of recommendations, and who wait for approval on calls that clearly sit inside their own roles. 

From there, many CEOs decide they hired people who weren’t senior enough and start planning their next round of hiring executives. Sometimes that’s the right call. More often, I’m looking at a team that has been trained, with the best intentions, to act exactly this way.

The training is easy to miss because each moment of it looks like good leadership. Someone brings you a problem, and since you’ve seen it before and can fix it in ninety seconds, you fix it. You feel useful, they feel supported, and the issue goes away. But the person also learns something: when this gets hard, the CEO handles it. Repeat that a few hundred times over two years and you end up with a team of capable people who are great at spotting issues and have almost no practice closing them.

I call this the answer machine problem. It does waste the CEO’s time, but the bigger cost is that it limits how far the company can grow. If every real decision runs through one person, the company can only move as fast as that person’s calendar allows, and no amount of C-suite hiring will change that. A new executive hire who walks into the same pattern will pick up the same habits within a quarter.

Why Your Team Keeps Bringing You Problems

Delegation is not on or off

The usual advice here is to delegate more. That’s fair, but it’s too vague to act on, because delegation works more like a ladder than a switch. There is a lot of room between “do exactly what I tell you” and “this is yours,” and most of the friction I see between CEOs and their executives comes from the two sides assuming different spots on that ladder.

It helps to name the levels out loud:

Level 1, do exactly this. You give instructions, they execute. You own the decision.

Level 2, research and report back. They gather the facts, you decide.

Level 3, research and recommend. They form a point of view and defend it, you approve.

Level 4, decide and inform me. They make the call and tell you what they did and why.

Level 5, own it. They own the outcome and involve you only when they judge that you should know.

Each level has its place. Level 1 fits a brand new hire running a high-risk process, and Level 5 fits a leader whose judgment you’ve watched deliver results for a year. Where CEOs go wrong is never choosing a level at all, because without a clear level people default to the safest guess, and the safest guess is always lower than what you wanted.

The most damaging version is telling someone they own a function while requiring your sign-off on every decision inside it. That’s Level 5 responsibility with Level 2 authority, and the people stuck in that spot tend to leave. When you’re hiring executives, it’s worth agreeing on the level of ownership during the search itself, so the new leader knows from day one which decisions are theirs.

How people actually move up

CEOs get stuck at the bottom of the ladder because moving up requires proof, and the answer machine habit wipes out that proof before it can build. You can’t tell whether someone’s judgment is any good if you’ve never let them use it in front of you, which is why “What do you recommend?” matters so much. It turns a Level 1 conversation into a Level 3 one at no cost, and it gives you exactly what you need to decide whether this person can handle Level 4.

From there, the path is fairly predictable. Someone who executes reliably is ready to research. Someone whose research comes with a solid opinion is ready to recommend. Someone whose recommendations match the call you would have made is ready to decide and keep you informed. And someone who delivers strong results without oversight is already working at Level 5, so your only job left is to say so out loud.

Context has to travel with authority, because people can’t make CEO-level decisions without access to CEO-level thinking. If you want better calls made without you, spend your time explaining why the goal matters, what good looks like, which tradeoffs are acceptable, and where the real risk sits. The more context someone carries, the less instruction they need, and that context keeps paying off long after the conversation ends.

A better question than “did I delegate this?”

When the same issue lands on your desk for the fourth time, the instinct is to fix it again. The more useful move is to ask why it still needs you at all. The answer is almost always one of four things: the owner lacks authority, the owner lacks skill, the expectations were never clear, or nobody actually owns it. Each has a fix, and none of those fixes is you handling it one more time. It’s worth running through that list before you open an executive search, because three of the four have nothing to do with the person in the seat, and a new hire will run into the same wall.

So take an hour and list everything you’re currently involved in. For each item, write down what level it sits at today, what level it should reach, who should own it, and what’s stopping that person from owning it now. Strategy, culture, capital allocation, and senior leadership calls may well stay with you, and that’s fine. The point is to delegate on purpose, with each decision sitting at the level you chose for it.

Then ask yourself one question: what responsibility in your organization sits one level lower on the ladder than it should?

Why Your Team Keeps Bringing You Problems
Picture of Y Scouts
Y Scouts

October 1, 2026

Share Post

Want To Learn Our Secret Sauce? We Share Our Entire Process In Our Book 'Hiring on Purpose'

We’re all about transparency. That’s why we’re giving away our book with all our secrets to hiring on purpose…for free.  If you are responsible for hiring at any level, this book is guaranteed to change the way you approach the critical skill of hiring great people.

Master Purpose-Driven Hiring with
‘Hiring on Purpose.’

This essential guide is designed for business leaders and HR professionals who aim to streamline their hiring process and secure top talent that aligns perfectly with their company’s mission and culture.