This is the fourth post in my CEO Mindset series, written to help Chiefs of Staff operate at the level of their principal. If you missed the earlier ones, you can catch up here:
The CEO Mindset for Chiefs of Staff (Set the Vision)
How CEOs Build the Executive Team (Build the Team)
The Quiet Power Behind Culture (Shape the Culture)
This week, we’re focused on decisions from the lens of how a Chief of Staff ensures their principal devotes the most impactful time to the hardest calls.
The Fourth Responsibility
The fourth responsibility of a CEO is to make the tough decisions, but not all of the decisions.
When I ran my company, that line blurred more often than it should have. The team would bring me questions they were fully capable of answering, questions that didn’t need my input but I gave it anyway.
Why? Because I didn’t want to slow things down. I thought I was unblocking the work. But instead, I was training the team that it was OK not to think, or worse I didn’t want them to. I became the default decider. I reinforced that they could bring me anything and I answered it.
It was frustrating. It drained my energy. And more importantly, it kept them from building real leadership muscle. The kind that comes from taking ownership and making calls.
That experience shaped how I think about the Chief of Staff role, and specifically, the team’s role in decision-making.
The CEO shouldn't make all the decisions only the tough ones. The Chief’s job is to ensure your principal spends energy only on the calls that truly require their judgment. That means building a system around decision-making that keeps things moving and protects the CEO’s attention.
After years of getting this wrong, I developed a framework I call decision architecture. It helps in two ways. First, it’s a tool I share with the team when I know they can make the call, prompting them to think it through before escalating. Second, it gives my principal a way to filter, frame and focus so the toughest calls get the attention they deserve, and everything else doesn’t.
Deciding When to Decide
Not every decision needs to go to the CEO. In fact, most shouldn’t.
One of the most valuable things a Chief of Staff can do is protect the principal’s time and attention by helping the team—and the organization—decide when a decision needs to be elevated, and when it should be made without them.
Here’s the simplest filter I use:
Can we reverse it?
If yes, move fast. Reversible decisions are how a company builds momentum. Waiting for perfect information slows the work and sends a signal that no one is empowered to act.
When I was running Spaeth Hill, I’d sometimes say out loud: “This is my best bad decision.” This was how I moved forward in ambiguity, openly acknowledging that we might need to pivot later. It reminded me (and the team) that decisiveness matters more than being right on the first try.
And behind that is a mindset I used constantly:
Every decision is a trade on problems.
You’re never choosing a perfect outcome. You’re selecting the problems you’d rather have.
That line helped me and the team move forward when we were stuck. It reminded us that the goal isn’t to eliminate risk. It’s to trade up for a better set of problems and keep going.
Irreversible decisions are different. These are the ones that carry weight, strategic impact, financial consequence, reputational risk. They shape what the company becomes. These are the decisions a CEO should make but only if the rest of the team is moving without them.
That’s where a Chief of Staff comes in.
You help triage decisions before they reach the top. You ask:
Is this something we can walk back?
What’s the cost of getting it wrong?
Does this decision require the CEO’s judgment or approval?
Helping your principal and team answer those questions early is one of the quietest forms of leverage. It keeps the company moving without overloading the top.
Build the Decision Architecture
Once you’ve filtered what truly needs your principal’s attention, your next job is to bring them a decision that’s ready to be made: a clean, structured moment of choice.
This is what I call Decision Architecture: the structure you build around a moment of choice to make it easy, fast, and clear.
Here’s how I do it:
Define the decision.
What are we solving for? What’s the goal, and what facts matter?Surface the options.
Think in trade-offs. What are the viable paths? Outline more than one.Pressure-test your thinking.
List pros and cons. Ask: What’s the risk? Could we live with the worst case?Form a point of view.
What’s the best, most rational move based on what we know?Set up the 6-inch putt.
Don’t bring a question. Bring a call. Line it up. Let your principal tap it in.
This is where many employees get it wrong. They avoid the thinking and hand over a problem instead of a recommendation. As Chief, it’s your job to model a better way and, when needed, coach others to do the same. Sharing this framework helps raise the quality of decisions around your principal, not just above them.
When you do this well, your principal doesn’t waste time figuring out the shape of the decision. They step in and make the call. That’s leverage. That’s trust. That’s the job.
What great Chiefs do:
Most people avoid decisions. Chiefs don’t.
They lean in. They filter. They shape the hard calls before they ever reach the top. And when they do it well, they don’t just make their principal faster, they make the whole company smarter.
Call the decision early.
They recognize what actually needs to go to the CEO and what doesn’t.
Move fast on the rest.
They keep the team from getting stuck by pushing reversible decisions forward.
Bring a point of view.
They don’t escalate questions. They show up with a recommendation.
Make it easy to decide.
They set up the 6-inch putt so the CEO can tap it in.
That’s how great Chiefs protect the CEO’s focus and move the business forward. Because the best decisions don’t just happen. They’re built. And great Chiefs know how to build them.